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117048-59-6 | Phenol, 2-methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-
CAS No: 117048-59-6 Catalog No: AG000DMO MDL No:MFCD03453309
Product Description
Catalog Number:
AG000DMO
Chemical Name:
Phenol, 2-methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-
CAS Number:
117048-59-6
Molecular Formula:
C18H20O5
Molecular Weight:
316.3484
MDL Number:
MFCD03453309
IUPAC Name:
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
InChI:
InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
InChI Key:
HVXBOLULGPECHP-WAYWQWQTSA-N
SMILES:
COc1cc(/C=C\c2ccc(c(c2)O)OC)cc(c1OC)OC
UNII:
16U6OP69RQ
NSC Number:
613729
Properties
Complexity:
358
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1
Exact Mass:
316.131g/mol
Formal Charge:
0
Heavy Atom Count:
23
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
316.353g/mol
Monoisotopic Mass:
316.131g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
57.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.7
Literature
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| A phase II trial of fosbretabulin in advanced anaplastic thyroid carcinoma and correlation of baseline serum-soluble intracellular adhesion molecule-1 with outcome. | Thyroid : official journal of the American Thyroid Association 20090301 |
| Up-regulation of connective tissue growth factor in endothelial cells by the microtubule-destabilizing agent combretastatin A-4. | Molecular cancer research : MCR 20090201 |
| A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P). | Expert opinion on investigational drugs 20090201 |
| In vitro and in vivo phase II metabolism of combretastatin A-4: evidence for the formation of a sulphate conjugate metabolite. | Xenobiotica; the fate of foreign compounds in biological systems 20090201 |
| Pt(II) complexes of a combretastatin A-4 analogous chalcone: effects of conjugation on cytotoxicity, tumor specificity, and long-term tumor growth suppression. | Journal of medicinal chemistry 20090122 |
| Design, synthesis and biological evaluation of novel stilbene-based antitumor agents. | Bioorganic & medicinal chemistry 20090115 |
| Treatment of rodent liver tumor with combretastatin a4 phosphate: noninvasive therapeutic evaluation using multiparametric magnetic resonance imaging in correlation with microangiography and histology. | Investigative radiology 20090101 |
| Combination of combretastatin A4 phosphate and doxorubicin-containing liposomes affects growth of B16-F10 tumors. | Acta biochimica Polonica 20090101 |
| Pharmacological inhibition of the hypertensive response to combretastatin A-4 phosphate in rats. | Vascular pharmacology 20090101 |
| Synthesis and structure-activity relationships of 2-amino-1-aroylnaphthalene and 2-hydroxy-1-aroylnaphthalenes as potent antitubulin agents. | Journal of medicinal chemistry 20081225 |
| Novel A-ring and B-ring modified combretastatin A-4 (CA-4) analogues endowed with interesting cytotoxic activity. | Journal of medicinal chemistry 20081009 |
| Vibrational spectra and ab initio molecular orbital calculations of the novel anti-cancer drug combretastatin A-4 prodrug. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20081001 |
| Naphthylphenstatins as tubulin ligands: synthesis and biological evaluation. | Bioorganic & medicinal chemistry 20081001 |
| Synthesis and biological evaluation of polymethoxylated 4-heteroarylcoumarins as tubulin assembly inhibitor. | Bioorganic & medicinal chemistry 20081001 |
| Tumour vascular disrupting agents: combating treatment resistance. | The British journal of radiology 20081001 |
| Design, synthesis, biochemical, and biological evaluation of nitrogen-containing trifluoro structural modifications of combretastatin A-4. | Bioorganic & medicinal chemistry letters 20080915 |
| Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-N,N-dimethylamino benzo[b]furan derivatives as inhibitors of tubulin polymerization. | Bioorganic & medicinal chemistry 20080915 |
| 1,2,3,4-tetrahydro-2-thioxopyrimidine analogs of combretastatin-A4. | European journal of medicinal chemistry 20080901 |
| Design, synthesis and biological evaluation of dihydronaphthalene and benzosuberene analogs of the combretastatins as inhibitors of tubulin polymerization in cancer chemotherapy. | Bioorganic & medicinal chemistry 20080901 |
| Antineoplastic agents. 552. Oxidation of combretastatin A-1: trapping the o-quinone intermediate considered the metabolic product of the corresponding phosphate prodrug. | Journal of natural products 20080901 |
| Asymmetric synthesis of 2,3-dihydro-2-arylquinazolin-4-ones: methodology and application to a potent fluorescent tubulin inhibitor with anticancer activity. | Journal of medicinal chemistry 20080814 |
| Synthesis and biological evaluation of new disubstituted analogues of 6-methoxy-3-(3',4',5'-trimethoxybenzoyl)-1H-indole (BPR0L075), as potential antivascular agents. | Bioorganic & medicinal chemistry 20080801 |
| Discovery of 4-amino and 4-hydroxy-1-aroylindoles as potent tubulin polymerization inhibitors. | Journal of medicinal chemistry 20080724 |
| Relationship between human tumour angiogenic profile and combretastatin-induced vascular shutdown: an exploratory study. | British journal of cancer 20080722 |
| Antivascular effects of combretastatin A4 phosphate in breast cancer xenograft assessed using dynamic bioluminescence imaging and confirmed by MRI. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080701 |
| Synthesis and antitumor activity of benzils related to combretastatin A-4. | Bioorganic & medicinal chemistry letters 20080601 |
| Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization. | Bioorganic & medicinal chemistry 20080601 |
| Design, synthesis, and biological evaluation of thiophene analogues of chalcones. | Bioorganic & medicinal chemistry 20080515 |
| 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines as a new class of potent antitubulin agents. | Journal of medicinal chemistry 20080508 |
| Synthesis and biological activity of fluorinated combretastatin analogues. | Journal of medicinal chemistry 20080508 |
| The tubulin-depolymerising agent combretastatin-4 induces ectopic aster assembly and mitotic catastrophe in lung cancer cells H460. | Apoptosis : an international journal on programmed cell death 20080501 |
| 1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin. | Bioorganic & medicinal chemistry 20080501 |
| Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives. | Bioorganic & medicinal chemistry letters 20080501 |
| p38 MAPK, but not ERK1/2, is critically involved in the cytotoxicity of the novel vascular disrupting agent combretastatin A4. | International journal of cancer 20080415 |
| Blood vessel maturation and response to vascular-disrupting therapy in single vascular endothelial growth factor-A isoform-producing tumors. | Cancer research 20080401 |
| Combretastatin A-4 activates AMP-activated protein kinase and improves glucose metabolism in db/db mice. | Pharmacological research 20080401 |
| Synthesis and biological evaluation of 1-methyl-2-(3',4',5'-trimethoxybenzoyl)-3-aminoindoles as a new class of antimitotic agents and tubulin inhibitors. | Journal of medicinal chemistry 20080313 |
| Preclinical studies to predict efficacy of vascular changes induced by combretastatin a-4 disodium phosphate in patients. | International journal of radiation oncology, biology, physics 20080301 |
| Efficacy of selected natural products as therapeutic agents against cancer. | Journal of natural products 20080301 |
| Combretastatin dinitrogen-substituted stilbene analogues as tubulin-binding and vascular-disrupting agents. | Journal of natural products 20080301 |
| The microtubule-targeting agent CA4P regresses leukemic xenografts by disrupting interaction with vascular cells and mitochondrial-dependent cell death. | Blood 20080215 |
| Design, synthesis, and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2-thione analogues. | Bioorganic & medicinal chemistry letters 20080201 |
| Segmentation of dynamic contrast enhanced magnetic resonance imaging data. | Acta oncologica (Stockholm, Sweden) 20080101 |
| Solution-phase parallel synthesis and biological evaluation of combretatriazoles. | Journal of combinatorial chemistry 20080101 |
| The effect of combretastatin A4 disodium phosphate and 5,6-dimethylxanthenone-4-acetic acid on water diffusion and blood perfusion in tumours. | Acta oncologica (Stockholm, Sweden) 20080101 |
| 3-(2'-Bromopropionylamino)-benzamides as novel S-phase arrest agents. | Bioorganic & medicinal chemistry letters 20071215 |
| In vitro metabolism study of combretastatin A-4 in rat and human liver microsomes. | Drug metabolism and disposition: the biological fate of chemicals 20071201 |
| Mechanism of retinoblastoma tumor cell death after focal chemotherapy, radiation, and vascular targeting therapy in a mouse model. | Investigative ophthalmology & visual science 20071201 |
| Combretastatin a-4 analogs as anticancer agents. | Mini reviews in medicinal chemistry 20071201 |
| Conformationally restricted macrocyclic analogues of combretastatins. | Bioorganic & medicinal chemistry letters 20071115 |
| Assessment of tumor response to the vascular disrupting agents 5,6-dimethylxanthenone-4-acetic acid or combretastatin-A4-phosphate by intrinsic susceptibility magnetic resonance imaging. | International journal of radiation oncology, biology, physics 20071115 |
| Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry. | Bioorganic & medicinal chemistry 20071101 |
| Design, synthesis, and biological testing of pyrazoline derivatives of combretastatin-A4. | Bioorganic & medicinal chemistry letters 20071101 |
| Tumour targeting by microtubule-depolymerizing vascular disrupting agents. | Expert opinion on therapeutic targets 20071101 |
| Combretastatin A4-induced differential cytotoxicity and reduced metastatic ability by inhibition of AKT function in human gastric cancer cells. | The Journal of pharmacology and experimental therapeutics 20071001 |
| Combination chemotherapy including combretastatin A4 phosphate and paclitaxel is effective against anaplastic thyroid cancer in a nude mouse xenograft model. | The Journal of clinical endocrinology and metabolism 20070801 |
| Novel potent antimitotic heterocyclic ketones: synthesis, antiproliferative activity, and structure-activity relationships. | Bioorganic & medicinal chemistry letters 20070701 |
| Synthesis and biological activity of naphthalene analogues of phenstatins: naphthylphenstatins. | Bioorganic & medicinal chemistry letters 20070615 |
| Arylthioindole inhibitors of tubulin polymerization. 3. Biological evaluation, structure-activity relationships and molecular modeling studies. | Journal of medicinal chemistry 20070614 |
| Synthesis and biological evaluation of 2- and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization. | Journal of medicinal chemistry 20070503 |
| The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4. | Bioorganic & medicinal chemistry 20070501 |
| Characterizing the tumor response to treatment with combretastatin A4 phosphate. | International journal of radiation oncology, biology, physics 20070501 |
| A Ramberg-Bäcklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212. | Chemical communications (Cambridge, England) 20070428 |
| Vascular disrupting agents in clinical development. | British journal of cancer 20070423 |
| Synthesis and evaluation of 4/5-hydroxy-2,3-diaryl(substituted)-cyclopent-2-en-1-ones as cis-restricted analogues of combretastatin A-4 as novel anticancer agents. | Journal of medicinal chemistry 20070419 |
| Tumor antivascular effects of radiotherapy combined with combretastatin a4 phosphate in human non-small-cell lung cancer. | International journal of radiation oncology, biology, physics 20070401 |
| N-Phenyl-N'-(2-chloroethyl)urea analogues of combretastatin A-4: Is the N-phenyl-N'-(2-chloroethyl)urea pharmacophore mimicking the trimethoxy phenyl moiety? | Bioorganic & medicinal chemistry letters 20070401 |
| Evaluation of the vascular targeting agent combretastatin a-4 prodrug on retinal neovascularization in the galactose-fed dog. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20070401 |
| Potent antitubulin tumor cell cytotoxins based on 3-aroyl indazoles. | Journal of medicinal chemistry 20070308 |
| Novel pyridinyl and pyrimidinylcarbazole sulfonamides as antiproliferative agents. | Bioorganic & medicinal chemistry letters 20070301 |
| Highly potent triazole-based tubulin polymerization inhibitors. | Journal of medicinal chemistry 20070222 |
| Synthesis and cytotoxic activities of 4,5-diarylisoxazoles. | Bioorganic & medicinal chemistry letters 20070215 |
| Synthesis and activity of Combretastatin A-4 analogues: 1,2,3-thiadiazoles as potent antitumor agents. | Bioorganic & medicinal chemistry letters 20070215 |
| MZ3 induces apoptosis in human leukemia cells. | Cancer chemotherapy and pharmacology 20070201 |
| Early effects of combretastatin-A4 disodium phosphate on tumor perfusion and interstitial fluid pressure. | Neoplasia (New York, N.Y.) 20070201 |
| Combretastatin CA-4 and combretastatin derivative induce mitotic catastrophe dependent on spindle checkpoint and caspase-3 activation in non-small cell lung cancer cells. | Apoptosis : an international journal on programmed cell death 20070101 |
| Dose-response relationship of ultrasound contrast agent in an in vivo murine melanoma model. | Cancer imaging : the official publication of the International Cancer Imaging Society 20070101 |
| Thrombospondins deployed by thrombopoietic cells determine angiogenic switch and extent of revascularization. | The Journal of clinical investigation 20061201 |
| Synthesis and biological properties of bioreductively targeted nitrothienyl prodrugs of combretastatin A-4. | Molecular cancer therapeutics 20061101 |
| Synthesis and structure-activity relationships of carbazole sulfonamides as a novel class of antimitotic agents against solid tumors. | Journal of medicinal chemistry 20061019 |
| 2-amino and 2'-aminocombretastatin derivatives as potent antimitotic agents. | Journal of medicinal chemistry 20061019 |
| Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors. | Journal of medicinal chemistry 20061019 |
| Structure-activity-relationship studies of conformationally restricted analogs of combretastatin A-4 derived from SU5416. | Bioorganic & medicinal chemistry 20061001 |
| Therapy-induced acute recruitment of circulating endothelial progenitor cells to tumors. | Science (New York, N.Y.) 20060922 |
| Synthesis and cytotoxic evaluation of combretafurans, potential scaffolds for dual-action antitumoral agents. | Journal of medicinal chemistry 20060824 |
| Interaction of 4-arylcoumarin analogues of combretastatins with microtubule network of HBL100 cells and binding to tubulin. | Biochemistry 20060801 |
| Low-dose combretastatin A4 phosphate enhances the immune response of tumor hosts to experimental colon carcinoma. | Clinical cancer research : an official journal of the American Association for Cancer Research 20060801 |
| 4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: synthesis and evaluation as anti-mitotic and cytotoxic agents. | Bioorganic & medicinal chemistry 20060701 |
| Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents. | Bioorganic & medicinal chemistry 20060701 |
| Promising new treatments for neovascular age-related macular degeneration. | Expert opinion on investigational drugs 20060701 |
| Effect of the second-generation vascular disrupting agent OXi4503 on tumor vascularity. | Clinical cancer research : an official journal of the American Association for Cancer Research 20060701 |
| Early effects of combretastatin A4 phosphate assessed by anatomic and carbogen-based functional magnetic resonance imaging on rat bladder tumors implanted in nude mice. | Neoplasia (New York, N.Y.) 20060701 |
| Synthesis and biological evaluation of 2-amino-3-(3',4',5'-trimethoxybenzoyl)-5-aryl thiophenes as a new class of potent antitubulin agents. | Journal of medicinal chemistry 20060629 |
| Isoxazole-type derivatives related to combretastatin A-4, synthesis and biological evaluation. | Bioorganic & medicinal chemistry 20060615 |
| Medicinal chemistry of combretastatin A4: present and future directions. | Journal of medicinal chemistry 20060601 |
| Novel combretastatin analogues endowed with antitumor activity. | Journal of medicinal chemistry 20060601 |
| Current development status of small-molecule vascular disrupting agents. | Current opinion in investigational drugs (London, England : 2000) 20060601 |
| A tumor vasculature targeted liposome delivery system for combretastatin A4: design, characterization, and in vitro evaluation. | AAPS PharmSciTech 20060407 |
| Benzoylphenylurea sulfur analogues with potent antitumor activity. | Journal of medicinal chemistry 20060406 |
| Oxadiazole derivatives as a novel class of antimitotic agents: Synthesis, inhibition of tubulin polymerization, and activity in tumor cell lines. | Bioorganic & medicinal chemistry letters 20060301 |
| C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties. | Bioorganic & medicinal chemistry letters 20060101 |
| NPI-2358 is a tubulin-depolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent. | Anti-cancer drugs 20060101 |
| In vivo antitumour effect of combretastatin A-4 phosphate added to fractionated irradiation. | Anticancer research 20060101 |
| The effects of the vascular disrupting agents combretastatin A-4 disodium phosphate, 5,6-dimethylxanthenone-4-acetic acid and ZD6126 in a murine tumour: a comparative assessment using MRI and MRS. | Acta oncologica (Stockholm, Sweden) 20060101 |
| Macular degeneration: the latest in current medical management. | Retina (Philadelphia, Pa.) 20060101 |
| Combretastatin A-1 phosphate potentiates the antitumor activity of carboplatin and paclitaxel in a severe combined immunodeficiency disease (SCID) mouse model of human ovarian carcinoma. | International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20060101 |
| A targeted liposome delivery system for combretastatin A4: formulation optimization through drug loading and in vitro release studies. | PDA journal of pharmaceutical science and technology 20060101 |
| Anti-vascular agent Combretastatin A-4-P modulates hypoxia inducible factor-1 and gene expression. | BMC cancer 20060101 |
| Conformationally restricted analogs of Combretastatin A-4 derived from SU5416. | Bioorganic & medicinal chemistry letters 20051215 |
| Synthesis and structure-activity relationships of 1,2,4-triazoles as a novel class of potent tubulin polymerization inhibitors. | Bioorganic & medicinal chemistry letters 20051201 |
| Plant-based anticancer molecules: a chemical and biological profile of some important leads. | Bioorganic & medicinal chemistry 20051101 |
| Effect of vascular targeting agent in rat tumor model: dynamic contrast-enhanced versus diffusion-weighted MR imaging. | Radiology 20051101 |
| Combretastatin A4 phosphate induces rapid regression of tumor neovessels and growth through interference with vascular endothelial-cadherin signaling. | The Journal of clinical investigation 20051101 |
| Antineoplastic strategy: irreversible tumor blood flow stasis induced by the combretastatin A-4 derivative AVE8062 (AC7700). | Chemotherapy 20051001 |
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| A common pharmacophore for a diverse set of colchicine site inhibitors using a structure-based approach. | Journal of medicinal chemistry 20050922 |
| Synthesis and preliminary biological evaluation of new anti-tubulin agents containing different benzoheterocycles. | Bioorganic & medicinal chemistry letters 20050915 |
| Taking down tumors: vascular disrupting agents entering clinical trials. | Journal of the National Cancer Institute 20050907 |
| Structure-based discovery of a boronic acid bioisostere of combretastatin A-4. | Chemistry & biology 20050901 |
| Stilbenophane analogues of deoxycombretastatin A-4. | The Journal of organic chemistry 20050805 |
| Synthesis and biological activity of mustard derivatives of combretastatins. | Bioorganic & medicinal chemistry letters 20050801 |
| Antineoplastic agents. 515. Synthesis of human cancer cell growth inhibitors derived from 3,4-methylenedioxy-5,4'-dimethoxy-3'-amino-Z-stilbene. | Journal of natural products 20050801 |
| Diffusion-weighted magnetic resonance imaging allows noninvasive in vivo monitoring of the effects of combretastatin a-4 phosphate after repeated administration. | Neoplasia (New York, N.Y.) 20050801 |
| Synthesis and biological evaluation of vinylogous combretastatin A-4 derivatives. | Organic & biomolecular chemistry 20050721 |
| Tumor physiologic response to combretastatin A4 phosphate assessed by MRI. | International journal of radiation oncology, biology, physics 20050701 |
| Vascular targeting and antiangiogenesis agents induce drug resistance effector GRP78 within the tumor microenvironment. | Cancer research 20050701 |
| Antineoplastic agents. 445. Synthesis and evaluation of structural modifications of (Z)- and (E)-combretastatin A-41. | Journal of medicinal chemistry 20050616 |
| New antitubulin derivatives in the combretastatin A4 series: synthesis and biological evaluation. | Bioorganic & medicinal chemistry 20050601 |
| Synthesis and cytotoxic evaluation of combretafurazans. | Journal of medicinal chemistry 20050505 |
| Novel vascular targeting/disrupting agents: combretastatin A4 phosphate and related compounds. | Current oncology reports 20050301 |
| Tumour parameters affected by combretastatin A-4 phosphate therapy in a human colorectal xenograft model in nude mice. | European journal of cancer (Oxford, England : 1990) 20050301 |
| Antimitotic activity and reversal of breast cancer resistance protein-mediated drug resistance by stilbenoids from Bletilla striata. | Bioorganic & medicinal chemistry letters 20050215 |
| Phase I trial of combretastatin a-4 phosphate with carboplatin. | Clinical cancer research : an official journal of the American Association for Cancer Research 20050215 |
| Heterocyclic and phenyl double-bond-locked combretastatin analogues possessing potent apoptosis-inducing activity in HL60 and in MDR cell lines. | Journal of medicinal chemistry 20050210 |
| Quantitative structure-activity relationship (5D-QSAR) study of combretastatin-like analogues as inhibitors of tubulin assembly. | Journal of medicinal chemistry 20050127 |
| Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety. | Journal of medicinal chemistry 20050127 |
| Combretastatin A-4 prodrug in the treatment of a murine model of retinoblastoma. | Investigative ophthalmology & visual science 20050101 |
| Evaluation of anti-vascular therapy with texture analysis. | Anticancer research 20050101 |
| Combretastatin A-4 resistance in H460 human lung carcinoma demonstrates distinctive alterations in beta-tubulin isotype expression. | Anticancer research 20050101 |
| Arylthioindoles, potent inhibitors of tubulin polymerization. | Journal of medicinal chemistry 20041202 |
| The tubulin-binding agent combretastatin A-4-phosphate arrests endothelial cells in mitosis and induces mitotic cell death. | The American journal of pathology 20041001 |
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| Consideration of QT/QTc interval data in a phase I study in patients with advanced cancer. | Clinical cancer research : an official journal of the American Association for Cancer Research 20040901 |
| Concise synthesis and structure-activity relationships of combretastatin A-4 analogues, 1-aroylindoles and 3-aroylindoles, as novel classes of potent antitubulin agents. | Journal of medicinal chemistry 20040812 |
| A new family of quinoline and quinoxaline analogues of combretastatins. | Bioorganic & medicinal chemistry letters 20040716 |
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| Synthesis and structure-activity relationships of 3-aminobenzophenones as antimitotic agents. | Journal of medicinal chemistry 20040520 |
| Examination of the 1,4-disubstituted azetidinone ring system as a template for combretastatin A-4 conformationally restricted analogue design. | Bioorganic & medicinal chemistry letters 20040503 |
| Combretastatin A4 phosphate. | Anti-cancer drugs 20040301 |
| Comparative preclinical pharmacokinetic and metabolic studies of the combretastatin prodrugs combretastatin A4 phosphate and A1 phosphate. | Clinical cancer research : an official journal of the American Association for Cancer Research 20040215 |
| Induction of tumour blood flow stasis and necrosis: a new function for epinephrine similar to that of combretastatin A-4 derivative AVE8062 (AC7700). | British journal of cancer 20040126 |
| Vascular targeting agents as cancer therapeutics. | Clinical cancer research : an official journal of the American Association for Cancer Research 20040115 |
| Combretastatin A-4 phosphate enhances CPT-11 activity independently of the administration sequence. | European journal of cancer (Oxford, England : 1990) 20040101 |
| Cardiovascular safety profile of combretastatin a4 phosphate in a single-dose phase I study in patients with advanced cancer. | Clinical cancer research : an official journal of the American Association for Cancer Research 20040101 |
| Abilities of 3,4-diarylfuran-2-one analogs of combretastatin A-4 to inhibit both proliferation of tumor cell lines and growth of relevant tumors in nude mice. | Anticancer research 20040101 |
| Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins. | Journal of medicinal chemistry 20031204 |
| Phase I trial of the antivascular agent combretastatin A4 phosphate on a 5-day schedule to patients with cancer: magnetic resonance imaging evidence for altered tumor blood flow. | Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20031201 |
| Thrombosis and Hemostasis Issues in Cancer - Second International Conference. 19-21 September, 2003, Bergamo, Italy. | IDrugs : the investigational drugs journal 20031101 |
| Combretastatin A-4 analogues as antimitotic antitumor agents. | Current medicinal chemistry 20030901 |
| Antitumor activity of TZT-1027 (Soblidotin) against vascular endothelial growth factor-secreting human lung cancer in vivo. | Cancer science 20030901 |
| Assessment of pharmacodynamic vascular response in a phase I trial of combretastatin A4 phosphate. | Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030801 |
| Combretastatin A4 phosphate has tumor antivascular activity in rat and man as demonstrated by dynamic magnetic resonance imaging. | Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030801 |
| Combretastatin A-4 phosphate suppresses development and induces regression of choroidal neovascularization. | Investigative ophthalmology & visual science 20030801 |
| Novel benzylidene-9(10H)-anthracenones as highly active antimicrotubule agents. Synthesis, antiproliferative activity, and inhibition of tubulin polymerization. | Journal of medicinal chemistry 20030717 |
| (E)-1-(2-Hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene. | Acta crystallographica. Section C, Crystal structure communications 20030701 |
| Vascular targeting effect of combretastatin A-4 phosphate dominates the inherent angiogenesis inhibitory activity. | International journal of cancer 20030520 |
| Novel 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues as cytotoxic agents. | Bioorganic & medicinal chemistry letters 20030519 |
| Synthesis, in vitro, and in vivo evaluation of phosphate ester derivatives of combretastatin A-4. | Bioorganic & medicinal chemistry letters 20030505 |
| Synthesis, anticancer activity, and inhibition of tubulin polymerization by conformationally restricted analogues of lavendustin A. | Journal of medicinal chemistry 20030424 |
| Antineoplastic agents. 487. Synthesis and biological evaluation of the antineoplastic agent 3,4-methylenedioxy-5,4'-dimethoxy-3'-amino-Z-stilbene and derived amino acid amides. | Journal of medicinal chemistry 20030213 |
| Structure-activity and crystallographic analysis of benzophenone derivatives-the potential anticancer agents. | Bioorganic & medicinal chemistry letters 20030106 |
| Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin. | Cell biochemistry and biophysics 20030101 |
| Vascular targeting: a potential additional anti-cancer treatment. | Verhandelingen - Koninklijke Academie voor Geneeskunde van Belgie 20030101 |
| Oxi4503, a novel vascular targeting agent: effects on blood flow and antitumor activity in comparison to combretastatin A-4 phosphate. | Anticancer research 20030101 |
| The vascular targeting agent combretastatin A-4-phosphate induces neutrophil recruitment to endothelial cells in vitro. | Anticancer research 20030101 |
| Drug based approaches for targeting tumor vasculature: development of combretastatin A4 phosphate. | Pathophysiology of haemostasis and thrombosis 20030101 |
| The development of combretastatin A4 phosphate as a vascular targeting agent. | International journal of radiation oncology, biology, physics 20021201 |
| Combination of vascular targeting agents with thermal or radiation therapy. | International journal of radiation oncology, biology, physics 20021201 |
| Enhancement of vascular targeting by inhibitors of nitric oxide synthase. | International journal of radiation oncology, biology, physics 20021201 |
| Combretastatin A4 phosphate has primary antineoplastic activity against human anaplastic thyroid carcinoma cell lines and xenograft tumors. | Thyroid : official journal of the American Thyroid Association 20021201 |
| Schedule dependence of combretastatin A4 phosphate in transplanted and spontaneous tumour models. | International journal of cancer 20021101 |
| The vascular response of tumor and normal tissues in the rat to the vascular targeting agent, combretastatin A-4-phosphate, at clinically relevant doses. | International journal of oncology 20021001 |
| Combretastatin-A4 prodrug induces mitotic catastrophe in chronic lymphocytic leukemia cell line independent of caspase activation and poly(ADP-ribose) polymerase cleavage. | Clinical cancer research : an official journal of the American Association for Cancer Research 20020801 |
| A phase I pharmacokinetic and translational study of the novel vascular targeting agent combretastatin a-4 phosphate on a single-dose intravenous schedule in patients with advanced cancer. | Cancer research 20020615 |
| Antineoplastic agents. 465. Structural modification of resveratrol: sodium resverastatin phosphate. | Journal of medicinal chemistry 20020606 |
| Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents. | Journal of medicinal chemistry 20020606 |
| One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization. | Journal of medicinal chemistry 20020606 |
| Vascular targeting agents enhance chemotherapeutic agent activities in solid tumor therapy. | International journal of cancer 20020501 |
| Acute effects of vascular modifying agents in solid tumors assessed by noninvasive laser Doppler flowmetry and near infrared spectroscopy. | Neoplasia (New York, N.Y.) 20020501 |
| The influence of combretastatin A-4 and vinblastine on interstitial fluid pressure in BT4An rat gliomas. | Cancer letters 20020425 |
| Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. | Journal of medicinal chemistry 20020411 |
| Differential sensitivity of two adenocarcinoma xenografts to the anti-vascular drugs combretastatin A4 phosphate and 5,6-dimethylxanthenone-4-acetic acid, assessed using MRI and MRS. | NMR in biomedicine 20020401 |
| Inhibition of proliferative retinopathy by the anti-vascular agent combretastatin-A4. | The American journal of pathology 20020301 |
| Synthesis and biological evaluation of 2-indolyloxazolines as a new class of tubulin polymerization inhibitors. Discovery of A-289099 as an orally active antitumor agent. | Bioorganic & medicinal chemistry letters 20020211 |
| The biology of the combretastatins as tumour vascular targeting agents. | International journal of experimental pathology 20020201 |
| Preclinical evaluations of therapies combining the vascular targeting agent combretastatin A-4 disodium phosphate and conventional anticancer therapies in the treatment of Kaposi's sarcoma. | Acta oncologica (Stockholm, Sweden) 20020101 |
| Activity of the vascular targeting agent combretastatin A-4 disodium phosphate in a xenograft model of AIDS-associated Kaposi's sarcoma. | Acta oncologica (Stockholm, Sweden) 20020101 |
| Anti-tumor and anti-vascular effects of the novel tubulin-binding agent combretastatin A-1 phosphate. | Anticancer research 20020101 |
| Critical assessment of angiogenesis inhibitors in clinical trials. | I supplementi di Tumori : official journal of Societa italiana di cancerologia ... [et al.] 20020101 |
| Tumor vasculature is targeted by the combination of combretastatin A-4 and hyperthermia. | Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20011201 |
| Novel syntheses of cis and trans isomers of combretastatin A-4. | The Journal of organic chemistry 20011130 |
| Combretastatin A-4 disodium phosphate: a vascular targeting agent that improves that improves the anti-tumor effects of hyperthermia, radiation, and mild thermoradiotherapy. | International journal of radiation oncology, biology, physics 20011115 |
| Antitumor Agents. 211. Fluorinated 2-phenyl-4-quinolone derivatives as antimitotic antitumor agents. | Journal of medicinal chemistry 20011108 |
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| The susceptibility of tumors to the antivascular drug combretastatin A4 phosphate correlates with vascular permeability. | Cancer research 20010915 |
| The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4. | Bioorganic & medicinal chemistry letters 20010903 |
| Mechanisms associated with tumor vascular shut-down induced by combretastatin A-4 phosphate: intravital microscopy and measurement of vascular permeability. | Cancer research 20010901 |
| Combretastatin A-4 and hyperthermia;a potent combination for the treatment of solid tumors. | Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20010801 |
| Interaction between combretastatin A-4 disodium phosphate and radiation in murine tumors. | Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20010801 |
| Eradication of colorectal xenografts by combined radioimmunotherapy and combretastatin a-4 3-O-phosphate. | Cancer research 20010615 |
| Combretastatin A-4 prodrug inhibits growth of human non-small cell lung cancer in a murine xenotransplant model. | The Annals of thoracic surgery 20010501 |
| Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents. | Bioorganic & medicinal chemistry letters 20010409 |
| Combretastatin A4 prodrug study of effect on the growth and the microvasculature of colorectal liver metastases in a murine model. | Clinical cancer research : an official journal of the American Association for Cancer Research 20010401 |
| Specific targeting of cytosine deaminase to solid tumors by engineered Clostridium acetobutylicum. | Cancer gene therapy 20010401 |
| Combretastatin-A4 disrupts neovascular development in non-neoplastic tissue. | British journal of cancer 20010301 |
| Improvement of Clostridium tumour targeting vectors evaluated in rat rhabdomyosarcomas. | FEMS immunology and medical microbiology 20010201 |
| In vivo antitumor effect of vascular targeting combined with either ionizing radiation or anti-angiogenesis treatment. | International journal of radiation oncology, biology, physics 20010201 |
| Comparative effects of combretastatin A-4 disodium phosphate and 5,6-dimethylxanthenone-4-acetic acid on blood perfusion in a murine tumour and normal tissues. | International journal of radiation biology 20010201 |
| Design, synthesis, and biological evaluation of a series of lavendustin A analogues that inhibit EGFR and Syk tyrosine kinases, as well as tubulin polymerization. | Journal of medicinal chemistry 20010201 |
| Targeting tumour vasculature: the development of combretastatin A4. | The Lancet. Oncology 20010201 |
| Antimitotic and cell growth inhibitory properties of combretastatin A-4-like ethers. | Bioorganic & medicinal chemistry letters 20010108 |
| Combretastatin A-4 and doxorubicin combination treatment is effective in a preclinical model of human medullary thyroid carcinoma. | Oncology reports 20010101 |
| Stoppage of blood flow in 3-methylcholanthrene-induced autochthonous primary tumor due to a novel combretastatin A-4 derivative, AC7700, and its antitumor effect. | Medical science monitor : international medical journal of experimental and clinical research 20010101 |
| Evaluation of combretastatin A-4 prodrug in a non-Hodgkin's lymphoma xenograft model: preclinical efficacy. | Anti-cancer drugs 20010101 |
| Effects of combretastatin A4 phosphate on endothelial cell morphology in vitro and relationship to tumour vascular targeting activity in vivo. | Anticancer research 20010101 |
| 6-Alkylamino- and 2,3-dihydro-3'-methoxy-2-phenyl-4-quinazolinones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. | Journal of medicinal chemistry 20001116 |
| Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4. | Experientia 19890215 |
| Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: a structure-activity study. | Molecular pharmacology 19880801 |
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