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292618-32-7 | 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, 11-[O-(1,1-dimethylethyl)oxime], [C(E),4S]-
CAS No: 292618-32-7 Catalog No: AG002XVK MDL No:
Product Description
Catalog Number:
AG002XVK
Chemical Name:
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, 11-[O-(1,1-dimethylethyl)oxime], [C(E),4S]-
CAS Number:
292618-32-7
IUPAC Name:
(19S)-19-ethyl-19-hydroxy-10-[(E)-(2-methylpropan-2-yl)oxyiminomethyl]-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
InChI:
InChI=1S/C25H25N3O5/c1-5-25(31)18-10-20-21-16(12-28(20)22(29)17(18)13-32-23(25)30)15(11-26-33-24(2,3)4)14-8-6-7-9-19(14)27-21/h6-11,31H,5,12-13H2,1-4H3/b26-11+/t25-/m0/s1
InChI Key:
UIVFUQKYVFCEKJ-OPTOVBNMSA-N
UNII:
7KKS9R192F
Properties
Complexity:
948
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
1
Exact Mass:
447.179g/mol
Formal Charge:
0
Heavy Atom Count:
33
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
447.491g/mol
Monoisotopic Mass:
447.179g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
101A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2
Literature
| Title | Journal |
|---|---|
| Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. | Scientific reports 20140101 |
| DNA damage persistence as determinant of tumor sensitivity to the combination of Topo I inhibitors and telomere-targeting agents. | Clinical cancer research : an official journal of the American Association for Cancer Research 20110415 |
| Antitumor activity and pharmacokinetics of oral gimatecan on pediatric cancer xenografts. | Cancer chemotherapy and pharmacology 20100901 |
| Phase II of oral gimatecan in patients with recurrent epithelial ovarian, fallopian tube or peritoneal cancer, previously treated with platinum and taxanes. | Annals of oncology : official journal of the European Society for Medical Oncology 20100401 |
| Docetaxel-ST1481 sequence exerts a potent cytotoxic activity on hormone-resistant prostate cancer cells by reducing drug resistance-related gene expression. | The Prostate 20100201 |
| Clinical pharmacokinetics of the new oral camptothecin gimatecan: the inter-patient variability is related to alpha1-acid glycoprotein plasma levels. | European journal of cancer (Oxford, England : 1990) 20100201 |
| Determination of total and lactone form of a new camptothecin derivative gimatecan (ST1481) and its metabolite ST1698 in human plasma by high-performance liquid chromatography with fluorimetric detection. | Journal of pharmaceutical and biomedical analysis 20091015 |
| An exploratory survival analysis of anti-angiogenic therapy for recurrent malignant glioma. | Journal of neuro-oncology 20090401 |
| Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors. | Drug metabolism and disposition: the biological fate of chemicals 20090401 |
| Optimized synthesis and enhanced efficacy of novel triplex-forming camptothecin derivatives based on gimatecan. | Bioconjugate chemistry 20090401 |
| Phase I and pharmacokinetic study of gimatecan given orally once a week for 3 of 4 weeks in patients with advanced solid tumors. | Clinical cancer research : an official journal of the American Association for Cancer Research 20090101 |
| Effects of drug efflux proteins and topoisomerase I mutations on the camptothecin analogue gimatecan. | Investigational new drugs 20080601 |
| E-ring-modified 7-oxyiminomethyl camptothecins: Synthesis and preliminary in vitro and in vivo biological evaluation. | Bioorganic & medicinal chemistry letters 20080501 |
| Synthesis and cytotoxic activity of new 9-substituted camptothecins. | Bioorganic & medicinal chemistry letters 20080501 |
| Combination of metronomic gimatecan and CpG-oligodeoxynucleotides against an orthotopic pancreatic cancer xenograft. | Cancer biology & therapy 20080401 |
| Metronomic chemotherapy and tumor immunomodulation. | Cancer biology & therapy 20080401 |
| Next generation topoisomerase I inhibitors: Rationale and biomarker strategies. | Biochemical pharmacology 20080315 |
| In vitro transport of gimatecan (7-t-butoxyiminomethylcamptothecin) by breast cancer resistance protein, P-glycoprotein, and multidrug resistance protein 2. | Molecular cancer therapeutics 20071201 |
| Concerted escalation of dose and dosing duration in a phase I study of the oral camptothecin gimatecan (ST1481) in patients with advanced solid tumors. | Annals of oncology : official journal of the European Society for Medical Oncology 20070301 |
| Sensitization to gimatecan-induced apoptosis by tumor necrosis factor-related apoptosis inducing ligand in prostate carcinoma cells. | Biochemical pharmacology 20060314 |
| The novel lipophilic camptothecin analogue gimatecan is very active in vitro in human neuroblastoma: a comparative study with SN38 and topotecan. | Biochemical pharmacology 20051015 |
| Gimatecan (sigma-tau industrie farmaceutiche riunite/novartis). | IDrugs : the investigational drugs journal 20050701 |
| Enhanced antitumour efficacy of gimatecan in combination with Bcl-2 antisense oligonucleotide in human melanoma xenografts. | European journal of cancer (Oxford, England : 1990) 20050501 |
| Phacilitate Cell and Gene Therapy Forum 2005. Cell and gene therapy: a corporate perspective. 24-26 January 2005, Washington, DC, USA. | IDrugs : the investigational drugs journal 20050301 |
| Cellular basis of antiproliferative and antitumor activity of the novel camptothecin derivative, gimatecan, in bladder carcinoma models. | Neoplasia (New York, N.Y.) 20050201 |
| Efficacy of the novel camptothecin gimatecan against orthotopic and metastatic human tumor xenograft models. | Clinical cancer research : an official journal of the American Association for Cancer Research 20041101 |
| Gimatecan, a novel camptothecin with a promising preclinical profile. | Anti-cancer drugs 20040701 |
| Subcellular localization of the camptothecin analogues, topotecan and gimatecan. | Biochemical pharmacology 20040315 |
| Novel camptothecin analogue (gimatecan)-containing liposomes prepared by the ethanol injection method. | Journal of liposome research 20040101 |
| Antiangiogenic effects of the novel camptothecin ST1481 (gimatecan) in human tumor xenografts. | Molecular cancer research : MCR 20031001 |
| Cellular bases of the antitumor activity of a 7-substituted camptothecin in hormone-refractory human prostate carcinoma models. | Biochemical pharmacology 20030415 |
| Pattern of antitumor activity of a novel camptothecin, ST1481, in a large panel of human tumor xenografts. | Clinical cancer research : an official journal of the American Association for Cancer Research 20021201 |
| Potent antitumor activity and improved pharmacological profile of ST1481, a novel 7-substituted camptothecin. | Cancer research 20011001 |
| Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity. | Journal of medicinal chemistry 20010927 |
| A novel 7-modified camptothecin analog overcomes breast cancer resistance protein-associated resistance in a mitoxantrone-selected colon carcinoma cell line. | Cancer research 20010815 |
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