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96203-70-2 | Pancratistatin
CAS No: 96203-70-2 Catalog No: AG01FNS3 MDL No:
Product Description
Catalog Number:
AG01FNS3
Chemical Name:
Pancratistatin
CAS Number:
96203-70-2
IUPAC Name:
(1R,2S,3S,4S,4aR,11bR)-1,2,3,4,7-pentahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
InChI:
InChI=1S/C14H15NO8/c16-8-5-3-1-4-13(23-2-22-4)9(17)6(3)14(21)15-7(5)10(18)12(20)11(8)19/h1,5,7-8,10-12,16-20H,2H2,(H,15,21)/t5-,7-,8-,10+,11+,12+/m1/s1
InChI Key:
VREZDOWOLGNDPW-ALTGWBOUSA-N
NSC Number:
349156
Properties
Complexity:
503
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
6
Defined Bond Stereocenter Count:
0
Exact Mass:
325.08g/mol
Formal Charge:
0
Heavy Atom Count:
23
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
6
Isotope Atom Count:
0
Molecular Weight:
325.273g/mol
Monoisotopic Mass:
325.08g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
149A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.6
Literature
| Title | Journal |
|---|---|
| Apoptosis-inducing effects of distichamine and narciprimine, rare alkaloids of the plant family Amaryllidaceae. | Bioorganic & medicinal chemistry letters 20121001 |
| A novel synthetic C-1 analogue of 7-deoxypancratistatin induces apoptosis in p53 positive and negative human colorectal cancer cells by targeting the mitochondria: enhancement of activity by tamoxifen. | Investigational new drugs 20120601 |
| Antineoplastic agents. 587. Isolation and structure of 3-epipancratistatin from Narcissus cv. Ice Follies. | Journal of natural products 20120427 |
| Enhancement of apoptotic and autophagic induction by a novel synthetic C-1 analogue of 7-deoxypancratistatin in human breast adenocarcinoma and neuroblastoma cells with tamoxifen. | Journal of visualized experiments : JoVE 20120101 |
| β-Silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone for the total synthesis of (±)-pancratistatin. | Organic letters 20111104 |
| Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation. | Bioorganic & medicinal chemistry letters 20110815 |
| Cooperative effects of Akt-1 and Raf-1 on the induction of cellular senescence in doxorubicin or tamoxifen treated breast cancer cells. | Oncotarget 20110801 |
| Pancratistatin induces apoptosis and autophagy in metastatic prostate cancer cells. | International journal of oncology 20110601 |
| Pancratistatin selectively targets cancer cell mitochondria and reduces growth of human colon tumor xenografts. | Molecular cancer therapeutics 20110101 |
| The efficacy of dandelion root extract in inducing apoptosis in drug-resistant human melanoma cells. | Evidence-based complementary and alternative medicine : eCAM 20110101 |
| A cobalt complex of a microbial arene oxidation product. | Chemistry Central journal 20110101 |
| Concentration-dependent effects of narciclasine on cell cycle progression in Arabidopsis root tips. | BMC plant biology 20110101 |
| Selective cytotoxicity against human osteosarcoma cells by a novel synthetic C-1 analogue of 7-deoxypancratistatin is potentiated by curcumin. | PloS one 20110101 |
| Potent and selective inhibition of human cytochrome P450 3A4 by seco-pancratistatin structural analogs. | Bioorganic & medicinal chemistry letters 20100401 |
| Pancratistatin induces apoptosis in clinical leukemia samples with minimal effect on non-cancerous peripheral blood mononuclear cells. | Cancer cell international 20100101 |
| A flexible strategy based on a C2-symmetric pool of chiral substrates: concise synthesis of (+)-valienamine, key intermediate of (+)- pancratistatin, and conduramines A-1 and E. | Organic letters 20091001 |
| Structure-activity studies on seco-pancratistatin analogs: potent inhibitors of human cytochrome P450 3A4. | Bioorganic & medicinal chemistry letters 20091001 |
| Synthesis of structurally simplified analogues of pancratistatin: truncation of the cyclitol ring. | The Journal of organic chemistry 20090918 |
| Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids. | Bioorganic & medicinal chemistry letters 20090615 |
| Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida. | Lipids 20090101 |
| Suzuki cross-coupling/reductive debenzyloxycarbonylation sequence for the syntheses of [c]annulated isoquinolines: application for the syntheses of pancratistatin-like isoquinolines. | The Journal of organic chemistry 20081017 |
| Chemistry, biology, and medicinal potential of narciclasine and its congeners. | Chemical reviews 20080601 |
| Synergy of Pancratistatin and Tamoxifen on breast cancer cells in inducing apoptosis by targeting mitochondria. | Cancer biology & therapy 20080301 |
| Sodium pancratistatin 3,4-o-cyclic phosphate, a water-soluble synthetic derivative of pancratistatin, is highly effective in a human colon tumor model. | Journal of natural products 20080301 |
| synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues. | Journal of natural products 20080301 |
| Synergy of Pancratistatin and Tamoxifen in inducing apoptosis in breast cancer cells. | Cancer biology & therapy 20080301 |
| Applications of total synthesis toward the discovery of clinically useful anticancer agents. | Chemical Society reviews 20070801 |
| Selective cytotoxicity of pancratistatin-related natural Amaryllidaceae alkaloids: evaluation of the activity of two new compounds. | Cancer cell international 20070101 |
| Annulation of beta-aryl-alpha-nitro-alpha,beta-enals and 2,2-dimethyl-1,3-dioxan-5-one: a one-step assembly of nitrocyclitols. Application to a short practical synthesis of (+/-)-7-deoxy-2-epi-pancratistatin tetraacetate. | Chemical communications (Cambridge, England) 20061028 |
| Synthesis and biological evaluation of aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F structurally related to the amaryllidaceae anticancer constituents. | The Journal of organic chemistry 20060721 |
| Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine. | Journal of natural products 20060101 |
| Cyclotrimerization strategy toward analogues of amaryllidaceae constituents. synthesis of deoxygenated pancratistatin core. | Organic letters 20051208 |
| A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore. | Bioorganic & medicinal chemistry letters 20051201 |
| Antineoplastic agents. 553. The Texas grasshopper Brachystola magna. | Journal of natural products 20050801 |
| Pancratistatin causes early activation of caspase-3 and the flipping of phosphatidyl serine followed by rapid apoptosis specifically in human lymphoma cells. | Cancer chemotherapy and pharmacology 20050701 |
| Pancratistatin: a natural anti-cancer compound that targets mitochondria specifically in cancer cells to induce apoptosis. | Apoptosis : an international journal on programmed cell death 20050501 |
| Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of beta-carbolin-1-one mimic of pancratistatin. | The Journal of organic chemistry 20050429 |
| Induction of apoptotic cell death specifically in rat and human cancer cells by pancratistatin. | Artificial cells, blood substitutes, and immobilization biotechnology 20050101 |
| A beta-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin: synthesis and biological evaluation. | Angewandte Chemie (International ed. in English) 20041011 |
| Synthesis and biological activity of some structural modifications of pancratistatin. | Bioorganic & medicinal chemistry letters 20040607 |
| An approach to pancratistatins via ring-closing metathesis: efficient synthesis of novel 1-aryl-1-deoxyconduritols F. cv. | Organic letters 20040304 |
| Antineoplastic agents. 511. Direct phosphorylation of phenpanstatin and pancratistatin. | Journal of natural products 20040301 |
| Total synthesis of pancratistatin relying on the [3,3]-sigmatropic rearrangement. | The Journal of organic chemistry 20040109 |
| Stereospecific biocatalytic synthesis of pancratistatin analogues. | Angewandte Chemie (International ed. in English) 20031013 |
| Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives. | The Journal of organic chemistry 20021213 |
| Stereocontrolled total synthesis of pancratistatin. | Organic letters 20020418 |
| A new strategy towards the total synthesis of phenanthridone alkaloids: synthesis of (+)-2,7-dideoxypancratistatin as a model study. | Chemical communications (Cambridge, England) 20020321 |
| Inhibition of cell cycle progression through specific phase by pancratistatin derivatives. | Biological & pharmaceutical bulletin 20020201 |
| In vitro activities of two antimitotic compounds, pancratistatin and 7-deoxynarciclasine, against Encephalitozoon intestinalis, a microsporidium causing infections in humans. | Antimicrobial agents and chemotherapy 20011201 |
| Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay(1a). | The Journal of organic chemistry 20010420 |
| Studies directed towards the refinement of the pancratistatin cytotoxic pharmacophore. | Bioorganic & medicinal chemistry letters 20010122 |
| Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances. | Journal of natural products 19921101 |
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