Home Thiazoles 189453-10-9
189453-10-9,MFCD27976357
Catalog No.:AA002DM2

189453-10-9 | Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-

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1mg
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5mg
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10mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002DM2
Chemical Name:
Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-
CAS Number:
189453-10-9
Molecular Formula:
C27H41NO5S
Molecular Weight:
491.6831
MDL Number:
MFCD27976357
SMILES:
O=C1O[C@@H](C/C=C(/C)\CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
Properties
Properties
 
BP:
663.7°C at 760 mmHg  
Form:
Solid  
MP:
63-66°C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
777  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
5  

Literature

Title: Identification of glycan structure alterations on cell membrane proteins in desoxyepothilone B resistant leukemia cells.

Journal: Molecular & cellular proteomics : MCP 20111101

Title: The characterization of microtubule-stabilizing drugs as possible therapeutic agents for Alzheimer's disease and related tauopathies.

Journal: Pharmacological research 20110401

Title: Synthesis of (Z)-trisubstituted olefins by decarboxylative grob-type fragmentations: epothilone D, discodermolide, and peloruside A.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20100111

Title: Simultaneous determination of epothilone D and its hydrolytic metabolite in human plasma by high performance liquid chromatography-tandem mass spectrometry for pharmacokinetic studies.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091101

Title: Determination of a novel epothilone D analog (AV-EPO-106) in human plasma using ultra-performance liquid chromatography-tandem mass spectrometry.

Journal: Biomedical chromatography : BMC 20090301

Title: Decarboxylative Grob-type fragmentations in the synthesis of trisubstituted Z olefins: application to peloruside A, discodermolide, and epothilone D.

Journal: Angewandte Chemie (International ed. in English) 20090101

Title: Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions.

Journal: The Journal of organic chemistry 20081219

Title: Epothilones and new analogues of the microtubule modulators in taxane-resistant disease.

Journal: Expert opinion on investigational drugs 20080401

Title: Preclinical investigations with epothilones in breast cancer models.

Journal: Seminars in oncology 20080401

Title: Clinical studies with epothilones for the treatment of metastatic breast cancer.

Journal: Seminars in oncology 20080401

Title: Phase II study of KOS-862 in patients with metastatic androgen independent prostate cancer previously treated with docetaxel.

Journal: Investigational new drugs 20071201

Title: Epothilone D, a microtubule-stabilizing compound, inhibits neointimal hyperplasia after rat carotid artery injury by cell cycle arrest via regulation of G1-checkpoint proteins.

Journal: Vascular pharmacology 20071001

Title: Epothilones induce human colon cancer SW620 cell apoptosis via the tubulin polymerization independent activation of the nuclear factor-kappaB/IkappaB kinase signal pathway.

Journal: Molecular cancer therapeutics 20071001

Title: Novel tubulin-targeting agents: anticancer activity and pharmacologic profile of epothilones and related analogues.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20070701

Title: Alterations in gamma-actin and tubulin-targeted drug resistance in childhood leukemia.

Journal: Journal of the National Cancer Institute 20061004

Title: Determination of desoxyepothilone B in nude mice plasma by liquid-liquid extraction and reversed-phase high-performance liquid chromatography.

Journal: Journal of pharmaceutical and biomedical analysis 20060918

Title: Heterologous production of epothilone C and D in Escherichia coli.

Journal: Biochemistry 20060131

Title: Current state of the art of new tubulin inhibitors in the clinic.

Journal: Current clinical pharmacology 20060101

Title: Total synthesis of 12,13-desoxyepothilone B (Epothilone D).

Journal: Bioorganic chemistry 20050401

Title: Total syntheses of epothilones B and d.

Journal: The Journal of organic chemistry 20041224

Title: Kinetics and mechanism of degradation of epothilone-D: an experimental anticancer agent.

Journal: Journal of pharmaceutical sciences 20041201

Title: A comparison of signaling activities induced by Taxol and desoxyepothilone B.

Journal: Journal of chemotherapy (Florence, Italy) 20041201

Title: Crystal structures of epothilone D-bound, epothilone B-bound, and substrate-free forms of cytochrome P450epoK.

Journal: The Journal of biological chemistry 20031107

Title: Creating polyketide diversity through genetic engineering.

Journal: Frontiers in bioscience : a journal and virtual library 20030101

Title: Probing the SAR of dEpoB via chemical synthesis: a total synthesis evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B.

Journal: The Journal of organic chemistry 20021101

Title: A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus.

Journal: Journal of natural products 20020701

Title: Optimizing the heterologous production of epothilone D in Myxococcus xanthus.

Journal: Biotechnology and bioengineering 20020505

Title: Large-scale isolation and crystallization of epothilone D from Myxococcus xanthus cultures.

Journal: Journal of natural products 20020401

Title: Total synthesis of epothilones B and D.

Journal: Organic letters 20010712

Title: New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies.

Journal: Journal of natural products 20010701

Title: Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D.

Journal: Journal of the American Chemical Society 20010613

Title: Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20010417

Title: Konner J, et al. Phase I clinical, pharmacokinetic, and pharmacodynamic study of KOS-862 (Epothilone D) in patients with advanced solid tumors and lymphoma. Invest New Drugs. 2012 Dec;30(6):2294-302.

Title: Brunden KR, et al. Epothilone D improves microtubule density, axonal integrity, and cognition in a transgenic mouse model of tauopathy. J Neurosci. 2010 Oct 13;30(41):13861-6.

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SDS
Tags:189453-10-9 Molecular Formula|189453-10-9 MDL|189453-10-9 SMILES|189453-10-9 Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-