Epothilone A

Base Information

• Chemical Name: Epothilone A
• CAS No.: 152044-53-6
• Molecular Formula: C26H39NO6S
• Molecular Weight: 493.665
• NSC Number: 684362
• UNII: 51E07YBX96
• DSSTox Substance ID: DTXSID10332288
• Nikkaji Number: J1.408.121F
• Wikidata: Q27104197
• NCI Thesaurus Code: C1622
• Metabolomics Workbench ID: 21312
• ChEMBL ID: CHEMBL329993
• Mol file: 152044-53-6.mol

Synonyms:epothilon A;epothilone A

Chemical Property of Epothilone A

Chemical Property:

• Vapor Pressure: 1.31E-19mmHg at 25°C
• Melting Point: 95 °C
• Refractive Index: 1.531
• Boiling Point: 683.317 °C at 760 mmHg
• PKA: 13.57±0.70(Predicted)
• Flash Point: 367.057 °C
• PSA: 137.49000
• Density: 1.143 g/cm³
• LogP: 4.08740
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 493.24980914
• Heavy Atom Count: 34
• Complexity: 770

Purity/Quality:

98%,99%, ^*data from raw suppliers

Epothilone A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCCC2C(O2)CC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C
• Isomeric SMILES: C[C@H]1CCC[C@@H]2[C@@H](O2)C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C
• Uses: The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell. Epothilone A is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Epothilone A acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity. Epothilone A has been investigated in clinical trials as an antitumour agent.

Technology Process of Epothilone A

There total 262 articles about Epothilone A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione (479485-03-5) → epithilone A (152044-53-6)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/1521-3765(20020816)8:16<3717::AID-CHEM3717>3.0.CO;2-G

Reference yield: 65.0%

desoxyepothilone A (186692-73-9) → epithilone A (152044-53-6)

Guidance literature:

With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃;

DOI:10.1021/ja971110h

Reference yield: 60.0%

desoxyepothilone A (186692-73-9) → epithilone A (152044-53-6) + [1R,3S,7S,10R,11S,12S,16S]-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-[2-methylthiazol-4-yl]prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione (193071-75-9)

Guidance literature:

With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃;

DOI:10.1021/ja971109i

upstream raw materials:

desoxyepothilone A

(7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

(1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

(4S,7R,8S,16S)-8-hydroxy-4-(4-methoxybenzyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxacyclohexadec-13-en-2,6-dione

Downstream raw materials:

epothilone E

epothilone E

[4S-[4R*,7S*,8R*,9R*,13R*,14R*,16R*(E)]]-14-Azido-5,5,7,9-tetramethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-13-[(4-nitrobenzoyl)oxy]-4,8-bis [(triethylsilyl)oxy]-1-oxacyclohexadecane-2,6-dione

Refernces

• 1、 Schinzer, Dieter,Limberg, Anja,Bauer, Armin,Boehm, Oliver M.,Cordes, Martin. "Total Synthesis of (-)-Epothilone A". . p. 523 - 524. Retrieved 1997.
• 2、 -. "Synthesis of epothilones, intermediates thereto, analogues and uses thereof". Page column 37. . Retrieved 2010/01/31.
• 3、 Liu, Zhi-Yu,Chen, Ze-G,Yu, Cheng-Zhi,Wang, Rui-Fang,Zhang, Ru-Zhou,Huang, Chu-Sheng,Yan, Zheng,Cao, De-Rong,Sun, Jian-Bo,Li, Gang. "Total synthesis of epothilone A through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C". . p. 3747 - 3756. Retrieved 2007/10/03.