(4S,7R,8S,9S,16S)-4,8,13,14-Tetrahydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadecane-2,6-dione | 198571-40-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (4S,7R,8S,9S,16S)-4,8,13,14-Tetrahydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadecane-2,6-dione
• 英文别名: (4S,7R,8S,9S,16S)-4,8,13,14-tetrahydroxy-5,5,7,9-tetramethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-oxacyclohexadecane-2,6-dione
• CAS: 198571-40-3
• 化学式: C₂₆H₄₁NO₇S
• 分子量: 511.68
• InChiKey: DKQJLZSTNWVSBB-OPQAWFADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  丙酮 、 (4S,7R,8S,9S,16S)-4,8,13,14-Tetrahydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadecane-2,6-dione 在 对甲苯磺酸 作用下， 反应 2.0h， 生成 (3aS,5S,9S,12R,13S,14S,17aR)-9,13-Dihydroxy-2,2,10,10,12,14-hexamethyl-5-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-dodecahydro-1,3,6-trioxa-cyclopentacyclohexadecene-7,11-dione 、 (3aR,5S,9S,12R,13S,14S,17aS)-9,13-Dihydroxy-2,2,10,10,12,14-hexamethyl-5-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-dodecahydro-1,3,6-trioxa-cyclopentacyclohexadecene-7,11-dione
  参考文献：
  名称：

  Derivatization of the C12C13 functional groups of epothilones A, B and C

  摘要：

  Epothilone A reacted with hydrohalic acids to C12-C13 halohydrin regioisomers (ratios: 2:1 - 4:1), whereas epothilone B gave under the same conditions the isomerically pure C12 halo C13 hydroxy derivative. With non-nucleophilic Bromstedt acids and with Lewis acids a highly solvent dependent product distribution and some unexpected rearrangement products were observed. Epothilone C bearing a double bond between C12 and C13 was regioselectively dihydroxylated or hydrogenated at that position. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00546-0
• 作为产物：
  描述：

  埃博霉素C 在 四氧化锇 、 N-甲基吲哚酮 、 水 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 1.25h， 以62%的产率得到(4S,7R,8S,9S,16S)-4,8,13,14-Tetrahydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadecane-2,6-dione
  参考文献：
  名称：

  Derivatization of the C12C13 functional groups of epothilones A, B and C

  摘要：

  Epothilone A reacted with hydrohalic acids to C12-C13 halohydrin regioisomers (ratios: 2:1 - 4:1), whereas epothilone B gave under the same conditions the isomerically pure C12 halo C13 hydroxy derivative. With non-nucleophilic Bromstedt acids and with Lewis acids a highly solvent dependent product distribution and some unexpected rearrangement products were observed. Epothilone C bearing a double bond between C12 and C13 was regioselectively dihydroxylated or hydrogenated at that position. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00546-0

文献信息

• Altmann, Karl-Heinz; Bold, Guido; Caravatti, Giorgio, Chimia, 2000, vol. 54, # 11, p. 612 - 621
  作者：Altmann, Karl-Heinz、Bold, Guido、Caravatti, Giorgio、End, Nicole、Flörsheimer, Andreas、Guagnano, Vito、O'Reilly, Terence、Wartmann, Markus

  DOI：——

  日期：——
• Designed Epothilones: Combinatorial Synthesis, Tubulin Assembly Properties, abd Cytotoxic Action against Taxol-Resistant Tumor Cells
  作者：K. C. Nicolaou、Dionisios Vourloumis、Tianhu Li、Joaquin Pastor、Nicolas Winssinger、Yun He、Sacha Ninkovic、Francisco Sarabia、Hans Vallberg、Frank Roschangar、N. Paul King、M. Ray V. Finlay、Pareskevi Giannakakou、Pascal Verdier-Pinard、Ernest Hamel

  DOI：10.1002/anie.199720971

  日期：1997.10.17

  A library of epothilone A and B analogues, which was constructed by solid‐phase combinatorial synthesis using SMART Microreactors and solution chemistry, was screened in two different tubulin binding assays. Selected compounds were subjected to cytotoxicity studies against a number of cell lines, including Taxol‐resistant cells. Important structure–activity relationship emerged from these studies, which sets the stage for further discoveries and developments in the anticancer field.