Epothilone H₁ | 198475-12-6

• 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: Epothilone H₁
• 英文别名: epothilone H1；(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(E)-1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• CAS: 198475-12-6
• 化学式: C₂₆H₃₉NO₆
• 分子量: 461.599
• InChiKey: RINOSSPYIGLHTK-QJKGZULSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Epothilone H₁ 在 Oxone 、 1,1,1-三氟丙酮 、 edetate disodium 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (1R,3S,7S,10R,11S,12S,16S)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach

  摘要：

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.

  DOI：

  10.1002/chem.19970031211
• 作为产物：
  描述：

  2-甲基-3-[4-甲基(3,5-噁唑)]-2-丙醛 在 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 (-)-B-methoxydiisopinocampheylborane 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 31.5h， 生成 Epothilone H₁
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach

  摘要：

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.

  DOI：

  10.1002/chem.19970031211

文献信息

• Epothilone side components
  申请人：Hoefle Gerhard

  公开号：US20060142584A1

  公开（公告）日：2006-06-29

  The invention concerns compounds which can be obtained by fermenting DSM 6773, especially epothilones A1, A2, A8, A9, B10, C1, C2, C3, C4, C5, C6, C7, C8, C9, D1, D2, D5, G1, G2, H1, H2, I1, I2, I3, I4, I5, I6 and K and trans-epothilones C1 and C2.

  本发明涉及通过发酵DSM 6773而获得的化合物，特别是epothilones A1、A2、A8、A9、B10、C1、C2、C3、C4、C5、C6、C7、C8、C9、D1、D2、D5、G1、G2、H1、H2、I1、I2、I3、I4、I5、I6和K以及trans-epothilones C1和C2。
• Production of polyketides
  申请人：——

  公开号：US20030073205A1

  公开（公告）日：2003-04-17

  Recombinant Myxococcus host cells can be used to produce polyketides, including epothilone and epothilone analogs that can be purified from the fermentation broth and crystallized.

  重组的Myxococcus宿主细胞可用于生产聚酮类物质，包括可从发酵液中纯化和结晶的Epothilone和Epothilone类似物。
• Epothilone derivatives and methods for making and using the same
  申请人：——

  公开号：US20020045609A1

  公开（公告）日：2002-04-18

  The present invention relates to 16-membered macrocyclic compounds. These compounds are cytotoxic agents and can be used to treat cancer and non-cancer disorders characterized by cellular hyperproliferation.

  本发明涉及16元大环化合物。这些化合物是细胞毒性剂，可用于治疗癌症和细胞过度增殖性的非癌症疾病。
• Epothilone minor constituents
  申请人：Gesellschaft fuer Biotechnologische Forschung, mbH (GBF)

  公开号：US06624310B1

  公开（公告）日：2003-09-23

  The invention relates to compounds which are obtained by fermenting DSM 6773, especially epothilones A1, A2, A8, A9, B10, C1, C2, C3, C4, C5, C6, C7, C8, C9, D1, D2, D5, G1, G2, H1, H2, I1, I2, I3, I4, I5, I6 and K and trans-epothilones C1 and C2.

  本发明涉及通过发酵DSM 6773获得的化合物，特别是epothilones A1，A2，A8，A9，B10，C1，C2，C3，C4，C5，C6，C7，C8，C9，D1，D2，D5，G1，G2，H1，H2，I1，I2，I3，I4，I5，I6和K以及转-epothilones C1和C2。
• PRODUCTION OF POLYKETIDES
  申请人：Arslanian L. Robert

  公开号：US20070281343A9

  公开（公告）日：2007-12-06

  Recombinant Myxococcus host cells can be used to produce polyketides, including epothilone and epothilone analogs that can be purified from the fermentation broth and crystallized.

  重组Myxococcus宿主细胞可用于生产聚酮类化合物，包括可以从发酵液中纯化和结晶的紫杉醇和紫杉醇类似物。