3,7-dihydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoic acid 2-methyl-3-(5-methylpyridin-2-yl)-5-styrylcyclopent-2-enyl ester | 923956-33-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,7-dihydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoic acid 2-methyl-3-(5-methylpyridin-2-yl)-5-styrylcyclopent-2-enyl ester
• 英文别名: [(1S,5S)-2-methyl-3-(5-methylpyridin-2-yl)-5-[(E)-2-phenylethenyl]cyclopent-2-en-1-yl] (3S,6R,7S,8S)-3,7-dihydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoate
• CAS: 923956-33-6
• 化学式: C₃₈H₅₁NO₅
• 分子量: 601.827
• InChiKey: PFPNWBZLDCTTEL-LHJMLPRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3S,6R,7S,8S,1'S,5'S)-3,7-dihydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoic acid 2-methyl-3-(5-methylpyridin-2-yl)-5-vinylcyclopent-2-enyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (3S,6R,7S,8S,1'S,5'S)-7,11-dihydroxy-3,8,8,10,12,16-hexamethyl-2-(5-methylpyridin-2-yl)-3a,7,8,10,11,12,13,14,15,17a-decahydro-1H,6H-4-oxacyclopentacyclohexadecene-5,9-dione 、 3,7-dihydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoic acid 2-methyl-3-(5-methylpyridin-2-yl)-5-styrylcyclopent-2-enyl ester 、 [5-[(E)-2-[2-(3,7-dihydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoyl)oxy-3-methyl-4-(5-methylpyridin-2-yl)cyclopent-3-en-1-yl]ethenyl]-2-methyl-3-(5-methylpyridin-2-yl)cyclopent-2-en-1-yl] 3,7-dihydroxy-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoate
  参考文献：
  名称：

  WO2007/15929

  摘要：

  公开号：

文献信息

• Total Synthesis and Selective Activity of a New Class of Conformationally Restrained Epothilones
  作者：Mamoun M. Alhamadsheh、Shuchi Gupta、Richard A. Hudson、Lalith Perera、L. M. Viranga Tillekeratne

  DOI：10.1002/chem.200701143

  日期：2008.1.7

  Stereoselective total syntheses of two novel conformationally restrained epothilone analogues are described. Evans asymmetric alkylation, Brown allylation, and a diastereoselective aldol reaction served as the key steps in the stereoselective synthesis of one of the two key fragments of the convergent synthetic approach. Enzyme resolution was employed to obtain the second fragment as a single enantiomer

  描述了两种新型构象限制埃坡霉素类似物的立体选择性全合成。埃文斯不对称烷基化、布朗烯丙基化和非对映选择性羟醛反应是聚合合成方法的两个关键片段之一的立体选择性合成的关键步骤。采用酶拆分以获得作为单一对映体的第二片段。分子通过酯化组装，然后进行闭环复分解。在初步的细胞毒性研究中，其中一种类似物对两种白血病细胞系表现出比人类实体肿瘤细胞系更强的选择性生长抑制活性。该类似物的精确生物学作用机制和高度选择性仍有待研究。
• Conformationally Restrained Epothilone Analogues as Anti-Leukemic Agents
  申请人：Tillekeratne Viranga

  公开号：US20100324094A1

  公开（公告）日：2010-12-23

  A method for synthesizing anti-leukemic epothilone analogues includes rigidifying a region between the macrolactone ring and the aromatic side-chain. The anti-leukemic compositions are non-naturally occurring epothilone analogue that are rigidified between the macrolactone ring and the aromatic side-chain.

  一种合成抗白血病环孢菌素类似物的方法包括在大环内酯环和芳香侧链之间加强刚性区域。这些抗白血病的组合物是非天然存在的环孢菌素类似物，它们在大环内酯环和芳香侧链之间被加强刚性。
• US8435983B2
  申请人：——

  公开号：US8435983B2

  公开（公告）日：2013-05-07
• [EN] CONFORMATIONALLY RESTRAINED EPOTHILONE ANALOGUES AS ANTI-LEUKEMIC AGENTS<br/>[FR] ANALOGUES D'ÉPOTHILONE RESTREINTS EN CONFORMATION EN TANT QU'AGENTS ANTI-LEUCÉMIQUES
  申请人：UNIV TOLEDO

  公开号：WO2008118327A1

  公开（公告）日：2008-10-02

  [EN] A method for synthesizing anti-leukemic epothilone analogues includes rigidifying a region between the macrolactone ring and the aromatic side-chain. The anti-leukemic compositions are non-naturally occurring epothilone analogue that are rigidified between the macrolactone ring and the aromatic side-chain.
  [FR] L'invention concerne un procédé pour synthétiser des analogues épothilone anti-leucémiques comprenant la rigidification d'une région entre le cycle de macrolactone et la chaîne latérale aromatique. Les compositions anti-leucémiques sont des analogues d'épothilone non présents à l'état naturel qui sont rigidifiés entre le cycle de macrolactone et la chaîne latérale aromatique.
• WO2007/15929
  申请人：——

  公开号：——

  公开（公告）日：——