(4S,7E,9R,10S,13E,16R)-9-hydroxy-4,10-dimethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione | 913563-27-6

• 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: (4S,7E,9R,10S,13E,16R)-9-hydroxy-4,10-dimethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione
• CAS: 913563-27-6
• 化学式: C₂₂H₂₇NO₇S
• 分子量: 449.525
• InChiKey: SONUAAGANURNMT-WFLVUFFESA-N

物化性质

• 熔点：
  102-104 °C(Solvent: Diethyl ether; Hexane)
• 沸点：
  741.5±60.0 °C(predicted)
• 密度：
  1.209±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (4S,7E,9R,10S,13E,16R)-9-hydroxy-4,10-dimethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到(4S,7E,10S,13E,16R)-4,10-dimethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,9,12-tetrone
  参考文献：
  名称：

  Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property

  摘要：

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.

  DOI：

  10.1021/ol061922v
• 作为产物：
  描述：

  (1E)(3R)-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-dien-3-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 89.0h， 生成 (4S,7E,9R,10S,13E,16R)-9-hydroxy-4,10-dimethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione
  参考文献：
  名称：

  Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property

  摘要：

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.

  DOI：

  10.1021/ol061922v

文献信息

• Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property
  作者：Yuji Matsuya、Takanori Kawaguchi、Kentaro Ishihara、Kanwal Ahmed、Qing-Li Zhao、Takashi Kondo、Hideo Nemoto

  DOI：10.1021/ol061922v

  日期：2006.9.1

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.