methyl (5β,8α,9β,10α,12α)-17-hydroxyatis-15-en-18-oate | 450359-95-2

• 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: methyl (5β,8α,9β,10α,12α)-17-hydroxyatis-15-en-18-oate
• 英文别名: methyl ent-17-hydroxy-15-atisene-19-oate；methyl (1R,4S,5R,9S,10S,12S)-13-(hydroxymethyl)-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadec-13-ene-5-carboxylate
• CAS: 450359-95-2
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: HPIOEXVWWAPGKL-LDQGEQLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (5β,8α,9β,10α,12α)-17-hydroxyatis-15-en-18-oate 在 TEA 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 sodium thiomethoxide 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 ent-17-methylsulfinyl-15-atisene-19-oic acid
  参考文献：
  名称：

  Synthesis and neuroprotective effects of serofendic acid analogues

  摘要：

  Analogues of serofendic acid were prepared and their protective effects against L-glutamate (Glu)-induced neurotoxicity were examined using primary cultures of rat cortical neurons. Some analogues exhibited similar neuroprotective activity to that of serofendic acid.

  DOI：

  10.1016/j.bmcl.2006.07.038
• 作为产物：
  描述：

  methyl (5β,8α,9β,10α,12α)-16-hydroxyatisan-18-oate 以28%的产率得到methyl (5β,8α,9β,10α,12α,15α)-15-hydroxyatis-16-en-18-oate
  参考文献：
  名称：

  Synthesis and pharmacological profile of serofendic acids A and B

  摘要：

  We present efficient syntheses of serofendic acids A and B (SA-A and SA-B), novel neuroprotective substances isolated from fetal calf serum. Biological and pharmacological evaluation showed that SA-A and SA-B have potent protective action aaainst glutarnate-induced neurotoxicity, but do not interact directly with glutamate receptors. A pharmacokinetic study showed that they have good oral bioavailability in rats. The results indicate that SA-A and SA-B are potential lead compounds for candidate drugs to treat various neuroloaical disorders. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.037

文献信息

• Synthesis and absolute configuration of serofendic acids
  作者：Taro Terauchi、Naoki Asai、Masahiro Yonaga、Toshiaki Kume、Akinori Akaike、Hachiro Sugimoto

  DOI：10.1016/s0040-4039(02)00651-2

  日期：2002.5

  The first synthesis of serofendic acids A and B, novel neuroprotective substances isolated from fetal calf serum, is described. This efficient process, starting from (−)-isosteviol, not only provided substantial amounts of serofendic acids, but also established their absolute configuration.

  描述了从胎儿小牛血清中分离出来的新型神经保护物质，血脂酸A和B的首次合成。从（-）-异甜菊醇开始的这一有效过程不仅提供了大量的血清铁酸，而且确立了它们的绝对构型。
• EP1382591
  申请人：——

  公开号：——

  公开（公告）日：——
• US7211589B2
  申请人：——

  公开号：US7211589B2

  公开（公告）日：2007-05-01
• Synthesis and pharmacological profile of serofendic acids A and B
  作者：Taro Terauchi、Naoki Asai、Takashi Doko、Ryota Taguchi、Osamu Takenaka、Hideki Sakurai、Masahiro Yonaga、Teiji Kimura、Akiharu Kajiwara、Tetsuhiro Niidome、Toshiaki Kume、Akinori Akaike、Hachiro Sugimoto

  DOI：10.1016/j.bmc.2007.07.037

  日期：2007.11

  We present efficient syntheses of serofendic acids A and B (SA-A and SA-B), novel neuroprotective substances isolated from fetal calf serum. Biological and pharmacological evaluation showed that SA-A and SA-B have potent protective action aaainst glutarnate-induced neurotoxicity, but do not interact directly with glutamate receptors. A pharmacokinetic study showed that they have good oral bioavailability in rats. The results indicate that SA-A and SA-B are potential lead compounds for candidate drugs to treat various neuroloaical disorders. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and neuroprotective effects of serofendic acid analogues
  作者：Taro Terauchi、Takashi Doko、Masahiro Yonaga、Akiharu Kajiwara、Tetsuhiro Niidome、Ryota Taguchi、Toshiaki Kume、Akinori Akaike、Hachiro Sugimoto

  DOI：10.1016/j.bmcl.2006.07.038

  日期：2006.10

  Analogues of serofendic acid were prepared and their protective effects against L-glutamate (Glu)-induced neurotoxicity were examined using primary cultures of rat cortical neurons. Some analogues exhibited similar neuroprotective activity to that of serofendic acid.