chloro(2-indanoyl)methyl dimethylphosphonate | 116679-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: chloro(2-indanoyl)methyl dimethylphosphonate
• 英文别名: 2-chloro-1-(2,3-dihydro-1H-inden-2-yl)-2-dimethoxyphosphorylethanone
• CAS: 116679-43-7
• 化学式: C₁₃H₁₆ClO₄P
• 分子量: 302.694
• InChiKey: UVWPXMTXJUEUCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  chloro(2-indanoyl)methyl dimethylphosphonate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 7.58h， 生成 <3aS-<2E,3aα,4α(1Z,3RS),5β,6aα>>-5--2(1H)-pentalenylidene>pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological activity of novel carbacyclins having bicyclic substituents on the .omega.-chain

  摘要：

  A number of carbacyclins having bicyclic substituents on the omega-chain have been synthesized and tested for antiplatelet aggregation activity in vitro (against collagen-induced aggregation of rat platelet), for reduction of systemic blood pressure in vivo (ability to reduce the blood pressure in anesthetized rat by iv injection), and for cytoprotective activity (protection against ethanol-induced rat gastric lesion). The most effective compound for each activity was [3aS-[2E,3a alpha,4 alpha (3R),5 beta,6a alpha]]-5-[hexahydro-5- hydroxy-4-[3-hydroxy-3-(2-indanyl)-1-propynyl]-2(1H)-pentalenylidene+ ++] pentanoic acid (compound 11a), while some 1,4-benzodioxan analogues had selectivity for organ-protective activity, and indan analogues showed selectivity in their antiaggregation activity.

  DOI：

  10.1021/jm00128a049
• 作为产物：
  描述：

  2-茚羧酸 在 N-氯代丁二酰亚胺 、 正丁基锂 、 硫酸 、 sodium hydride 作用下， 反应 4.5h， 生成 chloro(2-indanoyl)methyl dimethylphosphonate
  参考文献：
  名称：

  Synthesis and biological activity of novel carbacyclins having bicyclic substituents on the .omega.-chain

  摘要：

  A number of carbacyclins having bicyclic substituents on the omega-chain have been synthesized and tested for antiplatelet aggregation activity in vitro (against collagen-induced aggregation of rat platelet), for reduction of systemic blood pressure in vivo (ability to reduce the blood pressure in anesthetized rat by iv injection), and for cytoprotective activity (protection against ethanol-induced rat gastric lesion). The most effective compound for each activity was [3aS-[2E,3a alpha,4 alpha (3R),5 beta,6a alpha]]-5-[hexahydro-5- hydroxy-4-[3-hydroxy-3-(2-indanyl)-1-propynyl]-2(1H)-pentalenylidene+ ++] pentanoic acid (compound 11a), while some 1,4-benzodioxan analogues had selectivity for organ-protective activity, and indan analogues showed selectivity in their antiaggregation activity.

  DOI：

  10.1021/jm00128a049

文献信息

• TSUYOSHI, TOMIYAMA;SHUICHI, WAKABAYASHI;MASAYUKI, YOKOTA, J. MED. CHEM., 32,(1989) N, C. 1988-1996
  作者：TSUYOSHI, TOMIYAMA、SHUICHI, WAKABAYASHI、MASAYUKI, YOKOTA

  DOI：——

  日期：——
• US4730060A
  申请人：——

  公开号：US4730060A

  公开（公告）日：1988-03-08
• Synthesis and biological activity of novel carbacyclins having bicyclic substituents on the .omega.-chain
  作者：Tsuyoshi Tomiyama、Shuichi Wakabayashi、Masayuki Yokota

  DOI：10.1021/jm00128a049

  日期：1989.8

  A number of carbacyclins having bicyclic substituents on the omega-chain have been synthesized and tested for antiplatelet aggregation activity in vitro (against collagen-induced aggregation of rat platelet), for reduction of systemic blood pressure in vivo (ability to reduce the blood pressure in anesthetized rat by iv injection), and for cytoprotective activity (protection against ethanol-induced rat gastric lesion). The most effective compound for each activity was [3aS-[2E,3a alpha,4 alpha (3R),5 beta,6a alpha]]-5-[hexahydro-5- hydroxy-4-[3-hydroxy-3-(2-indanyl)-1-propynyl]-2(1H)-pentalenylidene+ ++] pentanoic acid (compound 11a), while some 1,4-benzodioxan analogues had selectivity for organ-protective activity, and indan analogues showed selectivity in their antiaggregation activity.