cis-1-bromo-4-chloro-2-butene

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: cis-1-bromo-4-chloro-2-butene
• 英文别名: (Z)-1-bromo-4-chlorobut-2-ene
• 化学式: C₄H₆BrCl
• 分子量: 169.449
• InChiKey: KGRDKGJNOYVKPM-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  cis-1-bromo-4-chloro-2-butene 、 山楂酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以78%的产率得到(2Z) 4-chlorobut-2-en-1-yl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate
  参考文献：
  名称：

  Esters and amides of maslinic acid trigger apoptosis in human tumor cells and alter their mode of action with respect to the substitution pattern at C-28

  摘要：

  Cancer is one of the most commonly diagnosed diseases worldwide; its mortality rate is high, and there is still a demand for the development of antitumor active drugs. Triterpenoic acids show many pharmacological effects, among them antitumor activity. One of these, maslinic acid-1 is of interest because of its antitumor profile. It is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize a series of esters and amides differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/propidium iodide assay, DNA laddering and cell cycle experiments. Esters containing small-chain, lipophilic residues increased the cytotoxicity whereas amides as well long-chain esters led to a decrease in activity. The antitumor activity seems to be independent from the substitution pattern at position C-28 for esters and amides but alters their mode of action. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.016

文献信息

• [EN] CHIRAL CONTROL<br/>[FR] CONTRÔLE CHIRAL
  申请人：ONTORII INC

  公开号：WO2014012081A3

  公开（公告）日：2014-03-06
• MEIJER J.; VERMEER P.; BRANDSMA L., REC. TRAV. CHIM. <RTCP-A3>, 1975, 94, NO 4, 83-84
  作者：MEIJER J.、 VERMEER P.、 BRANDSMA L.

  DOI：——

  日期：——
• Esters and amides of maslinic acid trigger apoptosis in human tumor cells and alter their mode of action with respect to the substitution pattern at C-28
  作者：Bianka Siewert、Elke Pianowski、René Csuk

  DOI：10.1016/j.ejmech.2013.10.016

  日期：2013.12

  Cancer is one of the most commonly diagnosed diseases worldwide; its mortality rate is high, and there is still a demand for the development of antitumor active drugs. Triterpenoic acids show many pharmacological effects, among them antitumor activity. One of these, maslinic acid-1 is of interest because of its antitumor profile. It is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize a series of esters and amides differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/propidium iodide assay, DNA laddering and cell cycle experiments. Esters containing small-chain, lipophilic residues increased the cytotoxicity whereas amides as well long-chain esters led to a decrease in activity. The antitumor activity seems to be independent from the substitution pattern at position C-28 for esters and amides but alters their mode of action. (C) 2013 Elsevier Masson SAS. All rights reserved.