(2RS,4R)-2-phenyl-3-propionyl-thiazolidine-4-carboxylic acid ethyl ester | 1044255-57-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2RS,4R)-2-phenyl-3-propionyl-thiazolidine-4-carboxylic acid ethyl ester
• 英文别名: (4R)-2-phenyl-3-propioloyl-thiazolidine-4-carboxylic acid ethyl ester；ALC67；ethyl (4R)-2-phenyl-3-prop-2-ynoyl-1,3-thiazolidine-4-carboxylate
• CAS: 1044255-57-3
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: VYDZOJXGXGQPPY-NBFOIZRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,4R)-2-phenyl-3-propionyl-thiazolidine-4-carboxylic acid ethyl ester 、 6-叠氮基-1-己醇 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 ethyl (4R)-3-[1-(6-hydroxyhexyl)triazole-4-carbonyl]-2-phenyl-1,3-thiazolidine-4-carboxylate
  参考文献：
  名称：

  Design, synthesis and evaluation of potent thymidylate synthase X inhibitors

  摘要：

  Three synthesized series of compounds based on a thiazolidine core allowed identification of potent inhibitors of thymidylate synthase X. The evaluation of the catalytic activity of the enzyme in the presence of these molecules revealed two distinct classes of compounds that inhibit ThyX with submicromolar concentrations, which could lead, after optimization, to effective inhibitors with potential biomedical interest. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.080
• 作为产物：
  描述：

  苯甲醛 在 氯化亚砜 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.17h， 生成 (2RS,4R)-2-phenyl-3-propionyl-thiazolidine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  A novel thiazolidine compound induces caspase-9 dependent apoptosis in cancer cells

  摘要：

  The forward chemogenomics strategy allowed us to identify a potent cytotoxic thiazolidine compound as an apoptosis-inducing agent. Chemical structures were designed around a thiazolidine ring, a structure already noted for its anticancer properties. Initially, we evaluated these novel compounds on liver, breast, colon and endometrial cancer cell lines. The compound 3 (ALC67) showed the strongest cytotoxic activity (IC50 similar to 5 mu M). Cell cycle analysis with ALC67 on liver cells revealed SubG1/G1 arrest bearing apoptosis. Furthermore we demonstrated that cytotoxicity of this compound was due to the activation of caspase-9 involved apoptotic pathway, which is death receptor independent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.016

文献信息

• Design, synthesis and evaluation of potent thymidylate synthase X inhibitors
  作者：F. Esra Önen、Yap Boum、Claire Jacquement、Maria Vittoria Spanedda、Nada Jaber、Daniel Scherman、Hannu Myllykallio、Jean Herscovici

  DOI：10.1016/j.bmcl.2008.04.080

  日期：2008.6

  Three synthesized series of compounds based on a thiazolidine core allowed identification of potent inhibitors of thymidylate synthase X. The evaluation of the catalytic activity of the enzyme in the presence of these molecules revealed two distinct classes of compounds that inhibit ThyX with submicromolar concentrations, which could lead, after optimization, to effective inhibitors with potential biomedical interest. (C) 2008 Elsevier Ltd. All rights reserved.
• A novel thiazolidine compound induces caspase-9 dependent apoptosis in cancer cells
  作者：F. Esra Onen-Bayram、Irem Durmaz、Daniel Scherman、Jean Herscovici、Rengul Cetin-Atalay

  DOI：10.1016/j.bmc.2012.07.016

  日期：2012.9

  The forward chemogenomics strategy allowed us to identify a potent cytotoxic thiazolidine compound as an apoptosis-inducing agent. Chemical structures were designed around a thiazolidine ring, a structure already noted for its anticancer properties. Initially, we evaluated these novel compounds on liver, breast, colon and endometrial cancer cell lines. The compound 3 (ALC67) showed the strongest cytotoxic activity (IC50 similar to 5 mu M). Cell cycle analysis with ALC67 on liver cells revealed SubG1/G1 arrest bearing apoptosis. Furthermore we demonstrated that cytotoxicity of this compound was due to the activation of caspase-9 involved apoptotic pathway, which is death receptor independent. (C) 2012 Elsevier Ltd. All rights reserved.