4-{4'-[2"-(2'''-chloroethyl)-1,2,4-thiadiazolidine-3,5-dionyl]} sodium benzoate | 1332857-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{4'-[2"-(2'''-chloroethyl)-1,2,4-thiadiazolidine-3,5-dionyl]} sodium benzoate
• 英文别名: Sodium;4-[[2-(2-chloroethyl)-3,5-dioxo-1,2,4-thiadiazolidin-4-yl]methyl]benzoate
• CAS: 1332857-20-1
• 化学式: C₁₂H₁₀ClN₂O₄S*Na
• 分子量: 336.731
• InChiKey: PKRCHEHMDDGLLJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.27
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(氨基甲基)苯甲酸叔丁酯 在 盐酸 、 N-氯代丁二酰亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 0.69h， 生成 4-{4'-[2"-(2'''-chloroethyl)-1,2,4-thiadiazolidine-3,5-dionyl]} sodium benzoate
  参考文献：
  名称：

  Discovery of 1,2,4-thiadiazolidine-3,5-dione analogs that exhibit unusual and selective rapid cell death kinetics against acute myelogenous leukemia cells in culture

  摘要：

  4-Benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione (TDZD-8) was previously identified as an antileukemic agent exhibiting no evident toxicity toward normal hematopoietic cells. An SAR study has been carried out to examine the effect of varying the C-2 and C-4- substituents on the thiadiazolidinone ring of TDZD-8 on antileukemic activity. These studies resulted in the identification of more druglike analogs that exhibited comparable potency to TDZD-8 in killing acute myelogenous leukemia (AML) cells in culture. Surprisingly, the cell death kinetics induced by several of these novel analogs on MV-411 cells were extremely fast, with commitment to death occurring within 30 min. At a concentration of 10 mu M, 3f (LD50 = 3.5 mu M) completely eradicated cell viability of MV-411 cells within 2 h, while analog 3e (LD50 = 2.0 mu M) decimated cell viability within 30 min at a concentration of 10 mu M and effectively abolished cell viability at 5 mu M within 1-2 h. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.027

文献信息

• Discovery of 1,2,4-thiadiazolidine-3,5-dione analogs that exhibit unusual and selective rapid cell death kinetics against acute myelogenous leukemia cells in culture
  作者：Shama Nasim、Monica L. Guzman、Craig T. Jordan、Peter A. Crooks

  DOI：10.1016/j.bmcl.2011.06.027

  日期：2011.8

  4-Benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione (TDZD-8) was previously identified as an antileukemic agent exhibiting no evident toxicity toward normal hematopoietic cells. An SAR study has been carried out to examine the effect of varying the C-2 and C-4- substituents on the thiadiazolidinone ring of TDZD-8 on antileukemic activity. These studies resulted in the identification of more druglike analogs that exhibited comparable potency to TDZD-8 in killing acute myelogenous leukemia (AML) cells in culture. Surprisingly, the cell death kinetics induced by several of these novel analogs on MV-411 cells were extremely fast, with commitment to death occurring within 30 min. At a concentration of 10 mu M, 3f (LD50 = 3.5 mu M) completely eradicated cell viability of MV-411 cells within 2 h, while analog 3e (LD50 = 2.0 mu M) decimated cell viability within 30 min at a concentration of 10 mu M and effectively abolished cell viability at 5 mu M within 1-2 h. (C) 2011 Elsevier Ltd. All rights reserved.