tert-butyl (4-((2-allyl-3,5-dioxo-1,2,4-thiadiazolidin-4-yl)methyl)benzyl)carbamate | 1346771-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl (4-((2-allyl-3,5-dioxo-1,2,4-thiadiazolidin-4-yl)methyl)benzyl)carbamate
• CAS: 1346771-63-8
• 化学式: C₁₈H₂₃N₃O₄S
• 分子量: 377.464
• InChiKey: SAUAZYUKCVSXBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  82.33
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-((2-allyl-3,5-dioxo-1,2,4-thiadiazolidin-4-yl)methyl)benzyl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-allyl-4-(4'-methylaminobenzyl)-1,2,4-thiadiazolidine-3,5-dione hydrochloride
  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
• 作为产物：
  描述：

  在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.34h， 生成 tert-butyl (4-((2-allyl-3,5-dioxo-1,2,4-thiadiazolidin-4-yl)methyl)benzyl)carbamate
  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