(2-{[5-(2-bromoacryloylamino)benzo[b]thiophene-2-carbonyl]amino}ethyl)carbamic acid tert-butyl ester | 871691-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (2-{[5-(2-bromoacryloylamino)benzo[b]thiophene-2-carbonyl]amino}ethyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[[5-(2-bromoprop-2-enoylamino)-1-benzothiophene-2-carbonyl]amino]ethyl]carbamate
• CAS: 871691-03-1
• 化学式: C₁₉H₂₂BrN₃O₄S
• 分子量: 468.371
• InChiKey: BMGSVXWCOBFTQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-{[5-(2-bromoacryloylamino)benzo[b]thiophene-2-carbonyl]amino}ethyl)carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 5-(2-Bromo-acryloylamino)-benzo[b]thiophene-2-carboxylic acid (2-amino-ethyl)-amide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Hybrid Molecules Containing α-Methylene-γ-Butyrolactones and α-Bromoacryloyl Moieties

  摘要：

  The synthesis and biological activity of hybrids 8-18 prepared combining alpha-methylene-gamma-butyrolactones and alpha-bromoacryloylamides have been described and their structure -activity relationships discussed. All these heterobifunctional compounds demonstrate good antileukemic activity, significantly superior to that of both alkylating units alone. Using the human leukemia HL-60 cell line, selected compounds 10, 11, 13, and 17 were found to induce morphological changes and internucleosomal DNA fragmentation characteristic of apoptotic cell death.

  DOI：

  10.1021/jm058012o
• 作为产物：
  描述：

  N-叔丁氧羰基-1,2-乙二胺 、 5-(2-Bromoprop-2-enoylamino)-1-benzothiophene-2-carboxylic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以62%的产率得到(2-{[5-(2-bromoacryloylamino)benzo[b]thiophene-2-carbonyl]amino}ethyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Hybrid Molecules Containing α-Methylene-γ-Butyrolactones and α-Bromoacryloyl Moieties

  摘要：

  The synthesis and biological activity of hybrids 8-18 prepared combining alpha-methylene-gamma-butyrolactones and alpha-bromoacryloylamides have been described and their structure -activity relationships discussed. All these heterobifunctional compounds demonstrate good antileukemic activity, significantly superior to that of both alkylating units alone. Using the human leukemia HL-60 cell line, selected compounds 10, 11, 13, and 17 were found to induce morphological changes and internucleosomal DNA fragmentation characteristic of apoptotic cell death.

  DOI：

  10.1021/jm058012o