4-Phenylsulfonylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester

• 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-Phenylsulfonylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester
• 英文别名: (3-Cyano-3,3-diphenylpropyl) 4-(benzenesulfonyl)piperazine-1-carbodithioate
• 化学式: C₂₇H₂₇N₃O₂S₃
• 分子量: 521.728
• InChiKey: BOYJQOXMTXQPOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  溴乙基二苯乙腈 在 potassium phosphate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 生成 4-Phenylsulfonylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester
  参考文献：
  名称：

  Dithiocarbamic acid esters as anticancer agent. Part 1: 4-Substituted-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl esters

  摘要：

  A variety of 4-N atom substituted derivatives were synthesized and evaluated for their in vitro anticancer activities using 4-methylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester 4 as lead compound. Among them, compound 6a without any substituent on 4-N atom (R-1 = H) was found to be the most active anticancer agent with IC50 = 5.3 mu M against HL-60 and IC50 = 11.5 mu M against Bel-7402, respectively. Increase in the polarity and/or introduction of suitable acyl groups at the 4-N atom of the lead compound 4 are favorable for the improvement of activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.085

文献信息

• Piperazine mono(dithio)carbamate ester compounds and analogs thereof: preparation method and uses thereof
  申请人：Medinox, Inc.

  公开号：US20030149021A1

  公开（公告）日：2003-08-07

  In accordance with the present invention, there is provided a new class of compounds, i.e., mono(dithio)carbamate esters of piperazine and analogs thereof, with or without substituents. Also provided are methods for the preparation of invention compounds and the pharmaceutical use thereof in the treatment of a variety of pathological conditions, especially for the treatment of cancers. A lead compound has shown good anticancer activity with low toxicity.

  根据本发明，提供了一种新的化合物类，即吡哆醇及其类似物的单（二硫代）氨基甲酸酯，带或不带取代基。还提供了制备发明化合物的方法，以及在治疗各种病理状况，特别是治疗癌症方面的药物使用。一种主导化合物表现出良好的抗癌活性和低毒性。
• [EN] PIPERAZINE MONO(DITHIO)CARBAMATE ESTER COMPOUNDS AND ANALOGS THEREOF: PREPARATION METHOD AND USE THEREOF<br/>[FR] COMPOSES D'ESTER DE PIPERAZINE MONO(DITHIO)CARBAMATE ET LEURS ANALOGUES: PROCEDE DE PREPARATION ET UTILISATION
  申请人：PEKING UNIVERSITY SCHOOL OF PH

  公开号：WO2002096869A2

  公开（公告）日：2002-12-05

  In accordance with the present invention, there is provided a new class of compounds,i.e., mono(dithio)carbamate esters of piperazine and analogs thereof, with or without substituents. Also provided are methods for the preparation of invention compounds and the pharmaceutical use thereof in the treatment of a variety of pathological condition, especially for the treatment of cancers. A lead compound has shown good anticancer activity with low toxicity.
• Dithiocarbamic acid esters as anticancer agent. Part 1: 4-Substituted-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl esters
  作者：Xueling Hou、Zemei Ge、Tingmin Wang、Wei Guo、Jingrong Cui、Tieming Cheng、Chingshan Lai、Runtao Li

  DOI：10.1016/j.bmcl.2006.05.085

  日期：2006.8

  A variety of 4-N atom substituted derivatives were synthesized and evaluated for their in vitro anticancer activities using 4-methylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester 4 as lead compound. Among them, compound 6a without any substituent on 4-N atom (R-1 = H) was found to be the most active anticancer agent with IC50 = 5.3 mu M against HL-60 and IC50 = 11.5 mu M against Bel-7402, respectively. Increase in the polarity and/or introduction of suitable acyl groups at the 4-N atom of the lead compound 4 are favorable for the improvement of activity. (c) 2006 Elsevier Ltd. All rights reserved.