3-chlorobenzyl carbamimidothioate hydrobromide | 169558-97-8

• 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: 3-chlorobenzyl carbamimidothioate hydrobromide
• 英文别名: 2-(3-chlorobenzyl)isothiouronium bromide；{[(3-Chlorophenyl)methyl]sulfanyl}methanimidamide hydrobromide；(3-chlorophenyl)methyl carbamimidothioate;hydrobromide
• CAS: 169558-97-8
• 化学式: BrH*C₈H₉ClN₂S
• 分子量: 281.604
• InChiKey: MCCIIEZGQVQPDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chlorobenzyl carbamimidothioate hydrobromide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 8-((3-chlorobenzyl)thio)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues

  摘要：

  In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl) sulfanyl] caffeine (IC50 = 0.223 mu M) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl] caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[( phenylethyl) sulfanyl] caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 mu M. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl) sulfanyl] caffeine analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.005
• 作为产物：
  描述：

  硫脲 、 3-氯苄溴 以 乙醇 为溶剂， 以100%的产率得到3-chlorobenzyl carbamimidothioate hydrobromide
  参考文献：
  名称：

  PYRIMIDINONE COMPOUNDS AND THEIR USE

  摘要：

  本发明提供公式（1）的化合物及其药学上可接受的盐，其中R1，R2，Y和Z如规范中所定义，其制备过程，含有它们的制药组合物以及它们在治疗中的应用。

  公开号：

  US20140248378A1

文献信息

• Structure-guided optimization of 4,6-substituted-1,3,5-triazin-2(1H)-ones as catalytic inhibitors of human DNA topoisomerase IIα
  作者：Kaja Bergant、Matej Janežič、Katja Valjavec、Izidor Sosič、Stane Pajk、Martina Štampar、Bojana Žegura、Stanislav Gobec、Metka Filipič、Andrej Perdih

  DOI：10.1016/j.ejmech.2019.04.055

  日期：2019.8

  exhibit cytotoxicity on cancer cell lines. Using an optimized synthetic route, a focused chemical library was designed aimed at further functionalizing substituents at the position 4 of the 1,3,5-triazin-2(1H)-one scaffold to enable additional interactions with the topo IIα ATP binding site. After virtual screening, selected 36 analogues were synthesized and experimentally evaluated for human topo IIα

  人类DNA拓扑异构酶代表了现代化学疗法的关键目标之一。新兴的人类DNA拓扑异构酶IIα催化抑制剂包括一种新的范式，旨在规避拓扑异构酶II毒物的已知局限性，例如心脏毒性和继发性肿瘤的诱导。在我们以前的研究中，发现4,6-取代的1,3,5-三嗪-2（1 H）-是topoIIα的催化抑制剂。在这里，我们报告了我们努力优化初始化学系列的一些特性的结果，这些化学特性在癌细胞系中不表现出细胞毒性。使用优化的合成路线，设计了一个集中的化学文库，旨在进一步官能化1,3,5-triazin-2（1 H）-一个支架，可与topoIIαATP结合位点进行其他相互作用。经过虚拟筛选后，合成了所选的36种类似物，并通过实验评估了其对人topoIIα的抑制作用。与最初的系列相比，优化的系列显示出对topoIIα的改善的抑制作用，并且对所选的活性化合物证实了抑制作用的催化模式。优化的系列还显示出对HepG2和MCF-7
• [EN] PYRIMIDINONE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS PYRIMIDINONES ET LEUR UTILISATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2013004995A8

  公开（公告）日：2013-03-07