o-Chlormercapto-benzoesaeureaethylester | 1441-80-1

• 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: o-Chlormercapto-benzoesaeureaethylester
• 英文别名: Ethyl 2-chlorosulfanylbenzoate
• CAS: 1441-80-1
• 化学式: C₉H₉ClO₂S
• 分子量: 216.688
• InChiKey: LFSFNXGCFGGQNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  o-Chlormercapto-benzoesaeureaethylester 、 靛红 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以68.9%的产率得到Ethyl 2-(2,3-dioxoindol-1-yl)sulfanylbenzoate
  参考文献：
  名称：

  Synthesis and evaluation of novel sulfenamides as novel anti Methicillin-resistant Staphylococcus aureus agents

  摘要：

  A total of 29 novel sulfenamide compounds were synthesized, spectroscopically characterized and evaluated in vitro for antimicrobial activity against various infectious pathogens. Compounds 1b and 2c exhibited potent inhibition against clinical Methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentration (MIC) values of 1.56 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.103
• 作为产物：
  描述：

  2,2-二硫代双苯甲酸二乙酯 在 氯化亚砜 作用下， 生成 o-Chlormercapto-benzoesaeureaethylester
  参考文献：
  名称：

  Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase

  摘要：

  46 Novel nonsymmetrical aromatic disulfides containing [1,3,4] thiadiazole or [1,3,4] oxadiazole groups were synthesized and their biological activities were evaluated as inhibitors of acetohydroxyacid synthase (AHAS, EC 2.2.1.6). Besides their strong in vitro inhibition against plant AHAS, compounds 3e and 3f also display 80-100% post-emergence herbicidal activities in greenhouse bioassay at 1500 g/ha dosage. The assay of exogenous branched-chain amino acids supplementation on rape root growth of 3e suggests that the herbicidal activity has relationship with AHAS inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.013

文献信息

• Discovery of unsymmetrical aromatic disulfides as novel inhibitors of SARS-CoV main protease: Chemical synthesis, biological evaluation, molecular docking and 3D-QSAR study
  作者：Li Wang、Bo-Bo Bao、Guo-Qing Song、Cheng Chen、Xu-Meng Zhang、Wei Lu、Zefang Wang、Yan Cai、Shuang Li、Sheng Fu、Fu-Hang Song、Haitao Yang、Jian-Guo Wang

  DOI：10.1016/j.ejmech.2017.05.045

  日期：2017.9

  outbreak of severe acute respiratory syndrome (SARS) in 2003 had caused a high rate of mortality. Main protease (Mpro) of SARS-associated coronavirus (SARS-CoV) is an important target to discover pharmaceutical compounds for the therapy of this life-threatening disease. During the course of screening new anti-SARS agents, we have identified that a series of unsymmetrical aromatic disulfides inhibited SARS-CoV

  2003年，世界范围内的严重急性呼吸道综合症（SARS）爆发导致了很高的死亡率。SARS相关冠状病毒（SARS-CoV）的主要蛋白酶（M pro）是发现用于治疗这种威胁生命的疾病的药物的重要靶标。在筛选新的抗SARS药物的过程中，我们发现一系列不对称的芳香族二硫化物首次显着抑制了SARS-CoV M pro。本文中，化学合成了40种新型不对称芳族二硫化物，并在体外评估了它们对SARS-CoV M pro的生物学活性。这些新型化合物显示出优异的IC 50数据范围为0.516–5.954μM。初步研究表明，这些二硫化物是可逆的和竞争性抑制剂。通过分子对接模拟生成了可能的结合模式，并构建了一个比较场分析（CoMFA）模型来理解结构-活性关系。因此，本研究为设计和鉴定具有全新化学结构的抗SARS药物提供了有意义的指导。
• Synthesis, Crystal Structure, in Vitro Acetohydroxyacid Synthase Inhibition, in Vivo Herbicidal Activity, and 3D-QSAR of New Asymmetric Aryl Disulfides
  作者：Jun Shang、Wei-Min Wang、Yong-Hong Li、Hai-Bin Song、Zheng-Ming Li、Jian-Guo Wang

  DOI：10.1021/jf302206x

  日期：2012.8.29

  Acetohydroxyacid synthase (AHAS; EC 2.2.1.6) is an important bioactive target for the design environmentally:., benign herbicides. On the basis of previous virtual screening, 50 asymmetric aryl disulfides containing [1,2,4]triazole groups were synthesized and characterized by H-1 NMR, HRMS, and crystal structure. Compounds I-a, I-b, and I-p show K-i values of 1.70, 4.69, and 5.57 mu M, respectively, for Wild type Arabidopsis thaliana AHAS (AtAHAS) and low resistance, against mutant type AtAHAS W574L. At 100 mg L-1 concentration, compounds. I-a, II-a, and II-b exhibit 86.6, 817, and 87.5% in vivo rape root growth inhibition. CoMFA steric and electrostatic contour maps were established, and a possible binding mode was suggested from molecular docking, which :provide valuable information to understand the key structural features. of these disulfide compounds. To the authors knowledge, this is the first comprehensive case suggesting that asymmetric aryl disulfides are novel AHAS inhibitors.