2-[(4-氯苄基)硫基]苯胺 | 43092-84-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-[(4-氯苄基)硫基]苯胺
• 英文名称: 2-[(4-Chlorobenzyl)thio]aniline
• 英文别名: 2-[(4-chlorophenyl)methylsulfanyl]aniline
• CAS: 43092-84-8
• 化学式: C₁₃H₁₂ClNS
• mdl: MFCD02152597
• 分子量: 249.764
• InChiKey: ICMGQEPYBCOVEA-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±27.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(4-氯苄基)硫基]苯胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 1-[2-[(4-Chlorophenyl)methylsulfanyl]phenyl]guanidine
  参考文献：
  名称：

  Novel fungicidal benzylsulfanyl-phenylguanidines

  摘要：

  A series of substituted benzylsulfanyl-phenylamines was synthesized, of which four substituted benzylsulfanyl-phenylguanidines (665, 666, 667 and 684) showed potent fungicidal activity (minimal fungicidal concentration, MFC <= 10 mu M for Candida albicans and Candida glabrata). A benzylsulfanyl-phenyl scaffold with an unsubstituted guanidine resulted in less active compounds (MFC = 50-100 mu M), whereas substitution with an unsubstituted amine group resulted in compounds without fungicidal activity. Compounds 665, 666, 667 and 684 also showed activity against single C. albicans biofilms and biofilms consisting of C. albicans and Staphylococcus epidermidis (minimal concentration resulting in 50% eradication of the biofilm, BEC50 <= 121 mu M for both biofilm setups). Compounds 665 and 666 combined potent fungicidal (MFC = 5 mu M) and bactericidal activity (minimal bactericidal concentration, MBC for S. epidermidis <= 4 mu M). In an in vivo Caenorhabditis elegans model, compounds 665 and 667 exhibited less toxicity than 666 and 684. Moreover, addition of those compounds to Candida-infected C. elegans cultures resulted in increased survival of Candida-infected worms, demonstrating their in vivo efficacy in a mini-host model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.075
• 作为产物：
  描述：

  4-氯氯苄 、 2-氨基苯硫醇 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-[(4-氯苄基)硫基]苯胺
  参考文献：
  名称：

  Novel fungicidal benzylsulfanyl-phenylguanidines

  摘要：

  A series of substituted benzylsulfanyl-phenylamines was synthesized, of which four substituted benzylsulfanyl-phenylguanidines (665, 666, 667 and 684) showed potent fungicidal activity (minimal fungicidal concentration, MFC <= 10 mu M for Candida albicans and Candida glabrata). A benzylsulfanyl-phenyl scaffold with an unsubstituted guanidine resulted in less active compounds (MFC = 50-100 mu M), whereas substitution with an unsubstituted amine group resulted in compounds without fungicidal activity. Compounds 665, 666, 667 and 684 also showed activity against single C. albicans biofilms and biofilms consisting of C. albicans and Staphylococcus epidermidis (minimal concentration resulting in 50% eradication of the biofilm, BEC50 <= 121 mu M for both biofilm setups). Compounds 665 and 666 combined potent fungicidal (MFC = 5 mu M) and bactericidal activity (minimal bactericidal concentration, MBC for S. epidermidis <= 4 mu M). In an in vivo Caenorhabditis elegans model, compounds 665 and 667 exhibited less toxicity than 666 and 684. Moreover, addition of those compounds to Candida-infected C. elegans cultures resulted in increased survival of Candida-infected worms, demonstrating their in vivo efficacy in a mini-host model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.075

文献信息

• Use of substituted anilides and sulfonamides in the treatment of cardiovascular diseases
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0453658A2

  公开（公告）日：1991-10-30

  A novel pharmaceutical composition and method is disclosed for the treatment of cardiovascular diseases, e.g. myocardial ischemia and/or arrhythmia. The method and composition include an effective amount of a compound of the formula wherein R and R₁each independently represent hydrogen, halo, lower alkyl, lower alkoxy, trihalomethyl, nitro, amino or hydroxy; Xrepresents oxa (-O-) or thia (-S-); Brepresents a basic nitrogen-containing radical of less than 12 carbon atoms; A and A'are independently selected from hydrogen or lower alkyl; mis zero or an integer from 1 to 3; nrepresents an integer from 2-5; p and p'are the same or different integer of 1 to 3; yis and R₂is lower alkyl, aryl, aralkyl, cyclo-alkyl (lower alkyl), lower alkenyl, lower alkadienyl, α-substituted phenyl alkyl, aralkenyl, aralkynyl or heteroaryl.

  本发明公开了一种新型药物组合物和方法，用于治疗心血管疾病，如心肌缺血和/或心律失常。该方法和组合物包括有效量的式化合物 式中 R和R₁各自独立地代表氢、卤素、低级烷基、低级烷氧基、三卤甲基、硝基、氨基或羟基； X代表羰基（-O-）或噻吩（-S-）； Brep 代表少于 12 个碳原子的碱性含氮基； A 和 A'独立地选自氢或低级烷基； 误为零或 1 至 3 的整数； n为2-5的整数； p 和 p'是相同或不同的 1 至 3 的整数； y 是和 R₂是低级烷基、芳基、芳烷基、环烷基（低级烷基）、低级烯基、低级烷二烯基、α-取代苯基烷基、芳烯基、芳炔基或杂芳基。
• Novel fungicidal benzylsulfanyl-phenylguanidines
  作者：Karin Thevissen、Klaartje Pellens、Katrijn De Brucker、Isabelle E.J.A. François、Kwok K. Chow、Els M.K. Meert、Wim Meert、Geert Van Minnebruggen、Marcel Borgers、Valérie Vroome、Jeremy Levin、Dirk De Vos、Louis Maes、Paul Cos、Bruno P.A. Cammue

  DOI：10.1016/j.bmcl.2011.04.075

  日期：2011.6

  A series of substituted benzylsulfanyl-phenylamines was synthesized, of which four substituted benzylsulfanyl-phenylguanidines (665, 666, 667 and 684) showed potent fungicidal activity (minimal fungicidal concentration, MFC <= 10 mu M for Candida albicans and Candida glabrata). A benzylsulfanyl-phenyl scaffold with an unsubstituted guanidine resulted in less active compounds (MFC = 50-100 mu M), whereas substitution with an unsubstituted amine group resulted in compounds without fungicidal activity. Compounds 665, 666, 667 and 684 also showed activity against single C. albicans biofilms and biofilms consisting of C. albicans and Staphylococcus epidermidis (minimal concentration resulting in 50% eradication of the biofilm, BEC50 <= 121 mu M for both biofilm setups). Compounds 665 and 666 combined potent fungicidal (MFC = 5 mu M) and bactericidal activity (minimal bactericidal concentration, MBC for S. epidermidis <= 4 mu M). In an in vivo Caenorhabditis elegans model, compounds 665 and 667 exhibited less toxicity than 666 and 684. Moreover, addition of those compounds to Candida-infected C. elegans cultures resulted in increased survival of Candida-infected worms, demonstrating their in vivo efficacy in a mini-host model. (C) 2011 Elsevier Ltd. All rights reserved.