4-(3,5-Dibromobenzylthio)Aniline | 1314034-15-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(3,5-Dibromobenzylthio)Aniline
• 英文别名: 4-[(3,5-dibromophenyl)methylsulfanyl]aniline
• CAS: 1314034-15-5
• 化学式: C₁₃H₁₁Br₂NS
• 分子量: 373.111
• InChiKey: UKXPYZPBUUSMAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4-(3,5-Dibromobenzylthio)Aniline 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-[4-[(3,5-Dibromophenyl)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：

  3,5-二溴苄基溴 、 4-氨基苯硫酚 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 4-(3,5-Dibromobenzylthio)Aniline
  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

• 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.