tert-butyl [2-(1,3-benzothiazol-2-ylamino)ethyl]carbamate | 1206541-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: tert-butyl [2-(1,3-benzothiazol-2-ylamino)ethyl]carbamate
• 英文别名: tert-butyl 2-(benzo[d]thiazol-2-ylamino)ethylcarbamate；tert-butyl N-[2-(1,3-benzothiazol-2-ylamino)ethyl]carbamate
• CAS: 1206541-03-8
• 化学式: C₁₄H₁₉N₃O₂S
• 分子量: 293.39
• InChiKey: ZSSRIHUELJDQDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl [2-(1,3-benzothiazol-2-ylamino)ethyl]carbamate 在 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  Preparation, antibacterial evaluation and preliminary structure–activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

  摘要：

  In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.079
• 作为产物：
  描述：

  2-氨基苯并噻唑 在 氯化亚砜 、 盐酸肼 、 potassium carbonate 、 一水合肼 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 tert-butyl [2-(1,3-benzothiazol-2-ylamino)ethyl]carbamate
  参考文献：
  名称：

  Preparation, antibacterial evaluation and preliminary structure–activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

  摘要：

  In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.079

文献信息

• SUBSTITUTED BENZOTHIAZOLE AND BENZOXAZOLE DERIVATIVES USEFUL AS INHIBITORS OF DPP-1
  申请人：Jordan Alfonzo D.

  公开号：US20110152287A1

  公开（公告）日：2011-06-23

  The present invention is directed to substituted benzothiazole and benzoxazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by DPP-1.

  本发明涉及替代苯并噻唑和苯并噁唑衍生物，包含它们的药物组合物以及它们在通过DPP-1调节的疾病和症状治疗中的应用。
• Substituted benzothiazole and benzoxazole derivatives useful as inhibitors of DPP-1
  申请人：Jordan Alfonzo D.

  公开号：US08481547B2

  公开（公告）日：2013-07-09

  The present invention is directed to substituted benzothiazole and benzoxazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by DPP-1.

  本发明涉及取代苯并噻唑和苯并噁唑衍生物、含有它们的药物组合物以及它们在治疗由DPP-1调节的疾病和病状中的应用。
• [EN] FUSED OXAZOLE AND THIAZOLE DERIVATIVES AS TRPMS MODULATORS<br/>[FR] DÉRIVÉS OXAZOLE ET THIAZOLE FUSIONNÉS EN TANT QUE MODULATEURS DE TRPM8
  申请人：GLENMARK PHARMACEUTICAL S A

  公开号：WO2010010435A3

  公开（公告）日：2010-12-23
• US8481547B2
  申请人：——

  公开号：US8481547B2

  公开（公告）日：2013-07-09
• [EN] SUBSTITUTED BENZOTHIAZOLE AND BENZOXAZOLE DERIVATIVES USEFUL AS INHIBITORS OF DPP-1<br/>[FR] DÉRIVÉS DE BENZOTHIAZOLE ET DE BENZOXAZOLE SUBSTITUÉS UTILES EN TANT QU'INHIBITEURS DE DPP-1
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011075631A1

  公开（公告）日：2011-06-23

  The present invention is directed to substituted benzothiazole and benzoxazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by DPP-1.