2,4,6-三氯苯并噻唑 | 25745-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2,4,6-三氯苯并噻唑
• 英文名称: 2,4,6-trichlorobenzothiazole
• 英文别名: 2,4,6-Trichlor-benzothiazol；2,4,6-Trichloro-benzothiazole；2,4,6-trichloro-1,3-benzothiazole
• CAS: 25745-12-4
• 化学式: C₇H₂Cl₃NS
• 分子量: 238.525
• InChiKey: VTCQHPHTMWSXKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  2,4,6-三氯苯并噻唑 、 6-氯-2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以48%的产率得到6-chloro-2-(4,6-dichloro-1,3-benzothiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Tryptoline-based benzothiazoles re-sensitize MRSA to β-lactam antibiotics

  摘要：

  Resistance-modifying agents (RMAs) offer a promising solution to combat bacterial antibiotic resistance. Here we report the discovery and structure-activity relationships of a new class of RMAs with a novel tryptoline-based benzothiazole scaffold. Our most potent compound in this series (4ad) re-sensitizes multiple MRSA strains to cephalosporins at low concentrations (2 mu g/mL) and has low mammalian cytotoxicity with a half growth inhibitory concentration (GI(50)) > 100 mu g/mL in human cervical carcinoma (HeLa) cells. In addition, the same core scaffold with different substitutions also gives good antibacterial activity against MRSA.

  DOI：

  10.1016/j.bmc.2019.115095
• 作为产物：
  描述：

  1,1-二氯-N-(2,4-二氯苯基)甲亚胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以70%的产率得到2,4,6-三氯苯并噻唑
  参考文献：
  名称：

  含有氮，磷，砷和硫的有机金属化合物

  摘要：

  DOI：

  10.1016/0022-328x(85)87091-1

文献信息

• [EN] TRYPTOLINE-BASED BENZOTHIAZOLES AND THEIR USE AS ANTIBIOTICS AND ANTIBIOTIC RESISTANCE-MODIFYING AGENTS<br/>[FR] BENZOTHIAZOLES À BASE DE TRYPTOLINE ET LEUR UTILISATION EN TANT QU'ANTIBIOTIQUES ET AGENTS MODIFIANT LA RÉSISTANCE AUX ANTIBIOTIQUES
  申请人：UNIV COLORADO REGENTS

  公开号：WO2021046194A1

  公开（公告）日：2021-03-11

  The present inventions relates to tryptoline-based benzothi azole compounds and their use as both novel resistance modifying agents, and antibiotics.

  本发明涉及基于色胺的苯并噻唑类化合物及其用作新型耐药修饰剂和抗生素的用途。
• DOU H. J. M.; HASSANALY P.; KISTER J.; VERNIN G.; METZGER J., HELV. CHIM. ACTA, 1978, 61, NO 8, 3143-3148
  作者：DOU H. J. M.、 HASSANALY P.、 KISTER J.、 VERNIN G.、 METZGER J.

  DOI：——

  日期：——
• Propionsäureester und deren Verwendung als Unkrautbekämpfungsmittel
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0121871B1

  公开（公告）日：1988-01-20
• Tryptoline-Based Benzothiazoles and their use as Antibiotics and Antibiotic Resistance-Modifying Agents
  申请人：The Regents of the University of Colorado, a body corporate

  公开号：US20220402914A1

  公开（公告）日：2022-12-22

  The present inventions relates to tryptoline-based benzothiazole compounds and their use as both novel resistance modifying agents, and antibiotics.
• Tryptoline-based benzothiazoles re-sensitize MRSA to β-lactam antibiotics
  作者：Xinfeng Wang、Jinsen Chen、Wei Wang、Anna Jaunarajs、Xiang Wang

  DOI：10.1016/j.bmc.2019.115095

  日期：2019.11

  Resistance-modifying agents (RMAs) offer a promising solution to combat bacterial antibiotic resistance. Here we report the discovery and structure-activity relationships of a new class of RMAs with a novel tryptoline-based benzothiazole scaffold. Our most potent compound in this series (4ad) re-sensitizes multiple MRSA strains to cephalosporins at low concentrations (2 mu g/mL) and has low mammalian cytotoxicity with a half growth inhibitory concentration (GI(50)) > 100 mu g/mL in human cervical carcinoma (HeLa) cells. In addition, the same core scaffold with different substitutions also gives good antibacterial activity against MRSA.