methyl 6-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-4-carboxylate | 752936-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 6-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-4-carboxylate
• CAS: 752936-52-0
• 化学式: C₁₃H₁₃ClN₂O₂
• 分子量: 264.711
• InChiKey: FEYYQAUNRGVMSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-4-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 6-chloro-2-(6-chloro-4-((methoxymethoxy)methyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)benzo[d]thiazole
  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：

  methyl 2-(5-chloro-1H-indol-3-yl)-3-nitropropanoate 在 盐酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成 methyl 6-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-4-carboxylate
  参考文献：
  名称：

  WO2020037155A5

  摘要：

  公开号：

  WO2020037155A5

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。
• 1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF
  申请人：Recreo Pharmaceuticals Inc.

  公开号：EP3836919A1

  公开（公告）日：2021-06-23
• 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.
• [EN] 1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DÉRIVÉS DE 1,3,4,9-TÉTRAHYDRO-2H-PYRIDO[3,4-B]INDOLE ET LEURS UTILISATIONS
  申请人：RECREO PHARMACEUTICALS LLC

  公开号：WO2020037155A1

  公开（公告）日：2020-02-20

  The present invention relates to 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole derivative compounds and uses thereof. In particular, compounds of the invention have antibacterial activity and/or are capable of re-sensitizing methicillin-resistant Staphylococcus aureus to a P-lactam antibiotic or a combination of a P-lactam antibiotic and a P-lactamase inhibitor. The present invention also relates to a method for producing and using said compounds.
• WO2020037155A5
  申请人：——

  公开号：WO2020037155A5

  公开（公告）日：2022-08-16