1,2-Dichloro-3-(2-isocyanato-ethyl)-benzene | 73075-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-Dichloro-3-(2-isocyanato-ethyl)-benzene
• 英文别名: 1,2-Dichloro-3-(2-isocyanatoethyl)benzene
• CAS: 73075-66-8
• 化学式: C₉H₇Cl₂NO
• mdl: MFCD16547715
• 分子量: 216.067
• InChiKey: DTRCRRCMRPREIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-Dichloro-3-(2-isocyanato-ethyl)-benzene 在 三氯化铝 、 硼烷 作用下， 以 四氢呋喃 、 四氯乙烯 为溶剂， 反应 21.0h， 生成 5,6-dichloro-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007
• 作为产物：
  描述：

  3-(2,3-二氯苯基)丙酸 在 氯化亚砜 、 sodium azide 、 N,N-二甲基甲酰胺 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 3.17h， 生成 1,2-Dichloro-3-(2-isocyanato-ethyl)-benzene
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007

文献信息

• [EN] INHIBITORS OF BACTERIAL GLYCOSYL TRANSFERASES<br/>[FR] INHIBITEURS DE GLYCOSYL TRANSFÉRASES BACTÉRIENNES
  申请人：HARVARD COLLEGE

  公开号：WO2016191658A1

  公开（公告）日：2016-12-01

  Described herein are compounds of Formula (I'), Formula (IA), Formulae (I)-(VII), pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrug sthereof. The invention also provides pharmaceutical compositions of the compounds for human and veterinary use. Compounds of the present invention are useful for inhibiting bacterial growth and therefore are useful in treating and/or preventing bacterial infections. Methods of using the compounds for treating and/or preventing a bacterial infection in a subject are also described.

  本文描述了式(I')、式(IA)、式(I)-(VII)的化合物，以及这些化合物的药用盐、溶剂合物、水合物、多型体、共晶体、互变异构体、立体异构体、同位素标记衍生物和前药。本发明还提供了这些化合物的用于人类和兽医用途的药物组合物。本发明的化合物对抑制细菌生长有用，因此在治疗和/或预防细菌感染方面具有用途。还描述了使用这些化合物治疗和/或预防受试者细菌感染的方法。
• BONDINELL W. E.; CHAPIN F. W.; GIRARD G. R.; KAISER C.; KROG A. J.; PAVLO+, J. MED. CHEM., 1980, 23, NO 5, 506-511
  作者：BONDINELL W. E.、 CHAPIN F. W.、 GIRARD G. R.、 KAISER C.、 KROG A. J.、 PAVLO+

  DOI：——

  日期：——
• INHIBITORS OF BACTERIAL GLYCOSYL TRANSFERASES
  申请人：President and Fellows of Harvard College

  公开号：EP3303338A1

  公开（公告）日：2018-04-11
• Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines
  作者：William E. Bondinell、Frederic W. Chapin、Gerald R. Girard、Carl Kaiser、Arnold J. Krog、Alex M. Pavloff、Mark S. Schwartz、Joanne S. Silvestri、Praful D. Vaidya

  DOI：10.1021/jm00179a007

  日期：1980.5

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.