2-(溴甲基)-6-氯-[1,3]噻唑并[5,4-b]吡啶 | 951122-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(溴甲基)-6-氯-[1,3]噻唑并[5,4-b]吡啶
• 英文名称: 2-(bromomethyl)-6-chloropyrido[3,2-d][1,3]thiazole
• 英文别名: 2-(bromomethyl)-6-chlorothiazolo[5,4-b]pyridine；2-(bromomethyl)-6-chloro-[1,3]thiazolo[5,4-b]pyridine
• CAS: 951122-66-0
• 化学式: C₇H₄BrClN₂S
• 分子量: 263.545
• InChiKey: QAMMELFTJCKUFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二氟-3-羟基苯甲酰胺 、 2-(溴甲基)-6-氯-[1,3]噻唑并[5,4-b]吡啶 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 以78%的产率得到3-[(6-氯噻唑并[5,4-b]吡啶-2-基)甲氧基]-2,6-二氟苯甲酰胺
  参考文献：
  名称：

  Creating an Antibacterial with in Vivo Efficacy: Synthesis and Characterization of Potent Inhibitors of the Bacterial Cell Division Protein FtsZ with Improved Pharmaceutical Properties

  摘要：

  3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.

  DOI：

  10.1021/jm9016366
• 作为产物：
  描述：

  2-溴-3-氨基-5-氯吡啶 在 吡啶 、 tetraphosphorus decasulfide 、 lithium bromide monohydrate 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 14.5h， 生成 2-(溴甲基)-6-氯-[1,3]噻唑并[5,4-b]吡啶
  参考文献：
  名称：

  A Facile Approach to the Synthesis of 3-(6-Chloro-thiazolo[5,4-b]pyridin-2-ylmethoxy)-2,6-difluoro-benzamide (PC190723)

  摘要：

  Practical synthesis of PC 190723, a bacterial cell division protein Ftsz inhibitor, has been achieved in a high overall yield of 45% in six steps from commercially available starting materials.

  DOI：

  10.1055/s-0031-1290777

文献信息

• Substitution of terminal amide with 1 H -1,2,3-triazole: Identification of unexpected class of potent antibacterial agents
  作者：Fangchao Bi、Shengli Ji、Henrietta Venter、Jingru Liu、Susan J. Semple、Shutao Ma

  DOI：10.1016/j.bmcl.2018.02.001

  日期：2018.3

  3-Methoxybenzamide (3-MBA) derivatives have been identified as novel class of potent antibacterial agents targeting the bacterial cell division protein FtsZ. As one of isosteres for the amide group, 1,2,3-triazole can mimic the topological and electronic features of the amide, which has gained increasing attention in drug discovery. Based on these considerations, we prepared a series of 1H-1,2,3-triazole-containing

  3-甲氧基苯甲酰胺（3-MBA）衍生物已被确定为针对细菌细胞分裂蛋白FtsZ的新型有效抗菌剂。作为酰胺基团的等排体之一，1,2,3-三唑可以模拟酰胺的拓扑和电子特征，这在药物开发中已引起越来越多的关注。基于这些考虑，我们通过用三唑等位取代末端酰胺，制备了一系列含有1 H -1,2,3-三唑的3-MBA类似物，从而提高了抗菌活性。这项研究证明了发展1 H -1,2,3-三唑基作为末端酰胺模拟元件的可能性，该模拟元件能够保持和调节酰胺相关的生物活性。令人惊讶的是，这些新的1观察到含有H -1,2,3-三唑的类似物，这可能为开发抗菌剂打开新的机会。
• ANTIBACTERIAL AGENTS
  申请人：Brown David Ryall

  公开号：US20100173933A1

  公开（公告）日：2010-07-08

  Compounds of formula (I) have antibacterial activity: wherein R represents hydrogen or 1, 2 or 3 optional substituents; W is ═C(R 1 )— or ═N—; R 1 is hydrogen or an optional substituent and R 2 is hydrogen, methyl, or fluorine; or R 1 and R 2 taken together are —CH 2 —, —CH 2 CH 2 —, —O—, or, in either orientation, —O—CH 2 — or —OCH 2 CH 2 —; R 3 is a radical of formula -(Alk 1 ) m -(Z) p -(Alk 2 ) n -Q wherein m, p and n are independently 0 or 1, provided that at least one of m, p and n is 1, Z is —O—, —S—, —S(O)—, —S(O 2 )—, —NH—, —N(CH 3 )—, —N(CH 2 CH 3 )—, —C(═O)—, —O—(C═O)—, —C(═O)—O—, or an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted divalent bicyclic heterocyclic radical having 5 to 10 ring atoms; Alk 1 and Alk 2 are optionally substituted C 1 -C 6 alkylene, C 2 -C 6 alkenylene, or C 2 -C 6 alkynylene radicals, which may optionally terminate with or be interrupted by —O—, —S—, —S(O)—, —S(O 2 )—, —NH—, —N(CH 3 )—, or —N(CH 2 CH 3 )—; and Q is hydrogen, halogen, nitrile, or hydroxyl or an optionally substituted monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted bicyclic heterocyclic radical having 5 to 10 ring atoms.

  化学式为（I）的化合物具有抗菌活性：其中R代表氢或1、2或3个可选取代基；W是═C（R1）-或═N-；R1是氢或可选取代基，R2是氢、甲基或氟；或R1和R2一起取-CH2-、-CH2CH2-、-O-，或者，在任何方向上，取-O-CH2-或-OCH2CH2-；R3是公式-(Alk1)m-(Z)p-(Alk2)n-Q的基团，其中m、p和n独立地为0或1，但至少有一个为1，Z是-O-、-S-、-S（O）-、-S（O2）-、-NH-、-N（CH3）-、-N（CH2CH3）-、-C（═O）-、-O-（C═O）-、-C（═O）-O-，或具有3至6个环原子的可选取代的单环碳环或杂环基团；或具有5至10个环原子的可选取代双环杂环基团；Alk1和Alk2是可选取代的C1-C6烷基、C2-C6烯基或C2-C6炔基基团，可以以-O-、-S-、-S（O）-、-S（O2）-、-NH-、-N（CH3）-或-N（CH2CH3）-结尾或被中断；Q是氢、卤素、腈或羟基，或具有3至6个环原子的可选取代的单环碳环或杂环基团；或具有5至10个环原子的可选取代的双环杂环基团。
• Creating an Antibacterial with in Vivo Efficacy: Synthesis and Characterization of Potent Inhibitors of the Bacterial Cell Division Protein FtsZ with Improved Pharmaceutical Properties
  作者：David J. Haydon、James M. Bennett、David Brown、Ian Collins、Greta Galbraith、Paul Lancett、Rebecca Macdonald、Neil R. Stokes、Pramod K. Chauhan、Jignesh K. Sutariya、Narendra Nayal、Anil Srivastava、Joy Beanland、Robin Hall、Vincent Henstock、Caterina Noula、Chris Rockley、Lloyd Czaplewski

  DOI：10.1021/jm9016366

  日期：2010.5.27

  3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.
• BENZAMIDE AND PYRIDYLAMIDE DERIVATIVES AS ANTIBACTERIAL AGENTS
  申请人：Biota Europe Ltd

  公开号：EP1996180B1

  公开（公告）日：2011-08-03
• US8088791B2
  申请人：——

  公开号：US8088791B2

  公开（公告）日：2012-01-03