2,6-difluoro-3-({6-phenylpyrido[3,2-d][1,3]thiazol-2-yl}methoxy)benzamide | 951121-95-2

• 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
• 英文名称: 2,6-difluoro-3-({6-phenylpyrido[3,2-d][1,3]thiazol-2-yl}methoxy)benzamide
• 英文别名: 2,6-Difluoro-3-[(6-phenyl-[1,3]thiazolo[5,4-b]pyridin-2-yl)methoxy]benzamide
• CAS: 951121-95-2
• 化学式: C₂₀H₁₃F₂N₃O₂S
• 分子量: 397.405
• InChiKey: DOVMRFVTOPZLEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-({6-bromopyrido[3,2-d][1,3]thiazol-2-yl}methoxy)-2,6-difluorobenzamide 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以40%的产率得到2,6-difluoro-3-({6-phenylpyrido[3,2-d][1,3]thiazol-2-yl}methoxy)benzamide
  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

文献信息

• 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。
• US8088791B2
  申请人：——

  公开号：US8088791B2

  公开（公告）日：2012-01-03
• 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.