3-benzyl-2-[2-(1-chloro-ethyl)-4-fluoro-phenoxy]-6-(4-phenyl-[1,2,3]triazol-1-yl)-quinoline | 1173292-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-benzyl-2-[2-(1-chloro-ethyl)-4-fluoro-phenoxy]-6-(4-phenyl-[1,2,3]triazol-1-yl)-quinoline
• 英文别名: 3-benzyl-2-[2-(1-chloroethyl)-4-fluorophenoxy]-6-(4-phenyltriazol-1-yl)quinoline
• CAS: 1173292-08-4
• 化学式: C₃₂H₂₄ClFN₄O
• 分子量: 535.02
• InChiKey: FSZFCVARIICDGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-吡啶基)哌嗪 、 3-benzyl-2-[2-(1-chloro-ethyl)-4-fluoro-phenoxy]-6-(4-phenyl-[1,2,3]triazol-1-yl)-quinoline 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以24%的产率得到3-benzyl-2-{4-fluoro-2-[1-(4-pyridin-2-yl-piperazin-1-yl)-ethyl]-phenoxy}-6-(4-phenyl-[1,2,3]triazol-1-yl)-quinoline
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis

  摘要：

  A new series of 20 quinoline derivatives possessing triazolo, ureido and thioureido substituents have been synthesized and their antimycobacterial properties have been evaluated. Compounds 10, 22 and 24 inhibited Mycobacterium tuberculosis H37Rv up to 96%, 98% and 94% respectively, at a fixed concentration of 6.25 mu g/mL. Minimum inhibitory concentration of 3.125 mu g/mL was obtained for compound 10 and 24, while for compound 22 it was 6.25 mu g/mL. Molecular docking calculations suggest critical hydrogen bonding and electrostatic interactions between polar functional groups (such as quinoline-nitrogen, urea-carbonyl and hydroxyl) of anti-mycobacterial (anti-TB) compounds and amino acids (Arg186 and Glu61) of ATP-synthase of M. tuberculosis, could be the probable reason for observed anti-mycobacterial action. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.069
• 作为产物：
  描述：

  1-{2-[3-benzyl-6-(4-phenyl-[1,2,3]triazol-1-yl)-quinolin-2-yloxy]-5-fluoro-phenyl}-ethanol 在 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以60%的产率得到3-benzyl-2-[2-(1-chloro-ethyl)-4-fluoro-phenoxy]-6-(4-phenyl-[1,2,3]triazol-1-yl)-quinoline
  参考文献：
  名称：

  [EN] QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATES AS ANTI-MYCOBACTERIAL AGENTS
  [FR] DÉRIVÉS DE QUINOLÉINE, DE NAPHTALÈNE, DE QUINOLÉINE OU DE NAPHTALÈNE CONTRAINT AU NIVEAU CONFORMATION EN TANT QU'AGENTS ANTIMYCOBACTÉRIENS

  摘要：

  该发明涉及一般式I、II、III、IV、V、VI、VII、VIII、IX、X的化合物，或其立体化学异构体或药学上可接受的盐，其N-氧化物形式或其前药。该化合物可用作治疗分枝杆菌病的药物。

  公开号：

  WO2009091324A1

文献信息

• [EN] QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATES AS ANTI-MYCOBACTERIAL AGENTS<br/>[FR] DÉRIVÉS DE QUINOLÉINE, DE NAPHTALÈNE, DE QUINOLÉINE OU DE NAPHTALÈNE CONTRAINT AU NIVEAU CONFORMATION EN TANT QU'AGENTS ANTIMYCOBACTÉRIENS
  申请人：CHATTOPADHYAYA JYOTI

  公开号：WO2009091324A1

  公开（公告）日：2009-07-23

  The invention relates to a compound of general formula I, II, III, IV, V, VI, VII, VIII, IX, X or a tautomer and the stereochemically isomeric forms thereof or pharmaceutically acceptable salts thereof, a N-oxide form thereof or a pro-drug thereof. The compound is usable as a medicament for the treatment of mycobacterial disease.

  该发明涉及一般式I、II、III、IV、V、VI、VII、VIII、IX、X的化合物，或其立体化学异构体或药学上可接受的盐，其N-氧化物形式或其前药。该化合物可用作治疗分枝杆菌病的药物。
• QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATIVES AS ANTI-MYCOBACTERIAL AGENTS
  申请人：Chattopadhyaya Jyoti

  公开号：US20110059948A1

  公开（公告）日：2011-03-10

  The invention relates to a compound of general formula I, II, III, IV, V, VI, VII, VIII, IX, X or a tautomer and the stereochemically isomeric forms thereof or pharmaceutically acceptable salts thereof, a N-oxide form thereof or a pro-drug thereof. The compound is usable as a medicament for the treatment of mycobacterial disease.

  本发明涉及一种符合以下公式I、II、III、IV、V、VI、VII、VIII、IX、X或其互变异构体，或其药学上可接受的盐、N-氧化物形式或前药的化合物。该化合物可用作治疗分枝杆菌病的药物。
• Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis
  作者：Ram Shankar Upadhayaya、Girish M. Kulkarni、Nageswara Rao Vasireddy、Jaya Kishore Vandavasi、Shailesh S. Dixit、Vivek Sharma、Jyoti Chattopadhyaya

  DOI：10.1016/j.bmc.2009.04.069

  日期：2009.7

  A new series of 20 quinoline derivatives possessing triazolo, ureido and thioureido substituents have been synthesized and their antimycobacterial properties have been evaluated. Compounds 10, 22 and 24 inhibited Mycobacterium tuberculosis H37Rv up to 96%, 98% and 94% respectively, at a fixed concentration of 6.25 mu g/mL. Minimum inhibitory concentration of 3.125 mu g/mL was obtained for compound 10 and 24, while for compound 22 it was 6.25 mu g/mL. Molecular docking calculations suggest critical hydrogen bonding and electrostatic interactions between polar functional groups (such as quinoline-nitrogen, urea-carbonyl and hydroxyl) of anti-mycobacterial (anti-TB) compounds and amino acids (Arg186 and Glu61) of ATP-synthase of M. tuberculosis, could be the probable reason for observed anti-mycobacterial action. (C) 2009 Elsevier Ltd. All rights reserved.