4-((1-methyl-1H-benzo[d]imidazol-2-yl)amino)-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2Hpyran-4-yl)methyl)benzamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-((1-methyl-1H-benzo[d]imidazol-2-yl)amino)-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2Hpyran-4-yl)methyl)benzamide
• 英文别名: 4-[(1-methylbenzimidazol-2-yl)amino]-N-[[4-(4-phenylthiazol-2-yl)tetrahydropyran-4-yl]methyl]benzamide；4-[(1-methylbenzimidazol-2-yl)amino]-N-[[4-(4-phenyl-1,3-thiazol-2-yl)oxan-4-yl]methyl]benzamide
• 化学式: C₃₀H₂₉N₅O₂S
• 分子量: 523.659
• InChiKey: BOFKDIYVBUFIII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(4-苯基-1,3-噻唑-2-基)乙腈 在 lithium aluminium tetrahydride 、 sodium hydride 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 4-((1-methyl-1H-benzo[d]imidazol-2-yl)amino)-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2Hpyran-4-yl)methyl)benzamide
  参考文献：
  名称：

  New direct inhibitors of InhA with antimycobacterial activity based on a tetrahydropyran scaffold

  摘要：

  Tetrahydropyran derivative 1 was discovered in a high-throughput screening campaign to find new inhibitors of mycobacterial InhA. Following initial in-vitro profiling, a structure-activity relationship study was initiated and a focused library of analogs was synthesized and evaluated. This yielded compound 42 with improved antimycobacterial activity and low cytotoxicity. Additionally, the crystal structure of InhA in complex with inhibitor 1 was resolved, to reveal the binding mode and provide hints for further optimization. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.02.008

文献信息

• New direct inhibitors of InhA with antimycobacterial activity based on a tetrahydropyran scaffold
  作者：Stane Pajk、Matej Živec、Roman Šink、Izidor Sosič、Margarete Neu、Chun-wa Chung、María Martínez-Hoyos、Esther Pérez-Herrán、Daniel Álvarez-Gómez、Emilio Álvarez-Ruíz、Alfonso Mendoza-Losana、Julia Castro-Pichel、David Barros、Lluís Ballell-Pages、Robert J. Young、Maire A. Convery、Lourdes Encinas、Stanislav Gobec

  DOI：10.1016/j.ejmech.2016.02.008

  日期：2016.4

  Tetrahydropyran derivative 1 was discovered in a high-throughput screening campaign to find new inhibitors of mycobacterial InhA. Following initial in-vitro profiling, a structure-activity relationship study was initiated and a focused library of analogs was synthesized and evaluated. This yielded compound 42 with improved antimycobacterial activity and low cytotoxicity. Additionally, the crystal structure of InhA in complex with inhibitor 1 was resolved, to reveal the binding mode and provide hints for further optimization. (C) 2016 Elsevier Masson SAS. All rights reserved.