(5-苯基-1H-咪唑-2-基)甲胺盐酸盐 | 945404-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (5-苯基-1H-咪唑-2-基)甲胺盐酸盐
• 英文名称: 2-aminomethyl-4-phenyl-1H-imidazol hydrochloride
• 英文别名: (4-phenyl-1H-imidazol-2-yl)methylamine hydrochloride；2-aminomethyl-4-phenyl-1H-imidazole hydrochloride；1-(4-phenyl-1H-imidazol-2-yl)methanamine monohydrochloride；(5-phenyl-1H-imidazol-2-yl)methanamine hydrochloride；(5-phenyl-1H-imidazol-2-yl)methanamine;hydrochloride
• CAS: 945404-25-1；175531-38-1
• 化学式: C₁₀H₁₁N₃*ClH
• 分子量: 209.678
• InChiKey: HPQQIZHQBBTZPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.7
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-苯基-1H-咪唑-2-基)甲胺盐酸盐 在 四丁基溴化铵 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 生成 4,5-difluoro-3-[2-(6-hydroxy-2-phenyl-6,7-dihydro-5H-imidazo[1,2-a][1,4]diazepin-8(9H)-yl)-2-oxoethyl]-1,3-benzoxazol-2(3H)-one
  参考文献：
  名称：

  IMIDAZODIAZEPINE COMPOUND

  摘要：

  公开号：

  EP3312181B1
• 作为产物：
  描述：

  benzyl (4-phenyl-1H-imidazol-2-yl)methylcarbamate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以76%的产率得到(5-苯基-1H-咪唑-2-基)甲胺盐酸盐
  参考文献：
  名称：

  Phenylimidazole derivatives as new inhibitors of bacterial enoyl-ACP reductase FabK

  摘要：

  Novel FabK inhibitors with antibacterial activity against Streptococcus pneuinoniae were synthesized and evaluated. Through SAR studies of our initial hit compound 2-(1H-benz[d]imidazol-2-ylthio)-N-(6-methoxycarbonylbenzo[d]thiazo1-2-yl)acetamide, a series of novel phenylimidazole derivatives were discovered as potent FabK inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.040

文献信息

• Phenylimidazole Derivatives of 4-Pyridone as Dual Inhibitors of Bacterial Enoyl-Acyl Carrier Protein Reductases FabI and FabK
  作者：Hideo Kitagawa、Tomohiro Ozawa、Sho Takahata、Maiko Iida、Jun Saito、Mototsugu Yamada

  DOI：10.1021/jm0705354

  日期：2007.9.1

  reductases that catalyze the final and rate-limiting step of bacterial fatty acid biosynthesis (FAS) and are potential targets of novel antibacterial agents. We have reported 4-pyridone derivative 3 as a FabI inhibitor and phenylimidazole derivative 5 as a FabK inhibitor. Here, we will report phenylimidazole derivatives of 4-pyridone as FabI and FabK dual inhibitors based on an iterative medicinal chemistry

  FabI和FabK是细菌烯酰酰基载体蛋白（ACP）还原酶，可催化细菌脂肪酸生物合成（FAS）的最终步骤和限速步骤，并且是新型抗菌剂的潜在靶标。我们已经报道了4-吡啶酮衍生物3作为FabI抑制剂，而苯基咪唑衍生物5作为FabK抑制剂。在此，我们将基于肺炎链球菌/化合物26的FabK的迭代药物化学和结晶学研究，报告4-吡啶酮的苯基咪唑衍生物作为FabI和FabK双重抑制剂。代表性化合物6具有较强的FabI抑制作用（IC50 = 0.38 microM），并且FabK抑制性活性（IC50 = 0.0045 microM），对肺炎链球菌有很强的抗菌活性（MIC = 0.5 microg / mL）。由于观察到针对S的MIC值升高。在FabK中具有一个氨基酸取代的肺炎突变体，该化合物的抗菌活性被认为是由于对FabK的抑制。此外，该化合物未显示明显的细胞毒性（IC50> 69 microM）。这些结果
• Phenylimidazole derivatives as specific inhibitors of bacterial enoyl-acyl carrier protein reductase FabK
  作者：Tomohiro Ozawa、Hideo Kitagawa、Yasuo Yamamoto、Sho Takahata、Maiko Iida、Yumi Osaki、Keiko Yamada

  DOI：10.1016/j.bmc.2007.08.050

  日期：2007.12

  Bacterial enoyl-acyl carrier protein (ACP) reductases (FabI and FabK) catalyze the final step in each cycle of bacterial fatty acid biosynthesis and are attractive targets for the development of new antibacterial agents. Here, we report the development of novel FabK inhibitors with antibacterial activity against Streptococcus pneumoniae. Based on structure-activity relationship (SAR) studies of our screening hits, we have developed novel phenylimidazole derivatives as potent FabK inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.
• Phenylimidazole derivatives as new inhibitors of bacterial enoyl-ACP reductase FabK
  作者：Hideo Kitagawa、Tomohiro Ozawa、Sho Takahata、Maiko Iida

  DOI：10.1016/j.bmcl.2007.06.040

  日期：2007.9

  Novel FabK inhibitors with antibacterial activity against Streptococcus pneuinoniae were synthesized and evaluated. Through SAR studies of our initial hit compound 2-(1H-benz[d]imidazol-2-ylthio)-N-(6-methoxycarbonylbenzo[d]thiazo1-2-yl)acetamide, a series of novel phenylimidazole derivatives were discovered as potent FabK inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
• IMIDAZODIAZEPINE COMPOUND
  申请人：Astellas Pharma Inc.

  公开号：EP3312181B1

  公开（公告）日：2019-08-07