1-[3-(trifluoromethyl)benzyl]-1H-imidazole-4-carboxylic acid | 1295542-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[3-(trifluoromethyl)benzyl]-1H-imidazole-4-carboxylic acid
• 英文别名: 1-[3-(Trifluoromethyl)benzyl]-1H-imidazole-4-carboxylic acid；1-[[3-(trifluoromethyl)phenyl]methyl]imidazole-4-carboxylic acid
• CAS: 1295542-29-8
• 化学式: C₁₂H₉F₃N₂O₂
• mdl: MFCD26096961
• 分子量: 270.211
• InChiKey: HFUORFFDYFVYEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[3-(trifluoromethyl)benzyl]-1H-imidazole-4-carboxylic acid 、 N-甲基-3-氨基吡唑 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 N-(1-methyl-1H-pyrazol-3-yl)-1-(3-(trifluoromethyl)benzyl)-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  N-Benzylimidazole carboxamides as potent, orally active stearoylCoA desaturase-1 inhibitors

  摘要：

  A potent, small molecule inhibitor with a favorable pharmacokinetic profile to allow for sustained SCD inhibition in vivo was identified. Starting from a low MW acyl guanidine (5a), identified with a RapidFire High-Throughput Mass Spectrometry (RF-MS) assay, iterative library design was used to rapidly probe the amide and tail regions of the molecule. Singleton synthesis was used to probe core changes. Biological evaluation of a SCD inhibitor (5b) included in vitro potency at SCD-1 and in vivo modulation of the plasma desaturation index (DI) in rats on a low essential fatty acid (LEFA) diet. In addition to dose-dependent decrease in DI, effects on rodent ocular tissue were noted. Therefore, in rat, these SCD inhibitors only recapitulate a portion of phenotype exhibited by the SCD-1 knockout mouse. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.113
• 作为产物：
  描述：

  在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-[3-(trifluoromethyl)benzyl]-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  N-Benzylimidazole carboxamides as potent, orally active stearoylCoA desaturase-1 inhibitors

  摘要：

  A potent, small molecule inhibitor with a favorable pharmacokinetic profile to allow for sustained SCD inhibition in vivo was identified. Starting from a low MW acyl guanidine (5a), identified with a RapidFire High-Throughput Mass Spectrometry (RF-MS) assay, iterative library design was used to rapidly probe the amide and tail regions of the molecule. Singleton synthesis was used to probe core changes. Biological evaluation of a SCD inhibitor (5b) included in vitro potency at SCD-1 and in vivo modulation of the plasma desaturation index (DI) in rats on a low essential fatty acid (LEFA) diet. In addition to dose-dependent decrease in DI, effects on rodent ocular tissue were noted. Therefore, in rat, these SCD inhibitors only recapitulate a portion of phenotype exhibited by the SCD-1 knockout mouse. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.113

文献信息

• SUBSTITUTED SULFONYL AMIDES FOR CONTROLLING ANIMAL PESTS
  申请人：Bayer Aktiengesellschaft

  公开号：US20190269134A1

  公开（公告）日：2019-09-05

  The present invention relates to the use of a compound of the general formula (I) in which M and D have the meanings given in the description for controlling animal pests, in particular nematodes.

  本发明涉及使用一种具有一般式(I)的化合物，其中M和D具有描述中给出的含义，用于控制动物害虫，特别是线虫。
• Synthesis of novobiocin derivatives and evaluation of their antigonococcal activity and pharmacokinetics
  作者：Kazushige Sasaki、Hisashi Takada、Chigusa Hayashi、Kouhei Ohya、Yuko Yamaguchi、Yoshiaki Takahashi、Masayuki Igarashi、Masakatsu Shibasaki

  DOI：10.1016/j.bmc.2023.117381

  日期：2023.9

  very potent antibacterial activity. This derivative also showed excellent antigonococcal activity against resistant strains in vitro, however it has poor water solubility and pharmacokinetics because it is the acidic lipid-soluble compound. Therefore, we considered introduction of a basic substituent into the molecule would result in an amphoteric compound with improved water solubility, and we investigated

  淋病已成为一个严重的问题，因为感染人数不断增加，而且致病菌淋病奈瑟菌的多重耐药性不断增强。为了开发针对耐药淋病奈瑟菌的新药，我们重点关注抗生素新生霉素 ( 1 )。这种天然产物与现有的淋病药物具有不同的作用机制，这可能使其能够有效对抗耐药菌株。实际上，它被应用于耐药性淋病奈瑟菌，并证实具有中等抗菌活性。基于这一结果，我们研究了以1为先导化合物的抗淋球菌药物的开发。药效团被认为是新生糖部分，特别是3′位周围，因此我们对这部分进行衍生化以提高抗菌活性。结果，我们发现具有甲基吡咯酯结构的5具有非常有效的抗菌活性。该衍生物在体外对耐药菌株也表现出优异的抗淋球菌活性，但由于它是酸性脂溶性化合物，其水溶性和药代动力学较差。因此，我们认为在分子中引入碱性取代基会产生具有改善水溶性的两性化合物，并且我们研究了进一步的衍生化。通过合成各种衍生物，我们发现47含有咪唑，具有很强的抗淋球菌活性，并且大大提高了水
• Substituted sulfonyl amides for controlling animal pests
  申请人：Bayer Aktiengesellschaft

  公开号：US10820591B2

  公开（公告）日：2020-11-03

  The present invention relates to the use of a compound of the general formula (I) in which M and D have the meanings given in the description for controlling animal pests, in particular nematodes.

  本发明涉及通式(I)化合物的用途，其中 M 和 D 的含义在描述中给出，用于控制动物害虫，特别是线虫。
• SUBSTITUIERTE SULFONYLAMIDE ZUR BEKÄMPFUNG TIERISCHER SCHÄDLINGE
  申请人：Bayer Aktiengesellschaft

  公开号：EP3534709A1

  公开（公告）日：2019-09-11
• N-Benzylimidazole carboxamides as potent, orally active stearoylCoA desaturase-1 inhibitors
  作者：Karen A. Atkinson、Elena E. Beretta、Janice A. Brown、Mayda Castrodad、Yue Chen、Judith M. Cosgrove、Ping Du、John Litchfield、Michael Makowski、Kelly Martin、Thomas J. McLellan、Constantin Neagu、David A. Perry、David W. Piotrowski、Claire M. Steppan、Richard Trilles

  DOI：10.1016/j.bmcl.2011.01.113

  日期：2011.3

  A potent, small molecule inhibitor with a favorable pharmacokinetic profile to allow for sustained SCD inhibition in vivo was identified. Starting from a low MW acyl guanidine (5a), identified with a RapidFire High-Throughput Mass Spectrometry (RF-MS) assay, iterative library design was used to rapidly probe the amide and tail regions of the molecule. Singleton synthesis was used to probe core changes. Biological evaluation of a SCD inhibitor (5b) included in vitro potency at SCD-1 and in vivo modulation of the plasma desaturation index (DI) in rats on a low essential fatty acid (LEFA) diet. In addition to dose-dependent decrease in DI, effects on rodent ocular tissue were noted. Therefore, in rat, these SCD inhibitors only recapitulate a portion of phenotype exhibited by the SCD-1 knockout mouse. (C) 2011 Elsevier Ltd. All rights reserved.