1-(3-chlorobenzyl)-1H-imidazole-4-carboxylic acid | 1295542-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-chlorobenzyl)-1H-imidazole-4-carboxylic acid
• 英文别名: 1-(3-Chlorobenzyl)-1H-imidazole-4-carboxylic acid；1-[(3-chlorophenyl)methyl]imidazole-4-carboxylic acid
• CAS: 1295542-31-2
• 化学式: C₁₁H₉ClN₂O₂
• 分子量: 236.658
• InChiKey: DDJFYFYMPDTGII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-chlorobenzyl)-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 1-(3-chlorobenzyl)-N-(1-methyl-1H-pyrazol-3-yl)-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-chlorobenzyl)-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。
• Imidazolylamide derivative
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：US10898469B2

  公开（公告）日：2021-01-26

  The present invention pertains to an imidazolylamide derivative represented by formula (1) that exhibits an exceptional suppressive effect on cancer cell sphere formation ability and that is useful as an antitumor agent that can be administered orally, or a pharmacologically acceptable salt thereof. [In the formula, ring Q1 represents a C6-10 aryl group or the like; m represents 0, 1, 2, 3, 4, or 5; R3, independently when multiple, represent(s) a halogen atom or the like; R1 and R2 independently represent a hydrogen atom or the like; W1 represents a C1-4 alkylene group (said group may be substituted by 1-3 fluorine atoms or C3-7 cycloalkyls); W2 represents —NR4aC(O)— or the like (where R4a represents a hydrogen atom or C1-6 alkyl group); and ring Q2 represents a C6-10 arylgroup or the like]

  该发明涉及一种由式（1）表示的咪唑酰胺衍生物，该衍生物对癌细胞球形成能力具有显著的抑制作用，并且可作为一种口服抗肿瘤剂或其药理学上可接受的盐。【在该式中，环Q1代表C6-10芳基或类似物；m代表0、1、2、3、4或5；R3，当多个时，独立地代表卤原子或类似物；R1和R2独立地代表氢原子或类似物；W1代表C1-4烷基（该基团可被1-3氟原子或C3-7环烷基取代）；W2代表—NR4aC(O)—或类似物（其中R4a代表氢原子或C1-6烷基）；环Q2代表C6-10芳基或类似物】
• 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.