3-(3-chloro-2-methylphenyl)propanoic acid | 879-50-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(3-chloro-2-methylphenyl)propanoic acid
• 英文别名: 3-(3-Chlor-2-methyl-phenyl)-propionsaeure；3-(3-Chloro-2-methylphenyl)propanoic acid
• CAS: 879-50-5
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: OPZLYNMAUSNXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-chloro-2-methylphenyl)propanoic acid 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 PPA 、 氢气 、 汞 、 锌 、 三氯氧磷 作用下， 以 乙醚 、 乙二醇 为溶剂， 反应 24.0h， 生成 5-Isopropyl-4-methyl-indan
  参考文献：
  名称：

  Munavalli,S.; Ourisson,G., Bulletin de la Societe Chimique de France, 1964, p. 3103 - 3112

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲醇 在 哌啶 、 吡啶 、 盐酸 、 manganese(IV) oxide 、 palladium 10% on activated carbon 、 氢气 、 copper(l) chloride 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， -5.0~20.0 ℃ 、206.85 kPa 条件下， 反应 54.0h， 生成 3-(3-chloro-2-methylphenyl)propanoic acid
  参考文献：
  名称：

  Synthesis, pharmacological evaluation and docking studies of pyrrole structure-based CB 2 receptor antagonists

  摘要：

  During the last years, there has been a continuous interest in the development of cannabinoid receptor ligands that may serve as therapeutic agents and/or as experimental tools. This prompted us to design and synthesize analogues of the CB2 receptor antagonist N-fenchyl-5-(4-chloro-3-methyl-phenyl)-1-(4-methyl-benzyl)-1H-pyrazole-3-carboxamide (SR144528). The structural modifications involved the bioisosteric replacement of the pyrazole ring by a pyrrole ring and variations on the amine carbamoyl substituents. Two of these compounds, the fenchyl pyrrole analogue 6 and the myrtanyl derivative 10, showed high affinity (K-i in the low nM range) and selectivity for the CB2 receptor and both resulted to be antagonists/inverse agonists in [S-35]-GTP gamma S binding analysis and in an in vitro CB2 receptor bioassay. Cannabinoid receptor binding data of the series allowed identifying steric constraints within the CB2 binding pocket using a study of Van der Waals' volume maps. Glide docking studies revealed that all docked compounds bind in the same region of the CB2 receptor inactive state model. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.057

文献信息

• [EN] NOVEL THREE-RING FUSED STRUCTURE COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] NOUVEAU COMPOSÉ DE STRUCTURE À TROIS CYCLES CONDENSÉS, SON PROCÉDÉ DE PRÉPARATION ET UTILISATION ASSOCIÉE<br/>[ZH] 一种新颖的三并环结构化合物及其制备方法和用途
  申请人：INNOVENT BIOLOGICS SUZHOU CO LTD

  公开号：WO2020119592A1

  公开（公告）日：2020-06-18

  本发明属于药物化学领域，公开了一种三并环结构化合物及其制备方法和用途。本发明的化合物可以作为PI3K-γ选择性抑制剂，具有抗肿瘤、抗神经退行性疾病(如阿尔茨海默病)、抗炎、抗病毒、抗多发性硬化症、免疫调节等多种药理活性。
• Synthesis, pharmacological evaluation and docking studies of pyrrole structure-based CB 2 receptor antagonists
  作者：Giulio Ragusa、María Gómez-Cañas、Paula Morales、Dow P. Hurst、Francesco Deligia、Ruth Pazos、Gerard A. Pinna、Javier Fernández-Ruiz、Pilar Goya、Patricia H. Reggio、Nadine Jagerovic、Moisés García-Arencibia、Gabriele Murineddu

  DOI：10.1016/j.ejmech.2015.06.057

  日期：2015.8

  During the last years, there has been a continuous interest in the development of cannabinoid receptor ligands that may serve as therapeutic agents and/or as experimental tools. This prompted us to design and synthesize analogues of the CB2 receptor antagonist N-fenchyl-5-(4-chloro-3-methyl-phenyl)-1-(4-methyl-benzyl)-1H-pyrazole-3-carboxamide (SR144528). The structural modifications involved the bioisosteric replacement of the pyrazole ring by a pyrrole ring and variations on the amine carbamoyl substituents. Two of these compounds, the fenchyl pyrrole analogue 6 and the myrtanyl derivative 10, showed high affinity (K-i in the low nM range) and selectivity for the CB2 receptor and both resulted to be antagonists/inverse agonists in [S-35]-GTP gamma S binding analysis and in an in vitro CB2 receptor bioassay. Cannabinoid receptor binding data of the series allowed identifying steric constraints within the CB2 binding pocket using a study of Van der Waals' volume maps. Glide docking studies revealed that all docked compounds bind in the same region of the CB2 receptor inactive state model. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Munavalli,S.; Ourisson,G., Bulletin de la Societe Chimique de France, 1964, p. 3103 - 3112
  作者：Munavalli,S.、Ourisson,G.

  DOI：——

  日期：——