trans-2-methyl-3-nitrocinnamic acid | 73323-63-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: trans-2-methyl-3-nitrocinnamic acid
• 英文别名: (E)-3-(2-methyl-3-nitrophenyl)propenoic acid；2-Methyl-3-nitro-zimtsaeure；2-methyl-3-nitro-cinnamic acid；2-Methyl-3-nitrocinnamic acid；(E)-3-(2-methyl-3-nitrophenyl)prop-2-enoic acid
• CAS: 73323-63-4
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: UGYGQUPNHYOWJW-AATRIKPKSA-N

物化性质

• 沸点：
  369.0±30.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-2-methyl-3-nitrocinnamic acid 在 盐酸 、 三氟甲磺酸 、 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 、 溴 、 silica gel 、 sodium hydride 、 溶剂黄146 、 copper(l) chloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， -5.0~110.0 ℃ 、206.85 kPa 条件下， 反应 71.83h， 生成 ethyl 6-chloro-2,5-dimethyl-1-(4-methylbenzyl)-1,4-dihydroindeno[1,2-b]pyrrole-3-carboxylate
  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
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲醇 在 哌啶 、 吡啶 、 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 trans-2-methyl-3-nitrocinnamic 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] SUBSTITUTED PYRIDYL-CYCLOALKYL-CARBOXYLIC ACIDS, COMPOSITIONS CONTAINING THEM AND MEDICAL USES THEREOF<br/>[FR] ACIDES PYRIDYL-CYCLOALKYL-CARBOXYLIQUES SUBSTITUÉS, COMPOSITIONS LES CONTENANT ET LEURS UTILISATIONS MÉDICALES
  申请人：BAYER PHARMA AG

  公开号：WO2016097013A1

  公开（公告）日：2016-06-23

  The present invention relates to substituted Pyridyl-cycloalkyl- carboxylic acids of general formula (I), to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular in mammals, such as diseases associated with pains, or for the treatment or prophylaxis of pain syndromes (acute and chronic), inflammatory-induced pain, pelvic pain, cancer-associated pain, endometriosis-associated pain as well as endometriosis and adenomyosis as such, cancer as such, and proliferative diseases as such like endometriosis.

  本发明涉及一般式(I)的取代吡啶基-环烷基-羧酸，涉及包括所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是在哺乳动物中，如与疼痛相关的疾病，或用于治疗或预防疼痛综合症（急性和慢性）、炎症诱导的疼痛、盆腔疼痛、癌症相关的疼痛、子宫内膜异位症相关的疼痛以及子宫内膜异位症和子宫腺肌症本身、癌症本身以及增生性疾病本身，如子宫内膜异位症。
• SUBSTITUTED 3-PHENYLPROPIONIC ACIDS AND THE USE THEREOF
  申请人：BAYER INTELLECTUAL PROPERTY GmbH

  公开号：US20140142069A1

  公开（公告）日：2014-05-22

  The present application relates to novel 3-phenylpropionic acid derivatives, to processes for their preparation, to their use for the treatment and/or prevention of diseases and to their use for preparing medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular disorders.

  本申请涉及新型3-苯丙酸衍生物，其制备过程，其用于治疗和/或预防疾病以及其用于制备治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病。
• Substituted pyridyl-cycloalkyl-carboxylic acids, compositions containing them and medical uses thereof
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US10172814B2

  公开（公告）日：2019-01-08

  The present invention relates to substituted Pyridyl-cycloalkyl-carboxylic acids of general formula (I), to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular in mammals, such as diseases associated with pains, or for the treatment or prophylaxis of pain syndromes (acute and chronic), inflammatory-induced pain, pelvic pain, cancer-associated pain, endometriosis-associated pain as well as endometriosis and adenomyosis as such, cancer as such, and proliferative diseases as such like endometriosis.

  本发明涉及通式（I）的取代吡啶基-环烷基-羧酸、包含上述化合物的药物组合物和组合物，以及使用上述化合物制造药物组合物，用于治疗或预防疾病，尤其是哺乳动物的疾病、如与疼痛相关的疾病，或用于治疗或预防疼痛综合征（急性和慢性）、炎症引起的疼痛、盆腔疼痛、癌症相关疼痛、子宫内膜异位症相关疼痛以及子宫内膜异位症和子宫腺肌症、癌症以及子宫内膜异位症等增殖性疾病。
• Photocyclization of 1-(1-chloroisoquinolin-6-yl)-1H-v-triazolo[4,5-c]pyridines to 10-chloro-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinolines (azaellipticines)
  作者：Christian Rivalle、Claire Ducrocq、Jean Marc Lhoste、Emile Bisagni

  DOI：10.1021/jo01299a028

  日期：1980.5
• SUBSTITUTED PYRIDYL-CYCLOALKYL-CARBOXYLIC ACIDS, COMPOSITIONS CONTAINING THEM AND MEDICAL USES THEREOF
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3233802A1

  公开（公告）日：2017-10-25