2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid | 5441-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid
• 英文别名: 2-methyl-5-phenyl-pyrrole-3-carboxylic acid；2-Methyl-5-phenyl-pyrrol-3-carbonsaeure
• CAS: 5441-73-6
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD16304976
• 分子量: 201.225
• InChiKey: XDXKXRVCTYULQN-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C (decomp)
• 沸点：
  432.2±33.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid 在 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以90%的产率得到4-Bromo-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Petruso, S.; Caronna, S.; Sferlazzo, M., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1277 - 1280

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯 在 氢氧化钾 、 乙醇 作用下， 生成 2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Lederer; Paal, Chemische Berichte, 1885, vol. 18, p. 2598

  摘要：

  DOI：

文献信息

• One-Step Continuous Flow Synthesis of Highly Substituted Pyrrole-3-carboxylic Acid Derivatives via in Situ Hydrolysis of <i>tert-</i>Butyl Esters
  作者：Ananda Herath、Nicholas D. P. Cosford

  DOI：10.1021/ol102216x

  日期：2010.11.19

  one-step, continuous flow synthesis of pyrrole-3-carboxylic acids directly from tert-butyl acetoacetates, amines, and 2-bromoketones is reported. The HBr generated as a byproduct in the Hantzsch reaction was utilized in the flow method to hydrolyze the t-butyl esters in situ to provide the corresponding acids in a single microreactor. The protocol was used in the multistep synthesis of pyrrole-3-carboxamides

  报道了直接从乙酰乙酸叔丁酯、胺和 2-溴酮合成吡咯-3-羧酸的第一步连续流动合成。在流动法中利用在 Hantzsch 反应中作为副产物产生的 HBr原位水解叔丁酯，以在单个微反应器中提供相应的酸。该协议用于 pyrrole-3-carboxamides 的多步合成，包括两种 CB1 反向激动剂，在单个连续过程中直接从市售起始材料中合成。
• ARYLPIPERAZINE-CONTAINING PYRROLE 3-CARBOXAMIDE DERIVATIVES FOR TREATING DEPRESSIVE DISORDERS
  申请人：Lee Jinhwa

  公开号：US20110178091A1

  公开（公告）日：2011-07-21

  The present invention relates to novel arylpiperazine-containing pyrrole 3-carboxamide derivatives of formula (I) or a pharmaceutically acceptable salt thereof which is useful for preventing or treating depressive disorders. The present invention also provides a method for preparing the arylpiperazine-containing pyrrole 3-carboxamide derivatives or the pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating depressive disorders.

  本发明涉及一种新的芳基哌嗪含有吡咯3-羧酰胺衍生物的化合物（I），或其药学上可接受的盐，用于预防或治疗抑郁症。本发明还提供了制备芳基哌嗪含有吡咯3-羧酰胺衍生物或其药学上可接受的盐的方法，包括含有它们的药物组合物，以及预防或治疗抑郁症的方法。
• Synthesis and biological evaluation of panaxadiol ester derivatives possessing pyrazole and pyrrole moiety as HIF-1α inibitors
  作者：Ye-Fang Lu、Chuang Liu、Juan Ma、Hu-Ri Piao、Changhao Zhang、Xuejun Jin、Cheng-Hua Jin

  DOI：10.1016/j.fitote.2024.106052

  日期：2024.9

  hypoxia response in tumor cells. Therefore, its inhibitors have become one of the targets for the treatment of a variety of cancers. Two series of panaxadiol (PD) ester derivatives containing pyrazole () and pyrrole () moiety were synthesized and their HIF-1α inhibitory activities were evaluated. Among all the target compouds, compounds , , and (IC = 8.7010.44 μM) showed better HIF-1α inhibitory activity

  缺氧诱导因子1α（HIF-1α）在多种肿瘤患者中过度表达，在调节肿瘤细胞缺氧反应中发挥重要作用。因此，其抑制剂已成为多种癌症的治疗靶点之一。合成了两个系列含有吡唑()和吡咯()结构的人参二醇(PD)酯衍生物，并评价了它们的HIF-1α抑制活性。在所有目标化合物中，化合物 、 和 (IC = 8.7010.44 μM) 显示出比 PD (IC = 13.35 μM) 更好的 HIF-1α 抑制活性。这些化合物均未表现出高于 100 μM 的细胞毒性，并以剂量​​依赖性方式抑制 HIF-1α 转录。这些化合物表现出良好的抗肿瘤活性，为PD酯衍生物的进一步设计和活性研究提供了先导化合物。
• Borsche; Fels, Chemische Berichte, 1906, vol. 39, p. 3881
  作者：Borsche、Fels

  DOI：——

  日期：——
• Arylpiperazine-containing pyrrole 3-carboxamide derivatives targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant
  作者：Suk Youn Kang、Eun-Jung Park、Woo-Kyu Park、Hyun Jung Kim、Daeyoung Jeong、Myung Eun Jung、Kwang-Seop Song、Suk Ho Lee、Hee Jeong Seo、Min Ju Kim、MinWoo Lee、Ho-Kyun Han、Eun-Jung Son、Ae Nim Pae、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2010.01.093

  日期：2010.3

  Arylpiperzine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated as novel antidepressant compounds. The various analogues were efficiently prepared and bio-assayed for binding to 5-HT2A, 5-HT2C receptor, and 5-HT transporter. Based on their in vitro and in vivo activities as well as selectivity over other neurotransmitter receptors and PK profiles, 33 and 34 were identified as lead compounds. Consequently, this pyrrole series of compounds appears to be promising enough to warrant further investigation. (C) 2010 Elsevier Ltd. All rights reserved.