2-amino-5-(4-methylphenyl)-1H-pyrrole-3-carboxylic acid ethyl ester | 873192-77-9

• 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-amino-5-(4-methylphenyl)-1H-pyrrole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-amino-5-(4-methylphenyl)-1H-pyrrole-3-carboxylate
• CAS: 873192-77-9
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: MQAVZMHIZBSQKP-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  501.9±50.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-(4-methylphenyl)-1H-pyrrole-3-carboxylic acid ethyl ester 在 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  3-Arylpiperazinylethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives as novel, high-affinity and selective α1-adrenoceptor ligands

  摘要：

  The discovery of a new series of selective and high-affinity alpha(1)-adrenoceptor (alpha(1)-AR) ligands, characterized by a 1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione system, is described in this paper. Some synthesized compounds, including 20, 22, and 30, displayed affinity in the nanomolar range for alpha(1)-ARs and substantial selectivity with respect to 5-HT1A and dopaminergic D-1 and D-2 receptors. Functional assays, performed on selected derivatives, showed antagonistic properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.027
• 作为产物：
  描述：

  3-乙氧基-3-亚氨基丙酸乙酯盐酸盐 在 potassium carbonate 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 2-amino-5-(4-methylphenyl)-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  3-Arylpiperazinylethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives as novel, high-affinity and selective α1-adrenoceptor ligands

  摘要：

  The discovery of a new series of selective and high-affinity alpha(1)-adrenoceptor (alpha(1)-AR) ligands, characterized by a 1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione system, is described in this paper. Some synthesized compounds, including 20, 22, and 30, displayed affinity in the nanomolar range for alpha(1)-ARs and substantial selectivity with respect to 5-HT1A and dopaminergic D-1 and D-2 receptors. Functional assays, performed on selected derivatives, showed antagonistic properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.027

文献信息

• 一种取代吡咯并嘧啶中间体的制备方法
  申请人：天津法莫西医药科技有限公司

  公开号：CN111303160A

  公开（公告）日：2020-06-19

  本发明涉及化学合成技术领域，具体涉一种取代吡咯并嘧啶中间体的制备方法。所述方法以对甲基苯乙酮为起始原料，经NBS溴代，与3‑脒基丙酸乙酯盐酸盐关环，再经甲酰胺关环、氯代试剂氯代得到取代吡咯并嘧啶中间体。本发明避免使用了重金属催化的C‑C偶联反应，原料廉价易得，操作简单，降低了成本，提高了产品收率，适合工业化生产。
• Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library
  作者：Buer Song、Lifei Nie、Khurshed Bozorov、Rustamkhon Kuryazov、Jiangyu Zhao、Haji Akber Aisa

  DOI：10.1007/s11030-022-10529-y

  日期：——

  A facile protocol was developed for the combinatorial synthesis of furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library via a one-pot condensation, from 2-amino furans/pyrroles. Herein reported process required a similar reaction condition, providing mild access to two diverse series of natural product-like heterocycles. Both furo[2,3-d]pyrimidinones and pyrrolo[2,3-d]pyrimidinones were evaluated

  开发了一种简便的方案，用于通过一锅缩合从 2-氨基呋喃/吡咯组合合成呋喃并[2,3- d ]嘧啶酮和吡咯并[2,3- d ]嘧啶酮库。本文报道的过程需要类似的反应条件，提供温和地获得两种不同系列的天然产物样杂环。呋喃并[2,3- d ]嘧啶酮和吡咯并[2,3- d ]嘧啶酮均针对一组人类癌细胞系进行了体外评估，包括针对人类癌症HeLa（宫颈）、MCF-7（乳腺癌）和HT- 29（结肠）细胞系。衍生物12n ((2-(4-氯苯基)-1-甲基-6,7,8,9-四氢吡啶并[1,2- a ]吡咯并[2,3- d ]嘧啶-4(1H ) -酮) ) 对 HeLa 细胞系表现出高活性 (IC 50 = 6.55 ± 0.31 µM)。这些产品可以进行各种修饰，因此代表了抗癌药物发现的重要骨架。 图形概要
• 3-Arylpiperazinylethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives as novel, high-affinity and selective α1-adrenoceptor ligands
  作者：Valeria Pittalà、Giuseppe Romeo、Loredana Salerno、Maria Angela Siracusa、Maria Modica、Luisa Materia、Ilario Mereghetti、Alfredo Cagnotto、Tiziana Mennini、Gabriella Marucci、Piero Angeli、Filippo Russo

  DOI：10.1016/j.bmcl.2005.09.027

  日期：2006.1

  The discovery of a new series of selective and high-affinity alpha(1)-adrenoceptor (alpha(1)-AR) ligands, characterized by a 1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione system, is described in this paper. Some synthesized compounds, including 20, 22, and 30, displayed affinity in the nanomolar range for alpha(1)-ARs and substantial selectivity with respect to 5-HT1A and dopaminergic D-1 and D-2 receptors. Functional assays, performed on selected derivatives, showed antagonistic properties. (c) 2005 Elsevier Ltd. All rights reserved.