2-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester | 945381-57-7

• 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-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester
• 英文别名: 2-(3-ethoxycarbonyl-4-methyl-1H-pyrrol-2-yl)acetic acid
• CAS: 945381-57-7
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: GHMVLVNSPMWKRS-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester 在 哌啶 、 硼烷四氢呋喃络合物 、 1-羟基苯并三唑 、 乙二醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 (Z)-2-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one
  参考文献：
  名称：

  Novel Potent Orally Active Multitargeted Receptor Tyrosine Kinase Inhibitors: Synthesis, Structure−Activity Relationships, and Antitumor Activities of 2-Indolinone Derivatives

  摘要：

  The inhibition of receptor tyrosine kinases (RTKs) has become a successful approach in the development of anticancer agents. Many potent small-molecule kinase inhibitors have been discovered. We report herein a series of pyrrolo-fused-heterocycle-2-indolinone analogues as inhibitors of vascular endothelial growth factor receptor (VEGFR), platelet-derived growth factor receptor (PDGFR). and c-Kit. Among them, some pyrrolo-fused six- and seven-membered-heterocycle derivatives such as 9, 15, 23, and 25 are potent inhibitors of VEGFR, PDGFR, and c-Kit both enzymatically ( < 50 nM) and cellularly, ( < 50 nM). Furthermore, compounds 9 and 25 possess favorable pharmacokinetic profiles and demonstrate good efficacies against human HT-29 cell colon tumor xenografts in nude mice. Further evaluations are in progress.

  DOI：

  10.1021/jm101036c
• 作为产物：
  描述：

  5-carboxymethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以85.7%的产率得到2-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Pyrrolo [3,2-C] Pyridine-4-One 2-Indolinone Protein Kinase Inhibitors

  摘要：

  本发明涉及Formula(I)中的吡咯[3,2-c]吡啶-4-酮-2-吲哚酮化合物及其在药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8X、Y等在说明书中有所描述。还披露了含有上述化合物的药物组合物、其制备方法和药用方法，特别是作为蛋白激酶抑制剂。Formula(I)。

  公开号：

  US20100004239A1

文献信息

• Pyrrolo [3,2-C] Pyridine-4-One 2-Indolinone Protein Kinase Inhibitors
  申请人：Tang Peng Cho

  公开号：US20100004239A1

  公开（公告）日：2010-01-07

  The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 X, Y and have the meaning cited in the specification. Also disclosed are the pharmaceutical compositions containing the foregoing compounds, methods for the preparation and pharmaceutical use thereof, particularly as protein kinase inhibitors. Formula (I).

  本发明涉及Formula(I)中的吡咯[3,2-c]吡啶-4-酮-2-吲哚酮化合物及其在药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8X、Y等在说明书中有所描述。还披露了含有上述化合物的药物组合物、其制备方法和药用方法，特别是作为蛋白激酶抑制剂。Formula(I)。
• PYRROLO [3,2-C] PYRIDINE-4-ONE 2-INDOLINONE PROTEIN KINASE INHIBITORS
  申请人：TANG Peng Cho

  公开号：US20120058107A1

  公开（公告）日：2012-03-08

  The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R 1 , R2, R3, R4, R5, R6, R7, R8 X, Y and have the meaning cited in the specification. Also disclosed are the pharmaceutical compositions containing the foregoing compounds, methods for the preparation and pharmaceutical use thereof, particularly as protein kinase inhibitors. Formula (I).

  本发明涉及公式(I)中的吡咯并[3,2-c]吡啶-4-酮2-吲哚酮化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8、X、Y具有规范中所述的含义。还公开了含有上述化合物的制药组合物、其制备方法和药物用途，特别是作为蛋白激酶抑制剂。公式(I)。
• Pyrrolo [3,2-c] pyridine-4-one 2-indolinone protein kinase inhibitors
  申请人：Shanghai Hengrui Pharmaceutical Co., Ltd.

  公开号：US08012966B2

  公开（公告）日：2011-09-06

  The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8X, Y and have the meaning cited in the specification. Also disclosed are the pharmaceutical compositions containing the foregoing compounds, methods for the preparation and pharmaceutical use thereof, particularly as protein kinase inhibitors. Formula (I).

  本发明涉及公式(I)的吡咯并[3,2-c]吡啶-4-酮-2-吲哚酮化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8X、Y和在说明书中有所说明。还公开了含有上述化合物的制药组合物，其制备方法和药物用途，特别是作为蛋白激酶抑制剂。公式(I)。
• Pyrrolo [3,2-C] pyridine-4-one 2-indolinone protein kinase inhibitors
  申请人：Tang Peng Cho

  公开号：US08362251B2

  公开（公告）日：2013-01-29

  The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8 X, Y and have the meaning cited in the specification. Also disclosed are the pharmaceutical compositions containing the foregoing compounds, methods for the preparation and pharmaceutical use thereof, particularly as protein kinase inhibitors. Formula (I).

  本发明涉及公式（I）的吡咯并[3,2-c]吡啶-4-酮2-吲哚酮化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8、X、Y和在规范中所述。还公开了含有上述化合物的制药组合物，其制备方法和药物用途，尤其是作为蛋白激酶抑制剂。公式（I）。
• WO2007/85188
  申请人：——

  公开号：——

  公开（公告）日：——