3-[[2-Chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidin-4-yl]amino]pyridine-2-carboxylic acid | 1223456-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[[2-Chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidin-4-yl]amino]pyridine-2-carboxylic acid
• 英文别名: 3-[[2-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidin-4-yl]amino]pyridine-2-carboxylic acid
• CAS: 1223456-31-2
• 化学式: C₁₉H₁₄ClN₅O₄S
• 分子量: 443.87
• InChiKey: GDUXOOFXNYMWPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[[2-Chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidin-4-yl]amino]pyridine-2-carboxylic acid 在 草酰氯 作用下， 以 四氢呋喃 为溶剂， 生成 17-Chloro-14-(4-methylphenyl)sulfonyl-1,4,9,14,16-pentazatetracyclo[8.7.0.03,8.011,15]heptadeca-3(8),4,6,9,11(15),12,16-heptaen-2-one
  参考文献：
  名称：

  Optimization of a series of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine inhibitors of IGF-1R: Elimination of an acid-mediated decomposition pathway

  摘要：

  Initial evaluation of a series 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidines revealed a C(10) carboxamide was preferred for sub-micromolar in vitro potency against IGF-1R. Subsequent solution stability studies with 1 revealed a susceptibility toward acid-induced intramolecular cyclization with the C(10) carboxamide. Herein, we describe several successful approaches toward generating both potent and acid-stable inhibitors of IGF-1R within the 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine template. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.065
• 作为产物：
  描述：

  在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-[[2-Chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidin-4-yl]amino]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Optimization of a series of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine inhibitors of IGF-1R: Elimination of an acid-mediated decomposition pathway

  摘要：

  Initial evaluation of a series 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidines revealed a C(10) carboxamide was preferred for sub-micromolar in vitro potency against IGF-1R. Subsequent solution stability studies with 1 revealed a susceptibility toward acid-induced intramolecular cyclization with the C(10) carboxamide. Herein, we describe several successful approaches toward generating both potent and acid-stable inhibitors of IGF-1R within the 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine template. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.065

文献信息

• [EN] PYRROLOPYRIMIDINE COMPOUNDS<br/>[FR] COMPOSÉS PYRROLOPYRIMIDINE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010045451A1

  公开（公告）日：2010-04-22

  Novel pyrrolopyrimidines as shown in formula (I): and pharmaceutically acceptable derivatives thereof. The compounds are useful in the inhibition of IGF-1R.
• Optimization of a series of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine inhibitors of IGF-1R: Elimination of an acid-mediated decomposition pathway
  作者：Stanley D. Chamberlain、Anikó M. Redman、Samarjit Patnaik、Keith Brickhouse、Yen-Chiat Chew、Felix Deanda、Roseanne Gerding、Huangshu Lei、Ganesh Moorthy、Mark Patrick、Kirk L. Stevens、Joseph W. Wilson、J. Brad Shotwell

  DOI：10.1016/j.bmcl.2008.11.065

  日期：2009.1

  Initial evaluation of a series 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidines revealed a C(10) carboxamide was preferred for sub-micromolar in vitro potency against IGF-1R. Subsequent solution stability studies with 1 revealed a susceptibility toward acid-induced intramolecular cyclization with the C(10) carboxamide. Herein, we describe several successful approaches toward generating both potent and acid-stable inhibitors of IGF-1R within the 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine template. (C) 2008 Elsevier Ltd. All rights reserved.