3-(2-(2-methoxy-4-(1-propylpiperidin-4-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxamide | 1223454-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(2-(2-methoxy-4-(1-propylpiperidin-4-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxamide
• 英文别名: 3-[[2-[2-methoxy-4-(1-propylpiperidin-4-yl)anilino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide
• CAS: 1223454-02-1
• 化学式: C₂₆H₃₁N₇O₂S
• 分子量: 505.644
• InChiKey: MMNHSQXMGMJMBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(2-(2-methoxy-4-(1-propylpiperidin-4-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxamide 在 盐酸 作用下， 以 水 为溶剂， 生成
  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：

  3-[[2-[2-Methoxy-4-(1-propylpiperidin-4-yl)anilino]-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(2-(2-methoxy-4-(1-propylpiperidin-4-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxamide
  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.