(S)-4-(2-(3-chlorophenyl)-2-hydroxyethylamino)-3-(6-(4-(dimethylamino)piperidin-1-yl)-4-methyl-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one | 1056877-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (S)-4-(2-(3-chlorophenyl)-2-hydroxyethylamino)-3-(6-(4-(dimethylamino)piperidin-1-yl)-4-methyl-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one
• 英文别名: 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[4-(dimethylamino)piperidin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one
• CAS: 1056877-49-6
• 化学式: C₂₈H₃₃ClN₆O₂
• 分子量: 521.062
• InChiKey: HEBKCUAEAWNUQL-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.5
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[6-(4-aminopiperidin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one 、 聚合甲醛 在 sodium cyanoborohydride 、 溶剂黄146 、 原甲酸三甲酯 作用下， 以 水 为溶剂， 生成 (S)-4-(2-(3-chlorophenyl)-2-hydroxyethylamino)-3-(6-(4-(dimethylamino)piperidin-1-yl)-4-methyl-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one
  参考文献：
  名称：

  Balancing oral exposure with Cyp3A4 inhibition in benzimidazole-based IGF-IR inhibitors

  摘要：

  3-(Benzimidazol-2-yl)-pyridine-2-one-based ATP competitive inhibitors of Insulin-like Growth Factor 1 Kinase (IGF-IR) were optimized for reduced Cyp3A4 inhibition and improved oral exposure. The use of malonate as methyl anion synthon via SNAr reaction and double decarboxylation under mild conditions is demonstrated. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.104

文献信息

• Balancing oral exposure with Cyp3A4 inhibition in benzimidazole-based IGF-IR inhibitors
  作者：Kurt Zimmermann、Mark D. Wittman、Mark G. Saulnier、Upender Velaparthi、David R. Langley、Xiaopeng Sang、David Frennesson、Joan Carboni、Aixin Li、Ann Greer、Marco Gottardis、Ricardo M. Attar、Zheng Yang、Praveen Balimane、Lorell N. Discenza、Dolatrai Vyas

  DOI：10.1016/j.bmcl.2008.05.104

  日期：2008.7

  3-(Benzimidazol-2-yl)-pyridine-2-one-based ATP competitive inhibitors of Insulin-like Growth Factor 1 Kinase (IGF-IR) were optimized for reduced Cyp3A4 inhibition and improved oral exposure. The use of malonate as methyl anion synthon via SNAr reaction and double decarboxylation under mild conditions is demonstrated. (c) 2008 Elsevier Ltd. All rights reserved.