(S)-1'-(tert-butyl)-3-((((R)-2,3-dihydro-1H-inden-1-yl)amino)methyl)-6,8-dihydrospiro[cyclopenta[b][1,8]naphthyridine-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one | 1279083-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-1'-(tert-butyl)-3-((((R)-2,3-dihydro-1H-inden-1-yl)amino)methyl)-6,8-dihydrospiro[cyclopenta[b][1,8]naphthyridine-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one
• CAS: 1279083-97-4
• 化学式: C₃₁H₃₁N₅O
• 分子量: 489.62
• InChiKey: KYIVSKQGEZUMEO-NJHZRGNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  71.01
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-1'-(tert-butyl)-3-((((R)-2,3-dihydro-1H-inden-1-yl)amino)methyl)-6,8-dihydrospiro[cyclopenta[b][1,8]naphthyridine-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 在 甲烷磺酸 作用下， 反应 2.0h， 以100%的产率得到(S)-3-((((R)-2,3-dihydro-1H-inden-1-yl)amino)methyl)-6,8-dihydrospiro[cyclopenta[b][1,8]naphthyridine-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one
  参考文献：
  名称：

  Novel CGRP receptor antagonists from central amide replacements causing a reversal of preferred chirality

  摘要：

  A previously utilized quinoline-for-N-phenylamide replacement strategy was employed against a central amide in a novel class of CGRP receptor antagonists. A unique and unexpected substitution pattern was ultimately required to maintain reasonable affinity for the CGRP receptor, while at the same time predicting acceptable heterocycle positioning for related analogs. Subsequently, specific quinoline and naphthyridine compounds were prepared which supported these structural predictions by displaying CGRP binding affinities in the 0.037-0.15 nM range. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.105
• 作为产物：
  描述：

  (S)-1'-(tert-butyl)-2'-oxo-1',2',6,8-tetrahydrospiro[cyclopenta[b][1,8]naphthyridine-7,3'-pyrrolo[2,3-b]pyridine]-3-carbaldehyde 、 (R)-(-)-1-氨基茚满 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 以29%的产率得到(S)-1'-(tert-butyl)-3-((((R)-2,3-dihydro-1H-inden-1-yl)amino)methyl)-6,8-dihydrospiro[cyclopenta[b][1,8]naphthyridine-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one
  参考文献：
  名称：

  Novel CGRP receptor antagonists from central amide replacements causing a reversal of preferred chirality

  摘要：

  A previously utilized quinoline-for-N-phenylamide replacement strategy was employed against a central amide in a novel class of CGRP receptor antagonists. A unique and unexpected substitution pattern was ultimately required to maintain reasonable affinity for the CGRP receptor, while at the same time predicting acceptable heterocycle positioning for related analogs. Subsequently, specific quinoline and naphthyridine compounds were prepared which supported these structural predictions by displaying CGRP binding affinities in the 0.037-0.15 nM range. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.105