7-benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile | 400754-74-7

• 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: 7-benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile
• 英文别名: 7-benzyl-3-chloro-1-morpholin-4-yl-6,8-dihydro-5H-2,7-naphthyridine-4-carbonitrile
• CAS: 400754-74-7
• 化学式: C₂₀H₂₁ClN₄O
• 分子量: 368.866
• InChiKey: CXWRUJBEQIKCKH-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  588.8±50.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile 在 吡啶 、 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 3-benzyl-8-(4-methylpiperazin-1-yl)-5-(morpholin-4-yl)-1,2,3,4-tetrahydropyrimido[4′,5′:4,5]thieno[2,3-c][2,7]naphthyridine
  参考文献：
  名称：

  基于7-苄基-3-氯-1-（吗啉-4-基）-5,6,7,8-四氢-2,7-萘啶-4-甲腈的新杂环体系的合成

  摘要：

  已开发出用于合成新的8-氨基-3-苄基-5-（吗啉-4-基）-1,2,3,4-四氢嘧啶基[4'，5'：4,5]噻吩并[2]的方法由3-苄基-3-氯-1-（吗啉-4-基）-5,6,7,8-四氢-2,7-萘啶-4-甲腈开始的，3- c ] [2,7]萘啶。8-肼基-3-苄基-5-（吗啉-4-基）-1,2,3,4-四氢嘧啶基[4'，5'：4,5]噻吩并[2,3- c ] [2,7萘啶已被三唑环转化为异构的五环结构，三唑环稠合在嘧啶环的[ c ]侧，并且它们的Dimroth重排已在酸性和碱性介质中完成。新的杂环系统含有吡咯并[1,2一]嘧啶酮和嘧啶并[1,2-一个在噻吩并[[2，3- c ] [2，7]萘啶衍生物的基础上获得]氮杂庚酮片段。

  DOI：

  10.1134/s1070428018060155
• 作为产物：
  描述：

  吗啉 、 7-benzyl-1,3-dichloro-5,6,7,8-tetrahydro-[2,7]-naphthyridine-4-carbonitrile 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile
  参考文献：
  名称：

  Synthesis of 7-benzyl-5-(piperidin-1-yl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-ylamine and its analogs as bombesin receptor subtype-3 agonists

  摘要：

  The original structure of a high-throughput screening hit obtained from an external vendor was revised based on multiple NMR studies. The active compound was re-synthesized via a novel route and its structure and biological activity as a BRS-3 agonist were unambiguously confirmed. Multi-gram quantities of the hit were prepared for pharmacokinetic and efficacy studies. The synthetic strategy allowed for the preparation of multiple analogs for SAR exploration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.065

文献信息

• Synthesis of 7-benzyl-5-(piperidin-1-yl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-ylamine and its analogs as bombesin receptor subtype-3 agonists
  作者：Cheng Guo、Peter R. Guzzo、Mark Hadden、Bruce J. Sargent、Larry Yet、Yanqing Kan、Oksana Palyha、Theresa M. Kelly、Xiaoming Guan、Kim Rosko、Karen Gagen、Joseph M. Metzger、Jasminka Dragovic、Kathryn Lyons、Linus S. Lin、Ravi P. Nargund

  DOI：10.1016/j.bmcl.2010.03.065

  日期：2010.5

  The original structure of a high-throughput screening hit obtained from an external vendor was revised based on multiple NMR studies. The active compound was re-synthesized via a novel route and its structure and biological activity as a BRS-3 agonist were unambiguously confirmed. Multi-gram quantities of the hit were prepared for pharmacokinetic and efficacy studies. The synthetic strategy allowed for the preparation of multiple analogs for SAR exploration. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of New Heterocyclic Systems on the Basis of 7-Benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthiridine-4-carbonitrile
  作者：S. N. Sirakanyan、V. G. Kartsev、E. K. Hakobyan、A. A. Hovakimyan

  DOI：10.1134/s1070428018060155

  日期：2018.6

  pentacyclic structures with a triazole ring fused through the [c] side of the pyrimidine ring, and their Dimroth rearrangement has been accomplished in both acidic and basic media. New heterocyclic systems containing pyrrolo[1,2-a]pyrimidinone and pyrimido[1,2-a]azepinone fragments were obtained on the basis of the thieno-[2,3-c][2,7]naphthyridine derivative.

  已开发出用于合成新的8-氨基-3-苄基-5-（吗啉-4-基）-1,2,3,4-四氢嘧啶基[4'，5'：4,5]噻吩并[2]的方法由3-苄基-3-氯-1-（吗啉-4-基）-5,6,7,8-四氢-2,7-萘啶-4-甲腈开始的，3- c ] [2,7]萘啶。8-肼基-3-苄基-5-（吗啉-4-基）-1,2,3,4-四氢嘧啶基[4'，5'：4,5]噻吩并[2,3- c ] [2,7萘啶已被三唑环转化为异构的五环结构，三唑环稠合在嘧啶环的[ c ]侧，并且它们的Dimroth重排已在酸性和碱性介质中完成。新的杂环系统含有吡咯并[1,2一]嘧啶酮和嘧啶并[1,2-一个在噻吩并[[2，3- c ] [2，7]萘啶衍生物的基础上获得]氮杂庚酮片段。