N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-4-chlorobenzamide | 1164524-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-4-chlorobenzamide
• 英文别名: (E)-4-chloro-N-(1-cyano-9,10-dimethoxy-6,7-dihydro-2H-pyrido[2,1-a]isoquinolin-4(3H)-ylidene)benzamide
• CAS: 1164524-78-0
• 化学式: C₂₃H₂₀ClN₃O₃
• 分子量: 421.883
• InChiKey: FJNIDXRQNOEFNU-YYADALCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-(2-(3,4-二甲氧基苯基)乙基)-2-次氮基乙酰胺 在 四磷十氧化物 、 sodium ethanolate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 反应 2.67h， 生成 N-{(4E)-9,10-dimethoxy-1-cyano-2,3,6,7-tetrahydro-4H-pyrido[2,1-a]isoquinolin-4-ylidene}-4-chlorobenzamide
  参考文献：
  名称：

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions

  摘要：

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and beta-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides.

  DOI：

  10.1134/s1070428011050137

文献信息

• SMALL MOLECULE INHIBITORS OF VIRAL PROTEIN INTERACTIONS WITH HUMAN T-RNA
  申请人：Sirga Advanced Biopharma, Inc.

  公开号：US20150190384A1

  公开（公告）日：2015-07-09

  Disclosed herein are compounds, compositions and methods of their use to treat HIV/AIDS disease in a subject in need thereof wherein the compositions comprise small molecule inhibitors that inhibit viral preparation or viral recruitment of human tRNA3Lys.
• US9775835B2
  申请人：——

  公开号：US9775835B2

  公开（公告）日：2017-10-03
• [EN] SMALL MOLECULE INHIBITORS OF VIRAL PROTEIN INTERACTIONS WITH HUMAN T-RNA<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DES INTERACTIONS DES PROTÉINES VIRALES AVEC L'ARNT HUMAIN
  申请人：SIRGA ADVANCED BIOPHARMA INC

  公开号：WO2014025749A2

  公开（公告）日：2014-02-13

  Disclosed herein are compounds, compositions and methods of their use to treat HIV/AIDS disease in a subject in need thereof, wherein the compositions comprise small molecule inhibitors that inhibit viral preparation or viral recruitment of human tRNA3Lys.
• 6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions
  作者：A. A. Afon’kin、M. L. Kostrikin、A. E. Shumeiko、A. F. Popov

  DOI：10.1134/s1070428011050137

  日期：2011.5

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and beta-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides.