6-amino-5-(hexahydro-2,5-methanopentalene-3a-carboxamido)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydropyrimidine | 136199-24-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-amino-5-(hexahydro-2,5-methanopentalene-3a-carboxamido)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydropyrimidine
• 英文别名: N-(6-amino-2,4-dioxo-3-propyl-1H-pyrimidin-5-yl)tricyclo[3.3.1.03,7]nonane-3-carboxamide
• CAS: 136199-24-1
• 化学式: C₁₇H₂₄N₄O₃
• 分子量: 332.403
• InChiKey: WSDPJSMZJGBRSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-5-(hexahydro-2,5-methanopentalene-3a-carboxamido)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydropyrimidine 在 potassium carbonate 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-(hexahydro-2,5-methanopentalen-3a-yl)-4,5-dihydro-9-propyl-6H,8H-pyrimido[1,2,3-cd]purine-8,10(9H)-dione
  参考文献：
  名称：

  Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones

  摘要：

  The alkylation of 3-substituted cycloalkylcarboxamido-6-aminouraciI derivatives with 3-bromo-1-propanol followed by ring closure yields 1,3,8-trisubstituted xanthine derivatives bearing a polar hydroxyl group. Use of the more reactive 1,3-dibromopropane or homologous dibromoalkanes for the alkylation reaction results in simultaneous alkylation at N1 and the exocyclic amino group (N-6) yielding imidazo-, pyrimido- and diazepino-pyrimidine derivatives. The pyrimidopyrimidine derivatives can subsequently be cyclised using hexamethyldisilazane at high temperature affording an easy, convenient and general access to tricyclic pyrimido[1,2,3-cd]purinediones. Alternatively, 3-substituted 6-amino-5-benzylideneaminouraciI derivatives can be reacted with 1,3-dibromopropane followed by an oxidative cyclisation using thionyl chloride to obtain the desired tricyclic pyrimido[1,2,3-cd]purinediones, which are sterically fixed analogues of pharmacologically active purine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01485-0
• 作为产物：
  描述：

  3-甲基碳酸胺 、 5,6-二氨基-3-丙基嘧啶-2,4(1h,3h)-二酮 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以66%的产率得到6-amino-5-(hexahydro-2,5-methanopentalene-3a-carboxamido)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones

  摘要：

  The alkylation of 3-substituted cycloalkylcarboxamido-6-aminouraciI derivatives with 3-bromo-1-propanol followed by ring closure yields 1,3,8-trisubstituted xanthine derivatives bearing a polar hydroxyl group. Use of the more reactive 1,3-dibromopropane or homologous dibromoalkanes for the alkylation reaction results in simultaneous alkylation at N1 and the exocyclic amino group (N-6) yielding imidazo-, pyrimido- and diazepino-pyrimidine derivatives. The pyrimidopyrimidine derivatives can subsequently be cyclised using hexamethyldisilazane at high temperature affording an easy, convenient and general access to tricyclic pyrimido[1,2,3-cd]purinediones. Alternatively, 3-substituted 6-amino-5-benzylideneaminouraciI derivatives can be reacted with 1,3-dibromopropane followed by an oxidative cyclisation using thionyl chloride to obtain the desired tricyclic pyrimido[1,2,3-cd]purinediones, which are sterically fixed analogues of pharmacologically active purine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01485-0

文献信息

• Xanthine compounds
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0415456B1

  公开（公告）日：1996-06-26
• KW-3902 CONJUGATES THAT DO NOT CROSS THE BLOOD-BRAIN BARRIER
  申请人：Novacardia, Inc.

  公开号：EP2061793A2

  公开（公告）日：2009-05-27
• US5290782A
  申请人：——

  公开号：US5290782A

  公开（公告）日：1994-03-01
• US5525607A
  申请人：——

  公开号：US5525607A

  公开（公告）日：1996-06-11
• [EN] KW-3902 CONJUGATES THAT DO NOT CROSS THE BLOOD-BRAIN BARRIER<br/>[FR] CONJUGUÉS KW-3902 NE TRAVERSANT PAS LA BARRIÈRE SANG-CERVEAU
  申请人：NOVACARDIA INC

  公开号：WO2008024277A2

  公开（公告）日：2008-02-28

  [EN] The present invention relates to certain compounds and to methods for the preparation of certain compounds that can be used in the fields of chemistry and medicine. Specifically, described herein are methods for the preparation of various compounds and intermediates, and the compounds and intermediates themselves. More specifically, described herein are methods for synthesizing KW-3902 derivatives of Formula (I), (II), (HI), (IV), (V), and (VI).
  [FR] La présente invention concerne certains composés et des procédés servant à la préparation de certains composés pouvant être utilisés dans les domaines de la chimie et de la médecine. De façon spécifique, l'invention concerne des procédés servant à la préparation de divers composés et intermédiaires, ainsi que les composés intermédiaires eux-mêmes. Plus spécifiquement, l'invention concerne des procédés servant à synthétiser des dérivés KW-3902 représentés par les Formules (I), (II), (HI), (IV), (V) et (VI).