2-[4-(2,4-dioxo-1-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)phenyloxy]acetic acid | 480994-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-[4-(2,4-dioxo-1-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)phenyloxy]acetic acid
• 英文别名: 2-[4-(2,4-dioxo-1-propyl-5H-pyrrolo[3,2-d]pyrimidin-6-yl)phenoxy]acetic acid
• CAS: 480994-18-1
• 化学式: C₁₇H₁₇N₃O₅
• 分子量: 343.339
• InChiKey: DGFVGPKFNKZNTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-苯基哌嗪 、 2-[4-(2,4-dioxo-1-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)phenyloxy]acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以20%的产率得到6-[4-(4-phenylpiperazin-1-yl)carbonylmethoxyphenyl]-1-propyl-1,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of novel substituted 9-deazaxanthines as A2B receptor antagonists

  摘要：

  A new series of 9-deazaxanthine derivatives with various substituents at the heterocyclic system were synthesized and evaluated for their binding affinities for the four human recombinant adenosine receptors, A(1)-A(3) subtypes. A number of the 9-deazaxanthines derivatives 3a-m showed moderate-to-high affinity for hA(2B) receptors, with compound 3f showing a 32-fold selectivity for A(2B) over A(1) and a 2750-fold selectivity for A(2B) over A(2A). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.011
• 作为产物：
  描述：

  (E)-2-(4-(2-(5-nitro-2,6-dioxo-3-propyl-1,2,3,6-tetrahydropyrimidin-4-yl)ethenyl)phenoxy)acetic acid 在 甲酸 、 sodium dithionite 作用下， 反应 18.0h， 以89%的产率得到2-[4-(2,4-dioxo-1-propyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)phenyloxy]acetic acid
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of novel substituted 9-deazaxanthines as A2B receptor antagonists

  摘要：

  A new series of 9-deazaxanthine derivatives with various substituents at the heterocyclic system were synthesized and evaluated for their binding affinities for the four human recombinant adenosine receptors, A(1)-A(3) subtypes. A number of the 9-deazaxanthines derivatives 3a-m showed moderate-to-high affinity for hA(2B) receptors, with compound 3f showing a 32-fold selectivity for A(2B) over A(1) and a 2750-fold selectivity for A(2B) over A(2A). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.011

文献信息

• 6-Phenyldihydropyrrolopyrimidinedione derivatives
  申请人：Vidal Juan Bernat

  公开号：US20050070558A1

  公开（公告）日：2005-03-31

  6-phenylpyrrolopyrimidinedione derivatives of the formula (I), and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 and R 5 are organic residues, L 1 is a spacer group and R 6 is C(O) NR 10 R 11 , —S(O) 2 NR 10 R 11 , ? —ON═CR 12 R 13 , or a heterocyclyl, aryl? or heteroaryl group, where R 10 , R 11 , R 12 and R 13 are organic residues, have therapeutic potential as A2 adenosine receptor inhibitors.

  式(I)的6-苯基吡咯嘧啶二酮衍生物及其药学上可接受的盐，其中R1、R2、R3、R4和R5均为有机残基，L1为间隔基，R6为C（O）NR10R11、—S（O）2NR10R11、？—ON═CR12R13或杂环基、芳基或杂芳基，其中R10、R11、R12和R13为有机残基，具有作为A2腺苷受体抑制剂的治疗潜力。
• Synthesis and pharmacological evaluation of novel substituted 9-deazaxanthines as A2B receptor antagonists
  作者：María Isabel Nieto、María Carmen Balo、José Brea、Olga Caamaño、Franco Fernández、Xerardo García-Mera、Carmen López、María Isabel Loza、José Enrique Rodríguez-Borges、Bernat Vidal

  DOI：10.1016/j.ejmech.2010.03.011

  日期：2010.7

  A new series of 9-deazaxanthine derivatives with various substituents at the heterocyclic system were synthesized and evaluated for their binding affinities for the four human recombinant adenosine receptors, A(1)-A(3) subtypes. A number of the 9-deazaxanthines derivatives 3a-m showed moderate-to-high affinity for hA(2B) receptors, with compound 3f showing a 32-fold selectivity for A(2B) over A(1) and a 2750-fold selectivity for A(2B) over A(2A). (C) 2010 Elsevier Masson SAS. All rights reserved.