1,3-dimethyl-6-phenylpyrrolo<3,2-d>pyrimidine-2,4(1H,3H)-dione | 59119-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,3-dimethyl-6-phenylpyrrolo<3,2-d>pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-dimethyl-6-phenyl-2,4(1H,3H,5H)pyrrolo[3,2-d]pyrimidinedione；1,3-Dimethyl-8-phenyl-9-deazaxanthine；1,3-dimethyl-6-phenyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione；1,3-dimethyl-6-phenyl-1,5-dihydropyrrolo[3,2-d]pyrimidine-2,4-dione；1,3-dimethyl-6-phenyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione；1,3-dimethyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine-2,4-dione
• CAS: 59119-44-7
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: HBWLTYRKABSIQR-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: isopropanol (67-63-0))
• 沸点：
  500.4±52.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-6-phenylpyrrolo<3,2-d>pyrimidine-2,4(1H,3H)-dione 在 三氯氧磷 作用下， 以 环丁砜 为溶剂， 反应 5.0h， 以100%的产率得到6-chloro-6-deoxy-8-phenyl-9-deazatheophylline
  参考文献：
  名称：

  Nishigaki, Sadao; Kanamori, Yukako; Senga, Keitaro, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 5, p. 1636 - 1641

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,4-三甲基尿嘧啶 在 哌啶 、 硫酸 、 硝酸 、 亚磷酸三乙酯 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 1,3-dimethyl-6-phenylpyrrolo<3,2-d>pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Deazaxanthines: Analogs of Potent A1- and A2-Adenosine Receptor Antagonists

  摘要：

  A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d] pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9-Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 2-3-fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2-naphthyl)-9-deazaxanthine (19e) showed high affinty (K-i = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9-deazaxanthines was unfavorable for A1 and A2a receptor binding. 7-Deazaxanthines were considerably less potent compared to xanthines and to 9-deazaxanthines at both receptor subtypes.

  DOI：

  10.1021/jm00036a019

文献信息

• Pyrimidine derivatives and related compounds. Part 47. A new synthesis of xanthines and pyrrolo[3,2-d]pyrimidines by intramolecular cyclisation of 6-substituted 5-nitrouracil derivatives
  作者：Kosaku Hirota、Tadashi Sugiyama、Yukio Kitade、Shigeo Senda、Yoshifumi Maki

  DOI：10.1039/p19840000583

  日期：——

  of 6-[2-(ethoxycarbonyl, acetyl, and cyano) ethyl] uracil (8h–j) with triethylamine led to the formation of the corresponding 6-vinyluracil (11 a–c). A one-step synthesis of the 7-hydroxy-9-deazaxanthines (9a–e) was accomplished by the treatment of the sodium salt (7) with arylalkyl chlorides in the presence of potassium carbonate in dry DMF. Deoxygenation of the 7-hydroxy-9-deazaxanthines (9a–e) smoothly

  通过在三乙胺存在下使6-氯-1,3-二甲基-5-硝基尿嘧啶（1）与芳基烷基胺反应，制得6-芳烷基氨基-1,3-二甲基-5-硝基尿嘧啶（2a–f）。其中，在氮原子和6-芳基烷基氨基部分中的苄基位置不具有取代基的6-芳基烷基氨基尿嘧啶（2a–d）在转化为相应的8-芳基-1,3-二甲基黄嘌呤（3a–d）时在二甲基甲酰胺（DMF）中加热回流。钠盐（反应7 1,3,6-三甲基-5- nitrouracil（的）6）用在无水DMF烷基和芳基烷基卤化物，得到相应的6-（取代甲基）-1,3-二甲基-5-硝基尿嘧啶（8a–j）。其中，对6-（2-芳基乙基）尿嘧啶（8b-f）进行碱催化的环化反应，得到8-芳基-7-羟基-9-脱氮黄嘌呤（9a-e）。另一方面，用三乙胺处理6- [2-（乙氧羰基，乙酰基和氰基）乙基]尿嘧啶（8h-j）导致形成相应的6-乙烯基尿嘧啶（11a-c）。在干燥的DMF中，在碳酸钾的存在下
• [EN] NEW-4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE 4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2003082873A1

  公开（公告）日：2003-10-09

  This invention is directed to new potent and selective antagonists of A2A and/or A2B adenosine receptors having the general formula (I) to process for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

  这项发明是针对新型高效选择性A2A和/或A2B腺苷受体拮抗剂的，其具有通用公式（I），用于其制备的过程；包含它们的药物组合物；以及它们在治疗中的应用。
• New-4-pyrrolopyrimidin-6-YL)benzenesulphonamide derivatives
  申请人：Vidal Juan Bernat

  公开号：US20050261248A1

  公开（公告）日：2005-11-24

  This invention is directed to selective antagonists of A 2A and/or A 2B adenosine receptors having the general formula (I); to processes for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

  本发明涉及选择性A2A和/或A2B腺苷受体拮抗剂，其具有一般式（I）；它们的制备方法；包括它们的药物组合物；以及它们在治疗中的使用。
• New pyrrolopyrimidin-6-yl benzenesulfonamides: Potent A2B adenosine receptor antagonists
  作者：Cristina Esteve、Arsenio Nueda、José Luis Díaz、Jorge Beleta、Alvaro Cárdenas、Estrella Lozoya、Maria Isabel Cadavid、Maria Isabel Loza、Hamish Ryder、Bernat Vidal

  DOI：10.1016/j.bmcl.2006.04.074

  日期：2006.7

  A new series of 4-(1,3-dialkyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamides has been identified as potent AZB adenosine receptor antagonists. The products have been evaluated for their binding affinities for the human A(2B), A(1) and A(3) adenosine receptors. 6-(4-[4-(4-Bromobenzyl)piperazin-1-yl]sulfonyl}phenyl)-1,3-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (16) showed a high affinity for the AZB adenosine receptor (IC50 = 1 nM) and selectivity (A(1): 183x; A(30): 12660x). Synthesis and SAR of this novel class of compounds showing improved absorption properties is presented herein. (c) 2006 Elsevier Ltd. All rights reserved.
• A Facile Synthesis of 7-Hydroxy-9-deazaxanthines
  作者：Kosaku Hirota、Tadashi Sugiyama、Yukio Kitade、Shigeo Senda、Yoshifumi Maki

  DOI：10.1055/s-1982-30088

  日期：——