5-硫代-2,4,8,9-四氮杂双环[4.3.0]壬-1,6-二烯-3-酮 | 5334-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 5-硫代-2,4,8,9-四氮杂双环[4.3.0]壬-1,6-二烯-3-酮
• 英文名称: Pyrazolo<3,4-d>-4-thioxopyrimidin-6-one
• 英文别名: 4,5-Dihydro-4-thioxo-1H-pyrazolo[3,4-d]pyrimidin-6(7H)-one；4-thioxo-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-6-one；4-Thioxo-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-6-on；Oxithiopurinol；4-sulfanylidene-1,7-dihydropyrazolo[3,4-d]pyrimidin-6-one
• CAS: 5334-33-8
• 化学式: C₅H₄N₄OS
• mdl: MFCD11040462
• 分子量: 168.179
• InChiKey: KDAAPQIIYTZQEZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

文献信息

• Facile and general syntheses of 3- and/or 5-substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidines as a new class of potential xanthine oxidase inhibitors†
  作者：Tomohisa Nagamatsu、Takayuki Fujita

  DOI：10.1039/a903676h

  日期：——

  Convenient syntheses of 3- and/or 5-substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidines as a new class of potent xanthine oxidase inhibitors, involving the oxidative cyclisation of 4-alkylidenehydrazino- or 4-arylmethylidenehydrazino-1H-pyrazolo[3,4-d]pyrimidines with 70% nitric acid as the key step, are described.

  方便合成3和/或5取代的7H-吡唑[4,3-e]-1,2,4-三氮唑[4,3-c]嘧啶作为一类新的强效黄嘌呤氧化酶抑制剂，涉及到4-烷基亚胺氮或4-芳基亚胺氮-1H-吡唑[3,4-d]嘧啶与70%硝酸氧化环化的关键步骤。
• Novel xanthine oxidase inhibitor studies. Part 3. Convenient and general syntheses of 3-substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-5(6H)-ones as a new class of potential xanthine oxidase inhibitors
  作者：Tomohisa Nagamatsu、Takayuki Fujita、Kazuki Endo

  DOI：10.1039/a907673e

  日期：——

  Convenient and general syntheses of 3-substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-5(6H)-ones (12), a new class of potent xanthine oxidase inhibitors, involving the oxidative cyclisation of 6-substituted 4-alkylidenehydrazino- or 4-arylmethylidenehydrazino-1H-pyrazolo[3,4-d]pyrimidines (3 and 11) with 70% nitric acid as the key step, are reported. The hydrazones 3 and 11 were obtained by a versatile synthetic route via the key intermediates, 6-chloro-4-hydrazino-1H-pyrazolo[3,4-d]pyrimidine 2 or oxypurinol 4, starting from 2,4,6-trichloropyrimidine-5-carbaldehyde 1. Their inhibitory activities against bovine milk xanthine oxidase in vitro are also described; i.e. the pyrazolotriazolopyrimidines 12 were several hundred times more potent than allopurinol.

  报道了一种方便且通用的合成方法，用于合成3取代的7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-5(6H)-酮（12），这是一类新型的强效黄嘌呤氧化酶抑制剂。该合成涉及到以70%浓硝酸进行的6取代4-烯基氨基或4-芳基甲烯基氨基-1H-pyrazolo[3,4-d]pyrimidines（3和11）的氧化环化作为关键步骤。氢肼衍生物3和11是通过一个多功能合成路线获得的，该路线以关键中间体6-氯-4-氨基-1H-pyrazolo[3,4-d]pyrimidine（2）或氧嘌呤醇（4）为起始物，开始自2,4,6-三氯嘧啶-5-醛（1）。同时也描述了它们对牛乳黄嘌呤氧化酶的体外抑制活性；即，pyrazolotriazolopyrimidines（12）的活性比别嘌呤明显强几百倍。
• Heilmittelchemische Studien in der heterocyclischen Reihe. 25. Mitteilung. Pyrazolo-pyrimidine III Paraxanthin-, Theobromin- und Theophyllin-Analoga der Pyrazolo[3,4-d]pyrimidin-Reihe
  作者：P. Schmidt、K. Eichenberger、J. Dreuey

  DOI：10.1002/hlca.19590420132

  日期：——

  The preparation of the paraxanthine, theobromine and theophylline isomers 1,5-; 2,5- and 1,7-; 2,7- and 5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro-pyrazolo[3,4-d]-pyrimidines is described and their structure established. A structurally specific synthesis of the caffeine and isocaffeine isomers 1,5,7- and 2,5,7-trimethyl-4,6- dioxo-4,5,6,7-tetrahydro-pyrazolo [3,4-d]pyrimidines has been realized.

  对黄嘌呤，可可碱和茶碱异构体1，5-的制备；2.5和1.7；描述了2,7-和5,7-二甲基-4,6-二氧代-4,5,6,7-四氢-吡唑并[3,4-d]-嘧啶并确定了它们的结构。咖啡因和异咖啡因异构体1,5,7-和2,5,7-三甲基-4,6-二氧代-4,5,6,7-四氢吡唑并[3,4-d]嘧啶的结构特异性合成实现。
• General route for the facile synthesis of pyrimidin-2-one-4-thione derivatives via the annulation of cyclic o-aminonitriles using carbonyl sulfide
  作者：Maria A. Hernandez、Fung-Lung Chung、Robert A. Earl、Leroy B. Townsend

  DOI：10.1021/jo00333a001

  日期：1981.9
• Robins, Journal of the American Chemical Society, 1957, vol. 79, p. 6407,6412
  作者：Robins

  DOI：——

  日期：——