5-氨基-7-羟基-3H-噻唑并[4,5-d]嘧啶-2-酮 | 22288-75-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 5-氨基-7-羟基-3H-噻唑并[4,5-d]嘧啶-2-酮
• 英文名称: 2,4-diamino-6-hydroxy-5-thiocyanatopyrimidine
• 英文别名: 2,6-Diamino-5-thiocyanatopyrimidin-4(3H)-one；(2,4-diamino-6-oxo-1H-pyrimidin-5-yl) thiocyanate
• CAS: 22288-75-1
• 化学式: C₅H₅N₅OS
• mdl: MFCD18447702
• 分子量: 183.194
• InChiKey: WXJXCKXWZOPRJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-氨基-7-羟基-3H-噻唑并[4,5-d]嘧啶-2-酮 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以78%的产率得到2,5-二氨基-噻唑并[4,5-d]嘧啶-7(4H)-酮
  参考文献：
  名称：

  [EN] 2-OXO-THIAZOLE DERIVATIVES AS A2A INHIBITORS AND COMPOUNDS FOR USE IN THE TREATMENT OF CANCERS
  [FR] DÉRIVÉS DE 2-OXO-THIAZOLE EN TANT QU'INHIBITEURS DE A2A ET COMPOSÉS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE CANCERS

  摘要：

  本发明涉及式（I）的化合物或其药用可接受的盐或溶剂化合物。该发明进一步涉及将式（I）的化合物用作A2A抑制剂。该发明还涉及将式（I）的化合物用于治疗和/或预防癌症。该发明还涉及一种制造式（I）化合物的方法。

  公开号：

  WO2018178338A1
• 作为产物：
  描述：

  硫氰酸铵 、 2,4-二氨基-6-羟基嘧啶 在 碘 作用下， 以 甲醇 为溶剂， 反应 0.42h， 以90%的产率得到5-氨基-7-羟基-3H-噻唑并[4,5-d]嘧啶-2-酮
  参考文献：
  名称：

  Iodine mediated an efficient and greener thiocyanation of aminopyrimidines by a modification of the Kaufmann’s reaction

  摘要：

  A new, safe, and efficient methodology for the thiocyanation of some aminopyrimidine derivatives has been implemented. The thiocyanation reactions proceeded at room temperature with high yields and selectivity. This route is a less toxic alternative to other common thiocyanation techniques because it uses molecular iodine as a halogen source, which is less reactive and easier to handle than chlorine or bromine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.058

文献信息

• Synthesis of Benzothiazinophenothiazine Derivatives and their Antimicrobial Screening
  作者：Emmanuel O Adekola、Benjamin E Ezema、Jude I Ayogu、David I Ugwu、Chidimma G Ezema、Abuekwu P Nwasi、Christian O Ike

  DOI：10.13005/ojc/300406

  日期：2014.12.31

  The synthesis of benzothiazinophenothiazine derivatives from simple heterocyclic compounds was thoroughly investigated. The intermediate, 6-chloro-5H-benzo[a]phenothiazin-5-one was afforded by the condensation of 2-aminothiophenol with 2,3-dichloro-1, 4-naphthoquinone in an alkaline medium. Further condensation of the intermediate with 2,4-diamino-6-hydroxypyrimidine-5-thiol obtained by alkaline hydrolysis of 2,4-diamino-6-hydroxy-5-thiacyanatopyrimidine gave 7-amino-9-hydroxy-6-8,diazabenzo[a][1,4]benzothiazino[3,2-c]phenothiazine. However, facile acid-catalyzed synthesis of four other benzothiazinophenothiazine ring systems was accomplished with improved yield and lesser reaction time. The Structural confirmation was done using UV-Visible spectroscopy, FT-IR, 1H and 13C-NMR and elemental analysis. The synthesized compounds were screened against some micro-organisms and the results showed that the complex derivatives were significantly active against the microorganisms.

  合成苯硫噻嗪苯噻嗪衍生物的研究从简单的杂环化合物入手，进行了深入探讨。中间体6-氯-5H-苯并[a]噻嗪-5-酮是通过将2-氨基硫酚与2,3-二氯-1,4-萘醌在碱性介质中缩合得到的。进一步将该中间体与通过碱水解2,4-二氨基-6-羟基-5-硫氰基嘧啶得到的2,4-二氨基-6-羟基-5-硫噻唑缩合，得到7-氨基-9-羟基-6-8-二氮苯并[a][1,4]苯硫噻嗪[3,2-c]苯噻嗪。然而，采用酸催化法成功实现了其他四种苯硫噻嗪环系的合成，且产率较高，反应时间较短。利用紫外-可见光谱、傅里叶变换红外光谱、氢核磁共振谱(1H NMR)、碳核磁共振谱(13C NMR)和元素分析进行了结构确认。合成的化合物对一些微生物进行了筛选，结果显示这些复合衍生物对微生物具有显著的活性。
• Studies in the heterocyclic series. XVIII. Utilization of 4-aminopyrimidine chemistry in 1,4,7,9-tetraazabenzo[<i>b</i>]phenothiazine synthesis
  作者：Charles O. Okafor

  DOI：10.1002/jhet.5570170747

  日期：1980.11

  The synthesis of 1,4,7,9-tetraazabenzo[b]phenothiazine ring system from 4-aminopyrimidine is reported. This new heterocyclic ring was obtained by converting a 4-aminopyrimidine to the corresponding 5-thiocyanato derivative followed by hydrolysis and subsequent treatment with 2,3-dichloroquinoxaline. Several derivatives were obtained by using suitable substituted starting materials. Nitration with mixed

  据报道由4-氨基嘧啶合成1,4,7,9-四氮杂苯并[ b ]吩噻嗪环系统。通过将4-氨基嘧啶转化为相应的5-硫氰酸根衍生物，然后水解并随后用2,3-二氯喹喔啉处理，获得了该新的杂环。通过使用合适的取代起始原料获得了几种衍生物。用硝酸和硫酸混合硝化得到相应的13-硝基衍生物。光谱分析与分配的结构一致。
• Synthesis of derivatives of thiazolo[4,5-d]pyrimidine. Part I
  作者：J. A. Baker、P. V. Chatfield

  DOI：10.1039/j39690000603

  日期：——

  which with alkali afforded di-(2,4-diamino-6-hydroxypyrimidin-5-yl) disulphide and not the thiazolo[4,5-d]pyrimidine claimed by an earlier worker. Kaufmann thiocyanation of 2,4-diamino-6-hydroxypyrimidine yielded the 5-thiocyanato-compound, which did not readily cyclise to a thiazolo[4,5-d]pyrimidine as previously claimed by other workers. Cyclisation of the thiocyanato-compound has been effected with

  2,4-二氨基-5-溴-6-羟基嘧啶与硫脲反应，得到异硫脲盐，与碱反应生成二硫化二-（2,4-二氨基-6-羟基嘧啶-5-基），而不是噻唑啉[4]。 ，5- d ]嘧啶由一个更早的工人所声称。2，4-二氨基-6-羟基嘧啶的考夫曼硫氰化产生了5-硫氰酸根化合物，该化合物不容易环化成噻唑并[4,5- d ]嘧啶，如先前其他工人所声称的那样。硫氰酸根化合物的环化反应已经用乙酸酐完成。所得二乙酰氨基衍生物的脱乙酰基作用得到2，5-二氨基-7-羟基噻唑并[4，5- d ]嘧啶。
• OKAFOR C. O., J. HETEROCYCL. CHEM., 1980, 17, NO 7, 1587-1592
  作者：OKAFOR C. O.

  DOI：——

  日期：——