7-Oxo-3-phenylthiazolo<4,5-d>pyrimidin-2-thion | 7052-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 7-Oxo-3-phenylthiazolo<4,5-d>pyrimidin-2-thion
• 英文别名: 3-phenyl-2-thioxo-2,3-dihydrothiazolo<4,5-d>pyrimidin-7(6H)-one；7-oxo-3-phenylthiazolo<4,5-d>pyrimidine-2(6H)-thione；3-Phenyl-6H-thiazolo<4,5-d>pyrimidon-(7)-2H-thion-(2)；3-phenyl-2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-one；3-phenyl-2-thioxo-2,3-dihydro[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one；3-phenyl-2-sulfanylidene-6H-[1,3]thiazolo[4,5-d]pyrimidin-7-one
• CAS: 7052-22-4
• 化学式: C₁₁H₇N₃OS₂
• 分子量: 261.328
• InChiKey: HRMVDGHIMMJLMB-UHFFFAOYSA-N

物化性质

• 熔点：
  234 °C
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Oxo-3-phenylthiazolo<4,5-d>pyrimidin-2-thion 在 sodium azide 、 sodium dithionite 、 五氯化磷 作用下， 以 乙醇 、 水 、 丙酮 、 三氯氧磷 为溶剂， 反应 8.0h， 生成 7-amino-3-phenylthiazolo[4,5-d]pyrimidin-2(3H)-thione
  参考文献：
  名称：

  Condensed thiazoles, II: Synthesis of 7-substituted thiazolo[4,5-d]pyrimidines as possible anti-HIV, anticancer, and antimicrobial agents

  摘要：

  Some 3-substituted 2-thioxothiazolo[4,5-d]pyrimidin-7(6H)-ones (2a, b; 4) have been synthesized and converted to their 7-chloro (3, 5), 7-diethanolamino (6a,b), 7-bis(2-chloroethyl)amino (7), 7-azido (8), 7-amino (9), 7-hydrazino (10), 7-mercapto (11a, b), and 7-methylthio (12) derivatives. These compounds were evaluated for their in vitro antimicrobial, anti-HIV, and anticancer activities.

  DOI：

  10.1007/bf00844697
• 作为产物：
  描述：

  4-amino-3-phenyl-2,3-dihydro-2-thioxothiazole-5-carboximide 、 甲酸 反应 3.0h， 以77%的产率得到7-Oxo-3-phenylthiazolo<4,5-d>pyrimidin-2-thion
  参考文献：
  名称：

  Zur Chemie der 4-Aminothiazolin-2-thione

  摘要：

  DOI：

  10.1007/bf00900005

文献信息

• Some 6-Substituted 3-Aryl-7-oxothiazolo[4,5-<i>d</i>]pyrimidin-2(3<i>H</i>)-thione Derivatives and Their Antimicrobial Activities
  作者：Seref Demirayak、Faten Dali Ali、Baland Sirvan Osman、Yagmur Tunali

  DOI：10.1080/10426500701323333

  日期：2007.6.14

  3-aryl-6-substituted thiazolopyrimidin-2(3H)-thione derivatives 4 and 6 have been synthesized by reacting thiazolopyrimidines 2 with ω -bromoacetophenone 3 and 2-chloro-N-(2-thiazolyl)acetamides 5 . The structure elucidation of the obtained compounds was performed by IR, 1 H-NMR, MASS spectroscopy, and elemental analyses. The antibacterial and antifungal activities of the compounds were investigated, and

  在本研究中，3-芳基-6-取代的噻唑并嘧啶-2(3H)-硫酮衍生物 4 和 6 已通过噻唑并嘧啶 2 与 ω-溴苯乙酮 3 和 2-氯-N-(2-噻唑基) 乙酰胺 5 反应合成。所得化合物的结构解析通过IR、 1 H-NMR、质谱和元素分析进行​​。研究了化合物的抗菌和抗真菌活性，据报道，这些化合物表现出显着的抗菌活性。
• Gewald,K., Journal fur praktische Chemie (Leipzig 1954), 1966, vol. 32, p. 26 - 30
  作者：Gewald,K.

  DOI：——

  日期：——
• Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.
  作者：K. Gewald、U. Hain、R. Schindler、M. Gruner

  DOI：10.1007/bf00811521

  日期：1994.10

  6-Amino-thiazolo[4,5-c]isothiazole derivatives 4 are obtained by addition of hydrogen sulfide to the 4-Amino-thiazoline-5-carbonitrile 2 followed by cyclooxidation of the intermediate thioamides 3. In the presence of sodium sulfite the hydrolysis of the 4-amino-2-methylthio-thiazolium salts 5 derived from the title compounds 1 yields the 4-amino-thiazolin-2-ones 6. By their further hydrolysis the 2,4-dioxo-thiazolidin-5-carboxamides 8 are formed. The 2-oxo-and 2-thioxo-thiazolo [4,5-d]pyrimidin-7-ones and -thiones available from 1 undergo ring opening by hydrolysis to give the substituted 4-amino-6-oxo- and 4-amino-6-thioxo-pyrimidine-5-thiols 15a-h and 13i-e. They have been isolated as their disulfides 14 or 5-alkyl derivatives i.e. the substituted 4-amino-5-alkylthiopyrimidin-6-ones and -thiones 16. In analogy, the intermediate 6-amino-7-oxo-thiazolo[4,5-d] pyrimidin-2-thione 18 and the 7-amino-thiazolo[4,5-d]-pyrimidin-2-thione 24 derived from 1 react by ring cleavage to yield the 1,4- and 4,6-diamino-pyrimidin-5-thiole derivatives 22 and 27, respectively, isolated as their disulfides or alkylthio-derivatives. From the pyrimidine 16b the pyrimido[5,4-b]1,4-thiazine derivative 18 can be obtained.
• Gewald K., Hain U., Schindler R., Gruner M., Monatsh. Chem, 125 (1994) N 10, S 1129-1143
  作者：Gewald K., Hain U., Schindler R., Gruner M.

  DOI：——

  日期：——
• GEWALD, K.;HAIN, U.;HARTUNG, P., MONATSH. CHEM., 1981, 112, N 12, 1393-1404
  作者：GEWALD, K.、HAIN, U.、HARTUNG, P.

  DOI：——

  日期：——