3-Allyl-2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-one | 159897-64-0

• 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: 3-Allyl-2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-one
• 英文别名: 3-allyl-2-thioxo-2,3-dihydro[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one；3-prop-2-enyl-2-sulfanylidene-6H-[1,3]thiazolo[4,5-d]pyrimidin-7-one
• CAS: 159897-64-0
• 化学式: C₈H₇N₃OS₂
• mdl: MFCD03056467
• 分子量: 225.295
• InChiKey: XMSJNOBHTISRAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 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：

  3-Allyl-2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-one 在 sodium metabisulfite 、 sodium hydroxide 作用下， 反应 1.0h， 生成 3-Allyl-3H,6H-thiazolo[4,5-d]pyrimidine-2,7-dione
  参考文献：
  名称：

  Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.

  摘要：

  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.

  DOI：

  10.1007/bf00811521
• 作为产物：
  描述：

  原甲酸三乙酯 、 3-烯丙基-4-氨基-2-硫氧代-2,3-二氢-噻唑-5-羧酸酰胺 以90%的产率得到3-Allyl-2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-one
  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

文献信息

• Synthesis and antimicrobial activity of rhodanine derivatives
  作者：NS Habib、SM Rida、EAM Badawey、HTY Fahmy、HA Ghozlan

  DOI：10.1016/s0223-5234(97)88919-2

  日期：1997.9
• 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：——
• Condensed thiazoles, II: Synthesis of 7-substituted thiazolo[4,5-d]pyrimidines as possible anti-HIV, anticancer, and antimicrobial agents
  作者：N. S. Habib、S. M. Rida、E. A. M. Badawey、H. T. Y. Fahmy

  DOI：10.1007/bf00844697

  日期：1996.11

  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.
• 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.