4-(ethoxymethylene)amino-3-phenlyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile | 159897-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(ethoxymethylene)amino-3-phenlyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile
• 英文别名: 4-Ethoxymethylenamino-3-phenyl-2-thioxo-thiazolin-5-carbonitril；4-(ethoxymethylene)-amino-3-(phenyl)-2-thioxo-1,3-thiazole-5-carbonitrile；ethyl N-(5-cyano-3-phenyl-2-sulfanylidene-1,3-thiazol-4-yl)methanimidate
• CAS: 159897-83-3
• 化学式: C₁₃H₁₁N₃OS₂
• 分子量: 289.382
• InChiKey: YYHSKKTZZRUJRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(ethoxymethylene)amino-3-phenlyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile 在 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以47%的产率得到7-amino-3-phenylthiazolo[4,5-d]pyrimidin-2(3H)-thione
  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 、 4-amino-3-phenyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile 在 乙酸酐 作用下， 反应 3.0h， 生成 4-(ethoxymethylene)amino-3-phenlyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile
  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

文献信息

• Novel 8-(furan-2-yl)-3-substituted thiazolo [5,4-e][1,2,4] triazolo[1,5-c] pyrimidine-2(3H)-thione derivatives as potential adenosine A2A receptor antagonists
  作者：Chandra Bhushan Mishra、Sandeep Kumar Barodia、Amresh Prakash、J.B. Senthil Kumar、Pratibha Mehta Luthra

  DOI：10.1016/j.bmc.2010.02.048

  日期：2010.4

  Novel thiazolotriazolopyrimidine derivatives (23-33) designed as potential adenosine A(2A) receptor (A(2A)R) antagonists were synthesized. Molecular docking studies revealed that all compounds (23-33) exhibited strong interaction with A(2A)R. The strong interaction of the compounds (23-33) with A(2A)R in silico was confirmed by their high binding affinity with human A(2A)R stably expressed in HEK293 cells using radioligand-binding assay. The compounds 24-26 demonstrated substantial binding affinity and selectivity for A(2A)R as compared to SCH58261, a standard A(2A)R antagonist. Decrease in A(2A)R-coupled release of endogenous cAMP in treated HEK293 cells demonstrated in vitro A(2A)R antagonist potential of the compounds 24-26. Attenuation in haloperidol-induced motor impairments (catalepsy and akinesia) in Swiss albino male mice pre-treated with compounds 24-26 further supports their role in the alleviation of PD symptoms. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of novel 7-imino-2-thioxo-3,7-dihydro-2H-thiazolo [4,5-d] pyrimidine derivatives as adenosine A2A receptor antagonists
  作者：Pratibha Mehta Luthra、Chandra Bhushan Mishra、Pawan Kumar Jha、Sandeep Kumar Barodia

  DOI：10.1016/j.bmcl.2009.11.133

  日期：2010.2

  Novel bicyclic thiazolopyrimidine compounds (15-26) were synthesized to develop adenosine A(2A) receptor (A(2A)R) antagonist for the treatment of Parkinson's disease (PD). The binding affinity of the compounds (15-26) with A(2A)R was evaluated using radioligand binding assay on isolated membranes from stably transfected HEK293 cells. Selectivity of the compounds towards A(2A)R was assessed by comparing their binding affinities with A(1) receptors (A(1)R). cAMP concentrations were measured from HEK293 cells treated with compounds (15-26) as compared to NECA (A(2A)R agonist). The compound (16) possessed strongest A(2A)R binding affinity (K-i value = 0.0038 nM) and selectivity (737-fold) versus A(1)R. Decrease in A(2A)R-coupled release of endogenous cAMP from HEK293 cells treated with compounds (15-26) is evocative of their potential as A(2A)R antagonist. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] A NOVEL 3-SUBSTITUTED 7-IMINO-2-THIOXO-3, 7-DIHYDRO-2H-THIAZOLO [4,5-DI PYRIMIDIN-6-YL - AND PROCESS FOR PREPARATION THEREOF<br/>[FR] (7-IMINO-2-THIOXO-3,7-DIHYDRO-2H-THIAZOLO[4,5-D]PYRIMIDIN-6-YLE SUBSTITUÉ EN POSITION 3 INÉDIT ET SON PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2011061754A9

  公开（公告）日：2012-07-05