4-amino-3-phenyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile | 13251-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-3-phenyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile
• 英文别名: 4-amino-3-phenyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile；4-amino-3-phenyl-2-thioxo-2,3-dihydro-1,3-thiazol-5-carbonitrile；4-amino-3-phenyl-2-thioxo-2,3-dihydrothiazol-5-carbonitrile；4-amino-N3-phenyl-2-thioxo-1,3-thiazole-5-carbonitrile；4-amino-3-phenyl-2-thioxo-2,3-dihydro-thiazole-5-carbonitrile；4-amino-3-phenyl-2-sulfanylidene-1,3-thiazole-5-carbonitrile
• CAS: 13251-19-9
• 化学式: C₁₀H₇N₃S₂
• mdl: MFCD00090047
• 分子量: 233.318
• InChiKey: SSNKVURLRWLXES-UHFFFAOYSA-N

物化性质

• 熔点：
  283-285 °C
• 沸点：
  412.3±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  4-amino-3-phenyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile 在 乙酸酐 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 6-Amino-7-imino-5-methyl-3-phenyl-[1,3]thiazolo[4,5-d]pyrimidine-2-thione
  参考文献：
  名称：

  El-Bendary; El-Sherbeny; Badria, Bollettino Chimico Farmaceutico, 1998, vol. 137, # 4, p. 115 - 119

  摘要：

  DOI：
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 丙二腈 在 sulfur 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到4-amino-3-phenyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile
  参考文献：
  名称：

  Mohareb, Rafat Milad; Wardakhan, Wagnat Wahba; El-Ablack, Fawzia Zakeria, Journal of Chemical Research, Miniprint, 1994, # 4, p. 747 - 760

  摘要：

  DOI：

文献信息

• [EN] (4E)-4-(4-SUBSTITUTED BENZYLIDENEAMINO)-2,3-DIHYDRO-3- SUBSTITUTED-2-THIOXOTHIAZOLE-5-CARBONITRILES AS A2AR ANTAGONIST AND PROCESS FOR PREPARATION THEREOF<br/>[FR] 2-THIOXOTHIAZOLE-5-CARBONITRILES À SUBSTITUTION (4E)-4-(À SUBSTITUTION BENZYLIDÈNEAMINO EN POSITION 4)-2,3-DIHYDRO EN POSITION 3 UTILISÉS COMME ANTAGONISTES DE L'A2AR ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014106861A1

  公开（公告）日：2014-07-10

  The present, invention relates to novel the (4E)-4-(4-substituted benzylideneamino)- 2,3-dihydro-3-substituted -2-thioxothiazole-5-carbonitriles of general formula A and a process for the preparation thereof. The compounds of present invention are useful in the treatment of central nervous disorders including, Parkinson disease, Huntington's disease, attention disorder, cognition, Alzheimer disease, depression and hypertension.

  本发明涉及一种新型的通式A的(4E)-4-(4-取代苯基亚甲基氨基)-2,3-二氢-3-取代-2-硫代噻唑-5-碳腈化合物及其制备方法。本发明的化合物可用于治疗包括帕金森病、亨廷顿病、注意力障碍、认知、阿尔茨海默病、抑郁症和高血压在内的中枢神经系统疾病。
• 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.
• Design and synthesis of (4E)-4-(4-substitutedbenzylideneamino)-3-substituted-2,3-dihydro-2-thioxothiazole-5-carbonitrile as novel A2A receptor antagonists
  作者：Chandra Bhushan Mishra、Dimpy Sharma、Amresh Prakash、Namrata Kumari、Nitin Kumar、Pratibha Mehta Luthra

  DOI：10.1016/j.bmc.2013.07.005

  日期：2013.10

  Novel 2-thioxothiazole derivatives (6-19) as potential adenosine A(2A) receptor (A(2A)R) antagonists were synthesized. The strong interaction of the compounds (6-19) with A(2A)R in docking study was confirmed by high binding affinity with human A(2A)R expressed in HEK293T cells using radioligand-binding assay. The compound 19 demonstrated very high selectivity for A(2A)R as compared to standard A(2A)R antagonist SCH58261. Decrease in A(2A)R-coupled release of endogenous cAMP in treated HEK293T cells demonstrated in vitro A(2A)R antagonist potential of the compound 19. Attenuation in haloperidol-induced impairment (catalepsy) in Swiss albino male mice pre-treated with compound 19 is evocative to explore its prospective in therapy of PD. (c) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of some urea and thiourea derivatives of 3-phenyl/ethyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidine and their antagonistic effects on haloperidol-induced catalepsy and oxidative stress in mice
  作者：Faizul Azam、Ismail A. Alkskas、Musa A. Ahmed

  DOI：10.1016/j.ejmech.2009.04.007

  日期：2009.10

  A series of 3-phenyl/ethyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-7-yl urea and thiourea derivatives were designed and synthesized. All the compounds have been evaluated for their anti parkinsonian activity in catalepsy induced by haloperidol in mice. A majority of the compounds exhibited significant anti parkinsonian activity after intraperitoneal administration. The most active compound carries methoxy group at 2-position of the phenyl ring. Some of the potent compounds were selected for biochemical estimations of malondialdehyde, glutathione, superoxide dismutase and glutathione peroxidase from brain homogenate to highlight the neuroprotective properties associated with them. The results obtained in the present study may lead to the development of a suitable approach to the treatment of Parkinson's disease and may be the starting point for the future drug design. (C) 2009 Elsevier Masson SAS. All rights reserved.