4-amino-3-butyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile | 1225513-71-2

• 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-butyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile
• 英文别名: 4-amino-3-butyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carbonitrile；4-amino-N3-butyl-2-thioxo-1,3-thiazole-5-carbonitrile；4-Amino-3-butyl-2-sulfanylidene-1,3-thiazole-5-carbonitrile；4-amino-3-butyl-2-sulfanylidene-1,3-thiazole-5-carbonitrile
• CAS: 1225513-71-2
• 化学式: C₈H₁₁N₃S₂
• 分子量: 213.327
• InChiKey: SCQGYTFNHXUPKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-3-butyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile 、 对氟苯甲醛 在 aluminum (III) chloride 作用下， 以 氯仿 为溶剂， 反应 8.0h， 以2 g的产率得到(4E)-4-(4-fluorobenzylideneamino)-3-butyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile
  参考文献：
  名称：

  [EN] (4E)-4-(4-SUBSTITUTED BENZYLIDENEAMINO)-2,3-DIHYDRO-3- SUBSTITUTED-2-THIOXOTHIAZOLE-5-CARBONITRILES AS A2AR ANTAGONIST AND PROCESS FOR PREPARATION THEREOF
  [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

  摘要：

  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。

  公开号：

  WO2014106861A1
• 作为产物：
  描述：

  丁基异硫氰酸酯 、 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 4.25h， 以84%的产率得到4-amino-3-butyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile
  参考文献：
  名称：

  Design and synthesis of (4E)-4-(4-substitutedbenzylideneamino)-3-substituted-2,3-dihydro-2-thioxothiazole-5-carbonitrile as novel A2A receptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.07.005

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20140329814A2

  公开（公告）日：2014-11-06

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及制药组合物，包括上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物，该化合物为公式A、公式B、公式C或公式D。本发明还涉及该制药组合物的制药配方，以及使用该组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• 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.
• (4E)-4-(4-SUBSTITUTED BENZYLIDENEAMINO)-2,3-DIHYDRO-3- SUBSTITUTED-2-THIOXOTHIAZOLE-5-CARBONITRILES AS A2AR ANTAGONIST AND PROCESS FOR PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：EP2941420A1

  公开（公告）日：2015-11-11
• (4E)-4-(4-SUBSTITUTED BENZYLIDENEAMINO)-2,3-DIHYDRO-3-SUBSTITUTED-2-THIOXOTHIAZOLE-5-CARBONITRILES AS A2AR ANTAGONIST AND PROCESS FOR PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20150336912A1

  公开（公告）日：2015-11-26

  The present invention provides (4E)-4-(4-substituted benzylideneamino)-2,3-dihydro-3-substituted-2-thioxothiazole-5-carbonitriles of general formula A, below, and a process for the preparation thereof.