4-amino-N3-(2-phenylethyl)-2-thioxo-1,3-thiazole-5-carbonitrile | 1454903-71-9

• 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-N3-(2-phenylethyl)-2-thioxo-1,3-thiazole-5-carbonitrile
• 英文别名: 4-amino-3-phenylethyl-2,3-dihydro-2-thioxo-1,3-thiazole-5-carbonitrile；4-Amino-3-(2-phenylethyl)-2-sulfanylidene-1,3-thiazole-5-carbonitrile；4-amino-3-(2-phenylethyl)-2-sulfanylidene-1,3-thiazole-5-carbonitrile
• CAS: 1454903-71-9
• 化学式: C₁₂H₁₁N₃S₂
• 分子量: 261.371
• InChiKey: PQLHTMKNAXXUHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-N3-(2-phenylethyl)-2-thioxo-1,3-thiazole-5-carbonitrile 、 对氟苯甲醛 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (E)-4-(4-flurobenzylideneamino)-N3-(2-phenylethyl)-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：

  2-苯基乙基异硫代氰酸酯 、 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75%的产率得到4-amino-N3-(2-phenylethyl)-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

• (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.
• US9518033B2
  申请人：——

  公开号：US9518033B2

  公开（公告）日：2016-12-13
• 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.
• [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。