6-amino-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile | 111971-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-amino-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile
• 英文别名: 2-Amino-6-mercaptopyridine-3,5-dicarbonitrile；2-amino-6-sulfanylidene-1H-pyridine-3,5-dicarbonitrile
• CAS: 111971-56-3
• 化学式: C₇H₄N₄S
• mdl: MFCD06382875
• 分子量: 176.202
• InChiKey: AOLHMHYTLZBBKT-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  270.5±50.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 3,6-Diamino-2-(4-nitrophenyl)thieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  吡啶并[3'，2'：4,5] thieno [2,3-c] cinnolines的合成—一种新的杂环系统

  摘要：

  DOI：

  10.1007/bf02290619
• 作为产物：
  描述：

  2,6-diamino-3,5-dicyano-thiopyran 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以91%的产率得到6-amino-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Elnagdi, Mohamed Hilmy; Ghozlan, Said Ahmed Soliman; Abdelrazek, Fathy Mohamed, Journal of Chemical Research, Miniprint, 1991, # 5, p. 1021 - 1032

  摘要：

  DOI：

文献信息

• Adenosine receptor ligands and their use in the treatment of disease
  申请人：——

  公开号：US20010027196A1

  公开（公告）日：2001-10-04

  The invention relates to cyclic heteroaromatic compounds, containing at least one nitrogen atom, and to their use in the manufacture of medicaments for the treatment of diseases, related to adenosine receptor modulators, such as Alzheimer's disease, Parkinson's disease, neuroprotection, schizophrenia, anxiety, pain, respiration deficits, depression, asthma, allergic responses, hypoxia, ischaemia, seizure, substance abuse, sedation and they may be active as muscle relaxants, antipsychotics, anti epileptics, anticonvulsants and cardiaprotective agents.

  这项发明涉及含有至少一个氮原子的环状杂芳化合物，以及它们在制造用于治疗与腺苷受体调节剂相关的疾病的药物中的应用，如阿尔茨海默病、帕金森病、神经保护、精神分裂症、焦虑、疼痛、呼吸功能障碍、抑郁症、哮喘、过敏反应、缺氧、缺血、癫痫、物质滥用、镇静，它们可能作为肌肉松弛剂、抗精神病药、抗癫痫药、抗惊厥药和心脏保护剂而具有活性。
• Reactions of N-(2-chloroacetyl)-α-amino acids with 3-cyanopyridine-2(1H)-thiones. New promising route to 3,4-dihydropyrido[3",2":4,5]thieno[3,2-e][1,4]diazepine-2(1H),5-diones
  作者：A. E. Fedorov、A. M. Shestopalov、P. A. Belyakov

  DOI：10.1023/b:rucb.0000011878.52263.c4

  日期：2003.10

  The reactions of N-(2-chloroacetyl)-α-amino acids with 3-cyanopyridine-2(1H)-thiones afforded N-(3-aminothieno[2,3-b]pyridin-2-ylcarbonyl)-α-amino acids. Heating of the latter smoothly produced 3,4-dihydropyrido[3",2":4,5]thieno[3,2-e][1,4]diazepine-2(1H),5-diones in high yields.

  N-(2-氯乙酰基)-α-氨基酸与 3-氰基吡啶-2(1H)-硫酮反应得到 N-(3-氨基噻吩并[2,3-b]吡啶-2-基羰基)-α-氨基酸。后者的加热平稳地以高产率产生 3,4-dihydropyrido[3",2":4,5]thieno[3,2-e][1,4]diazepine-2(1H),5-diones。
• Design, synthesis and biological study of novel pyrido[2,3-d]pyrimidine as anti-proliferative CDK2 inhibitors
  作者：Diaa A. Ibrahim、Nasser S.M. Ismail

  DOI：10.1016/j.ejmech.2011.09.041

  日期：2011.12

  The design and synthesis of a small library of 4-aminopyrido[2,3-d]pyrimidine derivatives is reported. The potential activity of these compounds as CDK2/Cyclin A, CDK4/Cyclin D, EGFR and anti-tumor was evaluated by cytotoxicity studies in A431a, SNU638b, HCT116 and inhibition of CDK2-Cyclin A, CDK4/Cyclin D and EGFR enzyme activity in vitro. The anti-proliferative and CDK2-Cyclin A inhibitory activity

  报道了4-氨基吡啶并[2,3-d]嘧啶衍生物的小文库的设计和合成。通过A431a，SNU638b，HCT116中的细胞毒性研究以及CDK2-Cyclin A，CDK4 / Cyclin D和EGFR酶活性的抑制，评估了这些化合物作为CDK2 / Cyclin A，CDK4 / Cyclin D，EGFR和抗肿瘤药的潜在活性。体外。化合物4c和11a的抗增殖和CDK2-Cyclin A抑制活性分别比roscovotine活性高，IC 50分别为0.3和0.09μM 。进行了分子建模研究，包括适应3D药效团模型，对接细胞周期蛋白依赖性激酶2（CDK2）活性位点和结合能的计算，这些研究表明，与ATP相比，这些类似物在CDK2结合口袋内的结合方向相同。
• Pyrolysis and photolysis processes of pyran and thiopyran derivatives
  作者：A. A. Atalla、A. M. Hussein、M. Z. A. Badr

  DOI：10.1007/bf00807636

  日期：1997.1

  Pyrolysis and photolysis of 2-amino-3,5-dicyano-6-phenyl-4H-pyran (1) afford HNCO, acrylonitrile, cinnamonitrile, and 2-hydroxy-3,5-dicyano-6-phenylpyridine. Pyrolysis of 2-carboxyimino-3,5-dicyano-6-phenyI-4H-pyran (2) gives HCN, acrylonitrile, cinnamonitrile and 2-hydroxy-3,5-dicyano-6-phenylpyridine. Furthermore, both pyrolysis and photolysis of 2,6-diamino-3,5-dicyanothiopyran (3a) gives rise to HNCS, acrylonitrile and 6-amino-3,5-dicyano-6-mercaptopyridin, Moreover, comparative studies of pyrolysis and photolysis of 2,6-dicyano-4-arylthiopyran derivatives 3b-d revealed similar results. The similarity of products obtained from pyrolysis and photolysis and the mechanistic implications of these data are discussed.
• A simple one-pot synthesis of new 4-unsubstituted 2-oxo(thioxo)-1,2-dihydropyridine-3-carbonitriles, -3-carboxamides, and -3-carboxylic acid esters and 2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitriles
  作者：I. V. Dyachenko、V. D. Dyachenko

  DOI：10.1134/s1070428015090146

  日期：2015.9

  One-pot condensations of formaldehyde with CH acids and enamines afforded new 4-unsubstituted derivatives of 2-oxo(thioxo)-1,2-dihydropyridine-3-carbonitrile, 2-oxo(thioxo)-1,2-dihydropyridine-3-carboxamide, ethyl 2-oxo(thioxo)-1,2-dihydropyridine-3-carboxylate, and 2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, which were subjected to alkylation.