3,6-diamino-4-(2-thiophene)thieno{2,3-b}pyridine | 136633-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3,6-diamino-4-(2-thiophene)thieno{2,3-b}pyridine
• 英文别名: Ethyl 3,6-diamino-5-cyano-4-thiophen-2-ylthieno[2,3-b]pyridine-2-carboxylate
• CAS: 136633-86-8
• 化学式: C₁₅H₁₂N₄O₂S₂
• 分子量: 344.418
• InChiKey: WVJNNHIFOZFXMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2-噻吩亚甲基)甲烷-1,1-二甲腈 在 N-甲基吗啉 、 氢氧化钾 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3,6-diamino-4-(2-thiophene)thieno{2,3-b}pyridine
  参考文献：
  名称：

  Cyclization reactions of nitriles

  摘要：

  The interaction of 2-thienylidene derivatives of malononitrile and cyanothioacetamide with methylene active nitriles gives 2,6-diamino-3,5-dicyano-4-(2-thienyl)-4H-thiopyran which is smoothly recrystallized into 6-amino-3,5-dicyano-4-(2-thienyl)-2-(1H)-pyridinethione. The latter is easily alkylated at the sulfur atom by alpha-halocarbonyl compounds. This reaction was used in the synthesis of 3,6-diamino-4-(2-thienyl)thieno[2,3-b]pyridines.

  DOI：

  10.1007/bf00961252

文献信息

• Cyclization reactions of nitriles
  作者：S. V. Matrosova、V. K. Zav'yalova、V. P. Litvinov、Yu. A. Sharanin

  DOI：10.1007/bf00961252

  日期：1991.7

  The interaction of 2-thienylidene derivatives of malononitrile and cyanothioacetamide with methylene active nitriles gives 2,6-diamino-3,5-dicyano-4-(2-thienyl)-4H-thiopyran which is smoothly recrystallized into 6-amino-3,5-dicyano-4-(2-thienyl)-2-(1H)-pyridinethione. The latter is easily alkylated at the sulfur atom by alpha-halocarbonyl compounds. This reaction was used in the synthesis of 3,6-diamino-4-(2-thienyl)thieno[2,3-b]pyridines.
• MATROSOVA, S. V.;ZAVYALOVA, V. K.;LITVINOV, V. P.;SHARANIN, YU. A., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1643-1646
  作者：MATROSOVA, S. V.、ZAVYALOVA, V. K.、LITVINOV, V. P.、SHARANIN, YU. A.

  DOI：——

  日期：——
• Thiophenethieno[2,3-b]pyridine-chitosan nanorods; synthesis, characterization, BSA-Binding and kinetic interactions with BSA, antibacterial and in-vitro release studies
  作者：Hanaa Mansour

  DOI：10.1016/j.molstruc.2020.128611

  日期：2020.11

  The current work aimed to developed and investigate the potential of thiophenethieno[2,3-b]pyridinechitosan nanorods (CS-TTP) for the drug delivery system, BSA-binding and antibacterial activity for biomedical applications. Thiophenethieno[2,3-b]pyridine (TTP), a new member of thieno[2,3-b]pyridine containing thiophene moiety, has been synthesized and loaded on chitosan nanoparticle to give CS-TTP nanorods. Interestingly, CS-TTP showed a rod-like structure with a thickness of 5 nm and a length of 40 nm with uniform size over their entire length. The in vitro TTP release from CS-TTP was investigated in different pH media and the basic medium was found to be the optimal release condition. In-vitro BSA-binding to TPT, TTP, and CS-TTP were investigated because the potential of these compounds to act as pharmaceutical agents depends on their binding ability. The stopped-flow technique was used to obtain the kinetic parameters and also to suggest a mechanism. The results showed that the formation of CS-TTP nanorods enhances the binding rate and kinetic stability through coordination affinity compared to TPT and TTP and also change the pathway mechanism. Additionally, the antibacterial assessments on four bacteria strain correlated very well with the kinetic stability as BSA-CS-UP is the kinetically most stable and also showed better antibacterial activity compared to BSA-TPT and BSA-TTP. (C) 2020 Elsevier B.V. All rights reserved.