2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetohydrazide | 1343898-18-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetohydrazide
• 英文别名: 2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazide；2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetohydrazide
• CAS: 1343898-18-9
• 化学式: C₉H₁₃N₃OS
• 分子量: 211.288
• InChiKey: SOXFKLVVKZHGHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetohydrazide 、 苯甲腈 在 4-二甲氨基吡啶 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以91%的产率得到5-((5-phenyl-1H-1,2,4-triazol-3-yl)methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
  参考文献：
  名称：

  Synthesis, docking and ADMET prediction of novel 5-((5-substituted-1-H-1,2,4-triazol-3-yl) methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine as antifungal agents

  摘要：

  A novel series of 5-((5-substituted-1H-1,2,4-triazol-3-yl)methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridines 5(a-i) has been synthesized from thienopyridine hydrazide, substituted aromatic nitriles using 4-dimethylaminopyridine (DMAP) as a catalyst under microwave irradiation and evaluated for their in vitro antifungal activity. Compound 5g is found to be more potent against Candida albicans when compared with miconazole. Docking study of the newly synthesized compounds was performed, and results showed good binding mode in the active site of fungal enzyme P450 cytochrome lanosterol 14 alpha-demethylase. ADMET properties of synthesized compounds were also analyzed and showed good drug like properties. The results of in vitro antifungal activity, docking study and ADMET prediction revealed that the synthesized compounds have potential antifungal activity and can be further optimized and developed as a lead compound. (C) 2014 Jaiprakash N. Sangshetti. Published by Elsevier B.V.

  DOI：

  10.1016/j.cclet.2014.04.003
• 作为产物：
  描述：

  ethyl 2(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetate 在 一水合肼 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 生成 2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetohydrazide
  参考文献：
  名称：

  Synthesis, antileishmanial activity and docking study of N′-substitutedbenzylidene-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazides

  摘要：

  A series of N '-substitutedbenzylidene-2-(6,7-dihydrothieno[ 3,2-c] pyridin-5(4H)-yl) acetohydrazide derivatives is synthesized and evaluated for antileishmanial activity against Leishmania donovani promastigotes. Compounds 9a and 9i were shown significant antileishmanial when compared with standard sodium stilbogluconate. Antimicrobial study revealed that compound 9b has potent as well as broad spectrum antibacterial activity when compared with ampicillin and compound 9e showed promising antifungal activity when compared with miconazole. Also, none of the synthesized compounds showed cytotoxicity up to tested concentration. Further, docking study against pteridine reductase 1 enzyme of L. donovani showed good binding interactions. ADME properties of synthesized compounds were also analyzed and showed potential to develop as good oral drug candidates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.035

文献信息

• Synthesis, docking and ADMET prediction of novel 5-((5-substituted-1-H-1,2,4-triazol-3-yl) methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine as antifungal agents
  作者：Jaiprakash N. Sangshetti、Firoz A. Kalam Khan、Rashmi S. Chouthe、Manoj G. Damale、Devanand B. Shinde

  DOI：10.1016/j.cclet.2014.04.003

  日期：2014.7

  A novel series of 5-((5-substituted-1H-1,2,4-triazol-3-yl)methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridines 5(a-i) has been synthesized from thienopyridine hydrazide, substituted aromatic nitriles using 4-dimethylaminopyridine (DMAP) as a catalyst under microwave irradiation and evaluated for their in vitro antifungal activity. Compound 5g is found to be more potent against Candida albicans when compared with miconazole. Docking study of the newly synthesized compounds was performed, and results showed good binding mode in the active site of fungal enzyme P450 cytochrome lanosterol 14 alpha-demethylase. ADMET properties of synthesized compounds were also analyzed and showed good drug like properties. The results of in vitro antifungal activity, docking study and ADMET prediction revealed that the synthesized compounds have potential antifungal activity and can be further optimized and developed as a lead compound. (C) 2014 Jaiprakash N. Sangshetti. Published by Elsevier B.V.
• Synthesis, antileishmanial activity and docking study of N′-substitutedbenzylidene-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazides
  作者：Jaiprakash N. Sangshetti、Rehan I. Shaikh、Firoz A. Kalam Khan、Rajendra H. Patil、Sayali D. Marathe、Wasudev N. Gade、Devanand B. Shinde

  DOI：10.1016/j.bmcl.2014.01.035

  日期：2014.3

  A series of N '-substitutedbenzylidene-2-(6,7-dihydrothieno[ 3,2-c] pyridin-5(4H)-yl) acetohydrazide derivatives is synthesized and evaluated for antileishmanial activity against Leishmania donovani promastigotes. Compounds 9a and 9i were shown significant antileishmanial when compared with standard sodium stilbogluconate. Antimicrobial study revealed that compound 9b has potent as well as broad spectrum antibacterial activity when compared with ampicillin and compound 9e showed promising antifungal activity when compared with miconazole. Also, none of the synthesized compounds showed cytotoxicity up to tested concentration. Further, docking study against pteridine reductase 1 enzyme of L. donovani showed good binding interactions. ADME properties of synthesized compounds were also analyzed and showed potential to develop as good oral drug candidates. (C) 2014 Elsevier Ltd. All rights reserved.