5-acetyl-1,2-dihydro-4-(1H-indol-3-yl)-6-methyl-2-thioxopyridine-3-carbonitrile | 952608-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-acetyl-1,2-dihydro-4-(1H-indol-3-yl)-6-methyl-2-thioxopyridine-3-carbonitrile
• 英文别名: 5-acetyl-4-(1H-indol-3-yl)-6-methyl-2-sulfanylidene-1H-pyridine-3-carbonitrile
• CAS: 952608-58-1
• 化学式: C₁₇H₁₃N₃OS
• 分子量: 307.376
• InChiKey: BCJXKUHEZYUABQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-acetyl-1,2-dihydro-4-(1H-indol-3-yl)-6-methyl-2-thioxopyridine-3-carbonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 1-[3-amino-4-(1H-indol-3-yl)-6-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl]ethanone
  参考文献：
  名称：

  Synthesis, Reactions, and Biological Activity of 4(1H-Indol-3-yl)-2-Thioxopyridine Derivatives

  摘要：

  2-cyanoethanthioamide 1 reacted with 1H-indole-3-carbaldehyde 2 to give the corm responding 2-cyano-3-(1H-indol-3-yl)prop-2-enethioamide 3 in a very good yield, which in turn reacted with 2,4-pentanedione 4 to give 5-acetyl-1,2-dihydro-4(1H-indol-3-yl)-6-methyl-2-thioxopyridine-3-carbonitrile. The synthetic potential of 5 was examined through its reaction with several active halogen-containing reagents, e.g., 1-chloropropan-2-one, chloroacetonitrile, 2-chloroacetamide, ethyl chloroacetate, chloroacetic acid, ethyl chloroformate, methyl iodide, and 2-bromo-1-arylethanones 13a-c to give the corresponding thieno[2,3-b]pyridine derivatives 15a-c. The data of elemental analysis as well as the data of IR (cm(-1)), H-1 NMR (delta ppm), and mass spectra elucidated structures of all newly synthesized heterocyclic compounds. All newly synthesized heterocyclic compounds were evaluated as antimicrobial and GST enzyme activity and at the GSH enzyme level.

  DOI：

  10.1080/10426500601013216
• 作为产物：
  描述：

  乙酰丙酮 、 (2E)-2-cyano-3-(1H-indol-3-yl)prop-2-enethioamide 在 哌啶 、 吡啶 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 5-acetyl-1,2-dihydro-4-(1H-indol-3-yl)-6-methyl-2-thioxopyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis, Reactions, and Biological Activity of 4(1H-Indol-3-yl)-2-Thioxopyridine Derivatives

  摘要：

  2-cyanoethanthioamide 1 reacted with 1H-indole-3-carbaldehyde 2 to give the corm responding 2-cyano-3-(1H-indol-3-yl)prop-2-enethioamide 3 in a very good yield, which in turn reacted with 2,4-pentanedione 4 to give 5-acetyl-1,2-dihydro-4(1H-indol-3-yl)-6-methyl-2-thioxopyridine-3-carbonitrile. The synthetic potential of 5 was examined through its reaction with several active halogen-containing reagents, e.g., 1-chloropropan-2-one, chloroacetonitrile, 2-chloroacetamide, ethyl chloroacetate, chloroacetic acid, ethyl chloroformate, methyl iodide, and 2-bromo-1-arylethanones 13a-c to give the corresponding thieno[2,3-b]pyridine derivatives 15a-c. The data of elemental analysis as well as the data of IR (cm(-1)), H-1 NMR (delta ppm), and mass spectra elucidated structures of all newly synthesized heterocyclic compounds. All newly synthesized heterocyclic compounds were evaluated as antimicrobial and GST enzyme activity and at the GSH enzyme level.

  DOI：

  10.1080/10426500601013216

文献信息

• Synthesis, Reactions, and Biological Activity of 4(1<i>H</i>-Indol-3-yl)-2-Thioxopyridine Derivatives
  作者：Fawzy A. Attaby、Mostafa M. Ramla、Eman M. Gouda

  DOI：10.1080/10426500601013216

  日期：2007.4.1

  2-cyanoethanthioamide 1 reacted with 1H-indole-3-carbaldehyde 2 to give the corm responding 2-cyano-3-(1H-indol-3-yl)prop-2-enethioamide 3 in a very good yield, which in turn reacted with 2,4-pentanedione 4 to give 5-acetyl-1,2-dihydro-4(1H-indol-3-yl)-6-methyl-2-thioxopyridine-3-carbonitrile. The synthetic potential of 5 was examined through its reaction with several active halogen-containing reagents, e.g., 1-chloropropan-2-one, chloroacetonitrile, 2-chloroacetamide, ethyl chloroacetate, chloroacetic acid, ethyl chloroformate, methyl iodide, and 2-bromo-1-arylethanones 13a-c to give the corresponding thieno[2,3-b]pyridine derivatives 15a-c. The data of elemental analysis as well as the data of IR (cm(-1)), H-1 NMR (delta ppm), and mass spectra elucidated structures of all newly synthesized heterocyclic compounds. All newly synthesized heterocyclic compounds were evaluated as antimicrobial and GST enzyme activity and at the GSH enzyme level.