4-chloro-6-(1H-indol-3-yl)-2-thioxo-1,2-dihydropyrimidine-5-carbonitrile | 1558023-11-2

• 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: 4-chloro-6-(1H-indol-3-yl)-2-thioxo-1,2-dihydropyrimidine-5-carbonitrile
• CAS: 1558023-11-2
• 化学式: C₁₃H₇ClN₄S
• 分子量: 286.744
• InChiKey: GEPFWLIHWNGAND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.26
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-chloro-6-(1H-indol-3-yl)-2-thioxo-1,2-dihydropyrimidine-5-carbonitrile 在 一水合肼 作用下， 反应 0.33h， 生成 7-(1H-indol-3-yl)-5-thioxo-5,6-dihydro[1,2,4]triazolo[1,5-c]pyrimidine-8-carbonitrile
  参考文献：
  名称：

  Novel indolyl-pyrimidine derivatives: synthesis, antimicrobial, and antioxidant evaluations

  摘要：

  In the present study, a novel series of indolyl-pyrimidines (1-13) were synthesized starting from 4-hydrazinopyrimidine-5-carbonitrile 3. Elemental analysis, IR, H-1-NMR, C-13-NMR, and mass spectral data elucidated structure of newly synthesized compounds. All compounds were screened for their in vitro antibacterial, antifungal, and some for antioxidant activities. Compounds 5, 9g, 9i, and 9j showed pronounced antimicrobial activity against Staphylococcus aureus, Bacillus cereus, Escherichia coli, Candida albicans, and Aspergillus flavus compared to the reference drugs, while compounds 3 and 9g displayed promising free radical scavenging activity and found to be more potent than standard, ascorbic acid (vitamin C). Further, some compounds were evaluated for cytotoxic activity by SRB assay method against human colon carcinoma (CaCo-2) and showed that compounds 4 and 9g were found to be the highly active compared to the reference drug doxorubicin. Their structure and activity relationship were discussed.

  DOI：

  10.1007/s00044-014-0916-1
• 作为产物：
  描述：

  6-(1H-indol-3-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 在 五氯化磷 、 三氯氧磷 作用下， 反应 8.0h， 以50%的产率得到4-chloro-6-(1H-indol-3-yl)-2-thioxo-1,2-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  Novel indolyl-pyrimidine derivatives: synthesis, antimicrobial, and antioxidant evaluations

  摘要：

  In the present study, a novel series of indolyl-pyrimidines (1-13) were synthesized starting from 4-hydrazinopyrimidine-5-carbonitrile 3. Elemental analysis, IR, H-1-NMR, C-13-NMR, and mass spectral data elucidated structure of newly synthesized compounds. All compounds were screened for their in vitro antibacterial, antifungal, and some for antioxidant activities. Compounds 5, 9g, 9i, and 9j showed pronounced antimicrobial activity against Staphylococcus aureus, Bacillus cereus, Escherichia coli, Candida albicans, and Aspergillus flavus compared to the reference drugs, while compounds 3 and 9g displayed promising free radical scavenging activity and found to be more potent than standard, ascorbic acid (vitamin C). Further, some compounds were evaluated for cytotoxic activity by SRB assay method against human colon carcinoma (CaCo-2) and showed that compounds 4 and 9g were found to be the highly active compared to the reference drug doxorubicin. Their structure and activity relationship were discussed.

  DOI：

  10.1007/s00044-014-0916-1