1-phenyl-3-(5-thioxo-1,2,4-triazol-3-yl) β-carboline | 1085708-94-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-phenyl-3-(5-thioxo-1,2,4-triazol-3-yl) β-carboline
• 英文别名: 5-(1-phenyl-9H-pyrido[3,4-b]indol-3-yl)-1,2-dihydro-1,2,4-triazole-3-thione
• CAS: 1085708-94-6
• 化学式: C₁₉H₁₃N₅S
• 分子量: 343.412
• InChiKey: YWOZPMPODRHUNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-phenyl-β-carboline-3-carboxylic acid hydrazide 在 盐酸 、 potassium hydrogensulfate 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 96.0h， 生成 1-phenyl-3-(5-thioxo-1,2,4-triazol-3-yl) β-carboline
  参考文献：
  名称：

  Discovery of β-Carboline Oxadiazole Derivatives as Fungicidal Agents against Rice Sheath Blight

  摘要：

  A series of beta-carboline oxadiazoles were synthesized, and their fungicidal activities and mechanism of action against rice sheath blight caused by Rhizoctonia solani was evaluated. The results showed that all of these compounds exhibited significant in vitro fungicidal activity. Significantly, compound Si (EC50 = 4.2 mu g/mL) displayed the best efficacy and superior fungicidal activity compared to validamycin A (EC50 = 197.6 mu g/mL). Moreover, the in vivo test also demonstrated that compound Si could effectively control rice sheath blight and showed higher in vivo protective and curative activities against R. solani than validamycin A. Preliminary mechanism studies revealed that compound Si caused the loss of mitochondrial membrane potential, reactive oxygen species accumulation, cell membrane destruction, and DNA synthesis interference. These findings indicated that compound Si displayed superior fungicidal activities against R solani and could be a potential fungicidal candidate against rice sheath blight.

  DOI：

  10.1021/acs.jafc.8b02124

文献信息

• Synthesis and antitumoral activity of novel 3-(2-substituted-1,3,4-oxadiazol-5-yl) and 3-(5-substituted-1,2,4-triazol-3-yl) β-carboline derivatives
  作者：Anelise S. Nazari Formagio、Lilian T. Düsman Tonin、Mary Ann Foglio、Christiana Madjarof、João Ernesto de Carvalho、Willian Ferreira da Costa、Flávia P. Cardoso、Maria Helena Sarragiotto

  DOI：10.1016/j.bmc.2008.10.008

  日期：2008.11

  Several novel 1-substituted-phenyl beta-carbolines bearing the 2-substituted-1,3,4-oxadiazol-5-yl and 5-substituted-1,2,4-triazol-3-yl groups at C-3 were synthesized and evaluated for their in vitro anticancer activity. The assay results pointed thirteen compounds with growth inhibition effect (GI(50) < 100 mu M) for all eight different types of human cancer cell lines tested. The b-carbolines 7a and 7h, bearing the 3-(2-metylthio-1,3,4-oxadiazol-5-yl) group, displayed high selectivity and potent anticancer activity against ovarian cell line with GI50 values lying in the nanomolar concentration range (GI(50) = 10 nM for both compounds). The 1-(N,N-dimethylaminophenyl)-3-(5-thioxo-1,2,4-triazol-3-yl) beta-carboline (8g) was the most active compound, showing particular effectiveness on lung (GI(50) = 0.06 mu M), ovarian and renal cell lines. The potent anticancer activity presented for synthesized compounds 7a, 7h, and 8g, together with their easiness of synthesis, makes these compounds promising anticancer agents. (C) 2008 Elsevier Ltd. All rights reserved.
• Discovery of β-Carboline Oxadiazole Derivatives as Fungicidal Agents against Rice Sheath Blight
  作者：Zhi-Jun Zhang、Zhi-Yan Jiang、Qi Zhu、Guo-Hua Zhong

  DOI：10.1021/acs.jafc.8b02124

  日期：2018.9.19

  A series of beta-carboline oxadiazoles were synthesized, and their fungicidal activities and mechanism of action against rice sheath blight caused by Rhizoctonia solani was evaluated. The results showed that all of these compounds exhibited significant in vitro fungicidal activity. Significantly, compound Si (EC50 = 4.2 mu g/mL) displayed the best efficacy and superior fungicidal activity compared to validamycin A (EC50 = 197.6 mu g/mL). Moreover, the in vivo test also demonstrated that compound Si could effectively control rice sheath blight and showed higher in vivo protective and curative activities against R. solani than validamycin A. Preliminary mechanism studies revealed that compound Si caused the loss of mitochondrial membrane potential, reactive oxygen species accumulation, cell membrane destruction, and DNA synthesis interference. These findings indicated that compound Si displayed superior fungicidal activities against R solani and could be a potential fungicidal candidate against rice sheath blight.