1-phenyl-3-[5-(2-mercapto)-1,3,4-oxazoline]-β-carboline | 1085708-76-4

• 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-(2-mercapto)-1,3,4-oxazoline]-β-carboline
• 英文别名: 1-phenyl-3-(2-thioxo-1,3,4-oxadiazol-5-yl)-9H-pyrido[3,4-b]indole；1-phenyl-3-(2-thioxo-1,3,4-oxadiazol-5-yl) β-carboline；5-(1-phenyl-9H-pyrido[3,4-b]indol-3-yl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 1085708-76-4
• 化学式: C₁₉H₁₂N₄OS
• 分子量: 344.396
• InChiKey: LLZUSGLHLQCCLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  94.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-[5-(2-mercapto)-1,3,4-oxazoline]-β-carboline 在 肼 作用下， 反应 96.0h， 生成 1-phenyl-3-(4-amino-5-thioxo-1,2,4-triazol-3-yl) β-carboline
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.10.008
• 作为产物：
  描述：

  methyl 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 potassium permanganate 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1-phenyl-3-[5-(2-mercapto)-1,3,4-oxazoline]-β-carboline
  参考文献：
  名称：

  鉴定含有 1,3,4-恶二唑基的 β-咔啉衍生物作为具有抗糖尿病活性的新型 α-葡萄糖苷酶抑制剂

  摘要：

  在本研究中，我们设计并合成了一类新型的含1,3,4-恶二唑基的β-咔啉衍生物，即化合物f1∼f35作为潜在的α-葡萄糖苷酶抑制剂。所有合成的化合物均具有出色的α-葡萄糖苷酶抑制活性，IC 50值在3.07–15.49 μM范围内，这表明它们的活性比阳性对照阿卡波糖（IC 50  = 564.28 μM）高36∼183倍。其中，化合物f26表现出最高的α-葡萄糖苷酶抑制活性（IC 50  = 3.07 μM），并被证明具有可逆且非竞争性抑制剂的作用。通过3D荧光光谱、圆二色光谱和分子对接等机理研究表明，化合物f26与α-葡萄糖苷酶通过氢键和疏水相互作用发生络合，导致α-葡萄糖苷酶的构象和二级结构发生变化，进一步抑制α-葡萄糖苷酶的活性。酶活性。体内实验结果表明，口服化合物f26 （50mg/kg/天）可明显降低糖尿病小鼠的空腹血糖水平，改善糖耐量和血脂异常。目前的研究结果表明，化合物f26可

  DOI：

  10.1016/j.ejmech.2023.115795

文献信息

• Design, Synthesis and Bioactivity Evaluation of Novel β-carboline 1,3,4-oxadiazole Derivatives
  作者：Zhi-Jun Zhang、Jing-Jing Zhang、Zhi-Yan Jiang、Guo-Hua Zhong

  DOI：10.3390/molecules22111811

  日期：——

  A series of novel β-carboline 1,3,4-oxadiazole derivatives were designed and synthesized, and the in vitro cytotoxic activity against Sf9 cells and growth inhibitory activity against Spodoptera litura were evaluated. Bioassay results showed that most of these compounds exhibited excellent in vitro cytotoxic activity. Especially, compound 37 displayed the best efficacy in vitro (IC50 = 3.93 μM), and

  设计并合成了一系列新型β-咔啉1,3,4-恶二唑衍生物，并评估了其体外对Sf9细胞的细胞毒活性和对斜纹夜蛾的生长抑制活性。生物测定结果表明，这些化合物中的大多数表现出优异的体外细胞毒活性。特别是，化合物 37 在体外表现出最佳功效（IC50 = 3.93 μM），并且比喜树碱（CPT）（IC50 = 18.95 μM）强五倍。此外，化合物 5 和 37 可以诱导细胞凋亡和细胞周期停滞并刺激 Sf9 细胞中的 Sf-caspase-1 活化。体内生物测定还表明，化合物5和37可以显着抑制斜纹夜蛾幼虫的生长，降低幼虫和蛹的重量。根据这些生物测定结果，
• Synthesis, antitumor and antimicrobial activity of novel 1-substituted phenyl-3-[3-alkylamino(methyl)-2-thioxo-1,3,4-oxadiazol-5-yl] β-carboline derivatives
  作者：Franciele C. Savariz、Anelise S. N. Formagio、Valéria A. Barbosa、Mary Ann Foglio、João E. de Carvalho、Marta C. T. Duarte、Benedito P. Dias Filho、Maria Helena Sarragiotto

  DOI：10.1590/s0103-50532010000200014

  日期：——

  With the purpose of activity enhancement of 1-substituted phenyl-3-(2-thioxo-1,3,4-oxadiazol-5-yl) beta-carbolines 1a-c, reported as potential antitumor agents in our previous study, herein we report the synthesis and antitumor activity evaluation of several novel Mannich bases 2-7(a-c), by the introduction of different alkylamino(methyl) groups in the 1,3,4-oxadiazole unity of 1a-c. The antimicrobial activities of 1a-c and of 2-7(a-c) were also evaluated. Additionally, an in silico study of the ADME properties of novel synthesized beta-carboline derivatives 2-7(a-c) was performed by evaluation of their Lipinski's parameters and topological polar surface area (TPSA) and percentage of absorption (% ABS) data.