N-phenyl-2-(1-methyl-1H-indole-2-carbonyl)hydrazinecarbothioamide | 1424699-44-4

• 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: N-phenyl-2-(1-methyl-1H-indole-2-carbonyl)hydrazinecarbothioamide
• 英文别名: 1-(1-methyl-1H-indole-2-carbonyl)-4-phenylthiosemicarbazide
• CAS: 1424699-44-4
• 化学式: C₁₇H₁₆N₄OS
• 分子量: 324.406
• InChiKey: FOIZENQFOWMMAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.09
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-phenyl-2-(1-methyl-1H-indole-2-carbonyl)hydrazinecarbothioamide 在 potassium carbonate 、 溶剂黄146 、 potassium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.11h， 生成 2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-3-{[4-(pyrrolidin-1-yl)piperidin-1-yl]methyl}-1H-indole
  参考文献：
  名称：

  Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition

  摘要：

  In our pursuit to develop new potential anticancer leads, we designed a combination of structural units of indole and substituted triazole; and a library of 1-{1-methyl-2-[4-phenyl-5-(propan-2-ylsulfanyl)-4H-1,2,4-triazol-3-yl]-1H-indol-3-yl}methanamine derivatives was synthesized and characterized. Cytotoxic evaluations of these molecules over a panel of three human cancer cell lines were carried out. Few molecules exhibited potent growth inhibitory action against the treated cancer cell lines at lower micro molar concentration. An in vitro assay investigation of these active compounds using recombinant human SIRT1 enzyme showed that one of the compounds (IT-14) inhibited the deacetylation activity of the enzyme. The in vivo study of IT-14 exemplified its promising action by reducing the prostate weight to the body weight ratio in prostate hyperplasia animal models. A remarkable decrease in the disruption of histoarchitecture of the prostate tissues isolated from IT-14 treated animal compared to that of the positive control was observed. The molecular interactions with SIRT1 enzyme were also supported by molecular docking simulations. Hence this compound can act as a lead molecule to treat prostatic hyperplasia. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.018
• 作为产物：
  描述：

  ethyl pyruvate phenylhydrazone 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 9.42h， 生成 N-phenyl-2-(1-methyl-1H-indole-2-carbonyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition

  摘要：

  In our pursuit to develop new potential anticancer leads, we designed a combination of structural units of indole and substituted triazole; and a library of 1-{1-methyl-2-[4-phenyl-5-(propan-2-ylsulfanyl)-4H-1,2,4-triazol-3-yl]-1H-indol-3-yl}methanamine derivatives was synthesized and characterized. Cytotoxic evaluations of these molecules over a panel of three human cancer cell lines were carried out. Few molecules exhibited potent growth inhibitory action against the treated cancer cell lines at lower micro molar concentration. An in vitro assay investigation of these active compounds using recombinant human SIRT1 enzyme showed that one of the compounds (IT-14) inhibited the deacetylation activity of the enzyme. The in vivo study of IT-14 exemplified its promising action by reducing the prostate weight to the body weight ratio in prostate hyperplasia animal models. A remarkable decrease in the disruption of histoarchitecture of the prostate tissues isolated from IT-14 treated animal compared to that of the positive control was observed. The molecular interactions with SIRT1 enzyme were also supported by molecular docking simulations. Hence this compound can act as a lead molecule to treat prostatic hyperplasia. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.018

文献信息

• Synthesis and antioxidant and antimicrobial evaluation of novel 4-substituted-1H-1,2,4-triazole derivatives
  作者：SULTAN BAYTAŞ、EVİN KAPÇAK、TÜLAY ÇOBAN、HATİCE ÖZBİLGE

  DOI：10.3906/kim-1202-62

  日期：——

  A series of 4-benzyl/phenyl-3-(1-methyl-1H-indole-2-yl)-1H- 1,2,4-triazole-5(4H)-thione (4a,b) and 2-4-[benzyl/phenyl-5- (substitutedbenzylthio)]-4H-1,2,4-triazole-3-yl}-1-methyl-1H-indole derivatives (5a-p) were synthesized and evaluated for their in vitro scavenging of DPPH and superoxide radical, and lipid peroxidation inhibition effects as well as their antimicrobial properties. DPPH radical scavenging capacity was found to be equipotent with BHT and found in compounds containing 1,2,4-triazole-5(4H)-thione moiety (4a,b). With regard to antimicrobial properties, compound 5k showed slight antimicrobial activity against all the test microorganisms.

  合成了一系列 4-苄基/苯基-3-(1-甲基-1H-吲哚-2-基)-1H- 1,2,4-三唑-5(4H)-硫酮（4a,b）和 2-4-[苄基/苯基-5-（取代的苄基硫代）]-4H-1,2、4-三唑-3-基}-1-甲基-1H-吲哚衍生物（5a-p）的合成，并对其体外清除 DPPH 和超氧自由基、抑制脂质过氧化反应的效果及其抗菌特性进行了评估。 结果发现，含有 1,2,4-三唑-5(4H)-硫酮分子的化合物（4a,b）的 DPPH 自由基清除能力与 BHT 相当。 在抗菌特性方面，化合物 5k 对所有测试微生物都显示出轻微的抗菌活性。