5-[(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)methyl]-4-butyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

• 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-[(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)methyl]-4-butyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: SGK 241；4-butyl-3-[(1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)methyl]-1H-1,2,4-triazole-5-thione
• 化学式: C₂₂H₃₀N₄OS
• 分子量: 398.572
• InChiKey: RGOHGAZFNVEKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  58.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  依托度酸 在 硫酸 、 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 5-[(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)methyl]-4-butyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Anti-cancer and anti-hepatitis C virus NS5B polymerase activity of etodolac 1,2,4-triazoles

  摘要：

  Arachidonic acid is an unsaturated fatty acid liberated from phospholipids of cell membranes. NSAIDs are known as targets of cyclooxygenase enzyme (COX-1, COX-2 and COX-3) in arachidonic acid metabolism. This mechanism of COX-2 in carcinogenesis causes cancer. In addition, COX-2 plays a role in the early stages of hepatocarcinogenesis. Hepatitis C virus (HCV) infection is cause of liver cirrhosis and hepatocellular carcinoma (HCC). The aim of our study was to improve effective agents against HCV. A novel series of new etodolac 1,2,4-triazoles derivatives (4a-h) have been synthesized and investigated for their activity against HCV NS5B polymerase. Compound 4a was found to be the most active with IC50 value of 14.8 mu M. In accordance with these results, compound 4a was screened for anti-cancer activity on liver cancer cell lines (Huh7, Mahlavu, HepG2, FOCUS). Compound 4a showed anti-cancer activity against Huh7 human hepatoma cell line with IC50 value of 4.29 mu M. Therefore, compound 4a could be considered as a new anti-cancer and anti-HCV lead compound.

  DOI：

  10.3109/14756366.2014.971780

文献信息

• [EN] SYNTHESIS OF THIOSEMICARBAZIDES AND TRIAZOLES DERIVED FROM ETODOLAC<br/>[FR] SYNTHÈSE DE THIOSEMICARBAZIDES ET DE TRIAZOLES DÉRIVÉS DE L'ÉTODOLAC
  申请人：KUCUKGUZEL S GUNIZ

  公开号：WO2014003694A1

  公开（公告）日：2014-01-03

  A novel series of new etodolac hydrazide derivatives, 1 -[2-(1,8-diethyI- 1,3,4,9- tetrahydropyrano[3,4-b]indol-1 -yl)acetyl]-4-alkyl/aryl thiosernicarbazides [SGK224-230, SGK313] and 5-[(l,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)methyl]-4- subsrituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones [SGK238-244, SGK315] have been synthesized in this study.

  在这项研究中合成了一系列新的依托咯酸酰肼衍生物，包括1-[2-(1,8-二乙基-1,3,4,9-四氢吡喃[3,4-b]吲哚-1-基)乙酰]-4-烷基/芳基硫脒卡巴齐德[SGK224-230, SGK313]和5-[(1,8-二乙基-1,3,4,9-四氢吡喃[3,4-b]吲哚-1-基)甲基]-4-取代-2,4-二氢-3H-1,2,4-三唑-3-硫酮[SGK238-244, SGK315]。
• SYNTHESIS OF THIOSEMICARBAZIDES AND TRIAZOLES DERIVED FROM ETODOLAC
  申请人：Kucukguzel, S. Guniz

  公开号：EP2864334A1

  公开（公告）日：2015-04-29
• Anti-cancer and anti-hepatitis C virus NS5B polymerase activity of etodolac 1,2,4-triazoles
  作者：Pelin Çıkla-Süzgün、Neerja Kaushik-Basu、Amartya Basu、Payal Arora、Tanaji T. Talele、Irem Durmaz、Rengül Çetin-Atalay、Ş.Güniz Küçükgüzel

  DOI：10.3109/14756366.2014.971780

  日期：2015.9.3

  Arachidonic acid is an unsaturated fatty acid liberated from phospholipids of cell membranes. NSAIDs are known as targets of cyclooxygenase enzyme (COX-1, COX-2 and COX-3) in arachidonic acid metabolism. This mechanism of COX-2 in carcinogenesis causes cancer. In addition, COX-2 plays a role in the early stages of hepatocarcinogenesis. Hepatitis C virus (HCV) infection is cause of liver cirrhosis and hepatocellular carcinoma (HCC). The aim of our study was to improve effective agents against HCV. A novel series of new etodolac 1,2,4-triazoles derivatives (4a-h) have been synthesized and investigated for their activity against HCV NS5B polymerase. Compound 4a was found to be the most active with IC50 value of 14.8 mu M. In accordance with these results, compound 4a was screened for anti-cancer activity on liver cancer cell lines (Huh7, Mahlavu, HepG2, FOCUS). Compound 4a showed anti-cancer activity against Huh7 human hepatoma cell line with IC50 value of 4.29 mu M. Therefore, compound 4a could be considered as a new anti-cancer and anti-HCV lead compound.