methyl 5-(3,4-(methylenedioxy)phenyl)pentanoate | 130670-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: methyl 5-(3,4-(methylenedioxy)phenyl)pentanoate
• 英文别名: 5-benzo[1,3]dioxol-5-yl-valeric acid methyl ester；5-Benzo[1,3]dioxol-5-yl-valeriansaeure-methylester；Methyl 5-(1,3-benzodioxol-5-yl)pentanoate
• CAS: 130670-03-0
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: BPTGDQHLMKVBQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(3,4-(methylenedioxy)phenyl)pentanoate 在 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-[4-(1,3-benzodioxol-5-yl)butyl]-4-cyclohexyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Design, Synthesis, Trypanocidal Activity, and Studies on Human Albumin Interaction of Novel S-Alkyl-1,2,4-triazoles

  摘要：

  Chagas disease is a neglected tropical disease caused by the hemoflagellated parasite Trypanosoma cruzi (Kinetoplastida). The only available drug to treat chagasic patients in Brazil, the nitroheterocycle benznidazole, is effective solely during the acute phase of the infection. There is accordingly a need to develop new therapeutic tools for the treatment of Chagas disease. This work reports the synthesis, trypanocidal evaluation and human serum albumin (HSA) interactions of a novel series of 1,2,4-triazoles. The new derivatives were synthesized via microwave irradiation in good yields. Most compounds showed toxic effects against T. cruzi with low toxicity to host cells. Three S-alkylated-triazoles showed the best activity profile against amastigotes, with half maximal inhibitory concentration (IC50) values of 3.95 +/- 1.41, 4.15 +/- 0.92 and 3.61 +/- 0.65 mu mol L-1, respectively. The interaction between HSA and 3-[(1E, 3E)-4-(1,3-benzodioxol-5-yl)buta-1,3-dien-1-yl]-5-(butylthio)-4-cyclohexyl-4,5-dihydro-1H-1,2,4-triazole was investigated using multiple spectroscopic techniques and molecular docking, revealing that serum albumin is a potential endogenous carrier to this compound in the human bloodstream.

  DOI：

  10.21577/0103-5053.20190033
• 作为产物：
  描述：

  5-（1,3-苯并二恶唑-5-基）-2,4-戊二烯酸 在 草酰氯 、 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 methyl 5-(3,4-(methylenedioxy)phenyl)pentanoate
  参考文献：
  名称：

  Design, Synthesis, Trypanocidal Activity, and Studies on Human Albumin Interaction of Novel S-Alkyl-1,2,4-triazoles

  摘要：

  Chagas disease is a neglected tropical disease caused by the hemoflagellated parasite Trypanosoma cruzi (Kinetoplastida). The only available drug to treat chagasic patients in Brazil, the nitroheterocycle benznidazole, is effective solely during the acute phase of the infection. There is accordingly a need to develop new therapeutic tools for the treatment of Chagas disease. This work reports the synthesis, trypanocidal evaluation and human serum albumin (HSA) interactions of a novel series of 1,2,4-triazoles. The new derivatives were synthesized via microwave irradiation in good yields. Most compounds showed toxic effects against T. cruzi with low toxicity to host cells. Three S-alkylated-triazoles showed the best activity profile against amastigotes, with half maximal inhibitory concentration (IC50) values of 3.95 +/- 1.41, 4.15 +/- 0.92 and 3.61 +/- 0.65 mu mol L-1, respectively. The interaction between HSA and 3-[(1E, 3E)-4-(1,3-benzodioxol-5-yl)buta-1,3-dien-1-yl]-5-(butylthio)-4-cyclohexyl-4,5-dihydro-1H-1,2,4-triazole was investigated using multiple spectroscopic techniques and molecular docking, revealing that serum albumin is a potential endogenous carrier to this compound in the human bloodstream.

  DOI：

  10.21577/0103-5053.20190033

文献信息

• An Investigation into the One-Pot Heck Olefination−Hydrogenation Reaction
  作者：Kimberly Geoghegan、Susan Kelleher、Paul Evans

  DOI：10.1021/jo200023r

  日期：2011.4.1

  Herein is described an operationally simple process concerning the observation that, following either inter-, or intramolecular Heck olefination, stirring of the so formed substituted alkenyl product under an atmosphere of hydrogen efficiently effects alkene hydrogenation. Overall this two-operation, one-pot "reductive Heck" sequence is notable since direct reductive Heck processes, using additives such as formate salts, are restricted to a limited range of substrates. In total 25 examples are reported (yields ranging from 0 to 95%), which were selected in order to probe the scope and limitations of this method. Finally, the utility of this sequence was demonstrated in a short synthesis of the calcimimetic agent, cinacalcet.
• HARA, SHOJI;KISHIMURA, KOTARO;SUZUKI, AKIRA;DHILLON, RANJIT S., J. ORG. CHEM., 55,(1990) N6, C. 6356-6360
  作者：HARA, SHOJI、KISHIMURA, KOTARO、SUZUKI, AKIRA、DHILLON, RANJIT S.

  DOI：——

  日期：——
• Design, Synthesis, Trypanocidal Activity, and Studies on Human Albumin Interaction of Novel S-Alkyl-1,2,4-triazoles
  作者：Tatiany Franklim、Leonardo Freire-de-Lima、Otávio Chaves、Isabel LaRocque-de-Freitas、Joana da Silva-Trindade、José Netto-Ferreira、Célio Freire-de-Lima、Debora Decoté-Ricardo、José Previato、Lucia Mendonça-Previato、Marco de Lima

  DOI：10.21577/0103-5053.20190033

  日期：——

  Chagas disease is a neglected tropical disease caused by the hemoflagellated parasite Trypanosoma cruzi (Kinetoplastida). The only available drug to treat chagasic patients in Brazil, the nitroheterocycle benznidazole, is effective solely during the acute phase of the infection. There is accordingly a need to develop new therapeutic tools for the treatment of Chagas disease. This work reports the synthesis, trypanocidal evaluation and human serum albumin (HSA) interactions of a novel series of 1,2,4-triazoles. The new derivatives were synthesized via microwave irradiation in good yields. Most compounds showed toxic effects against T. cruzi with low toxicity to host cells. Three S-alkylated-triazoles showed the best activity profile against amastigotes, with half maximal inhibitory concentration (IC50) values of 3.95 +/- 1.41, 4.15 +/- 0.92 and 3.61 +/- 0.65 mu mol L-1, respectively. The interaction between HSA and 3-[(1E, 3E)-4-(1,3-benzodioxol-5-yl)buta-1,3-dien-1-yl]-5-(butylthio)-4-cyclohexyl-4,5-dihydro-1H-1,2,4-triazole was investigated using multiple spectroscopic techniques and molecular docking, revealing that serum albumin is a potential endogenous carrier to this compound in the human bloodstream.