Novel Pyrazolo[1,5-a]Pyrimidines and Pyrazolo[5,1-c][1,2,4]Triazines Incorporating Indole Moiety as a New Class of Antioxidant Agents

被引:24
作者
El-Mekabaty, Ahmed [1 ]
Fadda, Ahmed A. [1 ]
机构
[1] Mansoura Univ, Fac Sci, Chem Dept, El Gomhoria St, ET-35516 Mansoura, Egypt
关键词
BIOLOGICAL EVALUATION; ANTICANCER AGENTS; PURINE ANALOGS; DERIVATIVES; CHEMISTRY; ANTIBACTERIAL; ALKALOIDS;
D O I
10.1002/jhet.3288
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This effort focuses on the construction of novel pyrazolo[1,5-a]pyrimidines bearing indole nucleus via the reaction of 3-(1H-indol-3-yl)-1H-pyrazol-5-amine (3) with the appropriate reagents or through solvent free condensations with active methylene components and triethyl orthoformate. The utility of (3) for the preparation of pyrazolo[5,1-c][1, 2, 4]triazines was also explored via coupling of diazonium salt of (3) with active methylene compounds. Antioxidant activity screening of the synthetic targets showed that compounds (13), (14), (16), and (17) exhibited a promising activity.
引用
收藏
页码:2303 / 2308
页数:6
相关论文
共 28 条
[1]   Synthesis and biological evaluation of fluorine substituted pyrazolo[4,3-e][1,2,4] triazines as purine analogues [J].
Abdel-Rahman, Reda M. ;
Angawi, Rihab F. ;
Al-Mehmadi, Aisha R. .
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 (04) :495-503
[2]  
Abdel-Rahman RM, 2013, CURR ORG SYNTH, V10, P136
[3]   A regioselective synthesis of some new pyrazol-1′-ylpyrazolo[1,5-a]pyrimidines in aqueous medium and their evaluation as antimicrobial agents [J].
Aggarwal, Ranjana ;
Sumran, Garima ;
Garg, Neelam ;
Aggarwal, Ashok .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) :3038-3046
[4]   Synthesis and antibacterial activity of some substituted 3-(aryl)- and 3-(heteroaryl)indoles [J].
Al-Hiari, YM ;
Qaisi, AM ;
El-Abadelah, MM ;
Voelter, W .
MONATSHEFTE FUR CHEMIE, 2006, 137 (02) :243-248
[5]   Indole Alkaloids from Catharanthus roseus: Bioproduction and Their Effect on Human Health [J].
Almagro, Lorena ;
Fernandez-Perez, Francisco ;
Angeles Pedreno, Maria .
MOLECULES, 2015, 20 (02) :2973-3000
[6]  
[Anonymous], 2014, INT J ORGANIC CHEM, DOI DOI 10.4236/ijoc.2014.44028
[7]   Applications of 2-arylhydrazononitriles in synthesis: Preparation of new indole containing 1,2,3-triazole, pyrazole and pyrazolo[1,5-a]pyrimidine derivatives and evaluation of their antimicrobial activities [J].
Behbehani, Haider ;
Ibrahim, Hamada Mohamed ;
Makhseed, Saad ;
Mahmoud, Huda .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (05) :1813-1820
[8]   Indole in the target-based design of anticancer agents: A versatile scaffold with diverse mechanisms [J].
Dadashpour, Sakineh ;
Emami, Saeed .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 150 :9-29
[9]   Liquid-phase synthesis of combinatorial libraries based on 7-trifluoromethyl-substituted pyrazolo[1,5-a]pyrimidine scaffold [J].
Dalinger, IL ;
Vatsadse, IA ;
Shevelev, SA ;
Ivachtchenko, AV .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (02) :236-245
[10]   Chemistry of 3-(2-Haloacyl)indoles [J].
El-Mekabaty, Ahmed .
SYNTHETIC COMMUNICATIONS, 2015, 45 (20) :2271-2302