Ultrasound promoted green synthesis of spiro[pyrano[2,3-c]pyrazoles] as antioxidant agents

被引:39
作者
Dandia, Anshu [1 ]
Saini, Deepti [1 ]
Bhaskaran, Sumit [1 ]
Saini, Dinesh Kumar [2 ]
机构
[1] Univ Rajasthan, Dept Chem, Ctr Adv Studies, Jaipur 302004, Rajasthan, India
[2] Univ Rajasthan, Dept Zool, Radiat & Canc Biol Lab, Jaipur 302004, Rajasthan, India
关键词
Indole-2,3-dione; 3-Methyl-1-phenyl-2-pyrazolin-5-one; Active methylene group; Antioxidant activity; SPIROOXINDOLES; DERIVATIVES; MELATONIN; FACILE;
D O I
10.1007/s00044-013-0671-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Ultrasound promoted, cerium ammonium nitrate catalyzed sustainable synthesis of spiro[indoline3,4'-pyrano[2,3-c]pyrazole] derivatives (4a-l) is reported herein. The synthesized compounds were screened for their antioxidant activities as free radical scavenging effect on diphenylpicryl hydrazine (DPPH center dot), 2,2'-azino-bis(3-ethylbenzthiazoline- 6-sulphonic acid) (ABTS(center dot+)) and nitric oxide (NO) radicals. The screened compounds showed potent scavenging activities against DPPH center dot, ABTS(center dot+) and NO radicals. In order to further extend on studies and to obtain a deep insight into structure activity relationship of this class of compounds, we designed N-substitution of indole moiety with the aim to study its antioxidant potential.
引用
收藏
页码:725 / 734
页数:10
相关论文
共 38 条
[1]   Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives [J].
Abdelrazek, Fathy M. ;
Metz, Peter ;
Kataeva, Olga ;
Jaeger, Anne ;
El-Mahrouky, Sherif F. .
ARCHIV DER PHARMAZIE, 2007, 340 (10) :543-548
[2]  
BUYUKBINGOL E, 1994, FARMACO, V49, P443
[3]   In vitro antioxidant properties of dantrolene sodium [J].
Büyükokuroglu, ME ;
Gülçin, I ;
Oktay, M ;
Küfrevioglu, Ö .
PHARMACOLOGICAL RESEARCH, 2001, 44 (06) :491-494
[4]   Potent neuroprotective properties against the Alzheimer β-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid [J].
Chyan, YJ ;
Poeggeler, B ;
Omar, RA ;
Chain, DG ;
Frangione, B ;
Ghiso, J ;
Pappolla, MA .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (31) :21937-21942
[5]   Ammonium salt catalyzed multicomponent transformation: simple route to functionalized spirochromenes and spiroacridines [J].
Dabiri, Minoo ;
Bahramnejad, Mahboobeh ;
Baghbanzadeh, Mostafa .
TETRAHEDRON, 2009, 65 (45) :9443-9447
[6]  
Dandia A, 2003, HETEROCYCL COMMUN, V9, P415
[7]   Microwave promoted and improved thermal synthesis of spiro[indole-pyranobenzopyrans] and spiro[indole-pyranoimidazoles] [J].
Dandia, A ;
Singh, R ;
Sachdeva, H ;
Gupta, R ;
Paul, S .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2003, 50 (02) :273-278
[8]   Targeting reactive oxygen species in hypertension [J].
Delles, Christian ;
Miller, William H. ;
Dominiczak, Anna F. .
ANTIOXIDANTS & REDOX SIGNALING, 2008, 10 (06) :1061-1077
[9]   Electrocatalytic multicomponent assembling of isatins, 3-methyl-2-pyrazolin-5-ones and malononitrile: facile and convenient way to functionalized spirocyclic [indole-3,4'-pyrano[2,3-c]pyrazole] system [J].
Elinson, Michail N. ;
Dorofeev, Alexander S. ;
Miloserdov, Fedor M. ;
Nikishin, Gennady I. .
MOLECULAR DIVERSITY, 2009, 13 (01) :47-52
[10]  
Floor E, 1998, J NEUROCHEM, V70, P268