Synthesis of Some Novel Isoxazolidine Derivatives via 1,3-Dipolar Cycloaddition and Their Biological Evaluation

被引:0
作者
Yanmaz, Volkan [1 ]
Disli, Ali [1 ]
Yavuz, Serkan [1 ]
Ogutcu, Hatice [2 ]
Dilek, Gulay [3 ]
机构
[1] Gazi Univ, Dept Chem, TR-06500 Ankara, Turkey
[2] Ahi Evran Univ, Dept Biol, TR-40100 Kirsehir, Turkey
[3] Zonguldak Bulent Ecevit Univ, Dept Basic Pharmaceut Sci, TR-67600 Zonguldak, Turkey
来源
GAZI UNIVERSITY JOURNAL OF SCIENCE | 2019年 / 32卷 / 01期
关键词
Isoxazolidine; Nitrone; 1,3-Dipolar cycloaddition reaction; Antimicrobial activity; ANTIBACTERIAL; ANTIFUNGAL; INHIBITORS; ARYL; EFFICIENT; NITRONES; AGENTS; ROUTE;
D O I
暂无
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
A series of novel substituted isoxazolidine derivatives were synthesized by 1,3-dipolar cycloaddition reactions of alpha-aryl-N-methyl nitrones with diethyl maleate. The structures of the synthesized compounds were characterized using spectroscopic methods. All the synthesized compounds were screened for their antibacterial activities against Gram-positive and Gram-negative bacteria and for their antifungal activities against a yeast strain. The results show that all the synthesized compounds displayed significant activity against S. epidermidis, M. luteus, B. cereus, B. abortus and C. albicans when compared to standard drugs.
引用
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页码:78 / 89
页数:12
相关论文
共 42 条
[1]  
ALI AS, 1998, TETRAHEDRON, V44, P5911
[2]   Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines [J].
Andrade, Marta M. ;
Barros, Maria Teresa ;
Pinto, Rui C. .
TETRAHEDRON, 2008, 64 (46) :10521-10530
[3]   Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry [J].
Berthet, Matheo ;
Cheviett, Thomas ;
Dujardin, Gilles ;
Parrot, Isabelle ;
Martinez, Jean .
CHEMICAL REVIEWS, 2016, 116 (24) :15235-15283
[4]   Dimethyl trans-3-(4-bromophenyl)-2-methylisoxazolidine-4,5-dicarboxylate [J].
Buyukgungor, Orhan ;
Yavuz, Serkan ;
Odabasoglu, Mustafa ;
Ozkan, Hamdi ;
Pamir, Ozguer ;
Yildirir, Yilmaz .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 :O2207-U2478
[5]   RING-OPENING OF ISOXAZOLIDINE NUCLEUS - COMPETITIVE FORMATION OF ALPHA,BETA-ENONES AND TETRAHYDRO-1,3-OXAZINES [J].
CASUSCELLI, F ;
CHIACCHIO, U ;
RESCIFINA, A ;
ROMEO, R ;
ROMEO, G ;
TOMMASINI, S ;
UCCELLA, N .
TETRAHEDRON, 1995, 51 (10) :2979-2990
[6]  
Chakraborty B., 2010, J CHEM PHARM RES, V2, P727
[7]  
Chakraborty B, 2010, INDIAN J CHEM B, V49, P209
[8]   Synthesis of phosphonated carbocyclic 2′-oxa-3′-aza-nucleosides:: Novel inhibitors of reverse transcriptase [J].
Chiacchio, U ;
Balestrieri, E ;
Macchi, B ;
Iannazzo, D ;
Piperno, A ;
Rescifina, A ;
Romeo, R ;
Saglimbeni, M ;
Sciortino, MT ;
Valveri, V ;
Mastino, A ;
Romeo, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (05) :1389-1394
[9]   Solvent-free synthesis of nitrones in a ball-mill [J].
Colacino, Evelina ;
Nun, Pierrick ;
Colacino, Francesco Maria ;
Martinez, Jean ;
Lamaty, Frederic .
TETRAHEDRON, 2008, 64 (23) :5569-5576
[10]   Antibacterial Activity, Quantitative Structure-Activity Relationship and Diastereoselective Synthesis of Isoxazolidine Derivatives Via 1,3-Dipolar Cycloaddition of d-glucose Derived Nitrone with Olefin [J].
Damodiran, Munusamy ;
Sivakumar, Ponnurengan Malliappan ;
SenthilKumar, Rathnasabapathy ;
Muralidharan, Duraisamy ;
Kumar, Bandara Venkata Narasimha Phani ;
Doble, Mukesh ;
Perumal, Paramasivan Thirumalai .
CHEMICAL BIOLOGY & DRUG DESIGN, 2009, 74 (05) :494-506