A Facile Microwave Assisted Synthesis, Characterization and Antibacterial Activity of 5-Phenyl-1,3,4-Oxadiazole Derivatives for Chemotherapeutic Use
DOI:
https://doi.org/10.12970/2308-8044.2014.02.01.3Keywords:
Microwave assisted synthesis, oxadiazoles, characterization, antibacterial activity.Abstract
This paper deals with an efficient synthesis of some 2-amino-5-substituted phenyl-1,3,4-oxadiazoles by using both conventional and microwave methods for chemotherapeutic use. The obtained results confirmed that, microwave assisted technique is efficient, eco-friendly, and inexpensive method which not only gives higher yield but also reduces the reaction time significantly. The structural elucidation of the prepared compounds was carried out by the aid of IR, 1H NMR, UV-Vis and mass spectral analyses. Compounds Sa-Sf showed antimicrobial activities against Escherichia coli, Serratia marcescens, Salmonella enterica and Proteus vulgaris (Gram-negative bacteria) and Bacillus subtilis and Staphylococcus aureus (Gram-positive bacteria) at low concentrations (10–1000 µg/mL).
References
Al-Etaibi AM, El-Apasery MA, Ibrahim MR, Al-Awadi NA. A facile synthesis of new monoazo disperse dyes derived from 4-hydroxyphenylazopyrazole-5-amines: Evaluation of microwave assisted dyeing behavior. Molecules 2012; 17: 13891-909. http://dx.doi.org/10.3390/molecules171213891
Zhang Z, Fang S, Liu Q, Zhang G. Microwave-assisted facile synthesis of furo [3,2-b] indole derivatives via silver(I)- mediated [3+2] cycloaddition. Adv Synth Catal 2012; 354: 927-32. http://dx.doi.org/10.1002/adsc.201100767
Jadon S, Khedr AM, Kumar S, Yadav S, Kumar V, Gupta KC. A facile microwave assisted synthesis and spectral analysis of 2-amino-5-substituted phenyl-1,3,4-oxadiazoles. Orient J Chem 2012; 28: 1845-8. http://dx.doi.org/10.13005/ojc/280441
Zhang YM, Liu P, Zhang HL, Feng GL, Geng LJ. Microwaveassisted synthesis of novel ferrocenyl pyrrolizidines. J Chem Res 2012; 36: 536-8. http://dx.doi.org/10.3184/174751912X13418562888522
Frank PV, Grish KS, Kalluraya B. Solvent-free microwaveassisted synthesis of oxadiazoles containing imidazole moiety. J Chem Sci 2007; 119: 41-6. http://dx.doi.org/10.1007/s12039-007-0007-7
Karabasanga T, Adhikari AV, Shetty NS. Synthesis and antimicrobial activities of some novel 1,3,4-oxadiazoles carrying alkylthio and alkylsulphonyl phenoxy moieties. Phosphorus, Sulfur, Silcon 2007; 182: 2925-41. http://dx.doi.org/10.1080/10426500701542981
Cacic M, Trkovnik M, Cacic F, Has-schon E. Synthesis and antimicrobial activity of some derivatives of (7- Hydroxy-2- oxo-2H-chromen-4-yl)-acetic acid hydrazide. Molecules 2006; 11: 134-47. http://dx.doi.org/10.3390/11010134
Radakrishnan TR. Synthesis and antibacterial activity of some147 2,5-di-substituted-1,3,4-oxadiazole,1,3,4- thiadiazole, 1,2,4-148 triazole and 4-thiazolidinone. J Het Chem 1995; 5: 133-8.
Karthikeyan MS, Prasad DJ, Mahalinga M, Holl BS, Kumari NS. Antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing oxadiazoles. Eur J Med Chem 2008; 43: 25-31. http://dx.doi.org/10.1016/j.ejmech.2007.03.013
Amir M, Kumar S. Synthesis and evaluation of antiinflammatory, analgesic, ulcerogenic and lipid peroxidation properties of ibuprofen derivatives. Acta Pharm 2007; 57: 31- 45. http://dx.doi.org/10.2478/v10007-007-0003-y
Ram YJ, Pandeya HN. Mannich bases derived from 5-(o-)Hydroxyphenyl-1,3,4-oxadiazole-2-thione. J Indian Chem Soc 1974; 51: 634-5.
Dubey AK, Sangwan NK, synthesis and antifungal activity of 5-(3,5-diphenylpyrazol-4-yl-methyl)-2-(4-oxo-2-substituted phenyl-3-thiazolidinyl)-oxadiazol/thiadiazoles and related compounds as potential pesticidal activity. Indian J Chem 1994; 33B: 1043-7.
Shawali AS, Abudllah MA, Zayed MEM. Synthesis, Antimicrobial Activity and Heterocyclic Ring Transformation of 5-(Pyrazol-5-yl)-1,3,4-oxadiazole-2(3H)-thiones. Naturforsch B 2000; 55: 546-52.
Mohan TP, Vishalakshi B, Bhat KS, Rao KS, Kendappa GN. Synthesis and insecticidal activity of some 1, 3, 4-oxadiazole derivatives containing phenoxy fluorophenyl group. Indian J Chem Soc 2004; 48B: 1798-801.
Holla B, Prasnna SCS, Boja P, Rao KS, Bhatt S, Ganesh U. Synthesis and insecticidal activity of some 1,3,4-oxadiazoles derived from 2-chloropyridine-5-acetic acid. Indian J Chem 2003; 43B: 864-8.
Yadav LDS, Singh S. Synthesis and antiviral activity of acylic C-nucleoside incorporating thiazolo-1,3,4-thiadiazole. Indian J Chem 2001; 40B: 440-2.
Hazarika J, Kataky JCS. Synthesis and Biological Activity of some new 3- substituted -5-(2-chlorophenyl)-1,3,4- oxadiazole-2-thioness and theirn derivatives. Indian J Heterocycl Chem 1998; 8: 83-4.
Liszkieicz H, Kowalska MW, Wietrzyk J, Opolski A. Synthesis and anti-proliferative activity invitro of new 5-(2-amino-3- pyridyl)-2-thioxo-3H-1,3,4-oxadizole derivatives. Indian J Chem 2003; 42B: 2846-52.
Tang H, Song N, Gao Z, Chen X, Fan X, Xiang Q, Zhou Q. Synthesis and properties of 1,3,4-oxadiazole-containing highperformance bismaleimide resins. Polym J 2007; 48: 129-38. http://dx.doi.org/10.1016/j.polymer.2006.10.040
Pridham TG, Lindenfelser LA, Shotwell O L, et al. Antibiotics against plant diseases: A laboratory and green house survey. Phytopathology 1956; 46: 568-75.
Hsueh PR, Chang JC, Teng LJ, et al. Comparison of Etest and agar dilution method for antimicrobial susceptibility testing of Flavobacterium isolates. J Clin Microbiol 1997; 35: 1021-3.
Moustafa ME, El-Mossalamy EH, Amin AS. Synthesis and efficiency of 5-(2-hydroxyphenylazo)-indazoles as new reagents for the determination of vanadium. Monatsh Chem 1995; 126: 901-8. http://dx.doi.org/10.1007/BF00811009
Issa RM, Khedr AM, Rizk H. 1 H NMR, IR and UV/VIS Spectroscopic Studies of Some Schiff Bases Derived From 2-Aminobenzothiazole and 2-Amino-3-hydroxypyridine. J Chin Chem Soc 2008; 55: 875-84.
Chandra S, Gupta LK. Spectroscopic and biological studies on newly synthesized nickel(II) complexes of semicarbazones and thiosemicarbazones. Spectrochim Acta A 2005; 62: 1089-94. http://dx.doi.org/10.1016/j.saa.2005.04.005
Azizi N, Saidi MR. Synthesis of tertiary a-amino phosphonate by one-pot three component coupling mediated by LPDE. Tetrahedron 2003; 59: 5329-32. http://dx.doi.org/10.1016/S0040-4020(03)00759-2