Vol-3, Issue-4, Suppl-3, Dec 2012 ISSN: Parikh et al PHARMA SCIENCE MONITOR SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 5-PYRAZOLONE DERIVATIVES
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1 PHARMA SCIENCE MONITOR AN INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 5-PYRAZOLONE DERIVATIVES Shaishavi Parikh*, Arun Parikh, Vijayalakshmi Gudaparthy Department of Pharmaceutical Chemistry, L.J. Institute of Pharmacy, S.G.Highway, Ahmedabad ABSTRACT 5-Pyrazolone derivatives were synthesized by the reaction of the indole aldehyde with ethyl cyanoacetate to form indolacrylate which on further condensed to hydrazine or hydrazide derivative to form pyrazolones. All synthesized compounds are characterized by the IR, Mass and NMR spectroscopy and evaluated for the antibacterial and antifungal activity by using B. cereus, S. aureus strains of Gram positive E. coli strain of Gram negative and C.albicans strain of fungus. The compound having isonicotinic and benzocaine substituent shows significant activity. Keywords: antibacterial activity, antifungal activity, 5-pyrazolones. INTRODUCTION Pyrazoles are the heterocyclic five-membered compounds which possess two nitrogen at 1 st and 2 nd position of the ring. Pyrazolones and aminopyrazolones are associated with the broad spectrum of biological activities like antimicrobial [1], anti-inflammatory [2], anticancer [3], analgesic [4], hypoglycemic [5], antimycobacterial [6], ACE-Inhibitory activity [7], anticonvulsant [8], ulcerogenic [9]. 5-Pyrazolone is also endorsed with similar biological activities as well as it can be easily fused to other rings to obtain the new heterocycles. They are used as key starting materials for the synthesis of commercial arylazopyrazolone dyes. Drugs like Aminopyrine, Antipyrine (2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) were the first pyrazolone derivatives used in the management of pain and inflammation. Nafazatrom, has arachidonate enzyme inhibition property. It exhibits antithrombotic and thrombolytic action. The chemistry of aminopyrazoles has been extensively investigated in the past. The considerable biological and medicinal activities of pyrazoles and azolopyrazoles, for IC Value
2 which amino pyrazoles are preferred precursors, have stimulated these investigations. Interest in aminopyrazoles synthesis and chemistry has been revived. The established activity of zaleplon, viagra as well as allopurinol is surely behind this interest 10. MATERIAL AND METHODS All the melting points were determined in open capillaries and are uncorrected. The purity of compounds was checked by TLC on silica gel G coated glass plates. IR spectra were recorded in KBr on shimadzu FT-IR 8300 spectrophotometer; 1 H NMR spectra in CDCl 3 on a Brucker DRX-300 at 200 MHz using TMS as an internal standard. Mass spectra were determined using direct inlet probe on a GCMS-QP2010 mass spectrometer, elemental analysis were performed on a Carlo Erba EA 1108 elemental analyser. Synthesis of ethyl 2-cyno-3-(indol-3-yl)acrylate(1) A mixture of indol-3-carboxaldehyde (1.44g, 0.01M) and ethyl-cynoacetate (1.02mL, 0.01M) Piperidine (2-3drops) in rectified spirit (20mL) were stirred for 4-5 hr at room temperature. The resulting liquid was poured into ice water and product was separated, isolated and recrystallized from ethanol. Step-2 Synthesis of 4-((1H-indol-3-yl)methylene)-3-amino-1-(substituted)-1Hpyrazol-5(4H)-one(2a-e) A mixture of ethyl-2-cyno-3-indole acrylate (2.4g, 0.01M), hydrazine hydrate or hydrazide derivative (0.02M) and methanol (10mL) were refluxed for 3 hours. The contents were poured in crushed ice to isolate the product; the completion of reaction was monitored through TLC. IC Value
3 SCHEME BIOLOGICAL STUDIES Antibacterial and antifungal activity by cup plate agar diffusion method All the compounds have been evaluated for their in vitro biological assay like antibacterial activity towards gram-positive bacteria viz., B.cereus, S.aureus, and gramnegative bacteria viz., E.coli and antifungal activity towards c. albicans at a concentration of 100 μg. The biological activities of synthesized compounds were compared with standard drugs viz., streptomycin, tetracycline for antibacterial activity and antifungal activity was compared with miconazole. IC Value
4 RESULT TABLE 1: PHYSICAL AND ANALYTICAL CHARACTERIZATION DATA OF SYNTHESIZED COMPOUNDS Compound code Substituent R Mol. Formula Mol. Wt. m.p. (⁰C) Yield (%) Calcd % (found) N 1 - C 14 H 12 N (11.44) 2a -H C 12 H 10 N 4 O 226 > (24.52) 2b -C6H5 C 18 H 14 N 4 O (18.34) 2c -COC6H4(NH2) C 20 H 19 N 5 O (20.01) 2d -COC6H4(γN) C 19 H 17 N 5 O (20.96) 2e -COC6H4(βN) C 19 H 17 N 5 O (21.01) TABLE 2: SPECTRAL DATA OF ALL THE SYNTHESIZED COMPOUNDS Compound code IR MASS NMR C-N str a -NH CO-N C-N str b -NH CO-N C-N str c -NH CO-N d 2e C-N str NH CO-N C-N str NH CO-N (-NH-, s, 1H), (Ar-H, 9H), 6.5 (=CH-, s, 1H), 5.4 (-NH 2, s, 2H), 4.4 (-NH 2, s, 2H) 10.1 (-NH-, s, 1H), (Ar-H, 9H),6.9 (=CH-, s, 1H), 3.7 (-NH 2, s, 2H) IC Value
5 TABLE 3: ANTIMICROBIAL ACTIVITY Zone of inhibition(mm) Compound code Gram +ve Gram ve Fungi B.cereus S.aureus E.coli C. albicans 2a b c d e Streptomycin Tetracycline miconazole DISCUSSION This presented research work was carried out to synthesize, purify, characterize the various derivative of the 3-amino 5-pyrazolone and all the synthesized compounds are evaluated for their antibacterial and antifungal activity. IC Value
6 Among the all synthesized compound, most of them showed the significant antibacterial activity against Gram +ve and Gram ve bacteria 100μg/mL concentration. The compound 2c, 2d shows significant activity than the rest of compounds. Among the all synthesized compound, most of them showed the significant antifungal activity against C. albicans at 100μg/mL concentration. The compound 2c, 2d shows significant activity than the rest of compounds. ACKNOWLEDGMENT The authors are thankful to authorities of L. J. Institute of Pharmacy, Ahmedabad for providing the research facilities, Department of chemistry, Saurastra University, Rajkot for providing necessary IR spectra, Cadila Pharmaceuticals for providing the Mass spectra and IICT, Hyderabad for providing NMR spectra. REFERENCES 1. Vijesh AM, Isloor AM, Isloor S, Shivananda KN, Shyma PC, Arulmoli T, Synthesis of some new pyrazolone derivatives as potene antimicrobial agents, der pharma chemical; 2011, 3(4), Antre VR, Cendilkumar A, Goli D, Andhale GS, Oswal RJ, Microwave assisted synthesis of novel pyrazolone derivatives attached to a pyrimidine moiety and evaluation of their anti-inflammatory, analgesic and antipyretic activities, Saudi pharmaceutical journal; 2011, 19, Faidallah HM, Rostom AF, Al-Saadi MS, Synthesis and biological evaluation of some new substituted fused pyrazole ring system as possible anticancer and antimicrobial agents, Journal of king abdulaziz university; 2010, 22(1), Takagi K, Tanaka M, Morita H, Ogura K, Ishii K, Nakata N, Ozeki M, Synthesis and analgesic activity of 4-amino-1,2-dihydro-5-(2-hydroxyphenyl)-3H-pyrazol- 3-ones and 5-amino-6-(2-hydroxyphenyl)pyrimidin-4(3H)-ones, European journal of medicinal chemistry; 1987, 22, IC Value
7 5. Das N, Verma A, Shrivastava PK, Shrivastava SK Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents, Indian journal of chemistry; 2008, 47B, Sidhaye RV, Dhanawade AE, Manasa K, Aishwarya G, Synthesis, antimicrobial and antimycobacterial activity of nicotinic acid hydrazide derivative, Current pharma research; 2011, 2, El-Sabbagh OI, Baraka MM, Ibrahim SM, Pannecouque P, Andrei G, Snoeck R, Balzarini J, Rashad AA, Synthesis and antiviral activity of new pyrazole and thiazole derivatives, European journal of medicinal chemistry; 2009, 44, Abdel-Aziz M, El-Din A, Abuo-Rahma G, Hassan AA, Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities, European journal of medicinal chemistry; 2009, 44, Amir M, Kumar S, Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of 3,5-dimethyl pyrazoles, 3-methyl pyrazol-5-ones and 3,5-disubstituted pyrazolines, Indian journal of chemistry; 2005, 45B Anwar HF, Elnagdi MH, Recent development in aminopyrazole chemistry, Arkivoc; 2009, 1, For Correspondence: Parikh Shaishavi N shaishavi21@rediffmail.com IC Value
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