Abstract
The present work describes the newly synthesized series of 4-(3H)-quinazolinone derivatives of hydrazones 5(a–j) starting from benzoxazine (4) by conventional method and substituted hydrazones 3(a–j) from substituted benzaldehydes and hydrazine hydrate. The reaction mixture was refluxed using ethanol as a solvent. All the synthesized compounds were obtained in good yields. The structures of all compounds have been deduced on the basis of spectroscopy and elemental analysis. The synthesized compounds 5(a–j) were screened for their potential in vivo anti-inflammatory activity using carrageenan-induced paw edema model and in vitro antibacterial activity against various strains of gram-positive and gram-negative bacteria.
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References
Alagarsamy V, Pathak US, Venkatesh PR, Meena S, Thirumurugan K, Solomon RV, Clercq DE (2003) Anti-HIV and antibacterial activities of 2-substituted thiadiazolo quinazolines. Indian J Pharm Sci 65(3):293–296
AnilKumar M (2010) Ethnomedicinal plants as anti-inflammatory and analgesic agents. Res Signpost 267–293
Belskaya NP, Dehaen W, Bakulev VA (2010) Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions. Arkivoc 1:275–332
Bhatt KR, Mehta RK, Srivastava PN (1977) Simple methods for recording anti-inflammatory effect on rat paw edema. Indian J Physiol Pharmacol 21:399–400
Billones JB, Buenaobra SM (2011) Quantitative structure-activity relationship (QSAR) study of cyclooxygenase-2 (COX-2) inhibitors. Philipp J Sci 140(2):125–132
Chandrika M, Yakaiah T, Rao AR, Narsaiah B, Reddy NC, Shridar V, Rao JV (2007) Synthesis of novel 4, 6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U 937 leukemia cell lines. Eur J Med Chem 43(4):846–852
Dandia A, Singh R, Sarawgi P (2005) Green chemical multi-component one-pot synthesis of fluorinated 2, 3- disubstituted quinazolin-4(3H)-ones under solvent-free conditions and their antifungal activity. J Fluorine Chem 126(3):307–312
Dinakaran M, Selvam P, DeClercq E, Sridhar SK (2003) Synthesis, antiviral and cytotoxic activity of 6-bromo -2,3-disubstituted-4(3H)quinazolinones. Biol Pharm Bull 26(9):1278–1282
Grover G, Kini SG (2006) Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents. Eur J Med Chem 41(2):256–262
Guzman A, Diaz A, Trejo BE, Munoz JL (2004) Synthesis of potential anti-inflammatory compounds, selective inhibitors of cyclooxygenase-2 (COX-2). Rev Soc Quim Mex 48:225–230
Habib OMO, Hassan HM, Makabety AE (2012) Studies on some benzoxazine-4-one derivatives with potential biological activity. Amer J Org Chem 2(3):45–51
Hamide Abdel SG (2000) Synthesis of some new quinazoline derivatives. Indian J Heterocycl Chem 10:59–64
Heravi MM, Javanmardi N, Oskooie HA, Baghernejad B (2011) Dabco as a novel and efficient catalyst for the synthesis of 4(3H)-quinazolinone derivatives. Bull Chem Soc Ethiop 25(2):305–308
Mohareb RM, Rehab AI, Moustafa HE (2010) Hydrazide-hydrazones in the synthesis of 1,3,4-oxadiazine, 1,2,4-triazine and pyrazole derivatives with antitumor activities. Open Org Chem J 4:8–14
Nanthakumar R, Muthumani P, Girija K (2011) Antibacterial and anti-inflammatory of some novel quinazolinones. Arab J Chem 1–6
Raghav N, Singh M (2011) Biological activities of hydrazones. Int J Pharm Pharm Sci 3(4):26–32
Rajveer CH, Kumaraswamy D, Sudharshini S, Rathina SB (2010) Synthesis of some 6-bromo quinazolinone derivatives for their pharmacological activities. Inter J Pharm and biosci 1(3):1–14
Ram VJ, Farhanullah, Tripathi BK, Srivastava AK (2003) Synthesis and antihyperglycemic activity of suitably functionalized 3H-quinazolin-4-ones. Bioorg Med Chem 1(11):2439–2444
Rollas S, Kucukguzel SG (2007) Biological activities of hydrazone derivatives. Molecules 12:1910–1939
Rollas S, Kucukguzel SG (2008) Hydrazone, amide, carbamate, macromolecular and other prodrugs of doxorubicin. Open Drug Deliv J 2:77–85
Sousa C, Freire C, Castro BD (2003) Synthesis and characterization of benzo-15-crown-5 ethers with appended n2o schiff bases. Molecules 6:894–900
Tiwari AK, Singh VK, Bajpai A, Shukla G, Singh S, Mishra AK (2007a) Synthesis and biological properties of 4-(3H)-quinazolone derivatives. Eur J Med Chem 42:1234–1238
Tiwari AK, Mishra AK, Bajpai A, Mishra P, Sharma RK, Pandey V, Kumar VK (2007b) Synthesis and pharmacological study of novel pyrido-quinazolone analogues as anti-fungal, antibacterial, and anticancer agents. Bioorg Med Chem Lett 16:4581–4585
Uppal G, Bala S, Kamboj S, Saini M (2011) Therapeutic review exploring antimicrobial potential of hydrazones as promising lead. Der Pharma Chemica 3(1):250–268
Winter CA, Risley EA, Nuss GW (1962) Carrageenan-induced edema in hind paw of the rats as an assay for anti-inflammatory drugs. Proc Soc Exp Biol Med 3:544–547
Acknowledgments
The authors thank Head, Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur for providing laboratory facilities and Director, SAIF, Chandigarh for providing necessary spectral data. The authors are grateful to Head, Department of Biotechnology, Sindhu Mahavidyalaya Nagpur, India for providing antimicrobial screening and Head, Sharad Pawar College of pharmacy Nagpur, India for providing facilities for anti-inflammatory activities.
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Kandpal, B., Meshram, J., Mohanram, I. et al. Evaluation of newly synthesized quinazolinone derivatives of hydrazones as potent anti-inflammatory and antibacterial agents. Med Chem Res 24, 1419–1426 (2015). https://doi.org/10.1007/s00044-014-1226-3
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DOI: https://doi.org/10.1007/s00044-014-1226-3