Abstract
A new series of 2-methyl-3H-quinazolinones substituted at the third position with amino acids (2–5) and aryl amine (6, 7) was designed, synthesized, and analyzed by infrared, NMR, and mass spectral analysis. Further, the compounds were screened for their in vivo antimalarial activity using the rodent malaria parasite Plasmodium yoelii (N-67) with the Swiss mice model. The compounds were also tested for their antibacterial activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alagarsamy V, Pathak US, Sriram D, Pandeya SN, De Clerq E (2000) Anti HIV and antibacterial activities of some disubstituted quinazolones and their Bio-isostere disubstituted thieno pyrimidones. Ind J Pharm Sci 62(6):433–437
Alagarsamy N, Rajesh R, Ramaseshu M, Vijaya Kumar S, Ramseshu KV, Duraianandakumar T (2004) Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-methylthio-3-substituted quinazolin-4-(3H)-ones. Biol Pharm Bull 27(5):652–666
Joshi AA, Narkhede SS, Viswanatha CL (2005) Design, synthesis and evaluation of 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b] quinolines as novel antimalarials. Bioorg Med Chem Lett 15(1):73–76
Kaylene R (1999) Invited review. Bisquinoline antimalarials: their role in malaria chemotherapy. J Parasitol 29(3):367–379
Koizomi M, Marakuni Y (1917) Jpn Kokai 77:51
Manabu H, Ryuichi I, Hideaki H, Akio O, Takayuki S, Hiroshi O (1990) Novel 4-phenoxy-2-(1-piperazinyl) quinazolines as potent anticonvulsive and antihypoxic agents. Chem Pharm Bull 38(3):681–687
Mei-Lin G, Tong Lan N, Agnes Lay CT, Kunnika K, Prapon W (1998) Structure–activity relationships of some indolo[3,2-c]quinolines with antimalarial activity. Eur J Pharm Sci 6(1):19–26
Michael F, Leann T (1998) Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacol Ther 79(1):55–87
Neerja J, Puri SK (2004) Plasmodium yoelii: activity of azithromycin in combination with pyrimethamine or sulfadoxine against blood and sporozoite induced infections in Swiss mice. Exp Parasitol 107(3–4):120–124
Nigam R, Sanjay S, Saxena VK, Dua PR, Srimal RC (1990) Synthesis and pharmacological screening of some new 2-(phenyl/chloromethyl)-3-[4(N, N-disubstituted aminocarbonyl)phenyl]-8-substituted-4(3H)-quinazolones. Ind Drugs 27(4):238–243
Puri SK, Naresh S (2000) Azithromycin: antimalarial profile against blood- and sporozoite-induced infections in mice and monkeys. Exp Parasitol 94(1):8–14
Singh C, Srivastav NC, Puri SK (2002) In vivo active antimalarial isonitriles. Bioorg Med Chem Lett 12(17):2277–2279
Singh C, Mailk H, Puri SK (2004) Orally active amino functionalized antimalarial 1, 2, 4- trioxanes. Bioorg Med Chem Lett 14(2):459–462
Acknowledgments
All the authors are grateful to Dr. A. K. Goel, Assistant Director, CDRI, Lucknow, India, for helping us conduct the antimalarial evaluation. The authors are also grateful to Sri Shivarathree Desikendra Mahaswamigalavaru of Suttur mutt for providing the facilities to carry out the synthetic work.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Meyyanathan, S.N., Ramu, M. & Suresh, B. Synthesis, antimalarial and antibacterial activities of 3-amino acid- and aryl amine-substituted 2-methyl-3H-quinalzolin-4-ones. Med Chem Res 19, 993–999 (2010). https://doi.org/10.1007/s00044-009-9245-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-009-9245-1