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Synthesis, characterization and antimicrobial studies of new 2-(2-chloroquinolin-3-yl)-3-(substituted phenyl/pyridinyl)quinazolin-4(3H)-one derivatives using l-proline as a catalyst

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Abstract

2-(2-Chloroquinolin-3-yl)-3-(substituted phenyl/pyridinyl)quinazolin-4(3H)-one derivatives 5am were synthesized in good yield using conventional as well as microwave heating conditions in presence of l-proline as a catalyst. Synthetic conditions were optimized using an orthogonal array system of Taguchi’s design. The structure of synthesized quinazolinone compounds 5am was established with the help of physico-chemical analysis and various spectroscopic techniques like FT-IR, mass, 1H-NMR and 13C-NMR. Further, all the synthesized compounds were screened for their antimicrobial (antibacterial, antifungal and antimalarial) activities. The results of antimicrobial screening showed that compounds 4g, 4j, 4m, 5e and 5g have good activity against bacterial species, whereas compounds 4d, 4g, 4m, 5b, 5d and 5g have good activity against malaria pathogen. In addition to this, compounds 4i, 4j and 4m exhibited good to moderate activity against fungal strains.

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References

  • Abdel-Jalil RJ, Voelter W, Saeed M (2004) A novel method for the synthesis of 4(3H)-quinazolinones. Tetrahedron Lett 45:3475

    Article  CAS  Google Scholar 

  • Bava S, Kumar S (2009) Synthesis of schiff’s bases of 8-methyltetrazolo[1,5-a]quinoline as potential anti-inflammatory and antimicrobial agents. Indian J Chem 48B:142–145

    Google Scholar 

  • Bhuiyan MH, Nessa H, Mahmud MM (2012) Multicomponent reactions: microwave-assisted efficient synthesis of dihydropyrimidinones (thiones) and quinazolinones under green chemistry protocol as probes for antimicrobial activities. J Sci Res 4:143

    CAS  Google Scholar 

  • Boyapati S, Kulandaivelu U, Sangu S, Vanga MR (2010) Synthesis, antimicrobial evaluation, and docking studies of novel 4-substituted quinazoline derivatives as DNA-gyrase inhibitors. Arch Pharm 343:570

    Article  CAS  Google Scholar 

  • Carvalho LH, Krettli AU (1991) Antimalarial chemotherapy with natural products and chemically defined molecules. Mem Inst Oswaldo Cruz 86(Suppl. II):181

    Article  PubMed  Google Scholar 

  • Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M, Kozehgary G, Mohammadi AA (2005) Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)2·12H2O as a reusable catalyst in water and ethanol. Tetrahedron Lett 46:6123

    Article  CAS  Google Scholar 

  • Dave SS, Ghatole AM, Rahatgaonkar AM, Chorghade MS, Chuhan PMS, Srivastava K (2009) Experimental and computational evaluation of new quinolyl chalcones as potent antiplasmodium agents. Indian J Chem 48B:1780–1793

    CAS  Google Scholar 

  • Gawad NMA, Georgey HH, Youssef RM, Sayed NA (2011) Design, synthesis, and anticonvulsant activity of novel quinazolinone analogues. Med Chem Res 20:1280

    Article  Google Scholar 

  • Gnana Ruba Priya M, Zulykama Y, Girija K, Murugesh S, Perumal PT (2011) Microwave-assisted synthesis of quinazolinone derivatives by efficient and rapid iron-catalyzed cyclization in water. Indian J Chem Sect B 50:98

    Google Scholar 

  • Isambert N, MdelMS Duque, Plaquevent JC, Génisson Y, Rodriguez J, Constantieux T (2011) Multicomponent reactions and ionic liquids: a perfect synergy for eco-compatible heterocyclic synthesis. Chem Soc Rev 40:1347

    Article  CAS  PubMed  Google Scholar 

  • Ismail ZH, Ghorab MM, Mohamed EMA, Aly HM, El-Gaby MSA (2008) Antitumor activity of some novel 1,2,5-thiadiazole derivatives. Phosphorus Sulfur Silicon Relat Elem 183:2541

    Article  CAS  Google Scholar 

  • Kalluraya B, Nayak J, Adhikari A, Sujith KV, Sucheta N, Shetty MW (2008) Synthesis and characterization of some novel quinolinothiazines of biological interest. Phosphorus Sulfur Silicon Relat Elem 183:1870–1883

    Article  CAS  Google Scholar 

  • Kumar D, Mishra BG, Rao VS (2006) An environmentally benign protocol for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones using solid acid catalysts under solvent-free conditions. Indian J Chem Sect B 45:2325

    Google Scholar 

  • Kumari K, Raghuvanshi DS, Singh KN (2012) Microwave assisted eco-friendly protocol for one pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water. Indian J Chem Sect B 51:860

    Google Scholar 

  • Lambros C, Vanderberg JP (1979) Synchronization of Plasmodium falciparum erythrocytic stages in culture. J Parasitol 65:418

    Article  CAS  PubMed  Google Scholar 

  • Liang Y, Ding M-W, Liu Z-J, Liu X-P (2003) A facile and selective synthesis of 2-alkylamino-4(3H)-quinazolinones. Synth Commun 33:2843

    Article  CAS  Google Scholar 

  • Meth-Cohn O, Narine B, Tarnowski B (1981) A versatile new synthesis of quinolines and related fused pyridines. Part 5. The synthesis of 2-chloroquinoline-3-carbaldehydes. J Chem Soc Perkin Trans 1:1520

  • Mossetti R, Pirali T, Saggiorato D, CesareTron G (2011) Imides: forgotten players in the Ugi reaction. One-pot multicomponent synthesis of quinazolinones. Chem Commun 47:6966

    Article  CAS  Google Scholar 

  • National Committee for Clinical Laboratory Standards (2002) Performance standards for antimicrobial susceptibility testing: twelfth informational supplement. ISBN:1-56238-454-6, M100-S12, M7

  • Pan N, Zhang W, Liu Q (2009) Methyl 6-methyl-4-(4-iodophenyl)-1,2,3,4-tetrahydro-thioxo-5-pyrimidinecarbohydrate. Molbank 4:M645

    Article  Google Scholar 

  • Pavia DL, Lampman GM, Kriz GS, Vyvyan JR (2008) Spectroscopy. Cengage Learning India Pvt. Ltd., New Delhi

    Google Scholar 

  • Perreux L, Loupy A (2001) A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 57:9199

    Article  CAS  Google Scholar 

  • Peyman S, Minoo D, Mostafa B, Mahboobeh B (2006) One-pot, three-component synthesis of 2,3-dihydro-4(1h)-quinazolinones by Montmorillonite K-10 as an efficient and reusable catalyst. Synth Commun 36:2287

    Article  Google Scholar 

  • Potewar TM, Nadaf RN, Thomas D, Lahoti RJ, Srinivasan KV (2005) A novel one-pot synthesis of 2-aryl-4(3H)-quinazolinones using room temperature ionic liquid as reaction medium as well as promoter. Synth Commun 35:231

    Article  CAS  Google Scholar 

  • Rana PB, Mistry BD, Desai KR (2008) Green chemistry: conventional and microwave induced synthesis of various thiazolidinone derivatives from 3-{[(1E)-(2′-chloro-7′-methoxyquinoline-3′-yl)methoxyquinoline-3’-yl)methylene]amino}-4 (substitutedphenyldiazenyl)phenol and their antimicrobial screening. Arkivoc xv:262–279

    Article  Google Scholar 

  • Sangani CB, Jardosh HH, Patel MP, Patel RG (2013) Microwave-assisted synthesis of pyrido[1,2-a]benzimidazole derivatives of β-aryloxyquinoline and their antimicrobial and antituberculosis activities. Med Chem Res 22:3035–3047

    Article  CAS  Google Scholar 

  • Sen D, Banerjee A, Ghosh AK, Chatterjee TK (2010) Synthesis and antimalarial evaluation of some 4-quinazolinone derivatives based on febrifugine. J Adv Pharm Technol Res 1:401

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Shaterian HR, Oveisi AR, Honarmand M (2010) Synthesis of 2,3-dihydroquinazoline-4(1H)-ones. Synth Commun 40:1231

    Article  CAS  Google Scholar 

  • Shi A, Nguyen TA, Battina SK, Rana S, Takemoto DJ, Chiang PK, Hua DH (2008) Synthesis and anti-breast cancer activities of substituted quinolines. Bioorg Med Chem Lett 18:3364–3368

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Siddiqui IR, Singh PK, Srivastava V, Yadav S, Singh J (2011) A novel versatile strategy for synthesis of new series of 4(3H)-quinazolinone N-nucleosides. ChemInform Abstr 42. doi:10.1002/chin.201111214

  • Silverstein RM, Webster FX (2007) Spectroscopic identification of organic compounds. Wiley India (P) Ltd., New Delhi

    Google Scholar 

  • Tang JH, Shi DX, Zhang LJ, Zhang Q, Li J-R (2010) Facile and one-pot synthesis of 1,2-dihydroquinazolin-4(3H)-ones via tandem intramolecular pinner/dimroth rearrangement. Synth Commun 40:632

    Article  CAS  Google Scholar 

  • Trager W, Jensen JB (1976) Human malaria parasites in continuous culture. Science 193:673

    Article  CAS  PubMed  Google Scholar 

  • Varma RS (1999) Solvent-free organic synthesis using supported reagents and microwave irradiation. Green Chem 1:43

    Article  CAS  Google Scholar 

  • Wang L, Xia J, Qin F, Qian C, Sun J (2003) Yb(OTf)3-catalyzed one-pot synthesis of quinazolin-4(3H)-ones from anthranilic-acid, amines and ortho esters (or formic acid) in solvent-free conditions. Synthesis 8:1241

  • Xu Y, Guo QX (2004) Syntheses of heterocyclic compounds under microwave irradiation. Heterocycles 63:903

    Article  CAS  Google Scholar 

  • Zhang X, Ye D, Sun H, Guo D, Wang J, Huang H, Zhang X, Jiang H, Liu H (2009) Microwave-assisted synthesis of quinazolinone derivatives by efficient and rapid iron-catalyzed cyclization in water. Green Chem 11:1881

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge the Director, ARIBAS and C. V. M. for providing all the necessary research facilities. We also thanks to Dr. Saurabh S. Soni, Assistant professor, Department of Chemistry, S. P. University for providing scientific microwave oven facility. We are also obliged by Director, SICART for providing analysis facilities.

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Correspondence to Ritu Dixit.

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Dixit, R., Mehta, H. & Dixit, B. Synthesis, characterization and antimicrobial studies of new 2-(2-chloroquinolin-3-yl)-3-(substituted phenyl/pyridinyl)quinazolin-4(3H)-one derivatives using l-proline as a catalyst. Med Chem Res 24, 773–786 (2015). https://doi.org/10.1007/s00044-014-1116-8

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