Volume : 09, Issue : 07, July – 2022
Title:
09.SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL EVALUATION OF STYRYL MOIETIES BASED NEW 4(3H)- QUINAZOLINONE DERIVATIVE
Authors :
Manmohan Gupta, Dr Alok Pal Jain*, Mr. Govind Nagar
Abstract :
Objective: The objective of the paper is synthesis and characterization of new 4(3H)- quinazolinone derivative based on styryl moieties and evaluate them for the antimicrobial activity.
Material and methods: The derivatives have been synthesized by the three steps process, in first step 2-methyl-4H-3,1-benzoxazin-4-one compounds was synthesized, in step 2, 2-methyl-3-peptido quinazolin-4-(3H)-ones compound was synthesized and in last step, 2-styryl-3-peptido quinazolin-4-(3H) ones compound have been synthesized by the reaction of synthesized compound of step 2, with different substituted aldehyde to from the final compounds. Total Sixteen compounds have been synthesized and characterized by physicochemical and spectral analysis. The final compounds (QP-1 to QP-16) have been evaluated for anti-microbial activity i.e., antibacterial and antifungal activity by agar based disk diffusion method.
Result and Discussion: The IR spectrum of the final compound QP-1 to QP16 have shown the IR spectrum with characteristics peak at 3442,57 (N-H str.); 1702.33 (C=O str., amide); 1457.55 (C=N str.); 1368.32 (N-O str.); 1565.22 (N=O str.); 852.22 (C-Cl); 1015.32 (C-Br); 1102.22 (C-F). The 1HNMR spectrum of the compound QP-1 to QP16 have shown the characteristics peak at 7.48-8.02 (4H, 1-benzene); 8.15 (1H, s ethylene); 6.66 (1H, s, ethylene), 1.46 (3H, s, methylene); 2.85 (1H, s, methine), 3.50 (3H, s, methyl), 4.62 (1H, s, methine). The Data of antibacterial activity against the gram-positive bacterial strains suggested that compound QP-1, QP-4, QP-6, QP-9, QP12 have shown best activity against gram positive bacteria. The Data of antibacterial activity against the gram-negative bacterial strains (Escherichia Coli, Klebsiella Penumoniae) suggested that among substituted quinazolinone derivatives, compound QP-1, QP-4, QP-6, QP-9, QP12 have shown best activity against gram positive bacteria. The compounds possessed the halogens on the aromatic ring reveals the positive contribution of electron withdrawing groups to the antibacterial and antifungal activity. Presence of electronegative group (Cl, NO2) is required for the potent antimicrobial activity.
Keywords: antimicrobial activity, quinazolinone, peptides, disk diffusion method, antibacterial, antifungal
Cite This Article:
Please cite this article in press Manmohan Gupta et al, Synthesis, Characterization And Antimicrobial Evaluation Of Styryl Moieties Based New 4(3h)- Quinazolinone Derivative., Indo Am. J. P. Sci, 2022; 09(7).,
Number of Downloads : 10
References:
1. Alagarswamy V, Raja Solomon V, Dhanabal K. Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic anti-inflammatory agents. Bioorg Med Chem 2007; 15: 235-241.
2. Hemalatha K, Girija K. Synthesis of some novel 2,3-disubstituted quinazolinone derivatives as analgesic and anti-inflammatory agents. Int J Pharm Pharm Sci 2011; 3(2): 103-106.
3. Abdallah AE, Eissa SI, Saleh-Al-Ward MM, Mabrouk RR, Ahmed BMM, El-Zahabi MA. Design, synthesis and molecular modelling of new quinazolin-4(3H)-one based VEGFR-2 kinase inhibitors for potential anticancer evaluation. Bioorg Chem 2021; 109; 104695.
4. Sharma D, Kumar S, Narasimhan B, Ramasamy K, Lim SM, Shah SA, et al. 4-(4-Bromophenyl)-thiazol-2-amine derivatives: synthesis, biological activity and molecular docking study with ADME profile. BMC Chem 2019;13(1):60.
5. Janardhanan J, Bouley R, Martínez-Caballero S, Peng Z, Batuecas-Mordillo M, Meisel JE. The quinazolinone allosteric inhibitor of PBP2a synergizes with piperacillin and tazobactam against methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother 2019; 63(5): e02637-18.
6. Hosseinzadeh L, Aliabadi A, Rahnama M, Sadeghi HM, Khajouei MR. Synthesis and cytotoxic evaluation of some new 3-(2-(2-phenylthiazol-4-yl) ethyl)-quinazolin-4 (3H) one derivative with potential anticancer effects. Res Pharm Sci 2017;12(4):290.
7. Zandhaghighi M, Ghazvini K, Meshkat Z, Rezaee SA, Derakhshan M, Soleimanpour S, et al. Screening of the anti-mycobacterial activity of novel lipophilic agents by the modified broth-based method. J Clin Tuberc Other Mycobact Dis 2016;3:1-5.
8. Rajasekhar KK, Nizamuddin ND, Surur AS, Mekonnen YT. Synthesis, characterization, anti-tubercular and antibacterial activity, and molecular docking of 2,3-disubstituted quinazolinone derivatives. Res Rep Med Chem 2016; 6:15-26.
9. Fedarovich A, Djordjevic KA, Swanson SM, Peterson YK, Nicholas RA, Davies C. High-throughput screening for novel inhibitors of Neisseria gonorrhoeae penicillin-binding protein 2. PLoS One 2012; 7(9): e44918.
10. Al-Said MS, Bashandy MS, Al-Qasoumi SI, Ghorab MM. Anti-breast cancer activity of some novel 1,2-dihydropyridine, quinazoline, thiophene and thiazole derivatives. Eur J Med Chem 2011; 46: 137-141.
11. Hemalatha K. and Girija K. Synthesis of some novel 2,3-disubstituted quinazolinone derivatives as analgesic and anti-inflammatory agents. Int J Pharm Pharm Sci 2011; 3(2): 103-106
12. Kumaraswamy D, Mallareddy V. Synthesis and biological activities of some new 2-S substituted aminomethylthio-3-aryl-4-(3H)quinazolinone. J Pharm Biomed Sci 2011; 5(15): 1-5
13. Shivananda MK, Shivarama HB. Synthesis and antifungal activity of 3-aryl-2-[(5-nitro-2-furfuryl)vinyl]quinazolin-4-ones. J Chem Pharm Res 2011; 3(3): 83-86.
14. Patel NB, Shaikh AR. Synthesis, characterization and in vitro antimicrobial studies of new 2,3-disubstituted quinazolin-4(3H)one of 2-[2-(2,6-dichlorophenyl)amino] phenyl acetic acid. Indian J Chem 2010; 49B: 929–936
15. Xu GF, Song BA, Bhadury PS, Yang S, Zhang PQ, Jin LH. Synthesis and antifungal activity of novel s-substituted 6-fluoro-4-alkyl (aryl) thioquinazoline derivatives. Bioorg Med Chem 2007; 15(11): 3768-74.