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Synthesis and Antimicrobial activity of some Quinazolinones Derivatives

Karumanchi Anupama Devi1*, M. Sarangapani2, Sriram3
  1. East West College of Pharmacy, Bangalore – 560091
  2. University College of Pharmaceutical Sciences, Kakatiya University, Andhra Pradesh – 506009
  3. University College of Pharmaceutical Sciences, Kakatiya University, Andhra Pradesh – 506009
Corresponding Author: Karumanchi Anupama Devi Email: anupamakarumanchi@gmail.com
Received:27 July 2012 Accepted: 11 August 2012
Citation: Karumanchi Anupama Devi 1*, M. Sarangapani 2, Sriram3 “Synthesis and Antimicrobial activity of some Quinazolinones Derivatives” Int. J. Drug Dev. & Res., July-September 2012, 4(3):324-327. doi: doi number
Copyright: © 2010 IJDDR, Karumanchi Anupama Devi et al. This is an open access paper distributed under the copyright agreement with Serials Publication, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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Abstract

Quinazolines are building blocks for approximately 150 naturally occurring alkaloids with a wide variety of biological responses. The substituents present on C-2 and N-3 of the quinazoline molecule plays in critical role in promoting several biological activities. Hence a new azaisatins derivative containing 4(3H) quinazolinones has been designed and synthesized. Their structures have been elucidated on the basis of elemental analysis and spectral studies. All the compounds synthesized were screened for their potential antimicrobial activities, which exhibited some authentic results towards testing organism invitro and invivo studies.

Keywords

Quinazoline, azaisatins, antimicrobial.

INTRODUCTION

The advancement and changes in the culture and lifestyle the new disease are being existed among the human population which indicated that the search for better drug is still necessary. Fused pyrimidine ring system is well known to possess important biological properties. Quinazoline and potent antibiotics that are known to inhibit the growth of gram positive bacteria and active transplantable tumors [1]. In many derivatives of quinazoline system more common is 4(3H) quinazolinone. First synthetic derivative of quinazoline was 2-cyano- 4(3H) quinazolinone. The most common method for the synthetic of 4(3H) quinazolinone is by the condensation of anthranilic acid with amides or primary amines. Quinazolinone derivatives have been reported for potential biological activities like anti-hypertension [2], [3], antifungal, anti-bacterial activity [4], [5] anti-cancer [6], anti HIV [7] and pharmacological compounds [8]
Literature survey reveals that azaisatins are biological active compounds that are reported for their application in antibacterial, antifungal, and antiobesity. In view of their biological importance we report the synthesis of new azaisatins derivatives containing 4(3H) quinazolinones. Representative compounds have been characterized for antimicrobial activities.

MATERIAL AND METHODS

Melting points were recorded by open capillary method and are uncorrected. Purity of compound was confirmed by TLC on silica gel-G using toluene: ethyl acetate (7:3) and iodine vapor as visualizing agent. The IR spectra were recorded on a Perkin Elmer BX 1 spectrometer using KBr cm-1.and 1HNMR on BRUCKER NMR spectrometer (400MHz) using CDCl3 as internal standard. Mass spectra were recorded on an Agilent Mass spectroscopy 1100 series using ESI technique

GENERAL PROCEDURE

A) Synthesis of Methyl-2-acetamidobenzoate [9] (II)
In 100ml of round bottomed flask, a solution of Methyl-2-aminobenzoate (I)(0.016 mole) in acetic anhydride (0.0127 mole) were taken and refluxed for 8-12 hours and the reaction was monitored by TLC for completion. The solution was cooled, poured into cold water (50ml) containing a drop of pyridine and stirred until the oil was solidified. The product was filtered, washed with cold water (4x50) and dried. The solid product was recrystallized from ethanol (6ml/gm). Yield: 80%, m.p: 98 – 100 0 C
B) Synthesis of 3-Amino-2-methylquinazolin- 4(3H)-one [9] (III)
In 100ml of round bottomed flask, a solution of hydrazine hydrate (10ml) and Methyl-2- acetoamidobenzoate (II, 0.01 moles) in ethanol were taken and refluxed for 8-12 hours and the reaction was monitored by TLC for completion. The solution was cooled, poured into cold water and the product was filtered, washed with cold water and dried. The solid product was recrystallized from ethanol. Yield: 84%, m.p: 151 – 152 0 C

C) Synthesis of 3-(1, 2-Dihydro-1-substituted- 2-oxopyrrolo [2, 3-b] pyridine-3- ylideneamino)-2-methylquinazolin-4(3H)- ones [10] (IV) a-d

A mixture of 3-Amino-2-methylquinazolin-4(3H)- one (III, 0.001 mole) and substituted azaisatin (0.01 mole) in 10ml of glacial acetic acid were refluxed for 10-15minutes at 140 watt in Catalyst Systems Scientific microwave System and the reaction was monitored by TLC for completion. The resultant solution was poured into cold water. The product was filtered, washed with cold water and dried. The solid product was recrystallized from absolute alcohol.

ANTI-MICROBIAL ACTIVITY

Newly synthesized compounds were screened for antibacterial activity against gram positive bacteria Bacillus subtilis, Staphylococcus aureus, Streptococcus pneumonia and gram negative bacteria Escherichia coli, Proteus vulgaris, Klebsiella pneumoniae, Pseudomonas aeruginosa and four fungus Aspergillus niger, Aspergillus flavus, Candida albicans and Fusarium oxysporium by using disc diffusion method at 10 μg/disc. The cultural media used for bacteria was nutrient agar medium and for fungi it was potato-dextrose-agar medium. Solutions of Ciprofloxacin and Fluconazole were used as standard antibacterial and antifungal drugs respectively. Amongst all of them compound IVd has been found to be relatively active against gram positive & gram negative bacteria and all four funguses in comparison to other compounds. IVc were moderately active against Bacillus subtilis, Proteus vulgaris and all four funguses.

ACKNOWLEDGEMENT

 
The authors are thankful to University College of Pharmaceutical Sciences, Kakatiya University, Warangal, and Andhra Pradesh for providing all the facilities and Heads of R and D institute, Vijayawada for providing the spectral data.

Tables at a glance

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Figure 1
Scheme 1

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