Hindawi Publishing Corporation Journal of Pharmaceutics Volume 2013, Article ID 907525, 7 pages http://dx.doi.org/10.1155/2013/907525 Research Article S�nthesis, Characterization, and Anti�In�a��ator � Acti�it�o� Newer Quinazolinone Analogs Chatrasal Singh Rajput 1, 2 and Shiwani Singhal 1 1 Medicinal Chemistry Division, Department of Pharmacology, L.L.R.M. Medical College, Meerut 250002, India 2 Jubilant Chemsys Ltd. R & D B-34, Sector 58, Noida 201301, India Correspondence should be addressed to Chatrasal Singh Rajput; chatrasalrajput@gmail.com Received 24 September 2012; Revised 29 October 2012; Accepted 1 November 2012 Academic Editor: Susana Zacchino Copyright © 2013 C. S. Rajput and S. Singhal. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. A series of 3-[2 ′ -(Substitutedbenzylideneamino)phenyl]-2-methyl-6-substituted quinazolin-4-ones (5–10), 3-[2 ′ -(3 ″ -chloro-2 ″ - oxo-4 ″ -substitutedphenylazetidin-1 ″ -yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11–16), and 3-[2 ′ -(2 ″ -substitutedphe- nyl-4 ″ -oxo-1 ″ ,3 ″ -thiazolidin-3 ″ -yl)phentl]-2-methyl-6-substitutedquinazolin-4-ones (17–22) have been synthesized in the present study. e structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1 H NMR, and mass spectral data. All the newly synthesized compounds were screened for anti-in�ammatory and analgesic activities. 1. Introduction Quinazolinone derivatives represent one of the most active classes of compounds possessing a wide spectrum of biolog- ical activity. ey are widely used in pharmaceuticals and agrochemicals. Several reports have been published on the biological activities of quinazolinone derivatives, including their anti-in�ammatory [1–7], antimalarial [8, 9], antimicro- bial, anti-fungal, antibacterial [10–16], anticonvulsant [17– 20], and antitumor [21, 22] activities. Moreover, large num- ber of quinazolinone derivatives having substitution at 2 and 3 position by different heterocyclic moieties increases anti- in�ammatory potential of quinazolinone derivatives. Simi- larly, various azetidinones [23–25] and thiazolidinones [26, 27] have been reported to possess potent anti-in�ammatory activity. Looking to the medicinal importance of 4(3H)- quinazolinone, 4-thiazolidinone, and azetidinones, we report here the synthesis of a new class of heterocyclic molecules in which all of these moieties are present and try to develop potential bioactive molecules. e structures of the com- pounds synthesized were assigned on the basis of elemen- tal analysis, IR, 1 H NMR, and Mass spectral data. ese compounds were evaluated for their anti-in�ammatory and analgesic activities. 2. Materials and Methods 2.1. Chemistry. e synthetic routes of compounds are outlined in Scheme 1. As shown in Scheme 1, compounds 2-methylsubstitued-4H-3,1-benzoxazin-4-ones (1,2) were synthesized by the known procedure of Bogert [28]. Substituted anthranilic acid reacted with acetic anhydride to give 2-methylsubstituted-4H-3,1-benzoxazin-4-ones (1,2), which further reacted with 2-amino phenyl amine in acetic acid to yield 3-(2 ′ -aminophenyl)-2-methyl-6-substituted quinazolin-4-ones (3,4). Compounds (3,4) when treated with different substituted aromatic aldehydes formed various substituted arylidene derivatives (5–10). ese arylidene derivatives on treatment with chloroacetylchloride in presence of triethylamine yielded 3-[2 ′ -(3 ′′ -chloro- 2 ′′ -oxo-4 ′′ -substituted phenylazetidin-1 ′′ -yl)phenyl]-2- methyl-6-substitutedquinazolin-4-ones (11–16). On the other hand, these arylidene derivatives on reaction with thioglycolic acid and anhydrous ZnCl 2 furnished 3-[2 ′ -(2 ′′ - substitutedphenyl-4 ′′ -oxo-1 ′′ ,3 ′′ -thiazolidin-3 ′′ -yl)phenyl]- 2-methyl-6-substitutedquinazolin-4-ones. (17–22). e structures of the compounds synthesized were assigned