TY - JOUR T1 - Synthesis of New 3-Substiuted Quinazolin-4(3H)-one Compounds AU - Saad-aldeen, Rand Arshad AU - Al-ıraqı, Mohammed Ahmed PY - 2019 DA - November JF - The Eurasia Proceedings of Science Technology Engineering and Mathematics JO - EPSTEM PB - ISRES Publishing WT - DergiPark SN - 2602-3199 SP - 93 EP - 98 VL - 7 LA - en AB - Quinazolin-4(3H)-one is a well-known heterocyclic compound with a unique place in medicinal chemistry, and it has drawn much attention due to its diversified biological activity. In this research we report the synthesis of some quinazolin-4-one derivatives containing acetylenic moiety. The quinazolin-4(3H)-one (1) was synthesized from the reaction of anthranilic acid with formamide under the conventional or microwave irradiation conditions. The quinazolin-4(3H)-one was converted to the corresponding 3-propargyl derivative (2) by its reaction with propargyl bromide in presence of potassium carbonate as a base and acetone as a solvent. The 3-propargyl quinazolin-4(3H)-one (2) was used as a precursor to synthesize new three series of heterocyclic compounds containing quinazolin-4(3H)-one moiety. Compound (2) was treated with ethyl magnesium bromide, then the resulted solution treated immediately with carbon disulfide and sublimed sulfur to synthesize 1,2-dithiol-3-thione compound (3). The 1,2,3-triazole compounds (5a-d) were synthesized by the reaction of compound (2) with alkyl azides (4a-d) according to Click reaction. The Mannich bases (6a-i) were synthesized via Mannich reaction by reaction of the acetylenic compound (2) with secondary amines in presence of paraformaldehyde in1,4-dioxane as a solvent. All the synthesized compounds were characterized by physical and spectral measurements. KW - Quinazolin-4-one KW - 2-dithiol-3-thione KW - 1 KW - 2 KW - 3-triazole KW - Click reaction KW - Mannich reaction CR - Hess, H. J.; Cronin, T. H.; Scriabine, A., (1968), J. Med. Chem. 11, 140. Ghorab, M. M. (2000), Farmco. 55, 249. Bartroli, J.; Turmo, E.; Alguero, M.; Boncompte, E.; Vericant, M. L.; Conte Ramis, J.; Merlos, M.; Gracia-Rafanell, J. F., (1998), J .Med .Chem. 48, 1869. Dohle, W.; Jourdan, F.L.; Menchon, G.; Prota, A.E.; Foster, P.A.; Mannion, P.; Hamel, E.; Thomas, M.P.; Kasprzyk, P.G.; Ferrandis, E.; (2018), J. Med. Chem. 61, 1031–1044. Abdel-Hamid, S. G. (1997), J. Indian Chem. Soc. 74, 613. El-Brollosy, N. R.; Abdel-Megeed, M. F.; Genady, A. R. (2003), Alexandria J. Pharm. Sci. 17(1), 17. Shab, B. R.; Bhatt, J. J.; Patel, H. H.; Undavia, N. K.; Trivedi, P. B.; Desai, N. C. (1995), Indian. J.Chem. 34B, 201. Khili, M. A.; Soliman, R.; Furghuli, A. M.; Bekhit, A. A. (1994), Arch. Pharm. 327, 27. Shivaram, H. B.; Padmaja, M. T.; Shivnanda, M. K.; Akbarali, P. M. (1998), Indian. J. Chem. 37B, 715. Noureldin, N.A.; Kothayer, H.; Lashine, E.-S.M.; Baraka, M.M.; El-Eraky, W.; El Awdan, S.A. (2017), Arch. Pharm. Chem. Life Sci. 350, e1600332. Saravanan G., Alagarsamy V., Prakash CR; (2010), Int. J. Pharm. Pharm. Sci., 2010, 2:83–86. Sasmal S, Balaji G, Kanna R. HR, Balasubrahmanyam D, Srinivas G, Kyasa S, Sasmal PK, Khanna I, Talwar R, Suresh J, Jadhav VP, Muzeeb S, Shashikumar D, Harinder Reddy K, Sebastian VJ, Frimurer TM, Rist Ø, Elster L, Högberg T; (2012), Bioorg. Med. Chem. Lett. 22:3157–3162. Sjoqvist F and Gilette J, (1965) Life Sci. 4, 1031. Leslie G.B. and MaxwellD. R. (1904), Nature, 202, 97. Tang C, Castoldi AF, Costa LG, (1993) Biochem. Mol. Biol. Int. 29 (6): 1047–54. Disingrini T, Muth M, Dallanoce C, Barocelli E, Bertoni S, Kellershohn K, Mohr K, De Amici M, Holzgrabe U; (2006), J. Med. Chem. 491, 366-372 . Dallanoce, C.; Conti, P.; De Amici, M.; De Micheli, C.; Barocelli, E.; Chiavarini, M.; Ballabeni, V.; Bertoni, S.; Impicciatore, M., (1999), Bioorg. Med. Chem. 7, 1539-1547. Xu J M, Zhang E, Shi X J, Wang Y C, Yu B, Jiao W W, Guo Y Z, Liu H M, (2014), Eur.J. Med. Chem. 80, 593. Saqlain H, A. Sarwar A M, Hinna H, Syed S, Abhijeet D, Firasat H, Perwez A, Sadiq U, Pasha M A Q, Sameena B, Syed N, Yakub A, Chetna K, (2014), Eur. J. Med. Chem. 81, 204. Lee W. W, Bueding E, (1986), Carcinogenesis, 7(8), 1379–1381. Kensler T W, Egner P A, Dolan P M, Groopman J D, B. D. Roebuck B D, (1987), Cancer Research, 47, 4271-4277. Furniss B S; Hannaford A J; Smith P W; Tatchell A R; (1989) "Vogel's Textbook of Practical Organic Chemistry", John Wiley & Sons. Inc. New York, pp.534. UR - https://dergipark.org.tr/en/pub/epstem/issue//653237 L1 - https://dergipark.org.tr/en/download/article-file/867626 ER -