Abstract
We reported the synthesis of a novel series of quinazolin-4(3H)-one derivatives bearing oxadiazole, thiadiazole, and other moieties in the 3-position of the quinazolinone nucleus using appropriate synthetic route. The compounds were evaluated for their anticonvulsant activity using picrotoxin model, GABA-A receptor antagonist. Five compounds showed significantly prolonged times for convulsions compared with the standard drug phenobarbital.
Graphical abstract
Similar content being viewed by others
References
Stefan H, Feuerstein T (2007) Pharmacol Ther 113:165
Pollard JR, French J (2006) Lancet Neurol 5:1064
Donner EJ, Snead OC III (2006) NeuroRX 3:170
McAuley JW, Biederman TS, Smith JC, Moore JL (2002) Ann Pharmacother 36:119
Rho JM, Sankar R (1999) Epilepsia 40:1471
Shorvon S (2000) Handbook of epilepsy treatment. Blackwell Science, MA
Guimarães J, Ribeiro JAM (2010) Neurol 16:353
Vitaku E, Smith DT, Njardarson JT (2014) J Med Chem 57:10257
Al-Salem HSA, Hegazy GH, El-Taher KEH, El-Messery SM, Al-Obaid AM, El-Subbagh HI (2015) Bioorg Med Chem 25:1490
Witt A, Bergman J (2003) Curr Org Chem 7:659 (references cited therein)
Al-Omary FA, Abou-Zeid LA, Nagi MN, El-Habib SE, Abdel-Aziz AA, El-Azab AS, Abdel-Hamide SG, Al-Omar MA, Al-Obaid AM, El-Subbagh HI (2010) Bioorg Med Chem 18:2849
Al-Obaid AM, Abdel-Hamide SG, El-Kashef HA, Abdel-Aziz AA, El-Azab AS, Al-Khamees HA, El-Subbagh HI (2009) Eur J Med Chem 4:2379
El-Azab AS, Al-Omar MA, Abdel-Aziz AA, Abdel-Aziz NI, El-Sayed MA, Aleisa AM, Sayed-Ahmed MM, Abdel-Hamid SG (2010) Eur J Med Chem 45:4188
Alafeefy AM, Kadi AA, El-Azab AS, Abdel-Hamide SG, Daba MH (2008) Arch Pharm (Weinheim) 341:377
Kumar A, Sharma S, Archana A, Bajaj K, Panwar H, Singh T, Srivastava VK (2003) Bioorg Med Chem 11:5293
Alagarsamy V, Solomon VR, Dhanabal K (2007) Bioorg Med Chem 15:235
Srivastava AVK, Kumar A (2002) Eur J Med Chem 37:873
Chapleo CB, Mayer M, Myer PL, Saville JF, Smith ACB, Stilling MR, Tulloch IF, Walter DS, Welbourn AP (1986) J Med Chem 29:2273
Srivastava AVK, Kumar A (2004) Bioorg Med Chem 12:1257
Aziza MA, Ibrahim MK, El-Helpy AG (1994) J Pharm Sci 14:193
Bekhit AA, Khalil MA (1998) Pharmazie 53:539
Ergenc N, Buyuktimkin S, Capan G, Baktir G, Rollas S (1991) Pharmazie 46:290
Kashaw SK, Kashaw V, Mishra P, Jain NK (2008) Arkivoc xiv:17
Gujral M, Saeen K, Kohli R (1957) Ind J Med Res 45:207
Boltze KH, Dell HD, Lehwald H, Loranz D, Ruberg-Schweer M (1963) Arzneim-Forsch Drug Res 13:688
Wolfe JF, Rathman TL, Sleevi MC, Campbell JA, Greenwood TD (1990) J Med Chem 33:161
Kashaw SK, Kashaw V, Mishra P, Jain NK, Stables JP (2009) Eur J Med Chem 44:4335
Kumar KA, Jayaroopa P, Kumar G (2012) Int J ChemTech Res 4:1782
Chapleo L, Saville JF, Smith ACB, Stilling MR, Tullock IF, Walter DS, Welbourn AP (1986) J Med Chem 29:2273
Srivastava K, Pandeya SN (1993) Bioorg Med Chem 3:547
Prakash A, Murthi KN, Singh RP, Pandeya SN (1994) Indian J Heterocycl Chem 4:65
Khazi IAM, Mahajanshetti CS, Gadad AK, Tarnalli AD, Sultanpur CM (1996) Arzneim Forsch 46:949
Jain SK, Mishra P (2000) Asian J Chem 12:1341
Mali JR, Pratap UR, Netankar PD, Mane RA (2009) Tetrahedron Lett 50:5025
El-Essawy FA, El-Sayed WA (2013) J Heterocycl Chem 50:E1
Sing I, Saxena AK, Sinha JN, Bhargava KP, Shanker K (1984) Indian J Chem 23:592
Pathak US, Rathod IS, Patel MB, Shirsath VS, Jain KS (1995) Indian J Chem 34:617
Abdel-Hamid SG (1997) J Indian Chem Soc 74:619
Singh S, Shukla M, Srivastava VK, Shanker K (1986) Indian J Chem 26:712
Darshan R, Firdous F, Sanjiv M, Krishnan K (1986) Heterocycles 24:2493
Suesse M, Johne S (1985) Helv Chim Acta 68:892
Louhimies S (2002) Altern Lab Anim 30(Suppl 2):217
Farag AA, Abd-Alrahman SN, Ahmed GF, Ammar RM, Ammar YA, Abbas SY (2012) Arch Pharm 345:703
Heidari MR, Mandegary A, Hosseini A, Vahedian M (2006) Pak J Biol Sci 9:772
Heidari MR, Khalili F, Ghazi-khansari M, Hashemi B, Zarrindast MR (1996) Pharmacol Toxicol 78:313
Gale K (1992) Epilepsia 33(Suppl 5):S3
Salami P, Lévesque M, Gotman J, Avoli M (2015) J Neurophysiol 113:2840
Kalueff AV (2007) Neurochem Int 50:61
Navarro RA, Bastidas RBE, García EJ, García LP, Garzón P (1995) J Ethnopharmacol 45:199
Shemchuk LA, Al-Asri JM, Levashov DV, Shenhof YO, Arzumanov PS (2011) Visnik Farmatsii 3:30
Ranganathan D, Farooqui F, Mehrotra S, Kesavan K (1986) Heterocycles 24:2493
Acknowledgments
We are grateful to Professor Gerhard Maas from Institute of Organic Chemistry I, University of Ulm, Germany for assistance with NMR measurements.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Boshta, N.M., El-Essawy, F.A., Ammar, R.M. et al. Synthesis of some new quinazolin-4(3H)-one derivatives and evaluation of their anticonvulsant activity. Monatsh Chem 147, 2031–2042 (2016). https://doi.org/10.1007/s00706-016-1710-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-016-1710-1