Conglomerate and Analgesic Activity of 6-bromo-2-(o-aminophenyl)-3-amino-Quinazolin-4(3H)-one from 6-bromo,2-(o-aminophenyl)-3,1-benzoxazin-4(3H)-one.

Volume 9, Issue 1, February 2024     |     PP. 1-12      |     PDF (343 K)    |     Pub. Date: March 5, 2024
DOI: 10.54647/materials430259    27 Downloads     106254 Views  

Author(s)

Osarumwense Peter Osarodion, Department of Chemical Science, Ondo State University of Science and Technology, Okitipupa, Ondo State, Nigeria.

Abstract
Introduction: Quinazolinone by–product disclosed various curative characteristics such as analgesic, anti-inflammatory and anticancer activities, as well as antimicrobial activity. These heterocycles are beneficial intermediates in organic synthesis. Methods/Experimental:The compound, 6-bromo,2-(o-aminophenyl)-3,1-benzoxazin-4(3H)-one(1) was integrated by dissolving 5-bromo anthranillic acid in 100 ml of pyridine. To this reaction mixture o-amino benzoyl chloride stirring at room temperature for 30 minutes this was refluxed with 75 mL of hydrazine hydrate for 3 hrs at 120-1300C. the reaction mixture was allowed to cool to room temperature to give 6-bromo-2-(o-aminophenyl)-3-amino-Quinazolin-4(3H)-one (2). These Compounds were evaluated for their analgesic activity using Acetic acid induced model. Study Design: This study was experimentally design and the analgesic activity was evaluated using Acetic acid induced model. Result: The compounds synthesized were evaluated pharmacologically for their in-vivo analgesic activities by acetic acid induced writhing in mice. The two scrutinized compounds exhibited significant analgesic activity in the range of 61.33 - 83.18% in comparison to control. Conclusions: From our findings, compound 2 synthesized have higher analgesic activities as compared to indomethacin a standard analgesic drug.

Keywords
Analgesic activity; Coglomerate; Quinazolinone derivatives; 6-bromo-2-(o-aminophenyl)-3-amino-Quinazolin-4(3H)-one; 6-bromo,2-(o-aminophenyl)-3,1-benzoxazin-4(3H)-one.

Cite this paper
Osarumwense Peter Osarodion, Conglomerate and Analgesic Activity of 6-bromo-2-(o-aminophenyl)-3-amino-Quinazolin-4(3H)-one from 6-bromo,2-(o-aminophenyl)-3,1-benzoxazin-4(3H)-one. , SCIREA Journal of Materials. Volume 9, Issue 1, February 2024 | PP. 1-12. 10.54647/materials430259

References

[ 1 ] Raghavendra N.M., Niranjan M.S., Venkatesh P., Prashantha Kumar B.R., Gowda N.B., Sripathi M.S., Synthesis and biological activity of some substituted  2-phenyl-quinazolin-4-one, Asian Journal of Chemistry, vol.17 no.1, 57-65, 2005.
[ 2 ] Mishra P., Namdeo K.P., Jain S.K., Jain S., Synthesis and Antimicrobial Activity of  4- Thiazolidinones, Asian Journal of Chemisry, vol. 11 no.1, 55-58, 1999.
[ 3 ] Jatav V., Mishra P., Kashaw S., Stables J.P., Synthesis and CNS depressant activity of some novel 3-[5-substituted-1,3,4-thiadiazole-2-yl]-2-styryl-quinazoline-4(3H)-one, European Journal of Medicinal Chemistry, Vol. XX, 1-7, 2007.
[ 4 ] Bhat A.R., Shenoy G., Kotain M., Synthesis and biological activities of Mannich bases of 7-nitro-2-methyl-quinazolin-4(3H)-one, Indian Journal of Heterocyclic Chemistry, vol. 9, 319-320, 2000
[ 5 ] Abdel-Hamide S.G., El-Hakim A.E., Abdel-Rahman R.M., Synthesis and biological activities of some new heterocyclic compounds bearing 2-phenyl-6-iodo-quinazolinyl-4-oxy moiety part-1, Indian Journal of Heterocyclic Chemistry, vol. 5, 219-222, 1996.
[ 6 ] Maggio B., Daidone G., Demetrio R., Plescia S., Mantione L, Cutuli V.M., Mangano N.G., Caruso A., Synthesis and pharmacological study of ethyl 1-methyl-5-(substituted3,4-dihydro-4-oxoquinazolin-3-yl)-1H-pyrazole-4-acetates, European Journal of Medicinal Chemistry, Vol. 36, 737-742, 2001.
[ 7 ] Murugan V., Bhaskaran M.V., Rama Sarma G.V.S., Ramanathan M.,Suresh B., Synthesis and estrogenic screening of some new quinazolinonyl triazoles, Indian Journal of Heterocyclic Chemistry, Vol. 9, 267-270, 2000.
[ 8 ] Srivastava V.K., Singh S., Gulati A., Shankar K., Antiparkinsonian agents from Quinazolinylthiazolidinones and Azetidinones, Indian Journal of Chemistry, Vol. 26B, 652-656, 1987.
[ 9 ] Zheng X, Li Z, Wang Y, Chen W, Huang Q, Liu C, Song G. Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles. J Fluorine Chem. 2003;123:163–169. doi:10.1016/S0022-1139(03)00168-4. 
[ 10 ] Chavan VP, Sonawane SA, Shingare MS, Karale BK. Synthesis, characterization, and biological activities of some 3,5,6-trichloropyridine derivatives. Chem Heterocyclic Compounds. 2006;42:625–630. doi:10.1007/s10593-006-0137-8. 
[ 11 ] Hollaa BS, Gonsalves R, Shenoy S. Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2,4-triazol-3-yl)ethanes. Eur J Med Chem. 2000;35:267–271. doi:10.1016/S0223-5234(00)00154-9.
[ 12 ] Liu F, Luo X, Song B, Bhadury PS, Yang S, Jin L, Xue W, Hu D. Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety. Bioorg Med Chem. 2008;16:3632–3640. doi:10.1016/j.bmc.2008.02.006.
[ 13 ] Narayana B, Raj KKV, Ashalatha BV, Kumari NS. Synthesis of some new 2-(6-methoxy-2-naphthyl)-5-aryl-1,3,4-oxadiazoles as possible non-steroidal anti-inflammatory and analgesic agents. Arch Pharm. 2005;338:373–377. doi:10.1002/ardp.200500974.
[ 14 ] Koksal M, Bilge SS, Bozkurt A, Sahin ZS, Isik S, Erol DD. Synthesis, characterization and anti-inflammatory activity of new 5-(3,4-dichlorophenyl)-2-(aroyl methyl)thio-1,3,4-oxadiaxoles. Arzneimittel-Forschung. 2008;58:510–514. 
[ 15 ] Zareef M, Iqbal R, Dominguez NG, Rodrigues J, Zaidi JH, Arfan M, Supuran CT. Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1,3,4-oxadiazole moieties. J Enz Inhib Med Chem. 2007;22:301–308. doi:10.1080/14756360601114569.
[ 16 ] Farghaly AR, El-Kashef H. Synthesis of some new azoles with antiviral potential1. Arkivoc. 2006;11:76–90. 
[ 17 ] El-Essawy FA, Khattab AF, Abdel-Rahman AAH. Synthesis of 1,2,4-triazol-3-ylmethyl-, 1,3,4-oxa-, and -thiadiazol-2-ylmethyl-1H-[1,2,3]-triazolo[4,5-d]pyrimidinediones. Monatsh Chem. 2007;138:777–785. doi:10.1007/s00706-007-0649-7. 
[ 18 ] Amr AEE, Mohamed SF, Abdel-Hafez NA, Abdalla MM. Antianexiety activity of pyridine derivatives synthesized from 2-chloro-6-hydrazino-isonicotinic acid hydrazide. Monatsh Chem. 2008;139:1491–1498. doi:10.1007/s00706-008-0949-6. 
[ 19 ] Kumar A, D’Souza SS, Gaonkar SL, Rai KML, Salimath BP. Growth inhibition and induction of apoptosis in MCF-7 breast cancer cells by a new series of substituted-1,3,4-oxadiazole derivatives. Invest New Drugs. 2008;26:425–435. doi:10.1007/s10637-008-9116-5.
[ 20 ] Zareef M, Iqbal R, Al-Masoudi NA, Zaidi JH, Arfan M, Shahzad SA. Synthesis, anti–HIV, and antifungal activity of new benzensulfonamides bearing the 2,5-disubstituted-1,3,4-oxadiazole moiety. Phosphorus Sulfur and Silicon. 2007;182:281–298. doi:10.1080/10426500600919074. 
[ 21 ] Macaev F, Rusu G, Pogrebnoi S, Gudima A, Stingaci E, Vlad L, Shvets N, Kandemirli F, Dimogloa A, Reynolds R. Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure-anti-mycobacterial activities. Bioorg Med Chem. 2005;13:4842–4850. doi:10.1016/j.bmc.2005.05.011.
[ 22 ] Zarghi A, Tabatabai SA, Faizi M, Ahadian A, Navabi P, Zanganeh V, Shafiee A. Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles. Bioorg Med Chem Lett. 2005;15:1863–1865. doi:10.1016/j.bmcl.2005.02.014.
[ 23 ] Alafeefy AM. Synthesis and antimicrobial activity of some new quinazolin-4(3H)-one derivatives. Pharm Biol. 2008;46:751–756. doi:10.1080/13880200802315907. 
[ 24 ] Sen Gupta AK, Misra HK. Synthesis and evaluation of substituted quinazolone derivatives for antibacterial, antifungal, and antiacetylcholinesterase activities. J Pharm Sci. 1980;69:1313–1317. doi:10.1002/jps.2600691120.
[ 25 ] Alagarsamy V, Murugesan S, Sheorey RV. Synthesis and pharmacological investigation of novel 3-(benzyl)-2-substituted amino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents. Med Chem Res. 2008;17:564–577. doi:10.1007/s00044-008-9098-z. 
[ 26 ] Jessy EM, Sambanthan AT, Alex J, Sridevi CH, Srinivasan KK. Synthesis and biological evaluation of some novel quinazolones. Indian J Pharm Sci. 2007;69:476–478. 
[ 27 ] Shukla JS, Agarwal K, Rastogi R. Synthesis of some new 2-substituted 3-[4-(N-arylsulphonylbiguanido)phenyl]quinazolin-4-one hydrochlorides as potential anthelminthic agents. Arch Pharm. 1983;316:525–529. doi:10.1002/ardp.19833160610.
[ 28 ] Khalil AA, Abdel Hamide SG, Al-Obaid AM, El-Subbagh HI. Substituted quinazolines, part 2. synthesis and in vitro anticancer evaluation of new 2-substituted mercapto-3H-quinazoline analogs. Arch Pharm. 2003;336:95–103. doi:0365-6233/02/0095.
[ 29 ] Laddha SS, Bhatnagar SP. Rapid microwave-assisted solution phase synthesis of 6,8-disubstituted 2-phenyl-3-(substitutedbenzothiazol-2-yl)-4-[3H]-quinazolinones as novel anticonvulsants. Phosphorus Sulfur and Silicon. 2008;183:2262–2273. doi:10.1080/10426500801957766. 
[ 30 ] Alagarsamy V, Prabakaran L, Murugan RD, Gurumurth G, Bindu P, Arunkumar M, Bothiraja C. Synthesis and antihistaminic activity of some novel 2-mercapto-3-(substitutedmethylamino)quinazolin-4(3H)-ones. Acta Pharm Turcica. 2000;42:33–38. 
[ 31 ] Alagarsamy V, Murugesan S, Dhanabal K, Murugan M, Clercq E. Anti-HIV, antibacterial and antifungal activities of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones. Indian J Pharm Sci. 2007;69:304–307. 
[ 32 ] Raffa D, Daidone G, Maggio B, Schillaci D, Plescia F. Synthesis and antiproliferative activity of novel 3-(indazol-3-yl)-quinazolin-4(3H)-one and 3-(indazol-3-yl)-benzotriazin-4(3H)-one derivatives. Arch Pharm. 1999;332:317–320. doi:10.1002/(SICI)1521-4184(19999)332:9<317::AID-ARDP317>3.0.CO;2-R.
[ 33 ] Mosaad SM, Mohammed KI, Ahmed MA, Abdel-Hamide SG. Synthesis of certain new 6-iodoquinazolines as potential antitubercular agents. J Applied Sci. 2004;4:302–307. 
[ 34 ] Selvam P, Babu K, Padamraj R, Persoons L, Clercq E. Synthesis, antiviral and cytotoxic activities of some novel 2-phenyl-3-disubstituted quinazolin-4(3H)-ones. African J Pharm Pharmacol. 2008;2:110–115. 
[ 35 ] Joshi KC, Singh VK, Mehta DS, Sharma RC, Gupta L. Fluorinated quinazolones iii: synthesis and CNS depressant activity of fluorinated quinazolone derivatives. J Pharm Sci. 1975;64:1428–1430. doi:10.1002/jps.2600640843.
[ 36 ] Raffa D, Edler MC, Daidone G, Maggio B, Merickech M, Plescia S, Schillaci D, Bai R, Hamel E. Synthesis, cytotoxicity, and inhibitory effects on tubulin polymerization of a new 3-heterocyclo substituted 2-styrylquinazolinones. Eur J Med Chem. 2004;39:299–304. doi:10.1016/j.ejmech.2003.12.009.
[ 37 ] Maarouf AR, El-Bendary ER, Goda FE. Synthesis and evaluation of some novel quinazolinone derivatives as diuretic agents. Arch Pharm. 2004;337:527–532. doi:10.1002/ardp.200400869.
[ 38 ] Kurogi Y, Inoue Y, Tsutsumi K, Nakamura S, Nagao K, Yoshitsugu H, Tsuda Y. Synthesis and hypolipidemic activities of novel 2-[4 [(diethoxyphosphoryl)methyl]phenyl]quinazolines and 4(3H)-quinazolinones. J Med Chem. 1996;39:1433–1437. doi:10.1021/jm9506938.
[ 39 ] Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. Vogel’s Textbook of Practical Organic Chemistry. 5th ed. New York: Wiley; 1989. p. 692. 
[ 40 ] Katritzky AR, Vvedensky V, Cai X, Rogovoy B, Steel PJ. Syntheses of 5-(2-arylazenyl)-1,2,4-triazoles and 2-amino-5-aryl-1,3,4-oxadiazoles. Arkivoc. 2002;6:82–90.