Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis, Characterization, Antimicrobial and Antioxidant Activities of 1,2,4-triazolyl-isoxazole Moieties via Dehydration Reactions of Carbohydrazides

Author(s): Asma K. Alshamari, Mahmoud A. Al-Qudah*, Fedaa Hamadeh, Lo’ay A. Al-Momani and Sultan T. Abu-Orabi

Volume 19, Issue 3, 2022

Published on: 21 June, 2021

Page: [228 - 235] Pages: 8

DOI: 10.2174/1570178618666210531095246

Price: $65

Abstract

For the reason of distinct place in the field of medicinal and pharmaceutical chemistry of 1,2,4-triazole derivatives, a new class of fused 1,2,4-triazolyl-isoxazole moieties was prepared from 3- (2,4,6-trimethoxyphenyl)isoxazolo-4,5-bis[carbonyl-(4̍-phenyl) thiosemicarbazide via dehydration reactions of carbohydrazides by using the appropriate chemical reagents. The structures of the compounds were elucidated by both elemental and spectral (IR, NMR and MS) analyses. The in vitro antioxidant activity of the new compounds was determined by free radical scavenging and metal chelating activity. All the synthesized compounds showed good activity according to free radical scavenging and metal chelating activity compared with standards. The new compounds were screened in vitro antibacterial activity against three gram-positive bacteria and three gram-negative bacteria.

Keywords: 1, 2, 4-triazolyl-isoxazole, 1, 3-dipolar cycloaddition, carbohydrazide, dehydration reactions, antibacterial activity, antioxidant activity, radical scavenging, metal chelating activity.

« Previous Next »
Graphical Abstract

[1]
Tornøe, C.W.; Christensen, C.; Meldal, M. J. Org. Chem., 2002, 67(9), 3057-3064.
[2]
Abu-Orabi, S.T. Molecules, 2002, 7(2), 302-314.
[http://dx.doi.org/10.3390/70200302]
[3]
Abu-Orabi, S.T.; Al-Hamdany, R.; Al-Momany, L.A.; Ta’an, E.A. Asian J. Chem., 1999, 11(4), 1276.
[4]
Abu-Orabi, S.T.; Jibril, I.; Obiedat, R.; Hatamleh, L. J. Chem. Eng. Data, 1988, 33(4), 540-541.
[5]
Abu-Orabi, S.T.; Saleh, M.; Al-Momani, L.; Jibril, I.; Yousef, Y. J. Chem., 2006, 1(2), 109-120.
[6]
Yamamoto, T.; Fujita, K.; Asari, S.; Chiba, A.; Kataba, Y.; Ohsumi, K.; Ohmuta, N.; Iida, Y.; Ijichi, C.; Iwayama, S.; Fukuchi, N.; Shoji, M. Bioorg. Med. Chem. Lett., 2007, 17(13), 3736-3740.
[http://dx.doi.org/10.1016/j.bmcl.2007.04.024] [PMID: 17467986]
[7]
Kuz’min, V.E.; Artemenko, A.; Muratov, A.; Artemenko, A.; Artemenko, G.E.; Volineckaya, N.; Makarov, I.L.; Riabova, V.A.; Wutzler, O.B.; Schmidtke, P. M. J. Med. Chem., 2007, 50(17), 4205-4213.
[http://dx.doi.org/10.1021/jm0704806] [PMID: 17665898]
[8]
Melo, P.; Teresa, M.V.D. Curr. Org. Chem., 2005, 9(10), 925-958.
[http://dx.doi.org/10.2174/1385272054368420]
[9]
Sim, K.M.; Chan, P.Q.; Boo, X.L.; Heng, K.S.; Lye, K.W.; Teo, K.C. Lett. Org. Chem., 2018, 15(7), 575-582.
[10]
Xu, Z.; Zhao, S.J.; Liu, Y. Eur. J. Med. Chem., 2019.
[11]
Kaku, Y.; Tsuruoka, A.; Kakinuma, H.; Yanagiawa, M. Chem. Pharm. Bull. (Tokyo), 1998, 46(7), 1125-1129.
[http://dx.doi.org/10.1248/cpb.46.1125]
[12]
Tozkpran, B.; Kupeli, E.; Yesilada, E.; Ertan, M. Bioorg. Med. Chem., 2007, 15(4), 1808-1814.
[http://dx.doi.org/10.1016/j.bmc.2006.11.029] [PMID: 17166724]
[13]
Holla, B.; Veerandra, S.B.; Shivananda, M.K.; Poojary, B. Eur. J. Med. Chem., 2003, 38(7-8), 759-767.
[http://dx.doi.org/10.1016/S0223-5234(03)00128-4] [PMID: 12932907]
[14]
Foroumadi, A.; Kiani, Z.; Soltani, F. Farmaco, 2003, 58(11), 1073-1076.
[15]
Maddila, S.; Pagadala, R.; Jonnalagadda, B. Lett. Org. Chem., 2013, 10(10), 693-714.https://doi.org/
[http://dx.doi.org/10.2174/157017861010131126115448]
[16]
Goss, P.E.; Strasser-Weippl, K. Best Pract., 2004, 18(1), 113-130.
[17]
Santen, R.J. Steroids, 2003, 68(7-8), 559-567.
[18]
Clemons, M.; Coleman, R.E.; Verma, S. Cancer Treat., 2004, 30(4), 325-332.
[19]
Gan, K.C.; Sim, K.M.; Lim, T.M.; Teo, K.C. Lett. Org. Chem., 2020, 17(3), 191-198.
[20]
Cihan-Ustundag, G.; Simsek, B.; Ilhan, E.; Capan, G. Lett. Drug Des. Discov., 2014, 11(3), 290-296.https://doi.org
[21]
Prior, R.L.; Wu, X.; Schaich, K. J. Agric. Food Chem., 2005, 53(10), 4290-4302.
[22]
Yehye, W.A.; Abdul Rahman, N.; Alhadi, A.A.; Khaledi, H.; Weng, N.S.; Ariffin, A. Molecules, 2012, 17(7), 7645-7665.
[http://dx.doi.org/10.3390/molecules17077645] [PMID: 22732881]
[23]
Alshamari, A.; Al-Qudah, M.; Hamadeh, F.; Al-Momani, L.; Abu-Orabi, S. Molecules, 2020, 25(18), 4271.
[http://dx.doi.org/10.3390/molecules25184271] [PMID: 32961855]
[24]
Al-Qudah, M.A.; Allahham, F.E.; Obeidat, S.M.; Al-Jaber, H.I.; Lahham, J.N.; Abu Orabi, S.T. Int. J. Pharm. Sci. Res., 2020, 12(3), 1226-1236.
[http://dx.doi.org/10.31838/ijpr/2020.12.03.183]
[25]
Al-Qudah, M. J. Biol. Act. Prod. Nat, 2016, 6(2), 101-111.
[http://dx.doi.org/10.1080/22311866.2016.1199286]
[26]
Al-Qudah, M.A.; Saleh, A.M.; Alhawsawi, N.L.; Al-Jaber, H.I.; Rizvi, S.A.; Afifi, F.U. Chem. Biodivers., 2017, 14(8)e1700146
[http://dx.doi.org/10.1002/cbdv.201700146] [PMID: 28544513]
[27]
Abu-Orabi, S.T.; Al-Qudah, M.A.; Saleh, N.R.; Bataineh, T.T.; Obeidat, S.M.; Al-Sheraideh, M.S.; Al-Jaber, H.I.; Tashtoush, H.I.; Lahham, J.N. Arab. J. Chem., 2020, 13(7), 6256-6266.
[http://dx.doi.org/10.1016/j.arabjc.2020.05.043]
[28]
Al-Qudah, M.A.; Obeidat, S.M.; Saleh, A.M.; El-Oqlah, A.A.; Al-Masaeed, E.; Al-Jaber, H.I.; Abu Orabi, S.T.J. Essent. Oil-Bear. Plants, 2018, 21(3), 583-599.
[http://dx.doi.org/10.1080/0972060X.2018.1489739]
[29]
Al-Humaidi, J.Y.; Al-Qudah, M.A.; Al-Saleem, M.S.; Alotaibi, S.M. Jordan. J. Chem., 2017, 12(4), 241-254.
[30]
Al-Qudah, M.A.; Tashtoush, H.I.; Khlaifat, E.F.; Ibrahim, S.O.; Saleh, A.M.; Al-Jaber, H.I.; Abu Zarga, M.H.; Abu Orabi, S.T. Nat. Prod. Res., 2020, 34(20), 2981-2985.
[http://dx.doi.org/10.1080/14786419.2019.1597349] [PMID: 31161797]

Rights & Permissions Print Cite
Article Metrics
15
3
1
© 2024 Bentham Science Publishers | Privacy Policy