Abstract
A literature survey revealed that a great deal of interest had been focused on the synthesis of functionalized heterocyclic compounds due to their wide range of biological activities such as antimicrobial, antitumor, anti-inflammatory, antiviral, antibiotic, antidepressant, antimalarial, antifungal and antihypertensive. Moreover, it is used as pharmaceuticals, agrochemicals and veterinary products. They are also found in sensitizers, developers, antioxidants, as corrosion inhibitors, as copolymers, and dyes. On the other hand, hydrazonoyl halides are interesting synthons for valuable bioactive heterocyclic compounds. Reaction of hydrazonoyl halides with various types of aryl-amines and hetaryl-amines generated a huge number of different heterocyclic systems. In this review, we collected all reactions of hydrazonoyl halides with aryl- and hetaryl amines and classified them according to the type of the amines up to the end of 2021. Most reaction types have been successfully applied and used in the production of biologically active compounds.
Graphical Abstract
[http://dx.doi.org/10.1016/j.biotechadv.2021.107813] [PMID: 34450199]
[http://dx.doi.org/10.1016/j.ejmcr.2021.100006]
(b) Althagafi, I.; Abdel-Latif, E. Synthesis and antibacterial activity of new imidazo[1,2-a]pyridines festooned with pyridine, thiazole or pyrazole moiety. Polycycl. Aromat. Compd., 2022, 42, 4487-4500.;
(c) Alqahtani, A.M.; Safi El-Din, A.G.; Abdou, R.; Amin, A.H.; Arab, H.H.; Abdelazeem, A.H. Novel S-Mercaptotriazolebenzothiazole-based derivatives as antimicrobial agents: design, synthesis, and in vitro evaluation. Lett. Drug Des. Discov., 2022, 19, 925-937.
[http://dx.doi.org/10.2174/1570180819666220301154851]
[http://dx.doi.org/10.1080/10406638.2019.1689514];
(b) Yadav, P.; Kumar, A.; Althagafi, I.; Nemaysh, V.; Rai, R.; Pratap, R. The recent development of tetrahydro-quinoline/isoquinoline based compounds as anticancer agents. Curr. Top. Med. Chem., 2021, 21, 1587-1622.
[http://dx.doi.org/10.2174/1568026621666210526164208];
(c) Shah, R.; Alharbi, A.; Hameed, A.M.; Saad, F.; Zaky, R.; Khedr, A.M.; El-Metwaly, N. Synthesis and Structural Elucidation for New Schiff Base Complexes; Conductance, Conformational, MOE-Docking and Biological Studies. J. Inorg. Organomet. Polym. Mater., 2020, 30, 3595-3607.
[http://dx.doi.org/10.2174/1389557518666180330101447] [PMID: 29600758];
(b) Katouah, H.A.; Al-Fahemi, J.H.; Elghalban, M.G.; Saad, F.A.; Althagafi, I.A.; El-Metwaly, N.M.; Khedr, A.M. Synthesis of new Cu (II)-benzohydrazide nanometer complexes, spectral, modeling, CT-DNA binding with potential anti-inflammatory and anti-allergic theoretical features. Mater. Sci. Eng. C, 2019, 96, 740-756.
[http://dx.doi.org/10.1016/j.ejmech.2016.05.043] [PMID: 27240271];
(b) Refat, M. S.; Sedayo, A. A.; Sayqal, A.; Alharbi, A.; Katouah, H. A.; Abumelha, H. M.; Alzahrani, S.; Alkhatib, F.; Althagafi, I.; El-Metwaly, N. Aurintricarboxylic acid and its metal ion complexes in comparative virtual screening versus lopinavir and hydroxychloroquine in fighting COVID-19 pandemic: Synthesis and characterization. Inorg. Chem. Commun., 2021, 126, 108472.
[http://dx.doi.org/10.1016/j.inoche.2021.108472]
[http://dx.doi.org/10.1016/j.bmcl.2019.07.024] [PMID: 31383589]
[http://dx.doi.org/10.1016/j.molstruc.2021.130369]
[http://dx.doi.org/10.1016/j.ejps.2019.105015] [PMID: 31344442]
[http://dx.doi.org/10.1016/j.bmcl.2020.127762] [PMID: 33359605]
[http://dx.doi.org/10.1016/j.pestbp.2021.104897] [PMID: 34301359]
[http://dx.doi.org/10.1016/j.bmc.2014.02.013] [PMID: 24602400]
[http://dx.doi.org/10.1016/j.bioorg.2021.104945] [PMID: 33964579]
[http://dx.doi.org/10.1016/j.molstruc.2020.129318]
[http://dx.doi.org/10.1007/s10904-019-01308-8]
[http://dx.doi.org/10.1016/j.steroids.2016.02.010] [PMID: 26930574]
[http://dx.doi.org/10.1016/j.cej.2020.127445]
[http://dx.doi.org/10.1016/j.dyepig.2021.109849]
[http://dx.doi.org/10.3998/ark.5550190.0009.102]
[http://dx.doi.org/10.2174/1385272821666170523115019]
[http://dx.doi.org/10.1016/0040-4039(84)80018-0]
[http://dx.doi.org/10.1002/ardp.19923250404]
[http://dx.doi.org/10.1002/jhet.307]
[http://dx.doi.org/10.1002/ardp.19973301204] [PMID: 9474896]
[http://dx.doi.org/10.3987/COM-97-7792]
[http://dx.doi.org/10.1080/10426509308032427]
[http://dx.doi.org/10.1002/ardp.19973301206]
[http://dx.doi.org/10.1002/(SICI)1521-4184(19993)332:2<39:AID-ARDP39>3.0.CO;2-F]
[http://dx.doi.org/10.1002/jhet.5570210251]
[http://dx.doi.org/10.3390/molecules19010740] [PMID: 24406785]
[http://dx.doi.org/10.1002/jhet.5570200326]
[http://dx.doi.org/10.1002/jhet.5570170511]
[http://dx.doi.org/10.1002/(SICI)1098-1071(1997)8:2<129:AID-HC4>3.0.CO;2-9]
[http://dx.doi.org/10.1002/jhet.5570280107]
[http://dx.doi.org/10.1016/S0040-4020(02)00157-6]
[http://dx.doi.org/10.1002/jhet.2096]
[http://dx.doi.org/10.1248//cpb.c12-00939] [PMID: 23649193]
[http://dx.doi.org/10.1246/bcsj.57.1650]
[http://dx.doi.org/10.1002/prac.19893310318]
[http://dx.doi.org/10.1039/p19820002663]
[http://dx.doi.org/10.1016/S0040-4020(01)90419-3]
[http://dx.doi.org/10.1055/s-1989-27382]
[http://dx.doi.org/10.1039/p19790000330]
[http://dx.doi.org/10.1016/j.arabjc.2013.11.040]
[http://dx.doi.org/10.1002/cber.19871200614]
[http://dx.doi.org/10.3998/ark.5550190.0010.b06]
[http://dx.doi.org/10.1002/jccs.200100012]
[http://dx.doi.org/10.1515/znb-2002-0512]
[http://dx.doi.org/10.2174/1389557519666191015130037] [PMID: 31613728]
[http://dx.doi.org/10.3906/kim-1504-13]
[http://dx.doi.org/10.1080/00397911.2017.1385084]
[http://dx.doi.org/10.1007/s00706-008-0099-x]
[http://dx.doi.org/10.4236/ijoc.2014.43023]
[http://dx.doi.org/10.1002/jhet.2320]
[http://dx.doi.org/10.1080/00304949209355692]
[http://dx.doi.org/10.1002/ardp.19873200913]
[http://dx.doi.org/10.1007/BF00911090]
[http://dx.doi.org/10.1246/bcsj.50.2969]
[http://dx.doi.org/10.3390/molecules13010170] [PMID: 18259139]
[http://dx.doi.org/10.1007/s00706-003-0113-2]
[http://dx.doi.org/10.1002/(SICI)1098-1071(2000)11:2<87:AID-HC1>3.0.CO;2-#]
[http://dx.doi.org/10.1002/jhet.5570390105]
[http://dx.doi.org/10.3184/0308234041423718]
[http://dx.doi.org/10.1002/(SICI)1521-3897(200001)342:1<96:AID-PRAC96>3.0.CO;2-M]
[http://dx.doi.org/10.1016/j.tet.2006.05.071]
[http://dx.doi.org/10.1002/jhet.2695]
[http://dx.doi.org/10.3390/molecules200815287] [PMID: 26307959]
[http://dx.doi.org/10.1002/jccs.200600123]
[http://dx.doi.org/10.1007/s007060170058]
[http://dx.doi.org/10.7868/S0132342314010072] [PMID: 25898730]
[http://dx.doi.org/10.1515/znb-2002-0617]
[http://dx.doi.org/10.3390/molecules171011538] [PMID: 23018926]