Abstract
Sulfonamides, with the general formula R-SO2NR1R2, have attracted great attention
since the early discovery of sulfonamide-containing antibacterial drugs. The combinations
of certain sulfonamides and other drug molecules to form sulfonamide hybrids
are being used to develop novel formulations with greater effectiveness and in a huge
range of therapeutic applications such as antimicrobial, antifungal, anti-inflammatory, antitubercular,
antiviral, antidiabetic, antiproliferative, carbonic anhydrase inhibitor, antimalarial,
anticancer and other medicinal agents. Part C of this review presents recent advances
in designing and developing multicomponent sulfonamide hybrids containing more
than one biologically active heterocycle, such as coumarin, indole, pyridine, pyrimidine,
pyrazole, triazole, oxazole, oxadiazole, triazine, quinazoline, and thiadiazol. This review
aims to highlight the status of the hybridization technique in synthesizing biological and
computational studies of novel sulfonamide hybrids that were designed and presented between
2016 and 2020.
Keywords:
Sulfonamides, multicomponent, hybrids, folic acid, synthesis, biological activity, computational studies.
[1]
Sunil, R.; Pal, S.; Jayashree, A. Molecular hybridization-an emanating tool in drug design. Med. Chem., 2019, 9(6), 93-95.
[86]
Butta, R.; Ummadi, N.; Adivireddy, P.; Venkatapuram, P. Synthesis and antimicrobial activity of pyrimidinylsulfamoyl azolylbenzamides. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem., 2019, 58, 907-915.
[92]
Ghorab, M.; Alsaid, M. Anticancer activity of some novel thieno [2, 3-d] pyrimidine derivatives. Biomed. Res., 2016, 27, 110-115.
[94]
Ramdas, V.; Talwar, R.; Kanoje, V.; Loriya, R.M.; Banerjee, M.; Patil, P.; Joshi, A.A.; Datrange, L.; Das, A.K.; Walke, D.S.; Kalhapure, V.; Khan, T.; Gote, G.; Dhayagude, U.; Deshpande, S.; Shaikh, J.; Chaure, G.; Pal, R.R.; Parkale, S.; Suravase, S.; Bhoskar, S.; Gupta, R.V.; Kalia, A.; Yeshodharan, R.; Azhar, M.; Daler, J.; Mali, V.; Sharma, G.; Kishore, A.; Vyawahare, R.; Agarwal, G.; Pareek, H.; Budhe, S.; Nayak, A.; Warude, D.; Gupta, P.K.; Joshi, P.; Joshi, S.; Darekar, S.; Pandey, D.; Wagh, A.; Nigade, P.B.; Mehta, M.; Patil, V.; Modi, D.; Pawar, S.; Verma, M.; Singh, M.; Das, S.; Gundu, J.; Nemmani, K.; Bock, M.G.; Sharma, S.; Bakhle, D.; Kamboj, R.K.; Palle, V.P. Discovery of potent, selective, and state-dependent NaV1. 7 inhibitors with robust oral efficacy in pain models: Structure-activity relationship and optimization of chroman and indane aryl sulfonamides.
J. Med. Chem., 2020,
63(11), 6107-6133.
[
http://dx.doi.org/10.1021/acs.jmedchem.0c00361] [PMID:
32368909]
[96]
Variya, H.H.; Panchal, V.; Patel, G.R. Synthesis, antituberculosis and anti-bacterial activities of sulfadimethoxine bearing N-(2, 6-dimethoxypyrimidin-4-yl)-4-(4-oxo-2-(substituted) phenylthiazolidin-3yl) benzenesulfonamide. Int. J. Res. Anal. Rev., 2019, 6(2), 168-180.
[124]
Rai, G.; Urban, D.J.; Mott, B.T.; Hu, X.; Yang, S.M.; Benavides, G.A.; Johnson, M.S.; Squadrito, G.L.; Brimacombe, K.R.; Lee, T.D.; Cheff, D.M.; Zhu, H.; Henderson, M.J.; Pohida, K.; Sulikowski, G.A.; Dranow, D.M.; Kabir, M.; Shah, P.; Padilha, E.; Tao, D.; Fang, Y.; Christov, P.P.; Kim, K.; Jana, S.; Muttil, P.; Anderson, T.; Kunda, N.K.; Hathaway, H.J.; Kusewitt, D.F.; Oshima, N.; Cherukuri, M.; Davies, D.R.; Norenberg, J.P.; Sklar, L.A.; Moore, W.J.; Dang, C.V.; Stott, G.M.; Neckers, L.; Flint, A.J.; Darley-Usmar, V.M.; Simeonov, A.; Waterson, A.G.; Jadhav, A.; Hall, M.D.; Maloney, D.J. Pyrazole-based lactate dehydrogenase inhibitors with optimized cell activity and pharmacokinetic properties.
J. Med. Chem., 2020,
63(19), 10984-11011.
[
http://dx.doi.org/10.1021/acs.jmedchem.0c00916] [PMID:
32902275]
[163]
Focken, T.; Chowdhury, S.; Zenova, A.; Grimwood, M.E.; Chabot, C.; Sheng, T.; Hemeon, I.; Decker, S.M.; Wilson, M.; Bichler, P.; Jia, Q.; Sun, S.; Young, C.; Lin, S.; Goodchild, S.J.; Shuart, N.G.; Chang, E.; Xie, Z.; Li, B.; Khakh, K.; Bankar, G.; Waldbrook, M.; Kwan, R.; Nelkenbrecher, K.; Karimi Tari, P.; Chahal, N.; Sojo, L.; Robinette, C.L.; White, A.D.; Chen, C.A.; Zhang, Y.; Pang, J.; Chang, J.H.; Hackos, D.H.; Johnson, J.P., Jr; Cohen, C.J.; Ortwine, D.F.; Sutherlin, D.P.; Dehnhardt, C.M.; Safina, B.S. Design of conformationally constrained acyl sulfonamide isosteres: Identification of N-([1,2,4]triazolo[4,3-a]pyridin-3-yl)methane-sulfonamides as potent and selective hNaV1.7 inhibitors for the treatment of pain.
J. Med. Chem., 2018,
61(11), 4810-4831.
[
http://dx.doi.org/10.1021/acs.jmedchem.7b01826] [PMID:
29737846]
[213]
Park, Y.; Pacitto, A.; Bayliss, T.; Cleghorn, L.A.T.; Wang, Z.; Hartman, T.; Arora, K.; Ioerger, T.R.; Sacchettini, J.; Rizzi, M.; Donini, S.; Blundell, T.L.; Ascher, D.B.; Rhee, K.; Breda, A.; Zhou, N.; Dartois, V.; Jonnala, S.R.; Via, L.E.; Mizrahi, V.; Epemolu, O.; Stojanovski, L.; Simeons, F.; Osuna-Cabello, M.; Ellis, L.; MacKenzie, C.J.; Smith, A.R.C.; Davis, S.H.; Murugesan, D.; Buchanan, K.I.; Turner, P.A.; Huggett, M.; Zuccotto, F.; Rebollo-Lopez, M.J.; Lafuente-Monasterio, M.J.; Sanz, O.; Diaz, G.S.; Lelièvre, J.; Ballell, L.; Selenski, C.; Axtman, M.; Ghidelli-Disse, S.; Pflaumer, H.; Bösche, M.; Drewes, G.; Freiberg, G.M.; Kurnick, M.D.; Srikumaran, M.; Kempf, D.J.; Green, S.R.; Ray, P.C.; Read, K.; Wyatt, P.; Barry, C.E. , III; Boshoff, H.I. Essential but not vulnerable: indazole sulfonamides targeting inosine monophosphate dehydrogenase as potential leads against Mycobacterium tuberculosis.
ACS Infect. Dis., 2017,
3(1), 18-33.
[
http://dx.doi.org/10.1021/acsinfecdis.6b00103] [PMID:
27704782]
[235]
Boutard, N.; Białas, A.; Sabiniarz, A.; Guzik, P.; Banaszak, K.; Biela, A.; Bień, M.; Buda, A.; Bugaj, B.; Cieluch, E.; Cierpich, A.; Dudek, Ł.; Eggenweiler, H.M.; Fogt, J.; Gaik, M.; Gondela, A.; Jakubiec, K.; Jurzak, M.; Kitlińska, A.; Kowalczyk, P.; Kujawa, M.; Kwiecińska, K.; Leś, M.; Lindemann, R.; Maciuszek, M.; Mikulski, M.; Niedziejko, P.; Obara, A.; Pawlik, H.; Rzymski, T.; Sieprawska-Lupa, M.; Sowińska, M.; Szeremeta-Spisak, J.; Stachowicz, A.; Tomczyk, M.M.; Wiklik, K.; Włoszczak, Ł.; Ziemiańska, S.; Zarębski, A.; Brzózka, K.; Nowak, M.; Fabritius, C.H. Synthesis of amide and sulfonamide substituted N-aryl 6-aminoquinoxalines as PFKFB3 inhibitors with improved physicochemical properties.
Bioorg. Med. Chem. Lett., 2019,
29(4), 646-653.
[
http://dx.doi.org/10.1016/j.bmcl.2018.12.034] [PMID:
30626557]