SULFONES: AN IMPORTANT CLASS OF ORGANIC COMPOUNDS WITH DIVERSE BIOLOGICAL ACTIVITIES

Authors

  • Irshad Ahmad American University of Ras Al Khaimah
  • Shagufta . Department of Mathematics and Natural Sciences, School of Arts and Sciences, American University of Ras Al Khaimah, P. O. Box 10021, Ras Al Khaimah, UAE

Keywords:

Sulfone, Therapeutic agents, Biological activity

Abstract

Sulfones have been studied broadly for various biological activities primarily as anti-inflammatory, antimicrobial, anticancer, anti-HIV, antimalarial, and anti-inflammatory. The review focused on the biological activity of various sulfones on different therapeutic targets. The aim of this review is to summarize the biological significance of sulfones, giving a comprehensive scenario and offer prospective in the development of new sulfone derivatives as therapeutic agents.

 

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Author Biography

Shagufta ., Department of Mathematics and Natural Sciences, School of Arts and Sciences, American University of Ras Al Khaimah, P. O. Box 10021, Ras Al Khaimah, UAE

Assistant Professor of Chemistry,

Department of Mathematics and Natural Sciences, School of Arts and Sciences, American University of Ras Al Khaimah, P.O.Box 10021, Ras Al Khaimah, UAE

References

Tozkoparan B, Kupeli E, Yesilada E, Ertan M. Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatory–analgesic activity. Bioorg Med Chem 2007;15:1808-14.

Hwang SH, Wagner KM, Morisseau C, Liu J-Y, Dong H, Wecksler AT, et al. Synthesis and structure-activity relationship studies of urea-containing pyrazoles as dual inhibitors of cyclooxygenase-2 and soluble epoxide hydrolase. J Med Chem 2011;54(8):3037-50.

Shaaban OG, Rizk OH, Bayad AE, El-Ashmawy IM. Synthesis of some 4,5-dihydrothieno[3,2-e][1,2,4]triazolo[4,3-a] pyrimidine-2-carboxamides as anti-inflammatory and analgesic agents. Open Med Chem J 2013;7:49-65.

Curti C, Laget M, Carle AO, Gellis A, Vanelle P. Rapid synthesis of sulfone derivatives as potential anti-infectious agents. Eur J Med Chem 2007;42:880-4.

Dixit Y, Dixit R, Gautam N, Gautam DC. Synthesis of bioactive fluorinated 10H-phenothiazines and their sulfone derivatives. E-J Chem 2008;5(S1):1063-8.

Kumar ABVK, Rao KSVK, Chandra MS, Subha MCS, Choi YL. Synthesis and antimicrobial evaluation of sulfides, sulfoxides, and sulfones. J Korean Soc Appl Biol Chem 2009;52(1):34-9.

Pilyugin VS, Kuznetsov SL, Sapozhnikov YE, Chikisheva GE, Kiseleva GV, Vorob’eva TP, et al. Synthesis and fungicidal activity of bis(2-arylcarbonylamino-1H-benzimidazol-5-yl) sulfones. Russ J Gen Chem 2008;78(3):446-50.

Stecoza CE, Caproiu MT, Draghici C, Chifiriuc MC, Dracea NO. Synthesis, characterization and antimicrobial activity evaluation of some new derivatives of 6,11-dihydrodibenzo[b,e]thiepin 5,5-dioxide. Rev Chem (Bucuresti) 2000;60(2):137-41.

Barbuceanu S, Almajan GL, Saramet I, Draghici C, Socoteanu R, Barbuceanu F. New S-alkylated 1,2,4-triazoles incorporating diphenylsulfone moieties with potential antibacterial activity. J Serb Chem Soc 2009;74(10):1041-9.

Kudryavtsev KV, Bentley ML, McCafferty DG. Probing of the cis-5-phenyl prolinescaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureussortase Srt Aisoform. Bioorg Med Chem 2009;17(7):2886-93.

Low E, Kim B, Francavilla C, Shiau TP, Turtle ED, O’Mahony DJR. Structure stability/ activity relationship of sulfone stabilized N, N-dichloroamines. Bioorg Med Chem Lett 2011;21:3682-5.

Soni S, Seth M, Sah P. Synthesis and in-vitro antimicrobial evaluation of some novel phthalyl substituted aryl sulphones and sulphonamides. Res J Pharm Biol Chem Sci 2012;3(1):898-907.

Guruswamy B, Arul RK, Chaitanya MVSRK, Darsi SSPK. Synthesis and biological evaluation of novel βâ€hydroxybenzimidazolylsulfonefluoroquinolones by selective oxidation using ammonium molybdate catalyzed H2O2. Eur J Chem 2013;4(4):329-35.

Kumar LV, Naik PJ, Naveen M, Chandrasekhar T, Reddy AB, Penchalaiah N, et al. Synthesis and biological evaluation of some new 2,5-disubstituted 1,3,4-oxadiazoles from 3-(arylsulfonyl) propanehdrazides. Ind J Chem 2014;53B:208-11.

Wani A, Mahajan S. Synthesis, antibacterial activity and preliminary QSAR studies of diarylsulfones. Am J Pharm Tech Res 2014;4(1):1058-66.

Meadows DC, Sanchez T, Neamati N, North TW, Gervay-Hague J. Ring substituent effects on biological activity of vinyl sulfones as inhibitors of HIV-1. Bioorg Med Chem 2007;15(2):1127-37.

Usera AR, Dolan P, Kensler TW, Posner GH. Novel alkyl side chain sulfone 1α,25-dihydroxyvitamin D3 analogs: a comparison of in vitro antiproliferative activities and in vivo calcemic activities. Bioorg Med Chem 2009;17(15):5627-31. b) Usera AR, Dolan P, Kensler TW, Posner GH. Antiproliferative, low-calcemic, fluorinated sulfone analogs of 1α,25-dihydroxyvitamin D3:chemical synthesis and biological evaluation. Bioorg Med Chem 2007;15(16):5509-18.

Barbosa EG, Bega LAS, Beatriz A, Sarkar T, Hamel E, Amaral MS, et al. A diaryl sulfide, sulfoxide, and sulfone bearing structural similarities to combretastatin A-4. Eur J Med Chem 2009;44(6):2685-88.

Cohen A, Crozet MD, Rathelot P, Azas N, Vanelle P. Synthesis and promising in vitro antiproliferative activity of sulfones of a 5-nitrothiazole series. Mol 2013;18:97-113.

Al-Said MS, Ghorab MM, Nissan YM. Dapson in heterocyclic chemistry, part VII: synthesis, molecular docking and anticancer activity of some novel sulfonylbiscompounds carrying biological active 1.3-dihydropyridine, chromene and chromenopyridine moieties. Chem Cent J 2012;6:64.

Rosenthal AS, Chen X, Liu JO, West DC, Hergenrother PJ, ShapiroT A, et al. Malaria-infected mice are cured by a single oral dose of new dimerictrioxane sulfones which are also selectively and powerfully cytotoxic to cancer cells. J Med Chem 2009;52(4): 1198-203.

Capela R, Oliveira R, Gonçalves LM, Domingos A, Gut J, Rosenthal PJ, et al. Artemisinin-dipeptidyl vinyl sulfone hybrid molecules: design, synthesis and preliminary SAR for antiplasmodial activity and falcipain-2 inhibition. Bioorg Med Chem Lett 2009;19(12):3229-32.

Lee PJ, Bhonsle JB, Gaona HW, Huddler DP, Heady TN, Kreishman-Deitrick M, et al. Targeting the fatty acid biosynthesis enzyme, β-ketoacyl-acyl carrier protein synthase III (PfKASIII), in the identification of novel antimalarial agents. J Med Chem 2009;52(4):952-63.

Shenai BR, Lee BJ, Alvarez-Hernandez A, Chong PY, Emal CD, Neitz RJ, et al. Structure-activity relationships for inhibition of cysteine protease activity and development of Plasmodium falciparum by peptidyl vinyl sulfones. Antimicrob Agents Chemother 2003;47(1):154-60.

Chen YT, Lira R, Hansell E, McKerrow JH, Roush WR. Synthesis of macrocyclictrypanosaomal cysteine protease inhibitors. Bioorg Med Chem Lett 2008;18(22):5860-63.

Brak K, Doyle PS, McKerrow JH, Ellman JA. Identification of a new class of nonpeptidic inhibitors of cruzain. J Am Chem Soc 2008;130(20):6404-10.

Chen YT, Brinen LS, Kerr ID, Hansell E, Doyle PS, McKerrow JH, et al. In vitro and in vivostudies of the trypanocidal properties of WRR-483 against Trypanosomacruzi. PLoS 2010;4(9):e825.

Bryant C, Kerr ID, Debnath M, Kenny KHA, Ratnam J, Ferreira RS, et al. Novel non-peptidicvinylsulfones targeting the S2 and S3 subsites of parasite cysteine proteases. Bioorg Med Chem Lett 2009;19(21):6218-21.

Bachovchin DA, Zuhl AM, Speers AE, Wolfe MR, Weerapana E, Brown SJ, et al. Discovery and optimization of sulfonylacrylonitriles as selective, covalent inhibitors of protein phosphatase methylesterase-1. J Med Chem 2011;54(14):5229-36.

Hwang JY, Huang W, Arnold LA, Huang R, Attia RR, Connelly M, et al. Methylsulfonylnitrobenzoates, a new class of irreversible inhibitors of the interaction of the thyroid hormone receptor and its obligate coactivators that functionally antagonizes thyroid hormone. J Biol Chem 2011;286:11895-908.

Hwang JY, Attia RR, Zhu F, Yang L, Lemoff A, Jeffries C, et al. Synthesis and evaluation of sulfonylnitrophenylthiazoles (SNPT's) as thyroid hormone receptor-coactivator interaction inhibitors. J Med Chem 2012;55(5):2301-10.

Su X, Pradaux-Caggiano F, Vicker N, Thomas MP, Halem H, Culler MD, et al. Adamantylethanonepyridyl derivatives: potent and selective inhibitors of human 11β-hydroxysteroiddehydrogenase type 1. Chem Med Chem 2011;6:1616-29.

Reid PR, Bridges TM, Sheffler DJ, Cho HP, Lewis LM, Days E, et al. Discovery and optimization of a novel, selective and brain penetrant M1 positive allosteric modulator (PAM): the development of ML169, an MLPCN Probe. Bioorg Med Chem Lett 2011;21(9):2697-701.

Strassmaier T, Karpen JW. Novel N7-and N1-substituted cGMP derivatives are potent activators of cyclic nucleotide-gated channels. J Med Chem 2007;50(17):4186-94.

Chen H, Tsalkova T, Chepurny OG, Mei FC, Holz GG, Cheng X, et al. Identification and characterization of small molecules as potent and specific EPAC2 antagonists. J Med Chem 2013;56(3):952-62.

Welker ME, Kulik G. Recent synthesis of PI3K/Akt/mTOR signaling pathway inhibitors. Bioorg Med Chem 2013;21(14):4063-91.

Wu P, Su Y, Liu X, Zhang L, Ye Y, Xu J, et al. Synthesis and biological evaluation of novel 2-arylamino-3-(arylsulfonyl)quinoxalines as PI3Kα inhibitors. Eur J Med Chem 2011;46:5540-8.

Finlay MRV, Buttar D, Critchlow SE, Dishington AP, Fillery SM, Fisher E, et al. Sulfonyl-morpholino-pyrimidines: SAR and development of a novel class of selective mTOR kinase inhibitor. Bioorg Med Chem Lett 2012;22:4163-8.

Liu KK.-C, Bailey S, Dinh DM, Lam H, LiC, Wells PA, et al. Conformationally-restricted cyclic sulfones as potent and selective mTOR kinase inhibitors. Bioorg Med Chem Lett 2012;22:5114-7.

Shaw D, Best J, Dinnell K, Nadin A, Shearman M, Pattison C, et al. 3,4-Fused cyclohexylsulfones as c-secretase inhibitors. Bioorg Med Chem Lett 2006;16:3073-7.

Setti EL, Reddy NAV, Phillips OA, Czajkowski DP, Atchison K, Atwal H, et al. Synthesis and β-lactamase inhibitory activity of 2β-alkoxycarbonylpenicillanic acid sulfones. J Antibiotics 1996;49(9):944-6.

Phillips OA, Reddy AVN, Setti EL, Spevak P, Czajkowski DP, Atwal H, et al. Synthesis and biological evaluation of penamsulfones as inhibitors of b-lactamases. Bioorg Med Chem 2005;13:2847-58.

Papp-Wallace KM, Bethel CR, Gootz TD, Shang W, Stroh J, Lau W, et al. Inactivation of a class A and a class C β-lactamase by 6β-(hydroxymethyl)penicillanic acid sulfone. Biochem Pharmacol 2012;83(4):462-71.

Nottingham M, Bethel CR, Pagadala SRR, Harry E, Pinto A, Lemons ZA, et al. Modification of the C6-substituent of penicillin sulfones with goal of improving inhibitor recognition and efficacy. Bioorg Med Chem Lett 2011;21(1):387-93.

Lee M, Hesek D, Shi Q, Noll BC, Fisher JF, Chang M, et al. Conformational analyses of thiirane-based gelatinase inhibitors. Bioorg Med Chem Lett 2008;18(10):3064-7.

Forbes C, Shi Q, Fisher JF, Lee M, Hesek D, Llarrull L, et al. Active site ring-opening of a thiirane moiety and picomolar inhibition of gelatinases. Chem Biol Drug Des 2009;74(6):527-34.

Gooyit M, Lee M, Hesek D, Boggers B, Oliver AG, Fridman R, et al. Synthesis, kinetic characterization and metabolism of diastereomeric 2-(1-(4-phenoxyphenylsulfonyl)ethylthiiranes as potent gelatinase and MT1-MMP inhibitors. Chem Biol Drug Des 2009;74(6):535-46.

Gooyit M, Lee M, Schroeder VA, Ikejiri M, Suckow MA, Mobashery S, et al. Selective water-soluble gelatinase inhibitor prodrugs. J Med Chem 2011;54(19):6676-90.

Published

01-03-2015

How to Cite

Ahmad, I., and S. . “SULFONES: AN IMPORTANT CLASS OF ORGANIC COMPOUNDS WITH DIVERSE BIOLOGICAL ACTIVITIES”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 7, no. 3, Mar. 2015, pp. 19-27, https://journals.innovareacademics.in/index.php/ijpps/article/view/4603.

Issue

Section

Review Article(s)