Sulfur containing scaffolds in drugs: Synthesis and application in medicinal chemistry

Current Topics in Medicinal Chemistry

Volumn 16, Issue 11, 2016, Pages 1200-1216

  Feng, Minghao ^a   Tang, Bingqing ^a   Liang, Steven H ^b   Jiang, Xuefeng ^a,c  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

^c NANKAI UNIVERSITY   (China)

Author keywords

Organic synthesis; Sulfonamide; Sulfones; Sulfur containing drugs; Sulfur dioxide fixation; Thioether

Indexed keywords

BENDROFLUMETHIAZIDE; CELECOXIB; CIMETIDINE; CLINDAMYCIN; DELAVIRDINE; DICLOFENAMIDE; DILTIAZEM; DILTIAZEM PLUS ENALAPRIL MALEATE; GLIMEPIRIDE; GLIPIZIDE; MELOXICAM; NAPROXEN PLUS SUMATRIPTAN SUCCINATE; NARATRIPTAN; PENICILLIN DERIVATIVE; PERGOLIDE; PERPHENAZINE; PROCHLORPERAZINE MALEATE; RANITIDINE; ROSUVASTATIN; SOTALOL; SULFADIAZINE; SULFIDE; SULFONAMIDE; SULFONE; SULFUR; SULFUR DIOXIDE; SUMATRIPTAN; TOLBUTAMIDE; UNINDEXED DRUG; ZONISAMIDE; SULFUR DERIVATIVE;

CATALYSIS; CHEMICAL BOND; CYCLIZATION; ESCHERICHIA COLI; MEDICINAL CHEMISTRY; OXIDATIVE COUPLING; REVIEW; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY; DRUG DEVELOPMENT; HUMAN;

CHEMISTRY, PHARMACEUTICAL; DRUG DISCOVERY; HUMANS; PENICILLINS; SULFIDES; SULFONAMIDES; SULFONES; SULFUR COMPOUNDS;

EID: 84961727004     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026615666150915111741     Document Type: Review

References (59)

1. Bernardi, F.; Csizmadia, I. G.; Mangini, A. Organic Sulfur Chemistry. Theoretical and Experimental Advances (Eds: F. Bernardi, I. G. Csizmadia, A. Mangini), Elsevier: Amsterdam, The Netherlands, 1985;
2. Block, E. Reactions of Organosulfur Compounds; Academic Press: New York, 1978;
3. Patai, S.; Rappoport, Z. The Chemistry of Organic Selenium and Tellurium Compounds, John Wiley & Sons: New York, 1986-1987;
4. McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis. Chem. Rev., 2004, 104, 2239-2258;
5. Ager, D. J. Silicon-containing carbonyl equivalents. Chem. Soc. Rev., 1982, 11, 493.
6. H. Guo, B. Sun; H. Gao; X. Chen; S. Liu; X. Yao; X. Liu; Y. Che. Diketopiperazines from the cordyceps-colonizing fungus Epicoccum nigrum. J. Nat. Prod., 2009, 72, 2115-2119
7. Wang, J.-M.; Ding, G.-Z.; Fang, L.; Dai, J.-G; Yu, S.-S.; Wang, Y.-H.; Chen, X.-G.; Ma, S.-G.; Qu, J.; Xu, S.; Du, D.; Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum. J. Nat. Prod., 2010, 73, 1240-1249.
8. Piscitelli, S. C.; Goss, T. F.; Wilton, J. H.; D'Andrea, D. T.; Goldstein, H.; Schentag, J. J. Effects of ranitidine and sucralfate on ketoconazole bioavailability. Antimicrob. Agents Chemother., 1991, 35, 1765-1771.
9. Thase, M. E.; MacFadden, W.; Weisler, R. H.; Chang, W.; Paulsson, B. R.; Khan, A.; Calabrese, J. R.; Bolder, G. Efficacy of quetiapine monotherapy in bipolar I and II depression: A double-blind, placebo-controlled study (The BOLDER II Study). J. Clini. Psychopharma., 2006, 26, 600-609.
10. Ayati, A.; Emami, S.; Asadipour, A.; Shafiee, A.; Foroumadi, A. Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery. Eur. J. Med. Chem., 2015, 97, 699-718.
11. Di Santo, N.; Ehrisman, J., A functional perspective of nitazoxanide as a potential anticancer drug. Mutat. Res., 2014, 768, 16-21.
12. Mishra, C. B.; Kumari, S.; Tiwari, M., Thiazole: a promising heterocycle for the development of potent CNS active agents. Eur. J. Med. Chem., 2015, 92, 1-34.
13. Keri, R. S.; Patil, M. R.; Patil, S. A.; Budagumpi, S. A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry. Eur. J. Med. Chem., 2015, 89, 207-51.
14. Mancuso, R.; Gabriele, B. Recent advances in the synthesis of thiophene derivatives by cyclization of functionalized alkynes. Molecules, 2014, 19, 15687-719.
15. Gramec, D.; Peterlin Masic, L.; Sollner Dolenc, M. Bioactivation potential of thiophene-containing drugs. Chem. Res. Toxicol., 2014, 27, 1344-58.
16. Ilardi E. A.; Vitaku, E.; Njardarson, J. T. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery, J. Med. Chem., 2014, 57, 2832−2842.
17. Lesch, J. E. The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine, Oxford University Press, 2007.
18. Sittig, M. Pharmaceutical Manufacturing Encyclopedia. Park Ridge, Noyes Publications: N.J., U.S.A., 1988. 1756.
19. For a list of top drugs by year, see: http://cbc.arizona.edu/njardarson/group/toppharmaceuticalsposter, (Accessed on April 24, 2015).
20. Anderson, K. K. Sulfonic Acids and Their Derivatives in Comprehensive Organic Chemistry Barton, D. H. R.; Ollis, W. D.; Jones, D. N. Eds.; Pergamon Press: Oxford, 1979; Vol. 3, pp. 331−350.
21. Deng, X.; Mani, N. S. A facile, environmentally benign sulfonamide synthesis in water. Green Chem., 2006, 8, 835-838.
22. Gioiello, A.; Rosatelli, E.; Teofrasti, M.; Filipponi, P.; Pellicciari, R. Building a sulfonamide library by eco-friendly flow synthesis. ACS Comb. Sci., 2013, 15, 235-239.
23. Tang, X.; Huang, L.; Qi, C.; Wu, X.; Wu, W.; Jiang, H. Coppercatalyzed sulfonamides formation from sodium sulfinates and amines. Chem. Commun., 2013, 49, 6102-6104.
24. Wei, W.; Liu, C.; Yang, D.; Wen, J.; You, j.; Wang, H. Metal-free direct construction of sulfonamides via iodine-mediated coupling reaction of sodium sulfinates and amines at room temperature. Adv. Synth. Catal., 2015, 357, 987-992.
25. Zhang, W.; Xie, J.; Rao, B.; Luo, M. Iron-catalyzed N-arylsulfonamide formation through directly using nitroarenes as nitrogen sources. J. Org. Chem., 2015, 80, 3504-3511.
26. Liu, G.; Fan, C.; Wu, J. Fixation of sulfur dioxide into small molecules. Org. Biomol. Chem., 2015, 13, 1592–1599.
27. Pandya, R.; Murashima, T.; Tedeschi, L.; Barrett, A. G. M. Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides. J. Org. Chem., 2003, 68, 8274-8276.
28. Bouchez, L. C.; Dubbaka, S. R.; Turks, M.; Vogel, P. Sulfur dioxide mediated one-pot, three- and four-component syntheses of polyfunctional sulfonamides and sulfonic esters: study of the stereoselectivity of the ene reaction of sulfur dioxide. J. Org. Chem., 2004, 69, 6413-6418.
29. Woolven, H.; Gonzalez-Rodriguez, C.; Marco, I.; Thompson A. L.; Willis, M. C. DABCO-bis(sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: utility in sulfonamide and sulfamide preparation. Org. Lett., 2011, 13, 4876-4878.
30. Nguyen, B.; Emmett, E. J.; Willis, M. C. Palladium-catalyzed aminosulfonylation of aryl halides. J. Am. Chem. Soc., 2010, 132, 16372-16373.
31. Ye S.; Wu, J. A palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines. Chem. Commun., 2012, 48, 7753–7755.
32. Wang, X.; Xue, L.; Wang, Z. A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines. Org. Lett., 2014, 16, 4056−4058.
33. Zheng, D.; Li, Y.; An, Y.; Wu, J. Aminosulfonylation of aromatic amines, sulfur dioxide and hydrazines. Chem. Commun., 2014, 50, 8886-8888.
34. An, Y.; Zheng, D.; Wu, J. Synthesis of 1-(2,3-dihydrobenzofuran- 3-yl)-methanesulfonohydrazides through insertion of sulfur dioxide. Chem. Commun., 2014, 50, 11746-11748.
35. Debergh, J. R.; Niljianskul, N.; Buchwald, S. L. Synthesis of aryl su-lfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids. J. Am. Chem. Soc., 2013, 135, 10638-10641.
36. Lindley, J. Copper assisted nucleophilic substitution of arylhalogen. Tetrahedron, 1984, 40, 1433-1456.
37. Kosugi, M.; Shimizu, T.; Migita, T. Reactions of aryl halides with thiolate anions in the presence of catalytic amounts of tetrakis(triphenylphosphine)palladium preparation of aryl sulfides. Chem. Lett., 1978, 13-14.
38. Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. A General and long-lived catalyst for the palladium-catalyzed Coupling of aryl halides with thiols. J. Am. Chem. Soc., 2006, 128, 2180-2181.
39. Ke, F.; Qu, F.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. An efficient copper- catalyzed carbon-sulfur bond formation protocol in water. Org. Lett., 2011, 13, 454-457.
40. Qiao, Z.; Liu, H.; Xiao, X.; Fu, Y.; Li, Y. Efficient access to 1, 4- benzothiazine: palladium-catalyzed double C-S bond formation using Na2S2O3 as sulfurating reagent. Org. Lett., 2013, 15, 2594-2597.
41. Qiao, Z.; Wei, J.; Jiang, X. Direct cross-coupling access to diverse aromatic sulfide: palladium catalyzed double C−S bond construction using Na2S2O3 as a sulfurating reagent. Org. Lett., 2014, 16, 1212-1215.
42. Li, Y.; Pu, J.; Jiang, X. A highly efficient Cu-Catalyzed S-transfer reaction: from amine to sulfide. Org. Lett., 2014, 16, 2692−2695.
43. Zhang, Y.; Li, Y.; Zhang, X.; Jiang, X. Sulfide synthesis through copper-catalyzed C–S bond formation under biomoleculecompatible conditions. Chem. Commun., 2015, 51, 941-944.
44. Xu, H.-J.; Zhao, Y.-Q.; Feng, T.; Feng, Y.-S. Chan−Lam-type Sarylation of thiols with boronic acids at room temperature. J. Org. Chem., 2012, 77, 2878-2884.
45. Timpa, S. D.; Pell, C. J.; Ozerov, O. V. A well-defined (POCOP)- Rh catalyst for the coupling of aryl halides with thiols. J. Am. Chem. Soc., 2014, 136, 14772−14779.
46. Hamersvelt, H. W. V; Kloke, H. J.; Jong, D. J. D, Koene, R. A.; Huysmans F. T. Oedema formation with the vasodilators nifedipine and diazoxide: direct local effect or sodium retention? J. Hypertens., 1996, 14, 1041–1045.
47. Su, W. An efficient method for the oxidation of sulfides to sulfones. Tetrahedron Lett., 1994. 35. 4955-4958.
48. Emmett, E. J.; Hayter, B. R.; Willis, M. C. Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: a gas- and reductant-free process. Angew. Chem. Int. Ed., 2014, 53, 10204-10208.
49. Rocke, B. N.; Bahnck, K. B.; Herr, M.; Lavergne, S.; Mascitti, V.; Perreault, C.; Polivkova, J.; Shavnya, A. Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides. Org. Lett., 2014, 16, 154-157.
50. Liu, X.; Li, W.; Zheng, D.; Fan, X.; Wu, In press, J. Tetrahedron, 2015, http://dx.doi.org/10.1016/j.tet.2015.03.101
51. Garrod, L. P. Relative antibacterial activity of three Penicillins. Br. Med. J., 1960, 1, 527-529.
52. Sheehan, J. C.; Henery L.; Kenneth R. The Total Synthesis of Penicillin V. J. Am. Chem. Soc., 1957, 79, 1262–1263.
53. Maki, Y.; Sako, M. Photochemical formation of 3- methylenecepham. Tetrahedron Lett., 1976, 17, 4291.
54. Maki, Y.; Sako, M. Concentration-dependent photoreaction of benzothiazolyldithioazetidinones: novel photochemical formation of penam derivatives. J. Chem. Soc., Chem. Commun., 1978, 19. 836.
55. Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. Metal-promoted thiyl radical cyclizations in β-lactam antibiotics. Tetrahedron Lett., 1992, 33, 4783.
56. Cabri, W.; Borghi, D.; Arlandini, E.; Sbraletta, P.; Bedeschi, A. Metal-catalyzed and -promoted cyclizations for the synthesis of cephalosporins: a possible DAOC/DAC synthetase biomimetic process. Tetrahedron, 1993, 49, 6837.
57. Cabri, W.; Candiani, L.; Bedeschi, A. Iron(III)–copper(II) and manganese(III)–copper(II) promoted cyclizations: a new stereoselective approach towards -methyl substituted penicillin derivatives. J. Chem. Soc., Chem. Commun., 1994, 5, 597.
58. Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. A Direct and Convergent Approach to Penams and Penems. J. Org. Chem., 1997, 62, 3438-3439.
59. Emtena1s, H.; Soto, D.; Hultgren, S. J.; Marshall, G. R.; Almqvist, F. Stereoselective Synthesis of Optically Active a-Lactams, Potential Inhibitors of Pilus Assembly in Pathogenic Bacteria. Org. Lett., 2000, 2, 2065-2067.