Facile Synthesis of Novel Benzoylthiophene C-Nucleoside Analogues via Coupling of Sugar Alkynes, Aroyl Chlorides, and 1,4-Dithiane-2,5-diol

Abstract

Concise synthesis of novel benzoylthiophene C-nucleoside analogues has been achieved by the reaction of various terminal sugar alkynes with substituted benzoyl chlorides and 1,4-dithiane-2,5-diol, and subsequent dilute HCl-promoted dehydration in one pot. The sugar alkynes include pyranosides, furanosides, and acyclic sugar. The benzoyl chloride has various substituents. Twenty-eight examples are given. The desired products are obtained in 70–89% yields, and the mechanism has been clarified by isolation of the intermediate.

Key words

C-nucleoside - analogue - sugar - alkyne - thiophene - heterocycle

• References


For selected references, see:
• 1a Walker JA, Liu W, Wise DS, Drach JC, Townsend LB. J. Med. Chem. 1998; 41: 1236
• 1b Aketani S, Tanaka K, Yamamoto K, Ishihama A, Cao H, Tengeiji A, Hiraoka S, Shiro M, Shionoya M. J. Med. Chem. 2002; 45: 5594
• 1c Wu QP, Simons C. Synthesis 2004; 1533
• 1d Matsuda S, Fillo JD, Henry AA, Rai P, Wilkens SJ, Dwyer TJ, Geierstanger BH, Wemmer DE, Schultz PG, Spraggon G, Romesberg FE. J. Am. Chem. Soc. 2007; 129: 10466
• 1e Leconte AM, Hwang GT, Matsuda S, Capek P, Hari Y, Romesberg FE. J. Am. Chem. Soc. 2008; 130: 2336
• 1f Adamo MF. A, Pergoli R. Curr. Org. Chem. 2008; 12: 1544
• 1g Leconte AM, Joubert N, Hocek M, Romesberg FE. ChemBioChem 2008; 9: 2796
• 1h Štefko M, Pohl R, Hocek M. Tetrahedron 2009; 65: 4471

For selected references, see:
• 2a El-Gazzar AB. A, Hafez HN, Abbas HS. Eur. J. Med. Chem. 2009; 44: 4249
• 2b El-Gazzar AB. A, Hafez HN, Nawwar GA. M. S. Eur. J. Med. Chem. 2009; 44: 1427
• 2c Štambaský J, Hocek M, Kočovský P. Chem. Rev. 2009; 109: 6729
• 2d Popsavin M, Spaić S, Svirčev M, Kojić V, Bogdanović G, Pejanović V, Popsavin V. Tetrahedron 2009; 65: 7637
• 2e Cai X, Ng K, Panesar H, Moon SJ, Paredes M, Ishida K, Hertweck C, Minehan TG. Org. Lett. 2014; 16: 2962
• 2f Fujita Y, Inagaki NJ. Diabetes Invest. 2014; 5: 265
• 2g Zhang Y, Liu ZP. Curr. Med. Chem. 2016; 23: 832
• 2h Goodwin NC, Ding ZM, Strobel BA. H, Harris AL, Smith M, Thompson AY, Xiong W, Mseeh F, Bruce DJ, Diaz D, Gopinathan S, Li L, O’Neill EO, Thiel M, Wilson AG. E, Carson KG, Powell DR, Rawlins DB. J. Med. Chem. 2017; 60: 710
• 3a Guckian KM, Krugh TR, Kool ET. J. Am. Chem. Soc. 2000; 122: 6841
• 3b Wu YQ, Ogawa AK, Berger M, McMinn DL, Schultz PG, Romesberg FE. J. Am. Chem. Soc. 2000; 122: 7621
• 3c Parsch J, Engels JW. J. Am. Chem. Soc. 2002; 124: 5664
• 3d Lai JS, Qu J, Kool ET. Angew. Chem. Int. Ed. 2003; 42: 5973
• 3e Lai JS, Kool ET. J. Am. Chem. Soc. 2004; 126: 3040

For selected references, see:
• 4a Matray TJ, Kool ET. Nature 1999; 399: 704
• 4b Ogawa AK, Wu YQ, McMinn DL, Liu JQ, Schultz PG, Romesberg FE. J. Am. Chem. Soc. 2000; 122: 3274
• 4c Yu CZ, Henry AA, Romesberg FE, Schultz PG. Angew. Chem. Int. Ed. 2002; 41: 3841
• 4d Kwon K, Jiang YL, Stivers JT. Chem. Biol. 2003; 10: 351
• 4e Krosky DJ, Song F, Stivers JT. Biochemistry 2005; 44: 5949
• 5a Gargano EM, Perspicace E, Hanke N, Carotti A, Marchais-Oberwinkler S, Hartmann RW. Eur. J. Med. Chem. 2014; 87: 203
• 5b Dexheimer TS, Rosenthal AS, Luci DK, Liang Q, Villamil MA, Chen J, Sun H, Kerns EH, Simeonov A, Jadhav A, Zhuang Z, Maloney DJ. J. Med. Chem. 2014; 57: 8099
• 5c Kojima N, Fushimi T, Tatsukawa T, Tanaka T, Okamura M, Akatsuka A, Yamori T, Dan S, Iwasaki H, Yamashita M. Eur. J. Med. Chem. 2014; 86: 684
• 5d Leitans J, Sprudza A, Tanc M, Vozny I, Zalubovskis R, Tars K, Supuran CT. Bioorg. Med. Chem. 2013; 21: 5130
• 5e Ismail MM, Kamel MM, Mohamed LW, Faggal SI, Galal MA. Molecules 2012; 17: 7217
• 5f Badland M, Compere D, Courte K, Dublanchet AC, Blais S, Manage A, Peron G, Wrigglesworth R. Bioorg. Med. Chem. Lett. 2011; 21: 528
• 6 Cappellacci L, Franchetti P, Grifantini M, Messini L, Abu Sheikha G, Nocentini G, Moraca R, Goldstein BM. Nucleosides Nucleotides 1995; 14: 637
• 7 Franchetti P, Cappellacci L, Grifantini M, Barzi A, Nocentini G, Yang H, O’Connor A, Jayaram HN, Carrell C, Goldstein BM. J. Med. Chem. 1995; 38: 3829
• 8 Franchetti P, Cappellacci L, Perlini P, Jayaram HN, Butler A, Schneider BP, Collart FR, Huberman E, Grifantini M. J. Med. Chem. 1998; 41: 1702
• 9 Sakamaki S, Kawanishi E, Koga Y, Yamamoto Y, Kuriyama C, Matsushita Y, Ueta K, Nomura S. Chem. Pharm. Bull. 2013; 61: 1037
• 10 Sharma GV. M, Kumar KR, Sreenivas P, Krishna PR, Chorghade MS. Tetrahedron: Asymmetry 2002; 13: 687
• 11 Yokoyama M, Tanabe T, Toyoshima A, Togo H. Synthesis 1993; 517
• 12a Lemaire S, Houpis IN, Xiao T, Li J, Digard E, Gozlan C, Liu R, Gavryushin A, Diéne C, Wang Y, Farina V, Knochel P. Org. Lett. 2012; 14: 1480
• 12b Wagschal S, Guilbaud J, Rabet P, Farina V, Lemaire S. J. Org. Chem. 2015; 80: 9328
• 12c Barroso S, Lemaire S, Farina V, Steib AK, Blanc R, Knochel P. J. Org. Chem. 2016; 81: 2804
• 13 Imamura M, Nakanishi K, Suzuki T, Ikegai K, Shiraki R, Ogiyama T, Murakami T, Kurosaki E, Noda A, Kobayashi Y, Yokota M, Koide T, Kosakai K, Ohkura Y, Takeuchi M, Tomiyama H, Ohta M. Bioorg. Med. Chem. 2012; 20: 3263
• 14 Gong H, Gagné MR. J. Am. Chem. Soc. 2008; 130: 12177
• 15 Dumoulin A, Matsui JK, Gutiérrez-Bonet Á, Molander GA. Angew. Chem. Int. Ed. 2018; 57: 6614
• 16a Ma DL, Shum TY. T, Zhang F, Che C.-M, Yang M. Chem. Commun. 2005; 4675
• 16b Zhang Q, Sun J, Zhu Y, Zhang F, Yu B. Angew. Chem. Int. Ed. 2011; 50: 4933
• 16c Yu J, Sun J, Niu Y, Li R, Liao J, Zhang F. Chem. Sci. 2013; 4: 3899
• 17a Liu H.-M, Zhang F, Zou DP. Chem. Commun. 2003; 2044
• 17b Zhang F, Liu H, Li YF, Liu H.-M. Carbohydr. Res. 2010; 345: 839
• 17c Zhang Q, Sun J, Zhang F, Yu B. Eur. J. Org. Chem. 2010; 3579
• 17d Liu H, Zhang F, Li JP, Yan X, Liu HM, Zhao Y. J. Chem. Crystallogr. 2011; 41: 1228
• 17e Zhang F, Liu H, Sheng Y, Liu H.-M. Chin. J. Chem. 2012; 30: 195
• 17f Zhang F, Wang L, Zhang C, Zhao Y. Chem. Commun. 2014; 50: 2046
• 17g Zhang F, Xi Y, Lu Y, Wang L, Liu L, Li J, Zhao Y. Chem. Commun. 2014; 50: 5771
• 17h Zhang F, Mu D, Wang L, Han F, Zhao Y. J. Org. Chem. 2014; 79: 9490
• 17i Liu H, Liang Y, Jia TT, Han F, Zhang F, Zhao Y. Eur. J. Org. Chem. 2017; 1443
• 18a Corey EJ, Fuchs PL. Tetrahedron Lett. 1972; 3769
• 18b Ayyagari VS, Kalanidhi P, Krishna PK. Chem. Eur. J. 2010; 16: 8545
• 19 Huang SL, Omura K, Swern D. J. Org. Chem. 1976; 41: 3329
• 20 Krishna PK, Ayyagari VS. Org. Lett. 2007; 9: 1121
• 21 Sinclair HB. Carbohydr. Res. 1984; 127: 146
• 22 Thiéry JC, Fréchou C, Demailly G. Tetrahedron Lett. 2000; 41: 6337
• 23 Dolhem F, Lièvre C, Demailly G. Tetrahedron 2003; 59: 155