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Synthesis 2013; 45(4): 479-490
DOI: 10.1055/s-0032-1318100
DOI: 10.1055/s-0032-1318100
paper
Thienopyrimidinedione Formation Versus Ester Hydrolysis from Ureido Carboxylic Acid Methyl Ester
Further Information
Publication History
Received: 10 October 2012
Accepted after revision: 20 December 2012
Publication Date:
17 January 2013 (online)
Abstract
The basic hydrolysis of ureidothienyl carboxylic esters was found to depend on the substitution pattern of the ureido moiety. While various hindered substituents led to carboxylic acid formation, unhindered substituents preferentially resulted in a cyclization step, yielding thienopyrimidinedione derivatives.
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References
- 1a Gautier B, Goncalves V, Diana D, Di Stasi R, Teillet F, Lenoir C, Huguenot F, Garbay C, Fattorusso R, D’Andrea LD, Vidal M, Inguimbert N. J. Med. Chem. 2010; 53: 4428
- 1b Goncalves V, Gautier B, Garbay C, Vidal M, Inguimbert N. J. Pept. Sci. 2008; 14: 767
- 1c Goncalves V, Gautier B, Coric P, Bouaziz S, Lenoir C, Garbay C, Vidal M, Inguimbert N. J. Med. Chem. 2007; 50: 5135
- 1d Goncalves V, Gautier B, Regazzetti A, Coric P, Bouaziz S, Garbay C, Vidal M, Inguimbert N. Bioorg. Med. Chem. Lett. 2007; 17: 5590
- 2 Gautier B, Miteva MA, Goncalves V, Huguenot F, Coric P, Bouaziz S, Seijo B, Gaucher J-F, Broutin I, Garbay C, Lesnard A, Rault S, Inguimbert N, Villoutreix B, Vidal M. Chem. Biol. 2011; 18: 1631
- 3a Häcker H-G, Leyers S, Wiendlocha J, Gütschow M, Wiese M. J. Med. Chem. 2009; 52: 4586
- 3b Arhin F, Bélanger O, Ciblat S, Dehbi M, Delorme D, Dietrich E, Dixit D, Lafontaine Y, Lehoux D, Liu J, McKay JA, Moeck G, Reddy R, Rose Y, Srikumar R, Tanaka K, Williams DM, Gros P, Pelletier J, Parr TR. Jr, Rafai Fara A. Bioorg. Med. Chem. 2006; 14: 5812
- 3c Rheault T, Donaldson K, Badiang-Alberti J, Davis-Ward R, Webb Andrews C, Bambal R, Jackson J, Cheung M. Bioorg. Med. Chem. Lett. 2010; 20: 4587
- 3d Laine E, Goncalves C, Karst JC, Lesnard A, Rault S, Tang W-J, Malliavin TE, Ladant D, Blondel A. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 11277
- 3e Pietsch M, Gütschow M. J. Biol. Chem. 2002; 277: 24006
- 3f Chan L, Das SK, Jagadeeswar ReddyT, Poisson C, Proulx M, Pereira O, Courchesne M, Roy C, Wang W, Siddiqui A, Yannopoulos CG, Nguyen-Ba N, Labrecque D, Bethell R, Hamel M, Courtemanche-Asselin P, L’Heureux L, David M, Nicolas O, Brunette S, Bilimoria D, Bédard J. Bioorg. Med. Chem. Lett. 2004; 14: 793
- 4a Venskutonyte R, Butini S, Sanna CocconeS, Gemma S, Brindisi M, Kumar V, Guarino E, Maramai S, Valenti S, Amir A, Anton ValadesE, Frydenvang K, Kastrup JS, Novellino E, Campiani G, Pickering DS. J. Med. Chem. 2011; 54: 4793
- 4b Miwa K, Hitaka T, Imada T, Sasaki S, Yoshimatsu M, Kusaka M, Tanaka A, Nakata D, Furuya S, Endo S, Hamamura K, Kitazaki K. J. Med. Chem. 2011; 54: 4998
- 4c Guile SD, Bantick JR, Cooper ME, Donald DK, Eyssade C, Ingall AH, Lewis RJ, Martin BP, Mohammed RT, Potter TJ, Reynolds RH, St-Gallay SA, Wright AD. J. Med. Chem. 2007; 50: 254
- 4d Tor Y, Del Valle S, Jaramillo D, Srivatsan SG, Rios A, Weizman H. Tetrahedron 2007; 63: 3608
- 4e Betz SF, Lio FM, Gao Y, Reinhart GJ, Guo Z, Mesleh MF, Zhu Y-F, Struthers RS. J. Med. Chem. 2006; 49: 6170
- 5a Munchhof MJ, Beebe JS, Casavant JM, Cooper BA, Doty JL, Higdon RC, Hillerman SM, Soderstrom CI, Knauth EA, Marx MA, Rossi AM. K, Sobolov SB, Sun J. Bioorg. Med. Chem. Lett. 2004; 14: 21
- 5b Wamhoff H, Ertas M. Synthesis 1985; 190
- 5c Romeo G, Materia L, Manetti F, Cagnotto A, Mennini T, Nicoletti F, Botta M, Russo F, Minneman KP. J. Med. Chem. 2003; 46: 2877
- 5d Meyer M, Altenbach R, Bai H, Basha F, Carroll W, Kerwin Jr J, Lebold S, Lee E, Pratt J, Sippy K, Tietje K, Wendt M, Brune M, Buckner S, Hancock DI. J. Med. Chem. 2001; 44: 1971
- 5e Russell R, Press J, Rampulla R, McNally J, Falotico R, Keiser J, Bright D, Tobia A. J. Med. Chem. 1988; 31: 1789
- 5f Sasaki S, Cho N, Nara Y, Harada M, Endo S, Suzuki N, Furuya S, Fujino M. J. Med. Chem. 2003; 46: 113
- 5g Sugiyama M, Sakamoto T, Tabata K, Endo K, Ito K, Kobayshi M, Fukumi H. Chem. Pharm. Bull. 1989; 37: 2091
- 6 Pietsch M, Gütschow M. J. Med. Chem. 2005; 48: 8270
- 7a Florence X, Sebille S, De Tullio P, Lebrun P, Pirotte B. Bioorg. Med. Chem. 2009; 17: 7723
- 7b Lichitsky B, Belyi R, Komogortsev A, Dudinov A, Krayushkin M. Russ. Chem. Bull. 2009; 58: 387
- 7c Brouillette Y, Lisowski V, Guillon J, Massip S, Martinez J. Tetrahedron 2007; 63: 7538
- 8a Le Foulon F-X, Braud E, Fabis F, Lancelot J-C, Rault S. Tetrahedron 2003; 59: 10051
- 8b Le Foulon F-X, Braud E, Fabis F, Lancelot J-C, Rault S. J. Comb. Chem. 2005; 7: 253
- 8c Fabis F, Jolivet-Fouchet S, Robba M, Landelle H, Rault S. Tetrahedron 1998; 54: 10789
- 9a Temple Burling M, Goldstein BM. J. Am. Chem. Soc. 1992; 114: 2313
- 9b Tanaka R, Oyama Y, Imajo S, Matsuki S, Ishiguro M. Bioorg. Med. Chem. 1997; 5: 1389
- 9c Nagao Y, Hirata T, Goto S, Sano S, Kakehi A, Iizuka K, Shiro M. J. Am. Chem. Soc. 1998; 120: 3104
- 9d Huang H, Chen Z, Ponce Ortiz R, Newman C, Usta H, Lou S, Youn J, Noh Y-Y, Baeg K-J, Chen LX, Facchetti A, Marks T. J. Am. Chem. Soc. 2012; 134: 10966
- 9e Ohkata K, Ohsugi M, Yamamoto K, Ohsawa M, Akiba K. J. Am. Chem. Soc. 1996; 118: 6355
- 10a Domínguez de María P, García-Burgos CA, Bargeman G, van Gemert RW. Synthesis 2007; 1439
- 10b Felluga F, Fermeglia M, Ferrone M, Pitacco G, Pricl S, Valentin E. Helv. Chim. Acta 2002; 85: 4046
- 10c Tanyeli C, Turkut E. Tetrahedron: Asymmetry 2004; 15: 2057
- 10d Kingery-Wood J, Johnson JS. Tetrahedron Lett. 1996; 37: 3975
- 10e Lou W, Zong M, Wu H. Biotechnol. Appl. Biochem. 2005; 41: 151
- 10f Das AK, Collins R, Ulijn RV. Small 2008; 4: 279
- 11 Neumann U, Gütschow M. Bioorg. Chem. 1995; 23: 72