Synthesis of Ring-Opened Analogues of Oxysterol-Binding Protein-Inhibiting Piperidinyl-thiazole Fungicides

Abstract

Novel aminoethyl-, aminopropyl-, and aminobutyl-substituted thiazole-4-carboxamides have been prepared which are ring-opened analogues of piperidinyl-thiazole fungicides. Depending of the chain length, completely different synthetic approaches had to be chosen which vary from a Sonogashira coupling with a 2-bromothiazole derivative to a thiazole ring construction from different β- and δ-amino acids.

Key words

ring opening - piperidine - thiazole - heterocycle - fungicide - crop protection

• References and Notes

• 1 Pasteris RJ. Hanagan MA. Bisaha JJ. Finkelstein BL. Hoffman LE. Gregory V. Andreassi JL. Sweigard JA. Klyashchitsky BA. Henry YT. Berger RA. Bioorg. Med. Chem. 2016; 24: 354
• 2 Pasteris RJ. Hanagan MA. Bisaha JJ. Finkelstein BL. Hoffman LE. Gregory V. Shepherd CP. Andreassi JL. Sweigard JA. Klyashchitsky BA. Henry YT. Berger RA. In Discovery and Synthesis of Crop Protection Products . Maienfisch P. Stevenson TM. American Chemical Society; Washington: 2015: 149
• 3 Sulzer-Mosse S. Cederbaum F. Lamberth C. Berthon G. Umarye J. Grasso V. Schlereth A. Blum M. Waldmeier R. Bioorg. Med. Chem. 2015; 23: 2129
• 4 Nicolaou KC. Yin J. Mandal D. Erande RD. Klahn P. Jin M. Aujay M. Sandoval J. Gavrilyuk J. Vourloumis D. J. Am. Chem. Soc. 2016; 138: 1698
• 5 Hoffmann J. Gorges J. Junk L. Kazmeier U. Org. Biomol. Chem. 2015; 13: 6010
• 6 Kubisch R. von Gamm M. Braig S. Ullrich A. Burkhart JL. Colling L. Hermann J. Scherer O. Müller R. Werz O. Kazmeier U. Vollmar AM. J. Nat. Prod. 2014; 77: 536
• 7 Burkhart JL. Müller R. Kazmeier U. Eur. J. Org. Chem. 2011; 3050
• 8 Ullrich A. Herrmann J. Müller R. Kazmeier U. Eur. J. Org. Chem. 2009; 6367
• 9 Ullrich A. Chai Y. Pistorius D. Elnakady YA. Herrmann JE. Weissman KJ. Kazmaier U. Müller R. Angew. Chem. Int. Ed. 2009; 48: 4422
• 10 Kambe T. Maruyama T. Nakai Y. Yoshida H. Oida H. Maruyama T. Abe N. Nishiura A. Nakai H. Toda M. Bioorg. Med. Chem. 2012; 20: 2235
• 11 Kambe T. Maruyama T. Nakano M. Nakai Y. Yoshida T. Matsunaga N. Oida H. Konaka A. Maruyama T. Nakai H. Toda M. Bioorg. Med. Chem. Lett. 2012; 22: 396
• 12 Durant GJ. Ganellin CR. Hills DW. Miles PD. Parsons ME. Pepper ES. White GR. J. Med. Chem. 1985; 28: 1414
• 13 Van Bogaert I. Haemers A. Bollaert W. Van Meirvenne N. Brun R. Smith K. Fairlamb AH. Eur. J. Med. Chem. 1993; 28: 387
• 14 Lu J.-Y. Riedrich M. Wojtas KP. Arndt H.-D. Synthesis 2013; 45: 1300
• 15 Lu J.-Y. Arndt H.-D. J. Org. Chem. 2007; 72: 4205
• 16 Nicolaou KC. King NP. Finlay MR. V. He Y. Roschangar F. Vourloumis D. Vallberg H. Sarabia F. Ninkovic S. Hepworth D. Bioorg. Med. Chem. 1999; 7: 665
• 17 Nicolaou KC. He Y. Roschangar F. King NP. Vourloumis D. Li T. Angew. Chem. Int. Ed. 1998; 37: 84
• 18 Yuan C. Chang C.-T. Siegel D. J. Org. Chem. 2013; 78: 5647
• 19 Ducharme Y. Blouin M. Brideau C. Chateauneuf A. Gareau Y. Grimm EL. Juteau H. Laliberte S. MacKay B. Masse F. Ouellet M. Salem M. Styhler A. Friesen RW. ACS Med. Chem. Lett. 2010; 1: 170
• 20 Cosford ND. P. Tehrani L. Roppe J. Schweiger E. Smith ND. Anderson J. Bristow L. Brodkin J. Jiang X. McDonald I. Rao S. Washburn M. Varney MA. J. Med. Chem. 2003; 46: 204
• 21 Sasaki H. Heterocycles 2008; 75: 1061
• 22 Quada JC. Boturyn D. Hecht SM. Bioorg. Med. Chem. 2001; 9: 2303