Synthesis of Glucuronic, Mannuronic, and Galacturonic Acid‐Derived Imidazoles as Inhibitors of Bovine Liver β‐Glucuronidase
作者： Jagadish Pabba , Narinder Mohal , Andrea Vasella
关键词:
摘要: The gluco-, manno-, and galacto-configured imidazopyridine-5-carboxylates 5–7, respectively, were synthesized evaluated as inhibitors of bovine liver β-glucuronidase. gluconolactam 15 was transformed into the gluco- manno-imidazoles 5 6 in nine steps an overall yield 9 12%, respectively. Oxidation esterification selectively protected manno-configured hydroxymethyl-imidazopyridines 23 25, respectively (both obtained from 15), provided benzhydryl esters 24 26, Hydrogenolysis afforded gluco-imidazopyridine-carboxylic acid manno-isomer 6. Similarly, hydroxymethyl-imidazopyridine 33, galactonolactam 27, subjected to oxidation, esterification, deprotection afford imidazopyridine-carboxylate 7 ten 27 13%. gluco-configured imidazole is strongest known inhibitor β-glucuronidases (Ki = 12 nM), while manno- imidazoles are micromolar small difference between inhibitory strength imidazopyridine-carboxylic tetrazolopyridine-carboxylic 1, configurational selectivity 5–7 compared unselectivity corresponding lactams 3 4 discussed.
sci-hub.se 参考文章(42)
Joseph Kiss, β-Eliminative Degradation of Carbohydrates Containing Uronic Acid Residues Advances in Carbohydrate Chemistry and Biochemistry Volume 29. ,vol. 29, pp. 229- 303 ,(1974) , 10.1016/S0065-2318(08)60251-6
Chih-Cheng Wang, Oscar Touster, Studies of Catalysis by β-Glucuronidase Journal of Biological Chemistry. ,vol. 247, pp. 2644- 2649 ,(1972) , 10.1016/S0021-9258(19)45259-9
J. Kiss, F. Burkhardt, Ungesättigte Zucker. Eine milde Sulfonat-β-Eliminierung bei Aminohexopyranosiduronat-Derivaten Helvetica Chimica Acta. ,vol. 52, pp. 2622- 2636 ,(1969) , 10.1002/HLCA.19690520843
Yoshitaka Ichikawa, Yasuhiro Igarashi, Mie Ichikawa, Yoshitomo Suhara, 1-N-Iminosugars: Potent and Selective Inhibitors of β-Glycosidases Journal of the American Chemical Society. ,vol. 120, pp. 3007- 3018 ,(1998) , 10.1021/JA973443K
Yoshio Nishimura, gem-Diamine 1-N-Iminosugars and Related Iminosugars, Candidate of Therapeutic Agents for Tumor Metastasis Current Topics in Medicinal Chemistry. ,vol. 3, pp. 575- 591 ,(2003) , 10.2174/1568026033452492
Michael K. Tong, George Papandreou, Bruce Ganem, Potent, broad-spectrum inhibition of glycosidases by an amidine derivative of D-glucose Journal of the American Chemical Society. ,vol. 112, pp. 6137- 6139 ,(1990) , 10.1021/JA00172A045
Helmer Søhoel, Xifu Liang, Mikael Bols, Isogalactofagomine lactam. A neutral nanomolar galactosidase inhibitor Journal of the Chemical Society, Perkin Transactions 1. pp. 1584- 1585 ,(2001) , 10.1039/B103831C
Yoshio Nishimura, Eiki Shitara, Hayamitsu Adachi, Minako Toyoshima, Motowo Nakajima, Yoshiro Okami, Tomio Takeuchi, Flexible synthesis and biological activity of uronic acid-type gem-diamine 1-N-iminosugars: a new family of glycosidase inhibitors. Journal of Organic Chemistry. ,vol. 65, pp. 2- 11 ,(2000) , 10.1021/JO982448C
KUNIAKI TATSUTA, SHOZO MIURA, SHIGERU OHTA, HIROKI GUNJI, Syntheses and Glycosidase Inhibiting Activities of Nagstatin Analogs The Journal of Antibiotics. ,vol. 48, pp. 286- 288 ,(1995) , 10.7164/ANTIBIOTICS.48.286
Jagadish Pabba, Brian P. Rempel, Stephen G. Withers, Andrea Vasella, Synthesis of Glycaro‐1,5‐lactams and Tetrahydrotetrazolopyridine‐5‐carboxylates: Inhibitors of β‐D‐Glucuronidase and α‐L‐Iduronidase Helvetica Chimica Acta. ,vol. 89, pp. 635- 666 ,(2006) , 10.1002/HLCA.200690066