Facile synthesis of novel glycosyl carboxamide with sugar in furanose and pyranose form using benzotriazole methodology

Letters in Organic Chemistry

Volumn 7, Issue 2, 2010, Pages 136-143

  Kale, Raju R ^a   Prasad, Virendra ^a   Tiwari, Vinod K ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

Acylbenzotriazole; Amines; Benzotriazole; Carboxamides; Glycoconjugate

Indexed keywords

EID: 77951602323     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017810790796363     Document Type: Article

References (46)

1. Valeur, E.; Bradley, M. Amide bond formation: beyond the mytgh of coupling reagents. Chem. Soc. Rev., 2009, 38, 606.
2. Humphrey, J. M.; Chamberlin, A. R. Chemical synthesis of natural product peptides: coupling methods for the incorporation of noncoded amino acids into peptides. Chem. Rev., 1997, 97, 2243.
3. Katritzky, A. R.; Suzuki, K.; Singh, S. K. N-acylation in combinatorial chemistry. ARKIVoC, 2004, 12.
4. Montalbetti, C. A.; G. N.; Falque, V. Amide bond formation and peptide coupling. Tetrahedron, 2005, 61, 10827.
5. Najera, C. From a-amino acids to peptides: all you need for the journey. Synlett, 2002, 1388.
6. (a) Patchett, A. A. Excursions in drug discovery. J. Med. Chem., 1993, 36, 2051.
7. 1 receptors Regul. Pept., 1995, 59, 303.
8. 2+ complex. J. Med. Chem., 1993, 36, 1324.
9. (d) Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Leahy, E. M.; Salvino, J.; Arison, B.; Cichy, M. A.; Spoors, P. G.; Shakespeare, W. C. De novo design and synthesis of somatostatin non-peptide peptidomimetics utilizing .beta.-D-glucose as a novel scaffolding. J. Am. Chem. Soc. 1993, 115, 12550.
10. (a) Varki, A. Biological roles of oligosaccharides: all of theories are correct. Glycobiology, 1993, 3, 97.
11. (b) Gagneau, P.; Varki, A. Evolutionary considerations in relating oligosaccharide diversity to biological function. Glycobiology, 1999, 9, 747.
12. (c) Zhu, X.; Schmidt, R. R. New Principles for Glycoside-Bond Formation. Angew Chem. Int. Ed. Engl., 2009, 48, 1900.
13. (a) Kunz, H.; Schultz, M. In Glycopeptide and related compounds: Synthesis, Analysis and Application, Large, D. G.; Warren, C. D.; Eds: Marcel Dekker Inc New York, 1997, 23.
14. (b) Wittmann, V.; In Glycoscience, Vol. III, Fraser-Reid, B.; Tatsuta, K.; Theim, J. Eds; Springer-Verlag, Berlag, Berlin, Heidelberg, 2001, p. 2254.
15. Pandey, J.; Sharma, A.; Tiwari, V. K.; Dube, D.; Ramachandran, R.; Chaturvedi, V.; Sinha, S. K.; Mishra, N. N.; Shukla, P. K.; Tripathi, R. P. Solution-phase synthesis of a library of carbapeptide analogues based on glycosylamino acid scaffolds and their in silico screening and antimicrobial evaluation. J. Comb. Chem, 2009, 11, 422.
16. Wang, W.; McMurray, A selective method for the preparation of primary amides: synthesis of Fmoc-L-4-carboxamidophenylalanine and other compounds. J. S. Tetrahedron Lett., 1999, 40, 2501.
17. Schmidt, M. A.; Movassaghi, M. N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols. org. Lett., 2005, 7, 2453.
18. (a) Williams, A.; TIbrahim, I. Carbodiimide chemistry: recent advances. Chem. Rev., 1981, 81, 589.
19. 2 site. Bioorg. Med. Chem. 1998, 6, 595.
20. (a) Furstner, A.; Thiel, o. R.; Blanda, G. Asymmetric synthesis of the fully functional macrolide core of salicylihalamide: remote control of olefin geometry during RCM. org. Lett. 2000, 2, 3731.
21. (b) Furstner, A.; Thiel, o. R.; Kindler, N.; Bartkowska, B. Total syntheses of (S)-(-)-Zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol- 2-ylidene ligands. J. org. Chem. 2000, 65, 7990.
22. Gotor, V. Non-conventional hydrolase chemistry: amide and carbamate bond formation catalyzed by lipases Bioorg. Med. Chem., 1999, 7, 2189.
23. (a) Tiwari. V. K.; Singh, A.; Hussain, H. A.; Mishra, B. B.; Tripathi, V. one-pot convenient & high yielding synthesis of dithiocarbamates. Monatsh Chem., 2007, 138, 1297.
24. 1H)-ones. ARKIVoC, 2008, xiv, 27.
25. (c) Tiwari, V. K.; Hussain, H. A.; Mishra, B. B.; Singh, D. D.; Tripathi, V. Benzotriazole mediated one pot convenient synthesis of Thioquinazolinones as potential Antifungal agents. Med. Chem. Res., 2007, 15, 325.
26. (d) Singh, A.; Kale, R. R.; Tiwari, V. K. Benzotriazole mediated one-pot facile synthesis of N/S-glycosyl dithiocarbamates. Trends Carbo. Res., 2009, 1, 80.
27. (e) Tiwari, V. K.; Singh, D. D.; Hussain, H. A.; Mishra, B .B.; Singh, A. one-pot, simple new, and convenient synthesis of 2- thioxo-2,3- dihydroquinazolin-4(1H)-ones. Monatsh Chem., 2008, 139, 43.
28. (a) Yu, H.; Cheng, J.; Ding, L.; Khedri, Z.; Chen, Y.; Chin, S.; Lau, K.; Tiwari, V. K.; Chen, X. Chemoenzymatic synthesis of GD3 oligosaccharides and other disialyl glycans containing natural and non-natural sialic acids. J. Am. Chem. Soc., 2009, 131, 18467.
29. (b) Pandey, J.; Tiwari, V. K.; Verma, S. S.; Chaturvedi, V.; Bhatnagar, S.; Sinha, S.; Gaikwad, A.; Tripathi, R. P. Synthesis and antitubercular screening of imidazole derivatives. Eur. J. Med. Chem., 2009, 44, 3350.
30. (c) Cheng, J.; Yu, H.; Lau, K.; Huang, S.; Chokhawala, H. A.; Li, Y.; Tiwari, V. K.; Chen, X. Multifunctionality of Campylobacter jejuni sialyltransferase-ase C stII. Glycobiology, 2008, 18, 686.
31. (d) Katiyar, D.; Tiwari, V. K.; Tiwari, N.; Verma, S. S.; Sinha, S.; Giakwad, A.; Srivastava, A.; Chaturvedi, V.; Srivastava, R.; Srivastava B. S., Tripathi, R. P. Synthesis and antimycobacterial activity of glycosylated b-amino alcohols and amines. Eur. J. Med. Chem.,2005, 40, 351.
32. n-diglycosylated beta- diamino alcohols as new class of antitubercular agents. Bioorg. Med. Chem., 2005, 13, 5668.
33. (f) Tewari, N.; Tiwari, V. K.; Tripathi, R. P.; Gaikwad, A.; Sinha, S.; Chaturvedi, A. K.; Shukla, P. K.; Srivastava, R.; Srivastava, B. S. Synthesis of Galactopyranosyl amino alcohols as a new class of Antitubercular and antifungal agents. Bioorg. Med. Chem. Lett. , 2004, 14, 329.
34. (g) Tewari, N.; Katiyar, D.; Tiwari, V. K. Tripathi, R. P. Amberlite IR -120 catalysed efficient synthesis of glycosyl enaminones and their application. Tetrahedron Lett., 2003, 44, 6639.
35. n- diglycosylated diaminoalkanes. Bioorg. Med. Chem., 2003, 11, 1789.
36. (i) Tewari, N.; Tiwari, V. K.; Mishra, R. C.; Tripathi, R. P.; Srivastava, A. K.; Ahmad, R.; Srivastava, R.; Srivastava B. S. Synthesis and Bioevaluation of glycosyl ureas as alpha-glucosidase inhibitors and their effect on Mycobacteriam. Bioorg. Med. Chem., 2003, 11, 2911.
37. Caprio, V. In Comprehensive organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier: New York, 2005, 135.
38. Katritzky, A. R.; Suzuki, K.; Wang, Z. Acylbenzotriazoles as Advantageous N-, C-, S-, and o-acylating agnets. Synlett, 2005, 1656.
39. (a) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Highly diastereoselctive peptide chain extensions of unprotected amino acids with N-(Z-α-aminoacyl) benzotriazoles. Synthesis 2004, 2645.
40. (b) Katritzky, A. R.; Angrish, P.; Suzuki, K. The efficient preparation of di-and tripeptides by coupling N-(Cbz- or fmoc-α- aminoacyl) benzotriazoles with unprotected amino acids. Synthesis, 2006, p. 411.
41. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Efficient conversion of carboxylic acids into N-acylbenzotriazoles. Synthesis, 2003, 2795.
42. Katritzky, A. R.; Chang, H.-X.; Yang, B. N-formylbenzotriazole: a stable and convenient N- and o-formylating agent. Synthesis, 1995, 503.
43. Katritzky, A. R.; Yang, B.; Semenzin, D. Trifluoroacetyl)ben- zotriazole: a convenient trifluoroacetylating reagent. J. org. Chem., 1997, 62, 726.
44. Katrizky, A. R.; Suzuki, K.; Singh, S. K.; He, H.-Y. Regiospecific C-acylation of pyrroles and indoles using N-acylbenzotriazoles. J. org. Chem., 2003, 68, 5720
45. 1H-benzotriazole. Synthesis, 1998, 153.
46. Katritzky, A. R.; Pastor, A. Synthesis of β-dicarbonyl compounds using 1-acylbenzotriazoles as regioselective C-acylating reagents. J. org. Chem., 2000, 65, 3679.