Synthesis of thioureido-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates using bis(benzotriazolyl)methanethione as thioacylating agent

Synlett

Volumn , Issue 5, 2010, Pages 715-720

  Sureshbabu, Vommina V ^a   Chennakrishnareddy, Gundala ^a   Hemantha, Hosahalli P ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Isothiocyanates; Peptidomimetics; Pseudoglycoconjugates; Thioureidopeptides

Indexed keywords

AMINO ACID; BIS(BENZOTRIAZOLYL)METHANETHIONE; GLYCOSYLATED AMINO ACID; PEPTIDOMIMETIC AGENT; THIOKETONE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77749334209     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219393     Document Type: Article

References (41)

1. Synthesis of Peptides and Peptidomimetics (Houben-Weyl) Vol. E22c, Goodman M, Felix A, Moroder L, Toniolo C, Thieme Stuttgart 2003; and references cited therein, Davis B G., Chem. Rev. 2002 102 579; and references cited therein
2. Sureshbabu V V., Patil B S., Venkataramanarao R, J. Org. Chem. 2006 71 7697; and references cited therein
3. Moree W J., vanderMarel G A., Liskamp R J., J. Org. Chem. 1995 60 5157
4. Gustafson G L., Gander J E., Methods Enzymol. 1984 107 172
5. Cho C Y., Moran E J., Cherry S R., Stephans J C., Fodor S P. A., Adams C L., Sundaram A, Jacobs J W., Schultz P G., Science 1993 261 1303
6. Sureshbabu V V., Hemantha H P., Naik S A., Tetrahedron Lett. 2008 49 5133, Wipf P, Venkatraman S, J. Org. Chem. 1996 61 8004, Angell Y L., Burgess K, Chem. Soc. Rev. 2007 36 1674, Hitotsuyanagi Y, Motegi S, Fukaya S, Takeya K, J. Org. Chem. 2002 67 3266
7. Nowick J S., Acc. Chem. Res. 2008 41 1319, Lam P Y., Jadhav P K., Eyermann C J., Hodge C N., Ru Y, Bacheler L T., Meek J L., Otto M J., Rayner M M., Wong Y N., Chang C.-H, Weber P C., Jackson D A., Sharpe T R., Erickson-Viitanen S, Science 1994 263 380
8. Blanco J L. J., Benito J M., Meiiet C O., Fernandez J M. G., Org. Lett. 1999 1 1217; and references cited therein
9. Tobe Y, Sasaki S.-I, Hirose K, Naemura K, Tetrahedron Lett. 1997 38 4791
10. Chalina E G., Chakarova L, Eur. J. Med. Chem. 1998 33 975
11. Todoulou O G., Papadaki-Valiraki A E., Filippatos E C., Ikeda S, DeClercq E, Eur. J. Med. Chem. 1994 29 127, Bloom J D., Dushin R G., Curran K J., Donahue F, Norton E B., Terefenko E, Jones T R., Ross A A., Feld B, Lang S A., DiGrandi M J., Bioorg. Med. Chem. Lett. 2004 14 3401
12. Zhang Y, Talalay P, Cancer Res. 1994 54 1976, Shusheng Z, Tianrong Z, Kun C, Youfeng X, Bo Y, Eur. J. Med. Chem. 2008 43 2778
13. Ren J, Diprose J, Warren J, Esnouf R M., Bird L E., Ikemizu S, Slater M, Milton J, Balzarini J, Stuart D I., Stammers D K., J. Biol. Chem. 2000 275 5633
14. Walpole C, Ko S Y., Brown M, Beattie D, Campbell E, Dickenson F, Ewan S, Hughes G A., Lemaire M, Lerpiniere J, Patel S, Urban L, J. Med. Chem. 1998 41 3159
15. Liav A, Angala S K., Brennan P J., Synth. Commun. 2008 38 1176
16. Rodriguez-Lucena D, Benito J, OrtizMellet C, GarciaFernandez J M., Chem. Commun. 2007 831, Lindhorst T K., Kieburg C, Angew. Chem., Int. Ed. Engl. 1996 35 1953
17. Doyle A G., Jacobsen E N., Chem. Rev. 2007 107 5713
18. Blanco J L. J., Bootello P, Benito J M., Mellet C O., Fernández J M. G., J. Org. Chem. 2006 71 5136
19. Blanco J L. J., Bootello P, Gallego R G., Mellet C O., Fernandez J M. G., Synthesis 2007 2545
20. Neville R G., McGee J J., Can. J. Chem. 1963 41 2123
21. Guy R G., Patai S, The Chemistry of Cyanide and Their Thio Derivatives Part 2 Wiley New York 1977 823
22. Hodgkissi J E., Ettlixger M G., J. Org. Chem. 1956 21 404
23. Dogadkin B A., Pavlov N N., Dokl. Akad. Nauk. SSSR 1961 138 1111
24. Tamura Y, Adachi M, Kawasaki T, Kita Y, Tetrahedron Lett. 1978 19 1753
25. Wong R, Dolman S J., J. Org. Chem. 2007 72 3969
26. Mohanta P K., Dhar S, Samal S K., Ila H, Junjappa H, Tetrahedron 2000 56 629
27. Kim S, Yi K Y., Tetrahedron Lett. 1985 26 1661
28. Chang H, Kim S, Bull. Korean Chem. Soc. 1986 7 407
29. Kim S, Yi K Y., J. Org. Chem. 1986 51 2613
30. Larsen C, Steliou K, Harpp D N., J. Org. Chem. 1978 43 337
31. Katritzky A R., Ledoux S, Witek R M., Nair S K., J. Org. Chem. 2004 69 2976
32. Birkofer P, Richter P, Ritter A, Chem. Ber. 1960 93 2804
33. Rodriguez M, Linares M, Doulut S, Heitz A, Martinez J, Tetrahedron Lett. 1991 32 923
34. Mondal S, Fan E, Synlett 2006 306
35. Boeijen A, Ameijde J V., Liskamp R M. J., J. Org. Chem. 2001 66 8454
36. Pal B, Jaisankar P, Giri V S., Synth. Commun. 2004 34 1317
37. Jarvinen A J., Cerrada-Gimenez M, Grigorenko N A., Khomutov A R., Vepsalainen J J., Sinervirta R M., Keinanen T A., Alhonen L I., Janne J E., J. Med. Chem. 2006 49 399
38. Ichikawa Y, Ohara F, Kotsuki H, Nakano K, Org. Lett. 2006 8 5009
39. Deng S, Gangadharmath U, Chang C T., J. Org. Chem. 2006 71 5179
40. Wang M, Gould S J., J. Org. Chem. 1993 58 5176
41. Zhang L.-H, Kauffman G S., Pesti J A., Yin J, J. Org. Chem. 1997 62 6918