Synthesis of diamino-furostan sapogenins and their use as scaffolds for positioning peptides in a preorganized form

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 5298-5305

  Rivera, Daniel G ^a   Concepción, Odette ^a   Pérez Labrada, Karell ^a   Coll, Francisco ^a  

^a UNIVERSITY OF HAVANA   (Cuba)

Author keywords

Cyclopeptides; Furostanes; Peptides; Steroidal sapogenins; Steroids

Indexed keywords

12ALPHA [N (TERT BUTOXYCARBONYL)AMINO] 5ALPHA FUROSTANE 3BETA,26 DIOL; 12ALPHA AMINO 5 ALPHA SPIROSTAN 3BETA OL; 3ALPHA AZIDO 12ALPHA [N (TERT BUTOXYCARBONYL)AMINO] 5ALPHA FUROSTAN 26 YL BENZOATE; 3ALPHA AZIDO 26 (TERT BUTYLDIPHNEYLSILYLOXY) 12ALPHA [N (TERT BTOXYCARBONYL)AMINO] 5ALPHA FUROSTANE; 3ALPHA,7ALPHA DI [N (TERT BUTOXYCARBONYL) AMINO] 5ALPHA FUROSTAN 26 OL; 3ALPHA,7ALPHA DIAMINO 5ALPHA SPIROSTANE; 3BETA ACETOXY SPIROST 5 EN 7 ONE; 5BETA SPIROSTANE 3BETA,7BETA DIOL; CYCLOPEPTIDOFUROSTANE; FUROSTANIC DICARBAMATE; PEPTIDOFUROSTANE; SAPOGENIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR RECOGNITION; PRIORITY JOURNAL; SYNTHESIS;

EID: 42749086674     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.023     Document Type: Article

References (95)

1. Yin H., and Hamilton A.D. Angew. Chem., Int. Ed. 44 (2005) 4130-4163
2. Lavigne J.J., and Anslyn E.V. Angew. Chem., Int. Ed. 40 (2001) 3118-3130
3. Wennemers H., Conza M., Nold M., and Krattiger P. Chem.-Eur. J. 7 (2001) 3342-3347
4. Peczuh M.W., and Hamilton A.D. Chem. Rev. 100 (2000) 2479-2494
5. Schneider H.-J. Adv. Supramol. Chem. 6 (2000) 185-216
6. Still W.C. Acc. Chem. Res. 29 (1996) 155-163
7. Chamorro C., and Liskamp R.J.M. Tetrahedron 60 (2004) 11145-11157
8. Chamorro C., and Liskamp R.J.M. J. Comb. Chem. 5 (2003) 794-801
9. Rump E.T., Rijkers D.T.S., Hilbers H.W., de Groot P.G., and Liskamp R.J.M. Chem.-Eur. J. 8 (2002) 4613-4621
10. Causton A.S., and Sherman J.C. Bioorg. Med. Chem. 7 (1999) 23-27
11. Castani A., Sansone F., and Ungaro R. Acc. Chem. Res. 36 (2003) 246-254
12. Lazzarotto M., Sansone F., Baldini L., Casnati A., Cozzini P., and Ungaro R. Eur. J. Org. Chem. (2001) 595-602
13. Sansone F., Barboso S., Casnati A., Fabbi M., Pochini A., Ugozzoli F., and Ungaro R. Eur. J. Org. Chem. (1998) 897-905
14. Park H.S., Lin Q., and Hamilton A.D. J. Am. Chem. Soc. 121 (1999) 8-13
15. Hamuro Y., Calama M.C., Park H.S., and Hamilton A.D. Angew. Chem., Int. Ed. 36 (1997) 2680-2683
16. Wright A.T., and Anslyn E.V. Chem. Soc. Rev. 35 (2006) 14-28
17. Wright A.T., Zhong Z., and Anslyn E.V. Angew. Chem., Int. Ed. 44 (2005) 5679-5682
18. Wright A.T., Griffin M.J., Zhong Z., MacCleskey S.C., Anslyn E.V., and McDevitt J.T. Angew. Chem., Int. Ed. 44 (2005) 6375-6378
19. Kwak J., Jefferson E.A., Bhumralkar M., and Goodman M. Bioorg. Med. Chem. 7 (1999) 153-160
20. Melacini G., Feng Y., and Goodman M. J. Am. Chem. Soc. 118 (1996) 10359-10364
21. Goodman M., Feng Y., Melacini G., and Taulane J.P. J. Am. Chem. Soc. 118 (1996) 5156-5157
22. del Amo V., Siracusa L., Markidis T., Baragaña B., Bhattarai K.M., Galobardes M., Naredo G., Pérez-Payán M.N., and Davis A.P. Org. Biol. Chem. 2 (2004) 3320-3328
23. Ding B., Taotofa U., Orsak T., Chadwell M., and Savage P.B. Org. Lett. 6 (2004) 3433-3436
24. Madder A., Li L., De Muynck H., Farcy N., Van Haver D., Fant F., Vanhoenacker G., Sandra P., Davis A.P., and De Clercq P.J. J. Comb. Chem. 4 (2002) 552-562
25. De Muynck H., Madder A., Farcy N., De Clercq P.J., Pérez-Payán M.N., Öhberg L.M., and Davis A.P. Angew. Chem., Int. Ed. 39 (2000) 145-148
26. Li H., and Wang L.-X. Org. Biol. Chem. 1 (2003) 3507-3513
27. Albert D., and Feigel M. Helv. Chim. Acta 80 (1997) 2168-2181
28. Cheng Y., Suenaga T., and Still W.C. J. Am. Chem. Soc. 118 (1996) 1813-1814
29. Boyce R., Li G., Nestler H.P., Suenaga T., and Still W.C. J. Am. Chem. Soc. 116 (1994) 7955-7956
30. Wess G., Bock K., Kleine H., Kurz M., Guba W., Hemmeric H., Lopez-Calle E., Baringhaus K.-H., Glombic H., Enhsen A., and Kramer W. Angew. Chem., Int. Ed. 35 (1996) 2222-2224
31. Davis A.P. Molecules 12 (2007) 2106-2122
32. Davis A.P. Coord. Chem. Rev. 250 (2006) 2939-2951
33. Clare J.P., Ayling A.J., Joos J.-B., Sisson A.L., Magro G., Pérez-Payán M.N., Lambert T.N., Shukla R., Smith B.D., and Davis A.P. J. Am. Chem. Soc. 127 (2005) 10739-10746
34. Virtanen E., and Kolehmainen E. Eur. J. Org. Chem. (2004) 3385-3399
35. Davis A.P., and Joss J.-B. Coord. Chem. Rev. 240 (2003) 143-156
36. Sisson A.L., Clare J.P., Taylor L.H., Charmant J.P.H., and Davis A.P. Chem. Commun. (2003) 2246-2247
37. Albert D., Feigel M., Benet-Buchholz J., and Boese R. Angew. Chem., Int. Ed. 37 (1998) 2727-2729
38. Albert D., and Feigel M. Tetrahedron Lett. 35 (1994) 565-568
39. Feigel M., Ladberg R., Engels S., Herbst-Irmer R., and Fröhlich R. Angew. Chem., Int. Ed. 45 (2006) 5698-5702
40. Rivera D.G., and Wessjohann L.A. J. Am. Chem. Soc. 128 (2006) 7122-7123
41. Wessjohann L.A., Voigt B., and Rivera D.G. Angew. Chem., Int. Ed. 44 (2005) 4785-4790
42. Bhattarai K.M., del Amo V., Magro G., Sisson A.L., Joss J.-B., Charmant J.P.H., Kantacha A., and Davis A.P. Chem. Commun. (2006) 2335-2337
43. Kallner A. Acta Chem. Scand. 21 (1967) 322-328
44. Rosenkranz G., Mancera O., Sondheimer F., and Djerassi C. J. Org. Chem. 21 (1956) 520-522
45. Ringold H.J., Rosenkranz G., and Sondheimer F. J. Am. Chem. Soc. 78 (1956) 820-825
46. Rosenkranz G., Pataki J., and Djerassi C. J. Am. Chem. Soc. 73 (1951) 4055-4056
47. Rivera D.G., León F., Coll F., and Davison G.P. Steroids 71 (2006) 1-11
48. Iglesias-Arteaga M.A., Pérez C.S., and Coll F. Steroids 67 (2002) 159-164
49. Seok J., and Fuchs P.L. Org. Lett. 5 (2003) 2247-2250
50. Li W., and Fuchs P.L. Org. Lett. 5 (2003) 2849-2852
51. Gryszkiewicz-Wojtkielewicz A., Jastrze{ogonek}bska I., Morzycki J.W., and Romanowska D.B. Curr. Org. Chem. 7 (2003) 1-22
52. Betancor C., Freire R., Pérez-Martín I., Prangé T., and Zuáres E. Org. Lett. 4 (2002) 1295-1297
53. Iglesias-Arteaga M.A., Pérez Martínez C.S., and Coll Manchado F. J. Chem. Res., Synop. (2001) 34-35
54. Zhang Y., Li Y., Zhu S., Guan H., Lin F., and Yu B. Carbohydr. Res. 339 (2004) 1753-1759
55. Suhr R., Lahmann M., Osacarson S., and Thiem F. Eur. J. Org. Chem. (2003) 4003-4011
56. Fragoso-Luna L.M., Frontana-Uribe B.A., and Cárdenas J. Tetrahdron Lett. 43 (2002) 1151-1155
57. Pettit G.R., and Bowyer W.J. J. Org. Chem. 25 (1960) 84-86
58. Wessjohann L.A., Rivera D.G., and Coll F. J. Org. Chem. 71 (2006) 7521-7526
59. Rivera D.G., Morejón O., and Coll F. Tetrahedron 62 (2006) 8327-8334
60. Li M., and Yu B. Org. Lett. 8 (2006) 2679-2682
61. Hu K., and Yao X. Cancer Invest. 21 (2003) 389-393
62. Hu K., Dong A., Yao X., Kobayashi H., and Iwasaki S. Planta Med. 63 (1997) 161-165
63. Shao Y., Poobrasert O., and Kenelly E.J. Planta Med. 63 (1997) 258-262
64. Nakamura T., Komori C., Lee Y.-y., Hashimoto F., Yahara S., Nohara T., and Ejima A. Biol. Pharm. Bull. 19 (1996) 564-566
65. Iglesias-Arteaga M.A., Pérez Gil R., Leliebre Lara V., Pérez Martínez C.S., and Coll Manchado F. J. Chem. Res., Synop. (1996) 504-505
66. Iglesias-Arteaga M.A., Pérez Gil R., Leliebre Lara V., Pérez Martínez C.S., Rosado A., and Coll Manchado F. Synth. Commun. 28 (1998) 1381-1386
67. Iglesias-Arteaga M.A., Pérez Gil R., Leliebre Lara V., Pérez Martínez C.S., and Coll Manchado F. Synth. Commun. 28 (1998) 1779-1784
68. Arsenou E.S., Koutsourea A.I., Fousteris M.A., and Nikolaropoulos S.S. Steroids 68 (2004) 407-414
69. Zhou X.-T., Rehman A., Li C., and Savage P.B. Org. Lett. 2 (2000) 3015-3018
70. For selected reviews, see:
71. Wessjohann L.A., Andrade C.K.Z., Vercillo O.E., and Rivera D.G. Targets Heterocycl. Systems 10 (2006) 24-63
72. von Nussbaum F., Brands M., Hinzen B., Weingand S., and Häbich D. Angew. Chem., Int. Ed. 45 (2006) 5072-5129
73. Gibson S.E., and Lecci C. Angew. Chem., Int. Ed. 45 (2006) 1364-1377
74. Tan N.-H., and Zhou J. Chem. Rev. 106 (2006) 840-895
75. Wessjohann L.A., Ruijter E., Rivera D.G., and Brandt W. Mol. Divers. 9 (2005) 171-186
76. Hamada Y., and Shioiri T. Chem. Rev. 105 (2005) 4441-4482
77. Nicolaou K.C., Boddy C.N.C., Bräse S., and Winssinger N. Angew. Chem., Int. Ed. 38 (1999) 2096-2152
78. Ueda S., Oishi S., Wang Z., Araki T., Tamamura H., Cluzeau J., Ohno H., Kusano S., Nakashima H., Tren J.O., Peiper S.C., and Fujii N. J. Med. Chem. 50 (2007) 192-198
79. Fletcher S., and Hamilton A.D. J. R. Soc. Interface 3 (2006) 215-233
80. Ying J., Gu X., Cai M., Dedek M., Vagner J., Trivedi D.V., and Hruby V.J. J. Med. Chem. 49 (2006) 6888-6896 and references therein
81. Ye Y., Li W.P., Anderson C.J., Kao J., Nikiforovich G.V., and Achilefu S. J. Am. Chem. Soc. 125 (2003) 7766-7767
82. Marinelli L., Lavecchia A., Gottschalk K.-E., Novellino E., and Kessler H. J. Med. Chem. 46 (2003) 4393-4404
83. Gottschalk K.-E., and Kessler H. Angew. Chem., Int. Ed. 41 (2002) 3767-3774
84. Goodman S.L., Hölzemann G., Sulyok G.A.G., and Kessler H. J. Med. Chem. 45 (2002) 1045-1051
85. Belvisi L., Bernardi A., Checchia A., Manzoni L., Potenza D., Scolastico C., Castorina M., Cupelli A., Giannini G., Carminati P., and Pisano C. Org. Lett. 3 (2001) 1001-1004
86. Haubner R., Gratias R., Diefenbach B., Goodman S.L., Jonczyk A., and Kessler H. J. Am. Chem. Soc. 118 (1996) 7461-7477
87. Rezai T., Yu B., Millhauser G.L., Jacobson M.P., and Lokey R.S. J. Am. Chem. Soc. 128 (2006) 2510-2511
88. March D.R., Abbenante G., Bergman D.A., Brinkworth R.I., Wickramasinghe W., Begun J., Martin J.L., and Fairlie D.P. J. Am. Chem. Soc. 118 (1996) 3375-3379
89. Burton P.S., Conradi R.A., Ho N.F.H., Hilgers A.R., and Borchardt R.T. J. Pharm. Sci. 85 (1996) 1336-1340
90. Kessler H. Angew. Chem., Int. Ed. Engl. 21 (1982) 512-523
91. Hruby V.J., al-Obeidi F., and Kazmierski W. Biochem. J. 268 (1990) 249-262
92. Doores K.J., Mimura Y., Dwek R.A., Rudd P.M., Elliott T., and Davis B.G. Chem. Commun. (2006) 1401-1403
93. For selected examples, see:
94. Cristau P., Martin M.-T., Dau M.T.H., Vors J.-P., and Zhu J. Org. Lett. 6 (2004) 3183-3186
95. Finks B.E., Kim P.R., and Katzenellenbogen J.A. J. Am. Chem. Soc. 120 (1998) 4334-4344