Design and synthesis of bile acid-based amino sterols as antimicrobial agents

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 18, 2009, Pages 5411-5414

  Aher, Nilkanth G ^a   Pore, Vandana S ^a   Mishra, Nripendra N ^b   Shukla, Praveen K ^b   Gonnade, Rajesh G ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Amino sterols; Antibacterial agent; Bile acid; Oxirane

Indexed keywords

BILE ACID; ETHYLENE OXIDE DERIVATIVE; ETHYLENEDIAMINE DERIVATIVE; GENTAMICIN; STEROL DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; IC 50; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REACTION ANALYSIS; STAPHYLOCOCCUS AUREUS;

AMINES; ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; BACTERIA; BILE ACIDS AND SALTS; FUNGI; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; STEROLS; STRUCTURE-ACTIVITY RELATIONSHIP;

STAPHYLOCOCCUS AUREUS;

EID: 68949119783     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.07.117     Document Type: Article

References (60)

1. Moore K.S., Wehrli S., Roder H., Rogers M., Forrest Jr. J.N., McCrimmon D., and Zasloff M. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 1354
2. Wehrli S.L., Moore K.S., Roder H., Durell S., and Zasloff M. Steroids 58 (1993) 370
3. Stone R. Science 259 (1993) 1125
4. Brunel J.M., Salmi C., Loncle C., Vidal N., and Letourneux Y. Curr. Cancer Drug Targets 5 (2005) 267
5. Rao M.N., Shinnar A.E., Noecker L.A., Chao T.L., Feibush B., Snyder B., Sharkansky I., Sarkhian A., Zhang X., Jones S.R., Kinney W.A., and Zasloff M. J. Nat. Prod. 63 (2000) 631
6. Pechulis A.D., Bellevue III F.H., Cioffi C.L., Trapp S.G., Fojtik J.P., McKitty A.A., Kinney W.A., and Frye L.L. J. Org. Chem. 60 (1995) 5121
7. Brunel J.M., and Letourneux Y. Eur. J. Org. Chem. (2003) 3897
8. Okumura K., Nakamura Y., Takeuchi S., Kato I., Fugimoto Y., and Ikekawa N. Chem. Pharm. Bull. 51 (2003) 1177
9. Zhou X.-D., Cai F., and Zhou W.-S. Tetrahedron 58 (2002) 10293
10. Zhang D.-H., Cai F., Zhou X.-D., and Zhou W.-S. Org. Lett. 5 (2003) 3257
11. Sadownik A., Deng G., Janout V., and Regen S.L. J. Am. Chem. Soc. 117 (1995) 6138
12. Kikuchi K., Bernard E.M., Sadownik A., Regen S.L., and Armstrong D. Antimicrob. Agents Chemother. 41 (1997) 1433
13. Jones S.R., Kinney W.A., Zhang X., Jones L.M., and Selinsky B.S. Steroids 61 (1996) 565
14. Shu Y., Jones S.R., Kinney W.A., and Selinsky B.S. Steroids 67 (2002) 291
15. Kim H.-S., Choi B.-S., Kwon K.-C., Lee S.-O., Kwak H.J., and Lee C.H. Bioorg. Med. Chem. 8 (2000) 2059
16. Choucair B., Dherbomez M., Roussakis C., and Kihel L.E. Tetrahedron 60 (2004) 11477
17. Barnett J., Ryman B.E., and Smith F. J. Chem. Soc. (1946) 528
18. Loncle C., Brunel J.M., Vidal N., Dherbomez M., and Letourneux Y. Eur. J. Med. Chem. 39 (2004) 1067
19. James S.P., Smith F., Stacy M., and Webb M. J. Chem. Soc. (1946) 665
20. Hilton M.L., Jones A.S., and Westwood J.R.B. J. Chem. Soc. (1955) 3449
21. Fini A., Fazio G., Roda A., Bellini A.M., Mencini E., and Guarneri M. J. Pharm. Sci. 81 (1992) 726
22. Blagbrough I.S., Carrington S., and Geall A. J. Pharm. Sci. 3 (1997) 223
23. Behr J.-P., Demeneix B., Loeffler J.-P., and Perez-Mutul J. Proc. Natl. Acad. Sci. U.S.A. 86 (1989) 6982
24. Donohue R., Mazzaglia A., Ravoo B.J., and Darcy R. Chem. Commun. (2002) 2864
25. Byk G., Dubertret C., Escriou V., Frederic M., Jaslin G., Rangara R., Pitard B., Crouzet J., Wils P., Schwartz B., and Scherman D. J. Med. Chem. 41 (1998) 224
26. Ewert K., Ahmed A., Evans H.M., Schmidt H.-W., and Safinya C.R. J. Med. Chem. 45 (2002) 5023
27. Nakaramura E., Isobe H., Tomita N., Sawamura M., Jinno S., and Okayama H. Angew. Chem., Int. Ed. 39 (2000) 4254
28. McGeorge C., Perrin C., Monck M., Camilleri P., and Kirby A.J. J. Am. Chem. Soc. 123 (2001) 6215
29. Savage P.B., and Li C. Exp. Opin. Invest. Drugs 9 (2000) 263
30. Savage P.B. Eur. J. Org. Chem. (2002) 759
31. Savage P.B., Li C., Taotafa U., Ding B., and Guan Q. FEMS Microbiol. Lett. 217 (2002) 1
32. Deng G., Dewa T., and Regen S.L. J. Am. Chem. Soc. 118 (1996) 8975
33. Merritt M., Lanier M., Deng G., and Regen S.L. J. Am. Chem. Soc. 120 (1998) 8494
34. Bandyopadhyay P., Janout V., Zhang L., and Regen S.L. J. Am. Chem. Soc. 123 (2001) 7691
35. Zhang J., Jing B., and Regen S.L. J. Am. Chem. Soc. 125 (2003) 13984
36. Chen W.-H., and Regen S.L. J. Am. Chem. Soc. 127 (2005) 6538
37. Mehiri M., Chen W.-H., Janout V., and Regen S.L. J. Am. Chem. Soc. 131 (2009) 1338
38. Salunke D.B., Ravi D.S., Pore V.S., Mitra D., and Hazra B.G. J. Med. Chem. 49 (2006) 2652
39. Salunke D.B., Hazra B.G., and Pore V.S. Curr. Med. Chem. 13 (2006) 813
40. Enhsen A., Kramer W., and Wess G. Drug Discovery Today 3 (1998) 409
41. Li C., Peters A.S., Meridith E.L., Allman G.W., and Savage P.B. J. Am. Chem. Soc. 120 (1998) 2961
42. Salunke D.B., Hazra B.G., Pore V.S., Bhat M.K., Nahar P.B., and Deshpande M.V. J. Med. Chem. 47 (2004) 1591
43. Hazra B.G., Pore V.S., Dey S.K., Datta S., Darokar M.P., Saikia D., Khanuja S.P.S., and Thakur A.P. Bioorg. Med. Chem. Lett. 14 (2004) 773
44. Pore V.S., Aher N.G., Kumar M., and Shukla P.K. Tetrahedron 62 (2006) 11178
45. Vatmurge N.S., Hazra B.G., Pore V.S., Shirazi F., Deshpande M.V., Kadreppa S., and Chattopadhyay S. Org. Biomol. Chem. 6 (2008) 3823
46. Bavikar S.N., Salunke D.B., Hazra B.G., Pore V.S., Dodd R.H., Thierry J., Shirazi F., Deshpande M.V., Kadreppa S., and Chattopadhyay S. Bioorg. Med. Chem. Lett. 18 (2008) 5512
47. Aher N.G., Pore V.S., Shiva Keshava G.B., Kumar A., Mishra N.N., Shukla P.K., Sharma A., and Bhat M.K. Bioorg. Med. Chem. Lett. 19 (2009) 759
48. Rapoport H., and Reist H.N. J. Am. Chem. Soc. 77 (1955) 480
49. Reagents for Organic Synthesis, Fieser & Fieser, Vol. 2, p 363.
50. Cook C.E., Corley R.C., and Wall M.E. Steroids 33 (1968) 2789
51. Bevins C.L., Bantia S., Pollack R.M., Bounds P.L., and Kayser R.H. J. Am. Chem. Soc. 106 (1984) 4957
52. Kashino S., Katz H., Glusker J.P., Pollack R.M., and Bounds P.L. J. Am. Chem. Soc. 109 (1987) 6765
53. Maltais R., Tremblay M.R., and Poirier D. J. Comb. Chem. 2 (2000) 604
54. Maltais R., Luu-The V., and Poirier D. J. Med. Chem. 45 (2002) 640
55. Single-crystal data and CIF file of compound 13 (CCDC # 725608) have been deposited at the Cambridge Crystallographic Data Centre and can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1123 336 033; or email: deposit@ccdc.ac.uk.
56. For the synthesis of N1-(Boc)-1,2-diaminoethane see Supplementary data.
57. National Committee for Clinical Laboratory Standard. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast, Approved Standard. Document M27-A; National Committee for Clinical Laboratory Standards: Wayne, PA, USA, 1997
58. National Committee for Clinical Laboratory Standard. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium Forming Filamentous Fungi: Proposed Standard. Document M38-P; National Committee for Clinical Laboratory Standard: Wayne, PA, USA, 1998
59. National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Approved Standard, 5th ed.; NCCLS: Villanova, PA, 2000; pp M7-A5
60. Yamamoto N., Fujita J., Shinzato T., Higa F., Tateyama M., Tohyama M., Nakasone I., and Yamane N. Int. J. Antimicrob. Agents 27 (2006) 171