Synthesis and biological activities of 3-polyamino-5β-cholane-7α,24-diols

Sharaf Nawaz Khan; Hong-Seok Kim

Journal of Industrial and Engineering Chemistry, Vol.15, No.4, 561-565, July, 2009

DOI10.1016/j.jiec.2009.01.013 Export Citation

Synthesis and biological activities of 3-polyamino-5β-cholane-7α,24-diols

Sharaf Nawaz Khan, and Hong-Seok Kim^†

Department of Applied Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea

E-mail:

A series of 3-polyaminochenodeoxycholic acid derivatives were synthesized and their in vitro antimicrobial and antifungal activities were assessed. The antimicrobial activity was evaluated against Gram-positive and Gram-negative bacteria, and the antifungal activity was assessed against two strains Candida albicans (ATCC MYA-1003) and Aspergillus fumigatus (ATCC 16424). The introduction of an amine group to steroid was accomplished by reductive amination of 3-oxosteroid 9 with Boc-spermidine and Boc-spermine, in the presence of NaBH(OAc)3. This afforded a high yield of 3-polyaminosteroids of 10-13. The 3β-sperminyl-5β-cholane 6 showed the highest antimicrobial activity against Streptococcus pyogenes 308A, Staphylococcus aureus 503, Escherichia coli DC2 and Pseudomonas aeruginosa 9027 with a MIC value of 3.13 μg/mL.

Keywords:3-Polyaminochenodeoxycholic acid;derivatives;Reductive amination;Antimicrobial activity;Antifungal activity

[References]

Moore KS, Wehrli SL, Roder H, Rogers M, Forrest Jr. JN, McCrimmon D, Zasloff M, Proc. Natl. Acad. Sci. U.S.A., 90, 1354 (1993)
Wehrli SL, Moore KS, Roder H, Durell S, Zasloff M, Steroids, 58, 370 (1993)
Herbst RS, Hammond LA, Carbone DP, Tran HT, Holroyd KJ, Desai A, Williams JI, Bekele BN, Hait H, Allgood V, Solomon S, Schiller JH, Clin. Cancer Res., 9, 4108 (2003)
Hao D, Hammond LA, Eckhardt SG, Patnaik A, Takimoto CH, Schwartz GH, Goetz AD, Tolcher AW, McCreery HA, Mamun K, Williams JI, Holroyd KJ, Rowinsky EK, Clin. Cancer Res., 9, 2465 (2003)
Rao MN, Shinnar AE, Noecker LA, Chao TL, Feibush B, Snyder B, Sharkansky I, Sarkahian A, Zhang X, Jones SR, Kinney WA, Zasloff M, J. Nat. Prod., 63, 631 (2000)
Jeong K, Kim MK, Chung WY, Kye YS, Kim JH, Suh J, J. Ind. Eng. Chem., 15(3), 342 (2009)
Lee IS, Kim SJ, Kwak YW, Choi MC, Park JW, Ha CS, J. Ind. Eng. Chem., 14(3), 344 (2008)
Okumura K, Nakamura Y, Takeuchi S, Kato I, Fujimoto Y, Kekawa N, Chem. Pharm. Bull., 51, 1177 (2003)
Zhang DH, Cai F, Zhou XD, Zhou WS, Org. Lett., 5, 3257 (2003)
Kinney WA, Zhang X, Williams JI, Johnston S, Michalak RS, Deshpande M, Dostal L, Rosazza JPN, Org. Lett., 2, 2921 (2000)
Weis AL, Bakes T, Alferiev I, Zhang X, Shao B, Kinney WA, Tetrahedron Lett., 40, 4863 (1999)
Jones SR, Selinsky BS, Rao MN, Zhang X, Kinney WA, Tham FS, J. Org. Chem., 63, 3786 (1998)
Pechulis AD, Bellevue FH, Cioffi CL, Trapp SG, Fojtik JP, McKitty AA, Kinney WA, Frye LL, J. Org. Chem., 60, 5121 (1995)
Moriarty RM, Enaehe LA, Kinney WA, Allen CS, Canary JW, Tuladhar SM, Guo L, Tetrahedron Lett., 36, 5139 (1995)
Salmi C, Loncle C, Letourneux Y, Brunel JM, Tetrahedron, references cited therein;, 64, 4453 (2008)
Chen WH, Shao XB, Moellering R, Wennersten C, Regen SL, Bioconjugate Chem., 17, 1582 (2006)
Zhang DH, Cai F, Zhou XD, Zhou WS, Chin. J. Chem., 23, 176 (2005)
Shu Y, Jones SR, Kinney WA, Selinsky BS, Steroids, 67, 291 (2002)
Kikuchi K, Bernard EM, Sadownik A, Regen SL, Armstrong D, Antimicrob. Agents Chemother., 41, 1433 (1997)
Jones SR, Kinney WA, Zhang X, Jones LM, Selinsky BS, Steroids, 61, 565 (1996)
Sadownik A, Deng G, Janout V, Regen SL, Bernard EM, Kikuchi K, Armstrong D, J. Am. Chem. Soc., 117(22), 6138 (1995)
Savage PB, Curr. Med. Chem., 1, 293 (2002)
Savage PB, Eur. J. Org. Chem., 759 (2002)
Kim HS, Choi BS, Kwon KC, Lee SO, Kwak HJ, Lee CH, Bioorg. Med. Chem., 8, 2059 (2000)
Kim HS, Kwon KC, Kim KS, Lee CH, Bioorg. Med. Chem. Lett., 11, 3065 (2001)
Khan SN, Kim HS, Kim BJ, Bioorg. Med. Chem. Lett., 17, 5139 (2007)
Khan SN, Cho NJ, Kim HS, Tetrahedron Lett., 48, 5189 (2007)
Khan SN, Jung YM, Kim BJ, Cho H, Lee J, Kim HS, Bioorg. Med. Chem. Lett., 18, 2558 (2008)
Salmi C, Loncle C, Vidal N, Letourneux Y, Brunel JM, Eur. J. Med. Chem., references cited therein;, 43, 540 (2008)
Brunel JM, Loncle C, Vidal N, Dherbomez M, Letourneux Y, Steroids, 70, 907 (2005)
Choucair B, Dherbomez M, Roussakis C, El Kihel L, Tetrahedron, 60, 11477 (2004)
Choucair B, Dherbomez M, Roussakis C, El Kihel L, Bioorg. Med. Chem. Lett., 14, 4213 (2004)
El Kihel L, Choucair B, Dherbomez M, Letourneux Y, Eur. J. Org. Chem., 4075 (2002)
Fouace S, El Kihel L, Dherbomez M, Letourneux Y, Bioorg. Med. Chem. Lett., 11, 3011 (2001)
Bellini AM, Mencini E, Quaglio MP, Guarneri M, Fini A, Arch. Pharm., 323, 201 (1990)
Bellini AM, Mencini E, Quaglio MP, Guarneri M, Fini A, Steroids, 56, 395 (1991)
Li CH, Budge LP, Driscoll CD, Willardson BM, Allman GW, Savage PB, J. Am. Chem. Soc., 121(5), 931 (1999)
Joyce MJ, Hiremath SV, Mattammal MB, Elliott WH, Steroids, 44, 95 (1984)
Khan SN, Bae SY, Kim HS, Tetrahedron Lett., 46, 7675 (2005)
Khan SN, Cho NJ, Kim HS, in: Robert SM, Whittall J (Eds.), Catalysts for Fine Chemical Synthesis, Vol. 5: Regio- and Stereo-Controlled Oxidations and Reductions, John Wiley & Sons, Chichester, 2007, pp. 175.181.

[Referenced By]

[Related Articles]

[1] Moore KS, Wehrli SL, Roder H, Rogers M, Forrest Jr. JN, McCrimmon D, Zasloff M, Proc. Natl. Acad. Sci. U.S.A., 90, 1354 (1993)

[2] Wehrli SL, Moore KS, Roder H, Durell S, Zasloff M, Steroids, 58, 370 (1993)

[3] Herbst RS, Hammond LA, Carbone DP, Tran HT, Holroyd KJ, Desai A, Williams JI, Bekele BN, Hait H, Allgood V, Solomon S, Schiller JH, Clin. Cancer Res., 9, 4108 (2003)

[4] Hao D, Hammond LA, Eckhardt SG, Patnaik A, Takimoto CH, Schwartz GH, Goetz AD, Tolcher AW, McCreery HA, Mamun K, Williams JI, Holroyd KJ, Rowinsky EK, Clin. Cancer Res., 9, 2465 (2003)

[5] Rao MN, Shinnar AE, Noecker LA, Chao TL, Feibush B, Snyder B, Sharkansky I, Sarkahian A, Zhang X, Jones SR, Kinney WA, Zasloff M, J. Nat. Prod., 63, 631 (2000)

[6] Jeong K, Kim MK, Chung WY, Kye YS, Kim JH, Suh J, J. Ind. Eng. Chem., 15(3), 342 (2009)

[7] Lee IS, Kim SJ, Kwak YW, Choi MC, Park JW, Ha CS, J. Ind. Eng. Chem., 14(3), 344 (2008)

[8] Okumura K, Nakamura Y, Takeuchi S, Kato I, Fujimoto Y, Kekawa N, Chem. Pharm. Bull., 51, 1177 (2003)

[9] Zhang DH, Cai F, Zhou XD, Zhou WS, Org. Lett., 5, 3257 (2003)

[10] Kinney WA, Zhang X, Williams JI, Johnston S, Michalak RS, Deshpande M, Dostal L, Rosazza JPN, Org. Lett., 2, 2921 (2000)

[11] Weis AL, Bakes T, Alferiev I, Zhang X, Shao B, Kinney WA, Tetrahedron Lett., 40, 4863 (1999)

[12] Jones SR, Selinsky BS, Rao MN, Zhang X, Kinney WA, Tham FS, J. Org. Chem., 63, 3786 (1998)

[13] Pechulis AD, Bellevue FH, Cioffi CL, Trapp SG, Fojtik JP, McKitty AA, Kinney WA, Frye LL, J. Org. Chem., 60, 5121 (1995)

[14] Moriarty RM, Enaehe LA, Kinney WA, Allen CS, Canary JW, Tuladhar SM, Guo L, Tetrahedron Lett., 36, 5139 (1995)

[15] Salmi C, Loncle C, Letourneux Y, Brunel JM, Tetrahedron, references cited therein;, 64, 4453 (2008)

[16] Chen WH, Shao XB, Moellering R, Wennersten C, Regen SL, Bioconjugate Chem., 17, 1582 (2006)

[17] Zhang DH, Cai F, Zhou XD, Zhou WS, Chin. J. Chem., 23, 176 (2005)

[18] Shu Y, Jones SR, Kinney WA, Selinsky BS, Steroids, 67, 291 (2002)

[19] Kikuchi K, Bernard EM, Sadownik A, Regen SL, Armstrong D, Antimicrob. Agents Chemother., 41, 1433 (1997)

[20] Jones SR, Kinney WA, Zhang X, Jones LM, Selinsky BS, Steroids, 61, 565 (1996)

[21] Sadownik A, Deng G, Janout V, Regen SL, Bernard EM, Kikuchi K, Armstrong D, J. Am. Chem. Soc., 117(22), 6138 (1995)

[22] Savage PB, Curr. Med. Chem., 1, 293 (2002)

[23] Savage PB, Eur. J. Org. Chem., 759 (2002)

[24] Kim HS, Choi BS, Kwon KC, Lee SO, Kwak HJ, Lee CH, Bioorg. Med. Chem., 8, 2059 (2000)

[25] Kim HS, Kwon KC, Kim KS, Lee CH, Bioorg. Med. Chem. Lett., 11, 3065 (2001)

[26] Khan SN, Kim HS, Kim BJ, Bioorg. Med. Chem. Lett., 17, 5139 (2007)

[27] Khan SN, Cho NJ, Kim HS, Tetrahedron Lett., 48, 5189 (2007)

[28] Khan SN, Jung YM, Kim BJ, Cho H, Lee J, Kim HS, Bioorg. Med. Chem. Lett., 18, 2558 (2008)

[29] Salmi C, Loncle C, Vidal N, Letourneux Y, Brunel JM, Eur. J. Med. Chem., references cited therein;, 43, 540 (2008)

[30] Brunel JM, Loncle C, Vidal N, Dherbomez M, Letourneux Y, Steroids, 70, 907 (2005)

[31] Choucair B, Dherbomez M, Roussakis C, El Kihel L, Tetrahedron, 60, 11477 (2004)

[32] Choucair B, Dherbomez M, Roussakis C, El Kihel L, Bioorg. Med. Chem. Lett., 14, 4213 (2004)

[33] El Kihel L, Choucair B, Dherbomez M, Letourneux Y, Eur. J. Org. Chem., 4075 (2002)

[34] Fouace S, El Kihel L, Dherbomez M, Letourneux Y, Bioorg. Med. Chem. Lett., 11, 3011 (2001)

[35] Bellini AM, Mencini E, Quaglio MP, Guarneri M, Fini A, Arch. Pharm., 323, 201 (1990)

[36] Bellini AM, Mencini E, Quaglio MP, Guarneri M, Fini A, Steroids, 56, 395 (1991)

[37] Li CH, Budge LP, Driscoll CD, Willardson BM, Allman GW, Savage PB, J. Am. Chem. Soc., 121(5), 931 (1999)

[38] Joyce MJ, Hiremath SV, Mattammal MB, Elliott WH, Steroids, 44, 95 (1984)

[39] Khan SN, Bae SY, Kim HS, Tetrahedron Lett., 46, 7675 (2005)

[40] Khan SN, Cho NJ, Kim HS, in: Robert SM, Whittall J (Eds.), Catalysts for Fine Chemical Synthesis, Vol. 5: Regio- and Stereo-Controlled Oxidations and Reductions, John Wiley & Sons, Chichester, 2007, pp. 175.181.