Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues
作者： Bassima Choucair , Michel Dherbomez , Cristos Roussakis , Laïla El Kihel
DOI: 10.1016/J.TET.2004.09.055
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摘要: Abstract Several novel squalamine-related polyaminosterols are reported. The synthesis of 7α- N -[3 -(4-aminobutyl)aminopropyl]aminocholestanol I , 6α- II 7α and 7β- -(4-aminobutyl)aminopropyl]aminocholesterol ( III IV ), was accomplished from cholesterol, they provide the first examples in which spermidine is introduced B steroidal ring. These molecules showed comparable antibacteria fungi activities to squalamine, were cytotoxic on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6). Therefore, these with antibiotic promising for immune-compromised patients cancer chemotherapy.
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sci-hub.se 参考文章(20)
Mark Donowitz, Henry Brem, John Laterra, Francis H. Gannon, Eric P. Sipos, Michael P. McLane, Darin S. Epstein, Jon I. Williams, Betty M. Tyler, John D. Davis, Tessa L. Chao, Simon Pitchford, William A. Kinney, Allen K. Sills, Kimberly Cheshire, Michael Zasloff, Squalamine Inhibits Angiogenesis and Solid Tumor Growth in Vivo and Perturbs Embryonic Vasculature Cancer Research. ,vol. 58, pp. 2784- 2792 ,(1998)
Daniel D. Von Hoff, Jennifer Marty, Kenneth J. Holroyd, Michael P. McLane, Carita H. Jundt, Jon I. Williams, Stephanie D. Stringer, Steven Weitman, Cristina M. Gonzalez, Qiming Chen, Michael Zasloff, Squalamine Treatment of Human Tumors in nu/nu Mice Enhances Platinum-based Chemotherapies Clinical Cancer Research. ,vol. 7, pp. 724- 733 ,(2001)
Meenakshi N. Rao, Melissa A. McGuigan, Xuehai Zhang, Ze'ev Shaked, William A. Kinney, Michel Bulliard, Blandine Laboue, Nancy E. Lee, PRACTICAL APPROACHES TO REMOTE ASYMMETRIC INDUCTION IN STEROIDAL SIDE-CHAINS UTILIZING OXAZABOROLIDINE REAGENTS Journal of Organic Chemistry. ,vol. 62, pp. 4541- 4545 ,(1997) , 10.1021/JO970227L
Anthony D. Pechulis, Frank H. Bellevue, Christopher L. Cioffi, Sean G. Trapp, John P. Fojtik, Anthony A. McKitty, William A. Kinney, Leah L. Frye, Synthesis of 24.xi.-Squalamine, an Anti-Infective Steroidal Polyamine Journal of Organic Chemistry. ,vol. 60, pp. 5121- 5126 ,(1995) , 10.1021/JO00121A033
Robert M. Moriarty, Sudersan M. Tuladhar, Liang Guo, Suzanne Wehrli, Synthesis of squalamine. A steroidal antibiotic from the shark Tetrahedron Letters. ,vol. 35, pp. 8103- 8106 ,(1994) , 10.1016/0040-4039(94)88254-1
Dan Li, Jon I Williams, Richard J Pietras, Squalamine and cisplatin block angiogenesis and growth of human ovarian cancer cells with or without HER-2 gene overexpression. Oncogene. ,vol. 21, pp. 2805- 2814 ,(2002) , 10.1038/SJ.ONC.1205410
Youheng Shu, Stephen R Jones, William A Kinney, Barry S Selinsky, The synthesis of spermine analogs of the shark aminosterol squalamine Steroids. ,vol. 67, pp. 291- 304 ,(2002) , 10.1016/S0039-128X(01)00161-1
B Choucair, M Dherbomez, C Roussakis, L El kihel, Synthesis of 7α- and 7β-spermidinylcholesterol, squalamine analogues Bioorganic & Medicinal Chemistry Letters. ,vol. 14, pp. 4213- 4216 ,(2004) , 10.1016/J.BMCL.2004.06.010
Meenakshi N. Rao, Ann E. Shinnar, Lincoln A. Noecker, Tessa L. Chao, Binyamin Feibush, Brad Snyder, Ilya Sharkansky, Ani Sarkahian, Xuehai Zhang, Stephen R. Jones, William A. Kinney, Michael Zasloff, Aminosterols from the Dogfish Shark Squalus acanthias Journal of Natural Products. ,vol. 63, pp. 631- 635 ,(2000) , 10.1021/NP990514F
Hong-Seok Kim, Bo-Seung Choi, Kyung-Chan Kwon, Sang-Ok Lee, Hyun Jung Kwak, Cheol Hae Lee, Synthesis and antimicrobial activity of squalamine analogue. Bioorganic & Medicinal Chemistry. ,vol. 8, pp. 2059- 2065 ,(2000) , 10.1016/S0968-0896(00)00128-0