Amides derived from heteroaromatic amines and selected steryl hemiesters.
作者： Uladzimir Bildziukevich , Lucie Rárová , David Šaman , Libor Havlíček , Pavel Drašar
DOI: 10.1016/J.STEROIDS.2013.10.003
关键词: Leukemia 、 N,N-Dicyclohexylcarbodiimide 、 Cell growth 、 HeLa 、 Stereochemistry 、 Lanosterol 、 Cytotoxicity 、 Chemistry 、 Amide 、 Cell culture
摘要: The current interest of the team has been focused on investigation novel amides with potential cytotoxicity. presented series compounds was synthesized from selected steryl hemiesters and heteroaromatic amines. synthetic protocol designed in a simple economic way, divided into several general methodologies applicable to synthesized. cytotoxicity tested cells derived human T-lymphoblastic leukemia, breast adenocarcinoma cervical cancer, compared tests normal fibroblasts. Most lanosterol-based (3-5 7-10) showed medium good cytotoxicity, while only two derivatives cholesterol (18 19) leukemia cell line. 8 9 displayed reasonable among this amides, lines [14.5±0.4 μM (8) 18.5±3.9 (9)], [19.5±2.1 23.1±4.0 (9)] cancer [24.8±5.3 29.1±4.7 (9)]. Only compound adequately less active fibroblasts (40.4±11.1 μM).
sci-hub.se 参考文章(26)
Bronwyn G Siim, Kevin O Hicks, Susan M Pullen, Pierre L van Zijl, William A Denny, William R Wilson, Comparison of aromatic and tertiary amine N-oxides of acridine DNA intercalators as bioreductive drugs Biochemical Pharmacology. ,vol. 60, pp. 969- 978 ,(2000) , 10.1016/S0006-2952(00)00420-2
Louis A. Carpino, Grace Y. Han, 9-Fluorenylmethoxycarbonyl amino-protecting group Journal of Organic Chemistry. ,vol. 37, pp. 3404- 3409 ,(1972) , 10.1021/JO00795A005
Louis A. Carpino, E. M. E. Mansour, Jerome Knapczyk, Piperazino-functionalized silica gel as a deblocking-scavenging agent for the 9-fluorenylmethyloxycarbonyl amino-protecting group Journal of Organic Chemistry. ,vol. 14, pp. 666- 669 ,(1983) , 10.1021/JO00153A009
Eric Valeur, Mark Bradley, Amide Bond Formation: Beyond the Myth of Coupling Reagents Chemical Society Reviews. ,vol. 38, pp. 606- 631 ,(2009) , 10.1039/B701677H
Hana Svobodová, Nonappa, Zdeněk Wimmer, Erkki Kolehmainen, Design, synthesis and stimuli responsive gelation of novel stigmasterol-amino acid conjugates. joint international conference on information sciences. ,vol. 361, pp. 587- 593 ,(2011) , 10.1016/J.JCIS.2011.05.084
Kari V. Ahonen, Manu K. Lahtinen, Miika S. Löfman, Anniina M. Kiesilä, Arto M. Valkonen, Elina I. Sievänen, Nonappa, Erkki T. Kolehmainen, Structural studies of five novel bile acid-4-aminopyridine conjugates. Steroids. ,vol. 77, pp. 1141- 1151 ,(2012) , 10.1016/J.STEROIDS.2012.06.003
Hoang L. Pham, Benjamin P. Ross, Ross P. McGeary, P. Nicholas Shaw, Nigel M. Davies, Synthesis of cationic derivatives of Quil A and the preparation of cationic immune-stimulating complexes (ISCOMs) International Journal of Pharmaceutics. ,vol. 376, pp. 123- 133 ,(2009) , 10.1016/J.IJPHARM.2009.04.011
Ikuro. Abe, Michel. Rohmer, Glenn D. Prestwich, ENZYMATIC CYCLIZATION OF SQUALENE AND OXIDOSQUALENE TO STEROLS AND TRITERPENES Chemical Reviews. ,vol. 93, pp. 2189- 2206 ,(1993) , 10.1021/CR00022A009
Komal Kalani, Dharmendra Kumar Yadav, Feroz Khan, Santosh K. Srivastava, Nitasha Suri, Pharmacophore, QSAR, and ADME based semisynthesis and in vitro evaluation of ursolic acid analogs for anticancer activity Journal of Molecular Modeling. ,vol. 18, pp. 3389- 3413 ,(2012) , 10.1007/S00894-011-1327-6
E. Rajanarendar, S. Raju, M. Nagi Reddy, S. Rama Krishna, L. Hari Kiran, A. Ram Narasimha Reddy, Y. Narasimha Reddy, Multi-component synthesis and in vitro and in vivo anticancer activity of novel arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides European Journal of Medicinal Chemistry. ,vol. 50, pp. 274- 279 ,(2012) , 10.1016/J.EJMECH.2012.02.004