Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells
Most sterols, such as cholesterol and ergosterol, become functional only after the removal of the two methyl groups at C-4 from their biosynthetic precursors. Nevertheless, some findings suggest that 4,4-dimethyl sterols might be involved in specific physiological processes. In this paper we present...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
Elsevier Inc.
2014
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 09711caa a22012977a 4500 | ||
|---|---|---|---|
| 001 | PAPER-23930 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250903102357.0 | ||
| 008 | 190411s2014 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84896482243 | |
| 024 | 7 | |2 cas |a Sterols | |
| 030 | |a STEDA | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Alonso, F. | |
| 245 | 1 | 0 | |a Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells |
| 260 | |b Elsevier Inc. |c 2014 | ||
| 270 | 1 | 0 | |m Ramírez, J.A.; Departamento de Química Orgánica and UMYMFOR, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 3, C1428EGA Buenos Aires, Argentina; email: jar@qo.fcen.uba.ar |
| 504 | |a Patterson, W.G., Phylogenetic distribution of sterols (1994) Isopentenoids and Other Natural Products, 562 VOL., pp. 5-90. , W.D. Nes, American Chemical Society | ||
| 504 | |a Nes, W.D., Patterson, G.W., (1991) Physiology and Biochemistry of Sterols, , The American Oil Chemists Society | ||
| 504 | |a Nes, W.D., Biosynthesis of cholesterol and other sterols (2011) Chem Rev, 111, pp. 6423-6451 | ||
| 504 | |a Rahier, A., Dissecting the sterol C-4 demethylation process in higher plants. from structures and genes to catalytic mechanism (2011) Steroids, 76, pp. 340-352 | ||
| 504 | |a Byskov, A.G., Andersen, C.Y., Nordholm, L., Thøgersen, H., Xia, G., Wassmann, O., Chemical structure of sterols that activate oocyte meiosis (1995) Nature, 374, pp. 559-562 | ||
| 504 | |a Hughes, A.L., Lee, C.-Y.S., Bien, C.M., Espenshade, P.J., 4-Methyl sterols regulate fission yeast SREBP-Scap under low oxygen and cell stress (2007) Journal of Biological Chemistry, 282 (33), pp. 24388-24396. , http://www.jbc.org/cgi/reprint/282/33/24388, DOI 10.1074/jbc.M701326200 | ||
| 504 | |a Hirota, M., Mori, T., Yoshida, M., Iiye, R., Suppression of tumor promoter-induced inflammation of mouse ear by ursolic acid and 4,4-dimethylcholestane derivatives (1990) Agric Biol Chem, 54, pp. 1073-1075 | ||
| 504 | |a Dávola, M.E., Alonso, F., Cabrera, G.M., Ramírez, J.A., Barquero, A.A., Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins (2012) Biochem Biophys Res Commun, 427, pp. 107-112 | ||
| 504 | |a Alonso, F., Cirigliano, A.M., Cabrera, G.M., Ramírez, J.A., Synthesis and preliminary biological screening of sterol analogues as new antifungal agents against plant pathogens (2010) Steroids, 75, pp. 659-664 | ||
| 504 | |a Sandoval, A., Thomas, G.H., Djerassi, C., Rosenkranz, G., Sondheimer, F., Steroids. LXI. Synthesis of 19-nor-desoxycorticosterone, a potent mineralocorticoid hormone (1954) J Am Chem Soc, 77, pp. 148-151 | ||
| 504 | |a Fei, X.-S., Tian, W.-S., Chen, Q.-Y., Synthesis of 4-trifluoromethylsteroids: A novel class of steroid 5α-reductase inhibitors (1997) Bioorganic and Medicinal Chemistry Letters, 7 (24), pp. 3113-3118. , DOI 10.1016/S0960-894X(97)10156-1, PII S0960894X97101561 | ||
| 504 | |a Hadacek, F., Greger, H., Testing of antifungal natural products: Methodologies, comparability of results and assay choice (2000) Phytochemical Analysis, 11 (3), pp. 137-147. , DOI 10.1002/(SICI)1099-1565(200005/06)11:3<137::AID-PCA514>3.0. CO;2-I | ||
| 504 | |a Kueng, W., Silber, E., Eppenberger, U., Quantification of cells cultured on 96-well plates (1989) Analytical Biochemistry, 182 (1), pp. 16-19 | ||
| 504 | |a Zhu, J., Bienaymé, H., (2006) Multicomponent Reactions, , Wiley | ||
| 504 | |a Zhang, N., O'Donnell, K., Sutton, D.A., Nalim, F.A., Summerbell, R.C., Padhye, A.A., Members of the Fusarium solani species complex that cause infections in both humans and plants are common in the environment (2006) J Clin Microbiol, 44, pp. 2186-2190 | ||
| 504 | |a Rassi, Jr.A., Rassi, A., Marin-Neto. Chagas disease (2010) Lancet, 375, pp. 1388-1402 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a Most sterols, such as cholesterol and ergosterol, become functional only after the removal of the two methyl groups at C-4 from their biosynthetic precursors. Nevertheless, some findings suggest that 4,4-dimethyl sterols might be involved in specific physiological processes. In this paper we present the synthesis of a collection of analogues of 4,4-dimethyl sterols with a diamide side chain and a preliminary analysis of their in vitro activity on selected biological systems. The key step for the synthesis involves an Ugi condensation, a versatile multicomponent reaction. Some of the new compounds showed antifungal and cytotoxic activity. © 2014 Elsevier Inc. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, UBACyT X-084 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP 0315 | ||
| 536 | |a Detalles de la financiación: This work was supported by grants from Universidad de Buenos Aires (UBACyT X-084) and CONICET (PIP 0315). We are grateful to UMYMFOR (UBA-CONICET) for the analytical and spectroscopic determinations. Appendix A | ||
| 593 | |a Departamento de Química Orgánica and UMYMFOR, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 3, C1428EGA Buenos Aires, Argentina | ||
| 593 | |a Departamento de Química Biológica and IQUIBICEN, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 4, C1428EGA Buenos Aires, Argentina | ||
| 593 | |a Laboratorio de Glicobilogía, Fundación Instituto Leloir e Instituto de Investigaciones Bioquímicas de Buenos Aires, Avenida Patricias Argentinas 435, C1405BWE Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 4,4-DIMETHYL STEROLS |
| 690 | 1 | 0 | |a ANTIFUNGAL |
| 690 | 1 | 0 | |a CYTOTOXIC |
| 690 | 1 | 0 | |a KEYWORDS |
| 690 | 1 | 0 | |a UGI REACTION |
| 690 | 1 | 0 | |a (17BETA) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXYLATE |
| 690 | 1 | 0 | |a (17BETA) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXYLIC ACID |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (2 CHLOROPHENYL) 4,4 DIMETHYL 3 HYDROXYANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (2 ETHYL 6 METHYLPHENYL) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (2 FLUOROPHENYL) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (2 NAPHTHYL) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (4 CHLOROPHENYL) 4,4 DIMETHYL 3 HYDROXYANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (4 CHLOROPHENYL) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (4 FLUOROPHENYL) 4,4 DIMETHYL 3 HYDROXYANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (4 FLUOROPHENYL) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (4 METHOXYPHENYL) 4,4 DIMETHYL 3 HYDROXYANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (4 METHOXYPHENYL) 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N (4 METHYLPHENYL) 4,4 DIMETHYL 3 HYDROXYANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N PHENYL 4,4 DIMETHYL 3 HYDROXYANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a (17BETA) N ((T BUTYLCARBAMOYL)METHYL) N PHENYL 4,4 DIMETHYL 3 OXOANDROST 5 ENE 17 CARBOXAMIDE |
| 690 | 1 | 0 | |a 2 (T BUTYLAMINO) 2 OXOETHYL (17BETA) 4,4 DIMETHYL 3 HYDROXYANDROST 5 ENE 17 CARBOXYLATE |
| 690 | 1 | 0 | |a ANTIFUNGAL AGENT |
| 690 | 1 | 0 | |a STEROL DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a STEROL |
| 690 | 1 | 0 | |a ANTIFUNGAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a BROTH DILUTION |
| 690 | 1 | 0 | |a DRUG CYTOTOXICITY |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a EUKARYOTIC CELL |
| 690 | 1 | 0 | |a FUSARIUM |
| 690 | 1 | 0 | |a MINIMUM INHIBITORY CONCENTRATION |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a STRUCTURE ACTIVITY RELATION |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANIMAL |
| 690 | 1 | 0 | |a BIOSYNTHESIS |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a CHLOROCEBUS AETHIOPS |
| 690 | 1 | 0 | |a DRUG EFFECTS |
| 690 | 1 | 0 | |a ELECTROSPRAY MASS SPECTROMETRY |
| 690 | 1 | 0 | |a EUKARYOTIC CELL |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a VERO CELL LINE |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a CERCOPITHECUS AETHIOPS |
| 690 | 1 | 0 | |a EUKARYOTIC CELLS |
| 690 | 1 | 0 | |a HUMANS |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION |
| 690 | 1 | 0 | |a STEROLS |
| 690 | 1 | 0 | |a VERO CELLS |
| 700 | 1 | |a Cirigliano, A.M. | |
| 700 | 1 | |a Dávola, M.E. | |
| 700 | 1 | |a Cabrera, G.M. | |
| 700 | 1 | |a García Liñares, G.E. | |
| 700 | 1 | |a Labriola, C. | |
| 700 | 1 | |a Barquero, A.A. | |
| 700 | 1 | |a Ramírez, Javier Alberto | |
| 773 | 0 | |d Elsevier Inc., 2014 |g v. 84 |h pp. 1-6 |p Steroids |x 0039128X |w (AR-BaUEN)CENRE-577 |t Steroids | |
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