Synthesis and preliminary biological screening of sterol analogues as new antifungal agents against plant pathogens
In this paperwereport the synthesis of anewfamily of sterol analogues that have two amidic bonds on the side chain. These azasterols were obtained by a straightforward procedure including an Ugi condensation that allows the facile attachment of a polyfunctionalized side chain into the steroidal fram...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2010
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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 | 07163caa a22010697a 4500 | ||
|---|---|---|---|
| 001 | PAPER-7630 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250903103104.0 | ||
| 008 | 190411s2010 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-77954315515 | |
| 024 | 7 | |2 cas |a Antifungal Agents; Azasteroids; Antifungal Agents; Azasteroids | |
| 030 | |a STEDA | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Alonso, F. | |
| 245 | 1 | 0 | |a Synthesis and preliminary biological screening of sterol analogues as new antifungal agents against plant pathogens |
| 260 | |c 2010 | ||
| 270 | 1 | 0 | |m Ramírez, J. A.; Departamento de Química Orgánica, UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Ciudad Universitaria, Pabellón 2, Piso 3, C1428EGA Buenos Aires, Argentina; email: jar@qo.fcen.uba.ar |
| 504 | |a Savary, S., Teng, P.S., Willocquet, L., Nutter Jr., F.W., Quantification and modeling of crop losses: A review of purposes (2006) Annu Rev Phytopathol, 44, pp. 89-112 | ||
| 504 | |a Knight, S.C., Anthony, V.M., Brady, A.M., Greenland, A.J., Heaney, S.P., Murray, D.C., Rationale and perspectives on the development of fungicides (1997) Annu Rev Phytopathol, 35, pp. 349-372 | ||
| 504 | |a Gros, L., Lorente, S.O., Jimenez, C., Yardley, V., Rattray, L., Wharton, H., Evaluation of azasterols as anti-parasitics (2006) J Med Chem, 49, pp. 6094-6103 | ||
| 504 | |a Brunel, J.M., Loncle, C., Vidal, N., Dherbomez, M., Letourneux, Y., Synthesis and antifungal activity of oxygenated cholesterol derivatives (2005) Steroids, 70, pp. 907-912 | ||
| 504 | |a Burbiel, J., Bracher, F., Azasteroids as antifungals (2003) Steroids, 68, pp. 587-594 | ||
| 504 | |a Zhu, J., Bienyamé, H., (2005) Multicomponet Reactions, , Wiley-VCH Verlag GmbH & Co. Weinheim | ||
| 504 | |a Dömling, A., Recent developments in isocyanide based multicomponent reactions in applied chemistry (2006) Chem Rev, 106, pp. 17-89 | ||
| 504 | |a Alonso, F., Acebedo, S.L., Bruttomesso, A.C., Ramírez, J.A., Synthesis of 4-azasteroids by an intramolecular Ugi reaction (2008) Steroids, 73, pp. 1270-1276 | ||
| 504 | |a Bruttomesso, A.C., Eiras, J., Ramírez, J.A., Galagovsky, L.R., Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry (2009) Tet Lett, 50, pp. 4022-4024 | ||
| 504 | |a Stauton, J., Eisenbaum, E.J., 3β-Acetoxyetienic acid (1962) Org Syn, 42, pp. 4-5 | ||
| 504 | |a Sato, Y., Sonoda, Y., Saito, H., Synthesis of [21-2H]- and [22-2H]-derivatives of 23, 24, 25, 26, 27-pentanorcholesterol and 23, 24, 25, 26, 27- pentanordihydrolanosterol and the stereochemical significance of the deuterium spin-lattice relaxation times (1980) Chem Pharm Bull, 28, pp. 1150-1156 | ||
| 504 | |a Sui, Q., Borchardt, D., Rabenstein, D.L., Kinetics and equilibria of cis/trans isomerization of backbone amide bonds in peptoids (2007) J Am Chem Soc, 129, pp. 12042-12048 | ||
| 504 | |a (2005) Antifungal Agents: Methods and Protocols, , E.J. Ernst, P.D. Rogers, 1st ed. Humana Press Inc. Totowa | ||
| 504 | |a Song, Z., Nes, D., Sterol biosynthesis inhibitors: Potential for transition state analogs and mechanism-based inactivators targeted at sterol methyltransferase (2007) Lipids, 42, pp. 15-33 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a In this paperwereport the synthesis of anewfamily of sterol analogues that have two amidic bonds on the side chain. These azasterols were obtained by a straightforward procedure including an Ugi condensation that allows the facile attachment of a polyfunctionalized side chain into the steroidal framework. Some of the new compounds showed an interesting inhibitory effect on the growth of two pathogenic fungi involved in plant diseases. © 2010 Elsevier Inc. All rights reserved. |l eng | |
| 593 | |a Departamento de Química Orgánica, UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Ciudad Universitaria, Pabellón 2, Piso 3, C1428EGA Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ANTIFUNGAL |
| 690 | 1 | 0 | |a AZASTEROLS |
| 690 | 1 | 0 | |a PLANT PATHOGENS |
| 690 | 1 | 0 | |a UGI REACTION |
| 690 | 1 | 0 | |a ANTIFUNGAL AGENT |
| 690 | 1 | 0 | |a AZASTEROL DERIVATIVE |
| 690 | 1 | 0 | |a DIETHYL[[N BENZYL N[(3BETA HYDROXYPREGN 5 ENE 20 YL)CARBONYL]GLYCYL]AMINO]METHYLPHOSPHONATE |
| 690 | 1 | 0 | |a N [(TERT BUTYLCARBAMOYL)METHYL)N BENZYL 3BETA HYDROXYANDROST 5 EN 17BETA CARBOXAMINE |
| 690 | 1 | 0 | |a N BENZYL N[(3BETA HYDROXYPREGN 5 ENE 20 YL)CARBONYL]GLYCYLGLYCINE |
| 690 | 1 | 0 | |a N[(CYCLOHEXYLCARBAMOYL)METHYL]N BENZYL 3BETA HYDROXYPREGN 5 ENE 20 CARBOXAMIDE |
| 690 | 1 | 0 | |a N[(CYCLOHEXYLCARBAMOYL)METHYL]N(2 (1H INDOL 3 YL)ETHYL] 3BETA HYDROXYPREGN 5 ENE 20 CARBOXAMIDE |
| 690 | 1 | 0 | |a N[(CYCLOHEXYLCARBAMOYL)METHYL]N(3,4 DIMETHOXYPHENETHYL) 3BETA HYDROXYANDROST 5 EN 17BETA CARBOXAMIDE |
| 690 | 1 | 0 | |a N[(CYCLOHEXYLCARBAMOYL)METHYL]N[3 (4 NITROPHENYLAMINO)PROPYL] 3BETA HYDROXYPREGN 5 ENE 20 CARBOXAMIDE |
| 690 | 1 | 0 | |a N[(TERT BUTYLCARBAMOYL)METHYL]N PHENYL 3BETA HYDROXYANDROST 5 EN 17BETA CARBOXAMIDE |
| 690 | 1 | 0 | |a N[(TERT BUTYLCARBAMOYL)METHYL]N(3 HYDROXYPHENYL)3BETA HYDROXYANDROST 5 EN 17BETA CARBOXAMIDE |
| 690 | 1 | 0 | |a N[(TERT-BUTYLCARBAMOYL)METHYL]N(4 CHLOROPHENYL) 3BETA HYDROXYANDROST 5 EN 17BETA CARBOXAMIDE |
| 690 | 1 | 0 | |a N[(TERTBUTYLCARBAMOYL)METHYL]N PHENYL 3BETA HYDROXYPREGN 5 ENE 20 CARBOXAMIDE |
| 690 | 1 | 0 | |a STEROL DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ANTIFUNGAL AGENT |
| 690 | 1 | 0 | |a AZASTEROID |
| 690 | 1 | 0 | |a ANTIFUNGAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PLANT DISEASE |
| 690 | 1 | 0 | |a STEROL SYNTHESIS |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a DRUG EFFECTS |
| 690 | 1 | 0 | |a FUSARIUM |
| 690 | 1 | 0 | |a MICROBIAL SENSITIVITY TEST |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a ANTIFUNGAL AGENTS |
| 690 | 1 | 0 | |a AZASTEROIDS |
| 690 | 1 | 0 | |a FUSARIUM |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MICROBIAL SENSITIVITY TESTS |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a FUNGI |
| 690 | 1 | 0 | |a ANTIFUNGAL AGENTS |
| 690 | 1 | 0 | |a AZASTEROIDS |
| 690 | 1 | 0 | |a FUSARIUM |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MICROBIAL SENSITIVITY TESTS |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 700 | 1 | |a Cirigliano, A.M. | |
| 700 | 1 | |a Cabrera, G.M. | |
| 700 | 1 | |a Ramírez, Javier Alberto | |
| 773 | 0 | |d 2010 |g v. 75 |h pp. 659-664 |k n. 10 |p Steroids |x 0039128X |w (AR-BaUEN)CENRE-577 |t Steroids | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-77954315515&doi=10.1016%2fj.steroids.2010.04.002&partnerID=40&md5=5a1a29823db3e2fb757fd9eac2c88871 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/j.steroids.2010.04.002 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_0039128X_v75_n10_p659_Alonso |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v75_n10_p659_Alonso |y Registro en la Biblioteca Digital |
| 961 | |a paper_0039128X_v75_n10_p659_Alonso |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 68583 | ||