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Abstract:

Thirty-seven brassinosteroid derivatives were tested for their antiviral activity against herpes simplex vires (HSV) type 1 and twenty-seven against HSV type 2, via a vires yield reduction assay. Most of the assayed compounds show selectivity indexes (SI) higher than those obtained with the reference drug, stigmasterol. The compounds that possessed a better structure-activity relationship are 6b [(22S,23S)-3β-bromo-5α ,22,23-trihydroxystigmastan-6-one], 7b [(22S,23S)-3β,5α ,22,23-tetrahydroxystigmastan-6-one] and 12b [(22S,23S)-5α-fluor-3β ,22,23-trihydroxy-stigmastan-6-one] with SI values of 100, 80 and 109 for HSV-1 and 71, 40 and 27 for HSV-2, respectively.

Registro:

Documento: Artículo
Título:Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures
Autor:Talarico, L.B.; Ramírez, J.A.; Galagovsky, L.R.; Wachsman, M.B.
Filiación:Depto. de Quím. Orgán., Fac. de Ciencias Exactas y Naturales, Pabellón 2, 1428, Buenos Aires, Argentina
Palabras clave:2alpa,3alpha dihydroxy 6alpha fluoro 5alpha stigmast 22 ene; 2alpha,3alpha dihydroxystigmast 22 en 6 one; 2alpha,3alpha,22,23 tetrahydroxy 5alpha fluorostigmastan 6 one; 2alpha,3alpha,22,23 tetrahydroxy 5alpha stigmastan 6 one; 2alpha,3alpha,22,23 tetrahydroxy beta homo 7 oxastigmastan 6 one; 2alpha,3alpha,5alpha,22,23 pentahydroxystigmastan 6 one; 3 beta hydroxystigmasta 5,22 diene; 3alpha fluoro 22,23 dihydroxystigmastan 6 one; 3alpha,22,23 trihydroxy 5alpha stigmastan 6 one; 3alpha,5alpha,22,23 tetrahydroxystigmastan 6 one; 3beta acetoxy 22,23 dihydroxy 5alpha stigmastan 6 one; 3beta acetoxy 5alpha,22,23 trihydroxystigmastan 6 one; 3beta bromo 22,23 dihydroxy 5alpha stigmastan 6 one; 3beta bromo 5alpha chloro 6beta hydroxystigmast 22 ene; 3beta bromo 5alpha hydroxystigmast 22 en 6 one; 3beta bromo 5alpha,22,23 trihydroxystigmastan 6 one; 3beta fluoro 22,23 dihydroxystigmastan 6 one; 3beta fluoro 5alpha 22,23 dihydroxystigmastan 6 one; 3beta fluoro 5alpha chlorostigmast 22 en 6 one; 3beta,22,23 trihydroxy 5alpha stigmastan 6 one; 3beta,5alpha dihydroxystigmast 22 en 6 one; 3beta,5alpha,22,23 tetrahydroxystigmastan 6 one; 5alpha fluoro 3beta 22,23 trihydroxystigmastan 6 one; 5alpha fluorostigmasta 2,22 dien 6 one; 6beta hydroxy 5alpha stigmast 22 en 3 one; 9 (2 hydroxyethoxymetyl)guanine; brassinosteroid; stigmasta 4,22 dien 3 one; stigmasterol; unclassified drug; unindexed drug; animal cell; antiviral activity; article; cell culture; controlled study; drug selectivity; Herpes simplex virus 1; Herpes simplex virus 2; nonhuman; structure activity relation
Año:2002
Volumen:11
Número:8
Página de inicio:434
Página de fin:444
Título revista:Medicinal Chemistry Research
Título revista abreviado:Med. Chem. Res.
ISSN:10542523
CODEN:MCREE
CAS:stigmasterol, 83-48-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico

Referencias:

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  • Wachsman, M.B., Ramírez, J.A., Galagovsky, L.R., Coto, C.E., Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures (2002) Antiviral Chem. Chemother., 13, pp. 61-66
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  • Ramírez, J., Gros, E., Galagovsky, L., Synthesis and bioactivity evaluation of brassinosteroid analogues (2000) Steroids, 65, pp. 329-337
  • Ramírez, J., Gros, E., Galagovsky, L., Synthesis of analogues of 28-homocastasterone, 28-homotyphasterol and 28-homoteasterone. Effects of heteroatom substituents at C-5 on bioactivity (2000) Tetrahedron, 56, pp. 6171-6180
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Citas:

---------- APA ----------
Talarico, L.B., Ramírez, J.A., Galagovsky, L.R. & Wachsman, M.B. (2002) . Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures. Medicinal Chemistry Research, 11(8), 434-444.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]
---------- CHICAGO ----------
Talarico, L.B., Ramírez, J.A., Galagovsky, L.R., Wachsman, M.B. "Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures" . Medicinal Chemistry Research 11, no. 8 (2002) : 434-444.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]
---------- MLA ----------
Talarico, L.B., Ramírez, J.A., Galagovsky, L.R., Wachsman, M.B. "Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures" . Medicinal Chemistry Research, vol. 11, no. 8, 2002, pp. 434-444.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]
---------- VANCOUVER ----------
Talarico, L.B., Ramírez, J.A., Galagovsky, L.R., Wachsman, M.B. Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures. Med. Chem. Res. 2002;11(8):434-444.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]