The catalytic hydrogenation of rifamycin S(2) over Pd/C, followed by oxidation with K3[Fe(CN)6], generates a pair of 16,17,18,19-tetrahydrorifamycins S(3/4), epimeric at C(16). The use of PtO2 as catalyst leads to the hydrogenation also of the C(28)=C(29) bond giving, after oxidation by K3[Fe(CN)6], a mixture of the epimers (16,R)- and (16S)-16,17,18,19,28,29-hexahydrorifamycins S(5/6). Furthermore, we synthesized the (16R)- and (16S)-3-bromo derivatives 7/8 and (16,R)- and (16S)-3-(piperidin-1-yl) derivatives 9/10. The determination of the X-ray crystal structure of the most abundant epimer 4 of the tetrahydrorifamycins allowed the assignment of the absolute configuration at C(16)of all derivatives. A structure-activity relationship study showed that in general the (16R)-epimers are more potent inhibitors of bacterial RNA polymerase than the (16S)-epimers.

HYDROGENATION OF THE ANSA-CHAIN OF RIFAMYCINS - X-RAY CRYSTAL-STRUCTURE OF (16S)-16, 17, 18, 19-TETRAHYDRORIFAMYCIN-S / Cecilia, Bartolucci; Luciano, Cellai; DI FILIPPO, Patrizia; Doriano, Lamba; Segre, Annalaura; Bianco, Armandodoriano; Guiso, Marcella; Vinicio, Pasquali; Brufani, Mario. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - STAMPA. - 76:4(1993), pp. 1459-1468. [10.1002/hlca.19930760406]

HYDROGENATION OF THE ANSA-CHAIN OF RIFAMYCINS - X-RAY CRYSTAL-STRUCTURE OF (16S)-16, 17, 18, 19-TETRAHYDRORIFAMYCIN-S

DI FILIPPO, PATRIZIA;SEGRE, ANNALAURA;BIANCO, Armandodoriano;GUISO, Marcella;BRUFANI, Mario
1993

Abstract

The catalytic hydrogenation of rifamycin S(2) over Pd/C, followed by oxidation with K3[Fe(CN)6], generates a pair of 16,17,18,19-tetrahydrorifamycins S(3/4), epimeric at C(16). The use of PtO2 as catalyst leads to the hydrogenation also of the C(28)=C(29) bond giving, after oxidation by K3[Fe(CN)6], a mixture of the epimers (16,R)- and (16S)-16,17,18,19,28,29-hexahydrorifamycins S(5/6). Furthermore, we synthesized the (16R)- and (16S)-3-bromo derivatives 7/8 and (16,R)- and (16S)-3-(piperidin-1-yl) derivatives 9/10. The determination of the X-ray crystal structure of the most abundant epimer 4 of the tetrahydrorifamycins allowed the assignment of the absolute configuration at C(16)of all derivatives. A structure-activity relationship study showed that in general the (16R)-epimers are more potent inhibitors of bacterial RNA polymerase than the (16S)-epimers.
1993
rifamycin derivative; drug structure; hydrogenation
01 Pubblicazione su rivista::01a Articolo in rivista
HYDROGENATION OF THE ANSA-CHAIN OF RIFAMYCINS - X-RAY CRYSTAL-STRUCTURE OF (16S)-16, 17, 18, 19-TETRAHYDRORIFAMYCIN-S / Cecilia, Bartolucci; Luciano, Cellai; DI FILIPPO, Patrizia; Doriano, Lamba; Segre, Annalaura; Bianco, Armandodoriano; Guiso, Marcella; Vinicio, Pasquali; Brufani, Mario. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - STAMPA. - 76:4(1993), pp. 1459-1468. [10.1002/hlca.19930760406]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/473612
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