The chloro substituted 3,3-di-(4'-hydroxyphenyl)-1-oxo-1H,3H-naphtho[1,8-cd]pyran was synthesized in a 40/60 mixture of C-6 or C-7 substituted isomers, respectively. The two isomers were separated by hplc. The X-ray crystal structure of the mixture was obtained. Both the mixture and the single isomers were tested against Lactobacillus Casei thymidylate synthase. The X-ray analysis clearly revealed co-crystallization of the two isomeric species. The apparent Ki of the mixture was 0.8 muM, while those of the C-6 and C-7 substituted isomers were 0.42 and 0.52 muM, respectively, thus showing that the position of the chlorine in the naphthalene ring was not critical for enzymatic activity.

Separation, structural determination and biological evaluation of the thymidylate synthase inhibitor 3,3-di(4'-hydroxyphenyl)-6(7)-chloro-1-oxo-1H,3H-naphtho[1,8-cd]pyran / Costi, Maria Paola; Tondi, Donatella; Pecorari, Piergiorgio; Rinaldi, M; Celentano, G; Ghelli, Stefano; Antolini, L; Barlocco, Daniela. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - STAMPA. - 36 (4):(1999), pp. 1043-1048.

Separation, structural determination and biological evaluation of the thymidylate synthase inhibitor 3,3-di(4'-hydroxyphenyl)-6(7)-chloro-1-oxo-1H,3H-naphtho[1,8-cd]pyran

COSTI, Maria Paola;TONDI, Donatella;PECORARI, Piergiorgio;GHELLI, Stefano;BARLOCCO, Daniela
1999

Abstract

The chloro substituted 3,3-di-(4'-hydroxyphenyl)-1-oxo-1H,3H-naphtho[1,8-cd]pyran was synthesized in a 40/60 mixture of C-6 or C-7 substituted isomers, respectively. The two isomers were separated by hplc. The X-ray crystal structure of the mixture was obtained. Both the mixture and the single isomers were tested against Lactobacillus Casei thymidylate synthase. The X-ray analysis clearly revealed co-crystallization of the two isomeric species. The apparent Ki of the mixture was 0.8 muM, while those of the C-6 and C-7 substituted isomers were 0.42 and 0.52 muM, respectively, thus showing that the position of the chlorine in the naphthalene ring was not critical for enzymatic activity.
36 (4)
1043
1048
Separation, structural determination and biological evaluation of the thymidylate synthase inhibitor 3,3-di(4'-hydroxyphenyl)-6(7)-chloro-1-oxo-1H,3H-naphtho[1,8-cd]pyran / Costi, Maria Paola; Tondi, Donatella; Pecorari, Piergiorgio; Rinaldi, M; Celentano, G; Ghelli, Stefano; Antolini, L; Barlocco, Daniela. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - STAMPA. - 36 (4):(1999), pp. 1043-1048.
Costi, Maria Paola; Tondi, Donatella; Pecorari, Piergiorgio; Rinaldi, M; Celentano, G; Ghelli, Stefano; Antolini, L; Barlocco, Daniela
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/611692
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