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Bismuth heterocycles based on a diphenyl sulfone scaffold: synthesis and substituent effect on the antifungal activity against Saccharomyces cerevisiae.

Abstract：

:A series of heterocyclic organobismuth(III) compounds 2 [ClBi(5-R-C6H(3)-2-SO2C6H(4)-1'-): R=Me, Ph, MeO, Cl, H, t-Bu, CF3, F, Me2N] was synthesized in order to study the relative importance of structure and specific substitutions in relation to their lipophilicity and antifungal activity against the yeast Saccharomyces cerevisiae. A clear structure-activity relationship between the size of the inhibition zone and the value of ClogP was found for 2. These results suggest that the higher the lipophilicity, the lower the antifungal activity. Thus, 2e (R=H) and 2h (R=F), which had ClogP values of 1.18 and 1.45, respectively, were most active. In contrast, 2b (R=Ph) and 2f (R=t-Bu) had ClogP values of 3.06 and 3.00, respectively, and exhibited no antifungal activity. Compound 6b ClBi[5-(OH)C6H(3)-2-SO(2)-5'-(OH)C6H(3)-1'-] had an estimated ClogP value of 0.81 but exhibited only low activity in spite of its low ClogP value, suggesting that such a considerable decrease in lipophilicity lowers inhibition activity. Bismuth carboxylate 7b derived from p-nitrobenzoic acid and 2e exhibited inhibition activity comparable to those of 2e and 2h despite its higher lipophilicity (ClogP=2.68).

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Murafuji T,Fujiwara Y,Yoshimatsu D,Miyakawa I,Migita K,Mikata Y

doi

10.1016/j.ejmech.2010.11.031

subject

Has Abstract

pub_date

2011-02-01 00:00:00

pages

519-25

issue

2

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(10)00826-3

journal_volume

46

pub_type

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