5-Bromoochrephilone

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Category Enzyme inhibitors
Catalog number BBF-00184
CAS
Molecular Weight 461.34
Molecular Formula C23H25BrO5

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Description

5-Bromoochrephilone is one of the products of Penicillum multicolor FO-2338 in broth containing potassium bromide. It has strong inhibitory activity on gP120-CD4 binding.

Specification

IUPAC Name (6aR,9R,9aR)-9-acetyl-5-bromo-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-6a-methyl-9,9a-dihydrofuro[2,3-h]isochromene-6,8-dione
Canonical SMILES CCC(C)C=C(C)C=CC1=CC2=C(C(=O)C3(C(C2=CO1)C(C(=O)O3)C(=O)C)C)Br
InChI InChI=1S/C23H25BrO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-28-15)19-18(14(4)25)22(27)29-23(19,5)21(26)20(16)24/h7-12,18-19H,6H2,1-5H3/b8-7+,13-9+/t12-,18-,19-,23+/m0/s1
InChI Key YVLXPVGJCIVWMQ-WJKJBVSTSA-N

Reference Reading

1. New brominated and halogen-less derivatives and structure-activity relationship of azaphilones inhibiting gp120-CD4 binding
K Matsuzaki, H Tahara, J Inokoshi, H Tanaka, R Masuma, S Omura J Antibiot (Tokyo). 1998 Nov;51(11):1004-11. doi: 10.7164/antibiotics.51.1004.
Novel brominated and halogen-less azaphilone (oxoisochromane) derivatives, 5-bromoochrephilone and dechloroisochromophilone IV, and known derivatives, dechloroisochromophilone III and isorotiorin, were isolated from the culture broth of a producing organism of isochromophilones I and II (azaphilones inhibiting gp120-CD4 binding), Penicillium multicolor FO-2338, fermented in a medium containing potassium bromide. Nineteen azaphilone-related compounds isolated from the above strain and from other fungi were tested for the inhibition of gp120-CD4 binding and the structure-activity relationship is discussed. Consequently, 5-bromoochrephilone is the strongest inhibitor (IC50, 2.5 microM). A halogen atom at C-5, a proton at C-8 and a diene structure in C-3 side chain of 6-oxoisochromane ring are necessary for gp120-CD4 binding.

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