Synthesis and β-lactamase inhibition of anacardic acids and their analogues

doi:10.1016/S0960-894X(01)80506-0

Bioorganic & Medicinal Chemistry Letters

Volume 4, Issue 12, 23 June 1994, Pages 1423-1428

https://doi.org/10.1016/S0960-894X(01)80506-0 Get rights and content

Abstract

Several anacardic acids and their analogues were symthesised and their β-lactamase inhibitory activities were determined. The structure-activity relationships suggested by these data are discussed.

Several anacardic acids (R₂ = CO₂H, R₃ = OH) and their analogues were synthesised and their β-lactamase inhibitory activities were determined. The structure-activity relationships suggested by these data are discussed.

Reference (10)

SutherlandR.
Trends Pharmacol. Sci.
(1991)
PiersonC.L. et al.
Diagn. Microbiol. Infect. Dis.
(1992)
Coates, N.J., Gilpin, M.L.; Gwynn, M.N.; Lewis, D.E.; Milner, P.H.; Spear, S.R. and Tyler, J.W. J. Nat. Products in...
SullivanJ.T. et al.
J. Med. Plant Research
(1982)
TymanJ.H.P.
Chem Soc. Rev.
(1979)
KuboI. et al.
Chem. Lett.
(1987)

There are more references available in the full text version of this article.

Cited by (9)

A Heck-Based Strategy to Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling
2018, Organic Letters
A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay.
Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative
2010, Bioorganic and Medicinal Chemistry
Several lines of evidence indicate that histone acetyltransferases (HATs) are novel drug targets for treatment of diseases like, for example, cancer and inflammation. The natural product anacardic acid is a starting point for development of small molecule inhibitors of the histone acetyltransferase (HAT) p300/CBP associated factor (PCAF). In order to optimize the inhibitory potency, a binding model for PCAF inhibition by anacardic acid was proposed and new anacardic acid derivatives were designed. Ten new derivatives were synthesized using a novel synthetic route. One compound showed a twofold improved inhibitory potency for the PCAF HAT activity and a twofold improved inhibition of histone acetylation in HEP G2 cells.
Bioactive phenolic lipids
2005, Studies in Natural Products Chemistry
This review is concerned with non-isoprenoid phenolic lipids typified by compounds biosynthesised by the polyketide pathway. Botanical, biological and entomological sources of such phenolic lipids are described which contain monohydric phenols, notably cardanol and relatives, dihydric phenols such as cardols, alk(en)ylresorcinols, urushiols and phenolic acids, particularly anacardic acids. Some recently investigated mixed types of dihydric phenolic lipids are included. Separatory methods are briefly reviewed. Synthetic methods for the saturated and unsaturated members of the three main classes of interest in structure/activity studies are summarised. Biological properties of members of the three main classes are given and discussed.
Synergistic effects of anacardic acids and methicillin against methicillin resistant Staphylococcus aureus
2004, Bioorganic and Medicinal Chemistry
The synergistic effects of 6-alk(en)ylsalcylic acids, also known as anacardic acids, in combination with methicillin against Staphylococcus aureus ATCC 33591 (MRSA) was investigated. The double bond in C₁₅-anacardic acids is not essential in eliciting the antibacterial activity but is associated with increasing the activity. The synergistic effects decreased with increasing the number of double bonds in the alkyl chain. On the other hand, the antibacterial activity of anacardic acids possessing different alkyl chain lengths against the same MRSA strain was found to be a parabolic function of their lipophilicity and maximized with the alkyl chain length of C₁₀ and C₁₂. Notably, the synergistic effects were noted to increase with increasing the alkyl chain length.
Inhibition of PCAF histone acetyltransferase, cytotoxicity and cell permeability of 2-acylamino-1-(3-or 4-carboxy-phenyl)benzamides
2012, Molecules
Inhibition of PCAF histone acetyltransferase and cytotoxic effect of N-acylanthranilic acids
2012, Archives of Pharmacal Research

View all citing articles on Scopus

View full text

Synthesis and β-lactamase inhibition of anacardic acids and their analogues

Abstract

Trends Pharmacol. Sci.

Diagn. Microbiol. Infect. Dis.

J. Med. Plant Research

Chem Soc. Rev.

Chem. Lett.