Efficient synthesis of anacardic acid analogues and their antibacterial activities

Mamidyala, Sreeman K., Ramu, Soumya, Huang, Johnny X., Robertson, Avril A. B. and Cooper, Matthew A. (2013) Efficient synthesis of anacardic acid analogues and their antibacterial activities. Bioorganic & Medicinal Chemistry Letters, 23 6: 1667-1670. doi:10.1016/j.bmcl.2013.01.074

Author Mamidyala, Sreeman K.
Ramu, Soumya
Huang, Johnny X.
Robertson, Avril A. B.
Cooper, Matthew A.
Title Efficient synthesis of anacardic acid analogues and their antibacterial activities
Journal name Bioorganic & Medicinal Chemistry Letters   Check publisher's open access policy
ISSN 0960-894X
Publication date 2013-03
Sub-type Article (original research)
DOI 10.1016/j.bmcl.2013.01.074
Volume 23
Issue 6
Start page 1667
End page 1670
Total pages 4
Place of publication Kidlington, Oxford, United Kingdom
Publisher Pergamon
Collection year 2014
Language eng
Abstract Anacardic acid derivatives exhibit a broad range of biological activities. In this report, an efficient method for the synthesis of anacardic acid derivatives was explored, and a small set of salicylic acid variants synthesised retaining a constant hydrophobic element (a naphthyl tail). The naphthyl side chain was introduced via Wittig reaction and the aldehyde installed using directed ortho-metalation reaction of the substituted o-anisic acids. The failure of ortho-metalation using unprotected carboxylic acid group compelled us to use directed ortho-metalation in which a tertiary amide was used as a strong ortho-directing group. In the initial route, tertiary amide cleavage during final step was challenging, but cleaving the tertiary amide before Wittig reaction was beneficial. The Wittig reaction with protected carboxylic group (methyl ester) resulted in side-products whereas using sodium salt resulted in higher yields. The novel compounds were screened for antibacterial activity and cytotoxicity. Although substitution on the salicylic head group enhanced antibacterial activities they also enhanced cytotoxicity.
Keyword Anacardic acid
Directed ortho-metalation reaction
Wittig reaction
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Medicine Publications
Institute for Molecular Bioscience - Publications
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