Synthesis of chlorogenic acid derivatives with promising antifungal activity

• Published in: Bioorganic & medicinal chemistry Vol. 15; no. 21; pp. 6830 - 6833
• Main Authors: Ma, Chao-Mei, Kully, Maureen, Khan, Jehangir K., Hattori, Masao, Daneshtalab, Mohsen
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01-11-2007; Elsevier Science
• Subjects: 1,3-β-Glucan; 1H NMR; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Aspergillus fumigatus; Aspergillus fumigatus - drug effects; Biological and medical sciences; Brine shrimp lethality assay; Candida - drug effects; Candida albicans; Chlorogenic acid; Chlorogenic Acid - analogs & derivatives; Cryptococcus neoformans; Cryptococcus neoformans - drug effects; Echinocandin B; ESI-MS; FAB-MS; H2N-aa-4-(octyloxy) aniline; Medical sciences; p-Octyloxyaniline; Pharmacology. Drug treatments; Candida albicans; p-Octyloxyaniline; H2N-aa-4-(octyloxy) aniline; Cryptococcus neoformans; Echinocandin B; Brine shrimp lethality assay; 1,3-β-Glucan; 1H NMR; ESI-MS; FAB-MS; Chlorogenic acid; Aspergillus fumigatus; Phenolic acid; Toxicity; Crustacea; Fungi; Antifungal agent; Structure activity relation; Fungi Imperfecti; Polyol; Mechanism of action; Chemical synthesis; Branchiopoda; Acylate; Artemia salina; Aminoamide; Benzene derivatives; In vitro; α-Aminoacid; Arthropoda; Carboxamide; Invertebrata; Candida alhicans
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2007.07.038

The synthesis of the chlorogenic acid derivatives with in vitro antifungal activity is reported.
Derivatives of chlorogenic acid or its analogues were synthesized by coupling protected chlorogenic acid or its analogues with
p-octyloxyaniline and selected amino acids. Most of the compounds exhibited significant potency against
Cryptococcus neoformans and
Candida species with low toxicity to brine shrimps. The 4,5-dihydroxyl groups in the quinic acid moiety were necessary for the activity and introduction of a free amino group increased the inhibitory activity against
Aspergillus fumigatus.