Ozonation of quinopimaric acid methyl ester and its 2,3-dihydro derivatives with sterically hindered double bonds

Tret’yakova, E. V.; Салимова, Е. В.; Medvedeva, N. I.; Куковинец, О. С.; Odinokov, V. N.

doi:10.1134/s1070428015030227

Cited by 4 publications

(1 citation statement)

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“…C(1), C(2), C(3), C(4) modified derivatives of dihydroquinopinaric acid (37)(38)(39)(40)(41)(42)(43)(44)(45)(46). Compounds 37 (Smirnova et al 2008), 38 (Tret'yakova et al 2015), 39 (Tret'yakova et al 2014), 40-42, 45, 46 (Smirnova et al 2011b), 43, 44 (Smirnova et al 2010).…”

Section: Figure S3mentioning

confidence: 99%

Synthetic modifications of abietane diterpene acids to potent antimicrobial agents

Смирнова

Tret’yakova

Baev

et al. 2021

Natural Product Research

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Among abietane type semisynthetic diterpenoids, a series of quinopimaric and maleopimaric acid derivatives modified at the carboxyl and carbonyl groups, and in ring E were synthesized to obtain new compounds with antimicrobial potency against Micobacterium tuberculosis H37Rv and key ESKAPE pathogens. It was found that dihydroquinopimaric N-{4'-[(3'-аminopropyl)amino]butyl} carboxamide (8) exhibited low toxicity to human embryonic kidney cell line HEK-293 (> 32 μg/mL) and showed significant bacteriostatic activity against methicillin-resistant Staphylococcus aureus (MRSA) (MIC ≤ 0.25 g/mL) and excellent antifungal activity against Cryptococcus neoformans var. grubii (MICs ≤0.25 g/mL) being 4 and 30 fold more active than vancomycin and fluconazole; it also showed moderate activity against fungi Candida albicans (MIC ≤ 0.25 g/mL). Methyl 1,4-bis(isonicotinoylhydrazono)dihydroquinopimarate (9) inhibited M. tuberculosis H37Rv with MIC of 1.25 µg/mL. The docking studies suggest possible interactions of the leading compounds with the molecular targets.

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