Synthesis and activity of (+)-usnic acid and (−)-usnic acid derivatives containing 1,3-thiazole cycle against Mycobacterium tuberculosis

Bekker, Olga B.; Sokolov, D. N.; Luzina, O. A.; Комарова, Н. И.; Gatilov, Yuriy V.; Andreevskaya, Sofya; Smirnova, Tatiana G.; Маслов, Д. А.; Черноусова, Л. Н.; Salakhutdinov, N. F.; Даниленко, В. Н.

doi:10.1007/s00044-015-1348-2

Cited by 58 publications

(22 citation statements)

References 27 publications

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“…The results of the studies by Shibata et al (1948) and Bekker et al (2015) revealed identical antibacterial Cladonia stellaris Kinoshita et al (1997) Cladonia foliacea Koparal (2015) Alectoria Alectoria lata Kinoshita et al (1997) Alectoria ochroleuca Melgarejo et al (2008) Mixture Flavocetraria Flavocetraria cucculata, F. nivalis The amount of (? )-usnic acid was one-fifth that of (-)-usnic acid Kinoshita et al (1997) F. nivalis The peak area ratio between the(-)-and (?…”

Section: Antibacterial Antifungal Antiviral Activitymentioning

confidence: 95%

Enantioselective activity of usnic acid: a comprehensive review and future perspectives

2019

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This review is focused on the comparison of the biological and pharmacological activities of usnic acid enantiomers. Most of the available data refer to (?)-usnic acid, while the left-handed isomer has been less often significantly studied. Special attention was paid to the experiments comparing both (?)-and (-)-usnic acid at the same time, the results of which indicated interesting differences, however no tendency as to which enantiomer was more potent could be observed. Nevertheless, more studies, especially on (-)-usnic acid, are needed to give a final explanation for the similarities and differences between both usnic acid enantiomers. These should be especially directed to steric structure-activity relationship of the enantiomers, tested under the same experimental conditions, which may help to explain the possible mechanisms of their actions.

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Section: Antibacterial Antifungal Antiviral Activitymentioning

confidence: 95%

Enantioselective activity of usnic acid: a comprehensive review and future perspectives

2019

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“…Natural sources have offered a consistent panel of antimycobacterial agents, and still represent a valid reservoir of chemical structures. Among them, usnic acid and a limited number of derivatives have proved antibacterial activity including mycobacteria, but, so far, the main limitation in its use was represented by its in vivo cytotoxicity. New derivatives have been synthesized, by simple conjugation of different moieties to the enolized β‐diketone system, resulting in enamines, hydrazones that show comparable or, in case of the quinoline derivatives, increased antimycobacterium activity.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and antimycobacterial activity of (+)‐usnic acid conjugates

Cirillo

Borroni

Festoso

et al. 2018

Archiv der Pharmazie

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New therapeutics are urgently needed to fight tuberculosis and mycobacteria-related diseases that are a major health hazard especially in poor countries. Natural products have been the source of important antitubercular drugs in the past and still need to receive attention as a potent reservoir of chemical structures. Fifteen known and two new (+)-usnic acid (a benzofurandione formerly isolated from lichens) enamines and hydrazones are here described and tested against sensitive and multidrug-resistant strains of mycobacteria. Among several (+)-usnic acid conjugates, PS14 and PS18 showed potent activity against both susceptible and resistant Mycobacterium tuberculosis strains (MIC values of 1-32 and 2-32 mg/L, respectively) comparable with MIC of other antitubercular drugs already in use for tuberculosis treatment.

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“…[10] The M. smegmatis test system exhibits a higher degree of resistance to antibiotics and antituberculosis agents than M. tuberculosis, therefore the selection criterion is a compound concentration of < 100 μg/ disc, in contrast to M. tuberculosis (MIC < 2 μg/ml). [11,12] All the results obtained for in vitro bioactivity of the compounds studied were compared to the activity of isoniazid (INH) and rifampicin (Rif), i. e., the first line drugs for tuberculosis treatment under these experimental conditions. The concentration of the compound at which the minimum visible zone of growth inhibition is observed is considered as the MIC (minimum inhibitory concentration, μg/disc).…”

Section: Antibacterial Activitymentioning

confidence: 99%

Improved In Vitro Antimycobacterial Activity of Trinuclear Complexes Cobalt(II,III) and Iron(III) with 2‐Furoic Acid againstMycolicibacterium smegmatis

et al. 2020

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The reaction of cobalt(II) and iron(III) pivalates with anions of 2furancarboxylic acid (pyromucic acid, Hfur) yielded trinuclear homometallic complexes with linear ([Co 3 (fur) 6 (phen) 2 ] (1, phen = 1,10-phenanthroline)) and triangular ([Co 3 O(fur) 6 (H 2 O) 3 ] (3), [Fe 3 O(fur) 6 (THF) 3 ] ⋅ 3THF (4)) structures of the metal moiety. The hexanuclear mixed carboxylate cobalt complex [Co 6 (piv) 8 (Hpiv) 4 (fur) 2 (OH) 2 ] (2, piv À = (CH 3) 3 COO À) was isolated as an intermediate in the synthesis of 3. According to CVA data, complex 3 contains bivalent and trivalent cobalt ions. According to Mossbauer spectroscopy data, all the iron(III) atoms in 4, which is an isostructural analogue of 3, are solely in the highspin state. The antibacterial activity of compounds 1-4, K(fur) (5) and Na(fur) (6) was determined in vitro against a nonpathogenic Mycolicibacterium smegmatis strain. The results of in vitro biological tests against Mycolicibacterium smegmatis showed a high bioactivity of complexes 1 and 4.

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Synthesis and activity of (+)-usnic acid and (−)-usnic acid derivatives containing 1,3-thiazole cycle against Mycobacterium tuberculosis

Cited by 58 publications

References 27 publications

Enantioselective activity of usnic acid: a comprehensive review and future perspectives

Enantioselective activity of usnic acid: a comprehensive review and future perspectives

Synthesis and antimycobacterial activity of (+)‐usnic acid conjugates

Improved In Vitro Antimycobacterial Activity of Trinuclear Complexes Cobalt(II,III) and Iron(III) with 2‐Furoic Acid againstMycolicibacterium smegmatis

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