Synthesis and Structure of Homodrimane Sesquiterpenoids Containing 1,2,4-Triazole and Carbazole Rings

Kuchkova, K. I.; Arycu, A. N.; Sekara, E. S.; Barba, Alic; Vlad, P. F.; Makaev, F. Z.; Melnik, E.I.; Kravtsov, Victor Ch.

doi:10.1007/s10600-015-1384-7

Cited by 11 publications

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References 16 publications

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“…Starting from sclareolide ( 1 ), carboxylic acids 2 , 5 , and 8 were obtained in five, six, and three steps, with overall yields of 81%, 62%, and 89%, respectively [ 13 , 21 , 22 ] ( Scheme 1 ). The intermediate carboxylic acid 12 was obtained based on (-)-sclareol 11 in two steps with the overall yield of 75% [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of terpene—heterocyclic compounds has seen a vertiginous development in the last 10 years. A great number of molecular hybrids containing a terpene unit and one of the following heterocycles: diazine [ 11 , 12 ], 1,2,4-triazole and carbazole [ 13 , 14 ], azaheterocyclic [ 15 , 16 ], hydrazinecarbothioamide and 1,2,4-triazole [ 17 ], 1,3,4-oxadiazole and 1,3,4-thiadiazole [ 18 ], thiosemicarbazone and 1,3-thiazole [ 19 ], or benzothiazole [ 20 ], many of which showed excellent antifungal and/or antibacterial activity, were reported elsewhere.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antimicrobial Activity Evaluation of Homodrimane Sesquiterpenoids with a Benzimidazole Unit

et al. 2023

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Herein we report a feasible study concerning the synthesis and the in vitro antimicrobial activity of some new homodrimane sesquiterpenoids with a benzimidazole unit. Based on some homodrimane carboxylic acids, on their acyl chlorides and intermediate monoamides, a series of seven N-homodrimenoyl-2-amino-1,3-benzimidazoles and 2-homodrimenyl-1,3-benzimidazoles was synthesized. The syntheses involved the decarboxylative cyclization and condensation of the said acids or acyl chlorides with o-phenylendiamine and 2-aminobenzimidazole, as well as the p-TsOH-mediated cyclodehydration of the said monoacylamides. The structures of the synthesized compounds have been fully confirmed, including by the X-ray diffraction. Their biological activities were evaluated on five species of fungi (Aspergillus niger, Fusarium solani, Penicillium chrysogenum, P. frequentans, and Alternaria alternata) and two strains of bacteria (Bacillus sp. and Pseudomonas aeruginosa). Compounds 7 and 20 showed higher antifungal (MIC = 0.064 and 0.05 μg/mL) and antibacterial (MIC = 0.05 and 0.032 μg/mL) activities compared to those of the standards: caspofungin (MIC = 0.32 μg/mL) and kanamycin (MIC = 2.0 μg/mL), and compounds 4, 10, 14, and 19 had moderate activities.

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Section: Resultsmentioning

confidence: 99%