Synthesis, antibacterial, and antifungal activities of new drimane sesquiterpenoids with azaheterocyclic units

Aricu, Aculina; Ciocârlan, Alexandru; Lungu, Lidia; Barba, Alic; Shova, Sergiu; Zbancioc, Gheorghiță; Mangalagiu, Ionel I.; D’Ambrosio, Michele; Vornicu, Nicoleta

doi:10.1007/s00044-016-1665-0

Cited by 18 publications

(8 citation statements)

References 48 publications

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“…Taking into consideration the above considerations and our expertise in the field of antibacterial and antifungal agents [ 13 , 15 , 20 , 21 , 22 , 23 , 24 , 25 ], we report here the design, synthesis, molecular docking, antibacterial and antifungal evaluation of some new benzo[f]quinoline derivatives.…”

Section: Introductionmentioning

confidence: 99%

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

et al. 2021

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We report here the design, synthesis, experimental and in silico evaluation of the antibacterial and antifungal activity of some new benzo[f]quinoline derivatives. Two classes of benzo[f]quinolinium derivatives—(benzo[f]quinolinium salts (BQS) and pyrrolobenzo[f]quinolinium cycloadducts (PBQC)—were designed and obtained in two steps via a direct and facile procedure: quaternization followed by a cycloaddition reaction. The synthesized compounds were characterized by elemental and spectral analysis (FT-IR, 1H-NMR, 13C-NMR). The antimicrobial assay reveals that the BQS salts have an excellent quasi-nonselective antifungal activity against the fungus Candida albicans (some of them higher that the control drug nystatin) and very good antibacterial activity against the Gram positive bacterium Staphylococcus aureus. The PBQC compounds are inactive. Analysis of the biological data reveals interesting SAR correlations in the benzo[f]quinolinium series of compounds. The in silico studies furnished important data concerning the pharmacodynamics, pharmacokinetics and ADMET parameters of the BQS salts. Studies of the interaction of each BQS salt 3a–o with ATP synthase in the formed complex, reveal that salts 3j, 3i, and 3n have the best fit in a complex with ATP synthase. Study of the interaction of each BQS salt 3a-o with TOPO II in the formed complex reveals that salts 3j and 3n have the best-fit in complex with TOPO II. The in silico ADMET studies reveal that the BQS salts have excellent drug-like properties, including a low toxicity profile. Overall, the experimental and in silico studies indicate that compounds 3e and 3f (from the aliphatic series), respectively, and 3i, 3j and 3n (from the aromatic series), are promising leading drug candidates.

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Section: Introductionmentioning

confidence: 99%

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

et al. 2021

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“…Encouraged by our recent results in the field of (di)azine with antimicrobial activity [ 11 , 15 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ], we report here the design, synthesis, antibacterial and antifungal evaluation of some newly hybrid quinoline-sulfonamide complexes.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

et al. 2020

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Two new series of hybrid quinoline-sulfonamide complexes (M2+: Zn2+, Cu2+, Co2+ and Cd2+) derivatives (QSC) were designed, synthesized and tested for their antimicrobial activity. The synthesis is straightforward and efficient, involving two steps: acylation of aminoquinoline followed by complexation with metal acetate (Cu2+, Co2+ and Cd2+) or chloride (Zn2+). The synthesized QSC compounds were characterized by FTIR and NMR spectroscopy and by X-ray diffraction on single crystal. The QSC compounds were preliminary screened for their antibacterial and antifungal activity and the obtained results are very promising. In this respect, the hybrid N-(quinolin-8-yl)-4-chloro-benzenesulfonamide cadmium (II), considered as leading structure for further studies, has an excellent antibacterial activity against Staphylococcus aureus ATCC25923 (with a diameters of inhibition zones of 21 mm and a minimum inhibitory concentration (MIC) of 19.04 × 10−5 mg/mL), a very good antibacterial activity against Escherichia coli ATCC25922 (with a diameters of inhibition zones of 19 mm and a MIC of 609 × 10−5 mg/mL), and again an excellent antifungal activity against Candida albicans ATCC10231 (with a diameters of inhibition zones of 25 mm and a MIC of 19.04 × 10−5 mg/mL).

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“…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%

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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Synthesis, antibacterial, and antifungal activities of new drimane sesquiterpenoids with azaheterocyclic units

Cited by 18 publications

References 48 publications

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

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

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