Synthesis of Novel Tetranorlabdane Derivatives with Unprecedented Carbon Skeleton

Ciocârlan, Alexandru; Aricu, Aculina; Lungu, Lidia; Edu, Carolina; Barba, Alic; Shova, Sergiu; Mangalagiu, Ionel I.; D’Ambrosio, Michele; Nicolescu, Alina; Deleanu, Călin; Vornicu, Nicoleta

doi:10.1055/s-0036-1588651

Cited by 11 publications

(6 citation statements)

References 17 publications

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Section: Introductionmentioning

confidence: 91%

“…The structures of intermediary compounds as well as final products were confirmed by 1 H, 13 C, 15 N, and 2D NMR spectroscopy and HRMS analysis. The formation of the The structures of intermediary compounds as well as final products were confirmed by 1 H, 13 C, 15 N, and 2D NMR spectroscopy and HRMS analysis. The formation of the desired hybrid compounds 4, 6, 8, and 9 was proved, first of all, with the presence of signals attributed to aromatic protons from a common 2-substituted-1,3-benzothiazole unit in a range of 7.32-7.96 ppm.…”

Section: Introductionmentioning

confidence: 91%

“…The IR spectra were recorded on a Spectrum 100 FT-IR spectrometer (Perkin-Elmer, Shelton, CT, USA) using an ATR technique. The 1 H, 13 C, and 15 N NMR (400, 100, and 40 MHz, respectively) and COSY, 1 H- 13 C HSQC, 1 H- 13 C HMBC, DEPT, and 1 H-15 N HSQC, 1 H-15 N HMBC spectra were acquired on a Bruker Avance DRX 400 spectrometer (Bruker BioSpin, Rheinstetten, Germany) in CDCl 3 (NMR spectra for all the compounds are available online, see the Supplementary Materials). The 1 H NMR chemical shifts were reported relative to the residual solvent protons as internal standards (7.26 ppm).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation

et al. 2022

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Based on some homodrimane carboxylic acids and their acyl chlorides, a series of fourteen 2-homodrimenyl-1,3-benzothiazoles, N-homodrimenoyl-2-amino-1,3-benzothiazoles, 4′-methyl-homodrimenoyl anilides and 4′-methyl-homodrimenthioyl anilides were synthesized and 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). The synthesis involved the decarboxylative cyclization, condensation and thionation of the said acids, anhydrides or their derivatives with 2-aminothiophenol, 2-aminobenzothiazole, p-toluidine and Lawesson’s reagent. As a result, together with the desired compounds, some unexpected products 8, 25, and 27 were obtained, and the structures and mechanisms for their formation have been proposed. Compounds 4, 9, and 25 showed higher antifungal and antibacterial activity compared to the standards caspofungin (MIC = 1.5 μg/mL) and kanamycin (MIC = 3.0 μg/mL), while compound 8 had comparable activities. In addition, compounds 6, 17, and 27 showed selective antifungal activity at MIC = 2.0, 0.25, and 1.0 μg/mL, respectively.

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Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 91%

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation

et al. 2022

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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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“…As part of our program studying Moroccan plants [ 5 , 6 ], our interest is focused on Dittrichia viscosa L. Greuter [ 7 , 8 ], an invasive perennial plant particularly abundant in wasteland areas. Its extract is used in traditional Moroccan medicine for its antipyretic, antiseptic and anti-inflammatory properties [ 9 , 10 ], and also exhibits antifungal activity [ 11 , 12 , 13 ]. Recent studies reported that the aerial parts of the plant are a rich source of eudesmane sesquiterpenes, among which ilicic acid ( 1 ) and isocostic acid ( 2 ) ( Figure 1 ) represent up to 2.5% and 2% of the aerial part dry weight, respectively [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Modification of Natural Eudesmane Scaffolds via Mizoroki-Heck Reactions

2017

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The Mizoroki-Heck reaction was applied to substrates derived from isocostic and ilicic acids, important sesquiterpene components of Dittrichia viscosa L. Greuter that were extracted directly from plant material collected in Morocco. After optimization of the metallo-catalysis conditions, various aryl-groups were successfully introduced on the exocyclic double bond with an exclusive E-configuration and without racemization.

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Synthesis of Novel Tetranorlabdane Derivatives with Unprecedented Carbon Skeleton

Cited by 11 publications

References 17 publications

Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation

Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation

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

Modification of Natural Eudesmane Scaffolds via Mizoroki-Heck Reactions

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