Norlabdane Compounds Containing Thiosemicarbazone or 1,3-Thiazole Fragments: Synthesis and Antimicrobial Activity

Blaja, Svetlana; Lungu, Lidia; Kuchkova, K. I.; Ciocârlan, Alexandru; Barba, Alic; Vornicu, Nicoleta; Aricu, Aculina

doi:10.1007/s10600-021-03292-3

Cited by 9 publications

(3 citation statements)

References 17 publications

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“…Certain biological applications of thiazoles were first identified in 1887 by Hantzsch and Weber. Since this discovery, thiazoles are a notable moiety present in several modern compounds of interest for their antitubercular [17], antidiabetic [18], antimalarial [19], antibacterial [19][20][21][22][23][24][25][26][27][28][29][30][31], antiviral [26,[32][33][34], antifungal [22, 24-27, 29, 30, 33, 34], antioxidant [35], anti-inflammatory [30,35], anti-cancer [36,37], and anti-proliferative [27,[38][39][40], activities.…”

Section: Biological Applications Of Thiazolesmentioning

confidence: 99%

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

Lozano¹,

Lewis-Bakker²,

Kotra³

2023

Strategies for the Synthesis of Heterocycles and Their Applications

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Pyrazoles and thiazoles belong to 5-membered aromatic heterocycles called azoles. In addition to a nitrogen, pyrazoles contain an additional nitrogen in a 1,2 linkage and thiazoles contain a sulfur atom in a 1,3 linkage. These compounds are useful pharmacophores that offer a broad range of therapeutic applications. Pyrazoles can be synthesized by (i) the condensation of 1,3 dipolar compounds and alkenes/alkynes, (b) cyclocondensation of hydrazines and dicarbonyl reagents, and (c) multi-component reactions. Access to thiazoles is typically via (a) the condensation of α-haloketones with nucleophilic thioamides containing the N-C-S fragment, (b) a reaction between α-aminonitriles and various reactants containing an X-C-S fragment, and (c) a reaction of acylaminocarbonyls and phosphorus pentasulfide. This chapter will focus on the strategies and our perspectives on the synthesis of pyrazoles and thiazoles including derivatives at the 1,5 positions and 2, 4, 5 positions respectively, reported during 2015–2022. Additionally, their therapeutic and biological evaluations will be discussed.

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Section: Biological Applications Of Thiazolesmentioning

confidence: 99%

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

Lozano¹,

Lewis-Bakker²,

Kotra³

2023

Strategies for the Synthesis of Heterocycles and Their Applications

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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 a typical heteroaromatic motif, the thiazole ring has been proved to be a pivotal structure in numerous pharmaceutical molecules, natural products as well as organic molecules possessing other versatile functions. 1 Rather recent works have revealed many more interesting thiazole compounds possessing attractive biological activities, such as anti-inflammatory, 2 antimicrobial, 3 anticancer, 4 antitumor, 5 antiproliferative, 6 fungicidal 7 activity etc. , which keeps enriching the application frontiers of thiazole scaffolds in discovering valuable lead compounds and drug candidates.…”

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confidence: 99%

Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization

et al. 2022

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Norlabdane Compounds Containing Thiosemicarbazone or 1,3-Thiazole Fragments: Synthesis and Antimicrobial Activity

Cited by 9 publications

References 17 publications

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

Synthetic Strategies and Biological Activities of 1,5-Disubstituted Pyrazoles and 2,5-Disubstituted Thiazoles

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

Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization

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