Design, synthesis and biological evaluation of new substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5 H )ones. Pharmacophore models for antifungal activity

Tratrat, Christophe; Haroun, Michelyne; Paparisva, Aliki; Geronikaki, Athina; Kamoutsis, Ch.; Ćirić, Ana; Glamočlija, Jasmina; Sokóvić, Marina; Fotakis, Charalambos; Zoumpoulakis, Panagiotis; Bhunia, Shome S.; Saxena, Anil Kumar

doi:10.1016/j.arabjc.2016.06.007

Cited by 29 publications

(19 citation statements)

References 78 publications

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“…Almost all the tested compounds showed antibacterial activity but on different levels and this activity was even better than that of Streptomycin against L. monocytogenes, and E. coli. [46] The results of the antimicrobial activity evaluations reveals that substances 2 exhibited maximum inhibitory activity against Pseudomonas aeruginosa with the inhibition zone at 6 to 13 mm. [39]…”

Section: Antimicrobial Activitymentioning

confidence: 97%

“…If (hetero)arylcarbaldehydes were added to the reaction mixture, various thiazolo [3,2-b] [1,2,4]triazole-6 (5H)-ones 3 with various 5-(het)arylidene substituents were formed (Scheme 2). [41][42][43][44][45][46] According to El-Sherief et al, [47] 5-phenyl-1,-2,4-triazole-3-thiol was treated with various cyanocompounds that contain the active methylene group in the boiling acetic acid in the presence of sulfuric acid. As a result, the corresponding 5-amino-2-phenyl- [1,3] thiazolo [3,2-b] [1,2,4]triazoles 4 were obtained in moderate yields (Scheme 3).…”

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

“…The development of effective routes for obtaining new fused triazoles is relevant because of their wide range of bioactivity and as a consequence-great perspective for usage. Obtained compounds exhibit fungicidal, [26,37,39,[46][47][48] antimicrobial, [26,[37][38][39][46][47][48]56] analgesic, [27,34,[42][43][44] antinociceptive, [28] ulcerogenic, [28,43] antioxidant, [27,39] antiinflammatory, [27][28][29]34,[42][43][44] and anticancer [41] activity. Thiazolo [3,2-b] [1,2,4]triazoles have the ability to act as a urease inhibitor, [36] stabilizers of G-quadruplex [32] and may be used as cationic surfactants.…”

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

“…All tested compounds 3 showed antifungal effect with MIC in the range of 3.67 to 34.6*10 −2 μmol/mL and MFC in the range of 7.35 to 39.6*10 −2 μmol/mL. [46] Compounds of 2 were tested for their antifungal activity against Aspergillus oryzae and Aspergillus niger. Results showed moderate activity with the inhibition zone in the range of 9 to 13 mm.…”

Section: Fungicidal Activitymentioning

confidence: 99%

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Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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Fused heterocyclic systems with 1,2,4‐triazole scaffold arouse great interest from researchers in the branch of heterocyclic and medical chemistry because of their wide biological activities as they are considered as fungicidal, antimicrobial, analgesic, bronchodilators, antioxidant, anti‐inflammatory agents, and they are G‐quadruple stabilizers; the molecular docking data for coumarin‐containing 1,2,4‐triazoles indicate their ability to act as a urease inhibitor. Therefore, the present review aims to investigate new trends in the chemistry of heterocycles incorporating thiazolo[3,2‐b][1,2,4]triazoles, thiazolo[2,3‐c][1,2,4]triazoles, thiazino[5,1‐b][1,2,4]triazoles, thiazino[3,4‐b][1,2,4]triazoles, triazolothiazepines, and their biological characteristics. The main sections discuss: (a) the synthetic routes to the production of substituted fused heterocyclic systems, which include condensation reactions, multiple bond annulation, and the reactions of electrophilic heterocyclization. (b) Description of chemical and biological characteristics of these fused heterocycles.

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Section: Antimicrobial Activitymentioning

confidence: 97%

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Section: Fungicidal Activitymentioning

confidence: 99%

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Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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“…The anti-inflammatory activity of the twenty five substituted 5-benzylideno-2adamantylthiazol [3,2-b] [1,2,4]triazol-6(5H)ones previously synthesized [42] was predicted using the PASS (Prediction of Activity Spectra for substances) program ( Table 1). Prediction was based on the comparison of structural characteristics of the compounds with that of known anti-inflammatory agents within a databank of 989,000 molecules.…”

Section: Prediction Of Anti-inflammatory Activity Of Designed Compoundsmentioning

confidence: 99%

New Substituted 5-Benzylideno-2-Adamantylthiazol[3,2-b][1,2,4]Triazol-6(5H)ones as Possible Anti-Inflammatory Agents

et al. 2021

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Background: Inflammation is a complex response to noxious stimuli promoted by the release of chemical mediators from the damaged cells. Metabolic products of arachidonic acid, produced by the action of cyclooxygenase and lipoxygenase, play important roles in this process. Several non-steroidal anti-inflammatory drugs act as cyclooxygenase inhibitors. However, almost all of them have undesired side effects. Methods: Prediction of the anti-inflammatory action of the compounds was performed using PASS Program. The anti-inflammatory activity was evaluated by the carrageenan paw edema test. COX and LOX inhibitory actions were tested using ovine COX-1, human recombinant COX-2 and soybean LOX-1, respectively. Docking analysis was performed using Autodock. Results: All designed derivatives had good prediction results according to PASS and were synthesized and experimentally evaluated. The compounds exhibited in vivo anti-inflammatory action with eleven being equal or better than indomethacin. Although, some of them had no or low inhibitory effect on COX-1/2 or LOX, certain compounds exhibited COX-1 inhibition much higher than naproxen and COX-2 inhibition, well explained by Docking analysis. Conclusions: A number of compounds with good anti-inflammatory action were obtained. Although, some exhibited remarkable COX inhibitory action this activity did not follow the anti-inflammatory results, indicating the implication of other mechanisms.

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Synthesis, in vitro cytotoxic and apoptotic effects, and molecular docking study of novel adamantane derivatives

Turk‐Erbul

Karaman

Duran

et al. 2021

Archiv der Pharmazie

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4-(Adamantane-1-carboxamido)-3-oxo-1-thia-4-azaspiro [4.4]nonan-2-yl]acetic acid (4a) and [4-(adamantane-1-carboxamido)-8-nonsubstituted/substituted-3-oxo-1-thia-4-azaspiro[4.5]decane-2-yl]acetic acid (4b-g) derivatives were synthesized; their structures were verified by elemental analysis, infrared spectroscopy, 1 H nuclear magnetic resonance (NMR), 13 C NMR, and mass spectroscopy data; and their in vitro cytotoxicity activities were investigated against human hepatocellular carcinoma, human prostate adenocarcinoma, and human lung carcinoma cell lines (HepG2, PC-3, and A549, respectively), and a mouse fibroblast cell line (NIH/3T3). All compounds, except compound 4e, were found as cytotoxic, especially on A549 cells as compared with the other cells (selectivity index = 2.01-11.6). As a further step, the effects of compounds 4a-c on apoptosis induction were tested and the expression of selected apoptosis genes was analyzed. Among the selected compounds, compound 4a induced apoptosis remarkably.Moreover, computational calculations of the binding of compounds 4a-c to the BIR3 domain of the human inhibitor of apoptosis protein revealed ligand-protein interactions at the atomistic level and emphasized the importance of a hydrophobic moiety on the ligands for better binding.

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Design, synthesis and biological evaluation of new substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5 H )ones. Pharmacophore models for antifungal activity

Cited by 29 publications

References 78 publications

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

New Substituted 5-Benzylideno-2-Adamantylthiazol[3,2-b][1,2,4]Triazol-6(5H)ones as Possible Anti-Inflammatory Agents

Synthesis, in vitro cytotoxic and apoptotic effects, and molecular docking study of novel adamantane derivatives

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