Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors

Navidpour, Latifeh; Shafaroodi, Hamed; Abdi, Khosrou; Amini, Mohsen; Ghahremani, Mohammad H.; Dehpour, Ahmad Reza; Shafiee, Abbas

doi:10.1016/j.bmc.2005.11.029

Cited by 144 publications

(82 citation statements)

References 21 publications

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“…Moreover, adamantane derivatives were also reported to exhibit marked anti-HIV [8][9][10], antibacterial [11][12][13], antimalarial [14], hypoglycemic [15,16], anti-inflammatory [17,18], and anticancer [19] activities. 1,2,4-Triazole derivatives were reported to possess significant anti-inflammatory [20,21] and antibacterial [22] activities. The title compound was prepared as an adamantanetriazole hybrid derivative as potential bioactive agent [23].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S

Al‐Shehri

Elsaman

Al‐Abdullah

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 18 H 20 FN 3 S, triclinic, P1, a = 7.3884(4) Å, b = 10.0741(6) Å, c = 12.6533(8) Å, α = 69.209(2)°, β = 73.778(2)°, γ = 72.638(2)°, The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. CCDC no.: 1507728 Source of material4-Fluorophenyl isothiocyanate (1.53 g, 0.01 mol) was added to a solution of adamantane-1-carbohydrazide (1.94 g, 0.01 mol), in ethanol (10 mL), and the mixture was heated under reflux with stirring for one hour. The solvent was then distilled off in vacuo; an aqueous sodium hydroxide solution (10%, 15 mL) was added to the residue and the mixture was heated under reflux for two hours then filtered hot. On cooling, the mixture was acidified with hydrochloric acid (pH 1-2) and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 3.03 g (92%) of the title compound (C 18 H 20 FN 3 S) as

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S

Al‐Shehri

Elsaman

Al‐Abdullah

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Thiocarbonyl diazoles as one of the highly reactive molecules are also used for the preparation of triazolones which are difficult to be prepared under common conditions. Treatment of amidrazone 36 with 1,1-thiocarbonyldiimidazole 37 as the donor of the remaining carbon atom in tetrahydrofuran (THF) gave the corresponding 1,2,4-triazol-5-thione 38 in yields of 47-55%, and further conversion afforded 3-alkylthio-1,2,4-triazoles in 41-47% overall yields which could be served as artificial cyclooxygenase-2 (COX-2) isozyme (Scheme 11) [64]. This approach provides a convenient synthetic strategy for the preparation of artificial COX-2 isozyme thio triazole derivatives with facile condition, easy operation and moderate yields using thiocarbonyldiimidazole as reaction agent.…”

Section: Amidrazonesmentioning

confidence: 99%

“…Oxadiazoles, including 1,2,4-oxadiazoles and 1,3,4-oxadiazoles which possess various bioactivities like antibacterial, antifungal and antitumor potencies [178], have relatively high reactivity due to the inductive effect of oxygen atom in the oxadiazole ring, and they have been investigated very well to transform into more stable heterocycles, especially 1,2,4-triazole derivatives [179][180][181][182][183][184][185][186][187]. In recent years, the prepared triazoles via rearrangement of oxadiazoles usually exhibited wide applications in medicinal chemistry especially as antitubercular [188] and antiproliferative agents [189], and also in supramolecular chemistry as progesterone receptors and ligands of coordination polymers [64,190,191].…”

Section: Transformations Of Five-membered Heterocyclic Compoundsmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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“…[19][20][21][22][23][24][25] The alterations in chemical structure of substituted 1,2,4-triazoles could affect their interactions with cells and tissues, thereby exhibiting different biological effects. Furthermore, much research manifested that incorporation of fluorine or chlorine moiety into an organic molecule could efficiently improve the pharmacological properties, [26][27][28][29] which resulted in increasing lipid solubility, accordingly enhancing the rate of absorption and transport of drugs in vivo.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Halobenzyloxy and Alkoxy 1,2,4-Triazoles and Evaluation for Their Antifungal and Antibacterial Activities

Wan¹,

Zhou

2010

Bulletin of the Korean Chemical Society

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A new class of halobenzyloxy or alkoxy 1,2,4-triazoles and their hydrochlorides were synthesized through cyclization starting from commercially available phenylhydrazine. The structures were characterized by MS, IR and 1 H NMR spectra as well as elemental analyses. All the synthesized compounds were screened for their antibacterial activities in vitro against Staphylococcus aureus (ATCC29213), methicillin-resistant Staphylococcus aureus (N315), Bacillus subtilis, Escherichia coli (ATCC25922), Pseudomonas aeruginosa, Shigella dysenteriae, Eberthella typhosa, and antifungal activities against Candida albicans (ATCC76615), Aspergillus fumigatus by broth microdilution assay method. The results of preliminary bioassay indicated that 3-(2,4-difluorobenzyloxy)-1-phenyl-1H-1,2,4-triazole hydrochloride exhibited the best inhibitory activity with an MIC value of 56.25 µM against P. aeruginosa superior to Chloramphenicol, and showed comparable activity with Chloramphenicol against E. coli (ATCC25922).

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Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors

Cited by 144 publications

References 21 publications

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Synthesis of Novel Halobenzyloxy and Alkoxy 1,2,4-Triazoles and Evaluation for Their Antifungal and Antibacterial Activities

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Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors

Cited by 144 publications

References 21 publications

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Synthesis of Novel Halobenzyloxy and Alkoxy 1,2,4-Triazoles and Evaluation for Their Antifungal and Antibacterial Activities

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Product

Resources

About

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S