New Acylated 1,2,4‐Triazoles as Antiviral Agents

Abstract

The syntheses and antiviral properties of the new acylated 1,2,4-triazole derivatives 4 are described. In cel1 culture experiments 6 out of 99 compounds specifically inhibit rubelia virus replication to a high degree. Structure-activity relationships are discussed. Neue acylierîe 1,2,4-Tnazoie als antivirale WirkstoffeDie Synthese und die antivirale Aktivität einiger neuer acylierten 1,2,4-Triazoie 4 wird beschrieben. In Zell-Kulturen erwiesen sich 6 von 99 Verbindungen als hoch wirksam und spezifisch gegen das Rubella Virus. Struktur-Aktivitäts-Beziehungen werden diskutiert. Antiviral chemotherapy must be directed to the development of compounds with activity against virus replication without affecting any cellular metabolic processes.The most valuable compounds specifically inhibit virus multiplication; 9-(2-hydroxyethoxymethy1)guanine and (E)-5-(2-bromovinyl)-deoxyuridine have been reported as exhibiting highly selective antiviral activity against the growth of herpes simplex virus14).Til1 the present time there have been only few papers about the triazole derivatives posessing antiviral activity . Thus 3-mercapto-5-(4-pyridyl)-4H-l,2,4-triazole is active oraily against neurovaccinia in mice". Other 1,2,4-triazole derivatives weakly inhibit the multiplication of ranikhet disease virus in a stationary culture of chorioallantoic membranes of chick embryo6). Triazolotriazino[5,6-blindole derivatives show some activity against herpes simplex virus7). 1-P-D-ribofuranosyl-1,2,4-triazole-3-carboxarnide is a nucleoside which inhibits some of the DNA-and RNA-virus rep~ications"~).The present study reports the synthesis of new acylated 1,2,4-triazoles with a selective antiviral activity against the rubella virus infected cell"'). The synthetic procedure followed the route below.The known reaction of N-cyano-carbonimidodithioic acid diaikyl esters 1 with hydrazine offered a good possibility to get large variable starting material~l'-'~), 3-alkylthio-S-amino-lH-l,2,4-triazoles 2 in a simple way.2 can be acylated in an organic aprotic solvent, e. g. dioxane in the presence of an organic base, e. g. pyridine at room temperature, to the I-benzoylated triazoles 3.3 can be submitted to a thermal rearrangement either in an organic inert solvent, e. g. sulfolane, dimethylformamide, dimethylsulfoxide or without solvent at a temperature of

Synthesis of Some New 3-(5-(Arylamino)-1,3,4-thiadiazol-2-yl)-2H-chromen-2-ones and 3-(4-Aryl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-YL)-2H-chromen-2-ones

“…29 It was converted into the corresponding hydrazide (1) by refluxing with hydrazine hydrate (80%) in methanol. 30 The IR spectrum of hydrazide exhibited a characteristic absorption band for primary NH 2 along with a shoulder at 3380 and for the secondary NH at 3287 cm −1 . The strong absorptions at 1732 and 1643 cm −1 were assigned to the coumarin and amide carbonyls, respectively.…”

Catalyst- and solvent-free synthesis of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement: X-ray structural and theoretical studies

“…FT-IR, 1D NMR and HRMS spectroscopy), the formation of tertiary amide (3) was confirmed. Although compound (3) is a known molecule (Somorai et al, 1986), no details about its spectroscopic and crystallographic analysis could be found. For that reason, a complete analytical and spectroscopic characterization was performed in this work (see Experimental).…”

“…[yield 948 mg, 94%; m.p. 428-429 K (amorphous), literature 430-432 K (Somorai et al, 1986)]. Recrystallization of (3) from methanol afforded white crystalline prisms suitable for single-crystal X-ray diffraction analysis.…”

“…The structure of (4) was confirmed by single-crystal X-ray diffraction analysis. Although compound (4) was reported three decades ago (Somorai et al, 1986), no spectroscopic or crystallographic analysis details could be found. For that reason, a complete analytical and spectroscopic characterization (i.e.…”

Antimicrobial and Anthelmintic Activities of Some Newly Synthesized Triazoles

“…It has become evident from the recent researches that the triazoles are not only antimicrobial or antifungal but also have many pharmacological activities [8]. Basic nucleus triazole, when fused to another heterocyclic ring, leads to widespread action and diverse biological applications such as antidepressant [9], anti-inflammatory [10], antitumor [11], and antiviral action [12]. Triazoles are distinguished class of heterocyclic compounds having broad spectrum biological properties.…”