Synthesis of hydroxymethyl compounds of 1,2,4-triazole and investigation of their antitumorigenic activity

Власова, Л. А.; Shamaeva, E. M.; Afanas'eva, G. B.; Postovskii, I. Ya.

doi:10.1007/bf00771732

Cited by 4 publications

(6 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cg2 and Cg5 are the centroids of the C1-C6 and C19-C24 rings, respectively. activities, such as anticonvulsant (Almasirad et al 2004;Kanazawa et al 1988), anticancer (Ibrahim 2009), antitubercular (Kalluraya et al 1996;Vlasova et al 1971), anti-inflammatory (Labanauskas et al, 2004), and their herbicidal (Kondo et al 1992) and analgesic properties (Amir & Shikha 2004;Tozkoparan et al 2007). Also, antifungal activity of aromatic ethers possessing a 1H-1,2,4-triazole ring has been reported (Wahbi et al 1995).…”

Section: Data Collectionmentioning

confidence: 99%

“…For the biological and pharmacological activity of 1,2,4-triazoles, see: Almasirad et al (2004); Amir & Shikha (2004); Ibrahim (2009); Kalluraya et al (1996); Kondo et al (1992); Kanazawa et al (1988); Labanauskas et al (2004); Tozkoparan et al (2007); Vlasova et al (1971); Wahbi et al (1995). For details of the synthesis, see: Drutkowski et al (2002).…”

Section: Related Literaturementioning

confidence: 99%

See 1 more Smart Citation

1-[4-(Difluoromethoxy)phenyl]-N-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-3-carboxamide

2010

View full text Add to dashboard Cite

Two crystallographically independent molecules, A and B, with similar conformations are present in the asymmetric unit of the title compound, C18H16F2N4O4. In molecule A, the plane of the 1,2,4-triazole ring is tilted relative of the 4-difluoromethoxy-substituted and the 3,4-dimethoxy-substituted benzene rings by 6.5 (2) and 16.4 (1)°, respectively. The –CHF2 group is twisted away from the plane of the benzene ring, with a dihedral angle between the O—C bond of the OCHF2 group and the plane of the adjacent phenyl ring of 38.6 (3)°. The corresponding parameters for molecule B are 7.7 (1), 9.5 (2) and 25.2 (2)°. In both molecules, the conformations are stabilized by intramolecular N—H⋯N and C—H⋯O hydrogen bonds. There are also C—H⋯π contacts between the methyl groups and the benzene rings, and π–π stacking interactions between the benzene rings of adjacent parallel A molecules [centroid–centroid distance = 3.8942 (17) Å]. π–π interactions are also observed between the triazole ring and one of the benzene rings of parallel B molecules [centroid–centroid distance = 3.7055 (16) Å].

show abstract

Section: Data Collectionmentioning

confidence: 99%

Section: Related Literaturementioning

confidence: 99%

1-[4-(Difluoromethoxy)phenyl]-N-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-3-carboxamide

2010

View full text Add to dashboard Cite

show abstract

“…This reaction is common to all azoles (pyrazole in acid 15 and neutral conditions, 16 , 18 , 19 imidazole, 20 , 21 triazoles, 22 − 24 tetrazole, 25 benzimidazole, 16 , 26 and benzotriazole). 27 − 29 In the case of indazole, previous to our works, 15 − 17 Pozharskii et al carried the reaction in 1964 in acid media.…”

Section: Introductionmentioning

confidence: 95%

Study of the Addition Mechanism of 1H-Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions

et al. 2022

View full text Add to dashboard Cite

The reaction of NH -indazoles with formaldehyde in aqueous hydrochloric acid has been experimentally studied by solution and solid-state nuclear magnetic resonance (NMR) and crystallography. The mechanism of the formation of N 1 -CH 2 OH derivatives was determined. For the first time, 2-substituted derivatives have been characterized by multinuclear NMR. Theoretically, calculations with gauge-invariant atomic orbitals (GIAOs) at the Becke three-parameter (exchange) Lee–Yang–Parr B3LYP/6-311++G(d,p) level have provided a sound basis for the experimental observations. The first X-ray structures of four (1 H -indazol-1-yl)methanol derivatives are reported.

show abstract

“…For general background regarding the biological and pharmacological activities of 1,2,4-triazoles and their derivatives, see: Wahbi et al (1995); Chai et al (2003); Hashimoto et al (1990); Kalluraya et al (1996); Almasirad et al (2004); Amir & Shikha (2004); Kanazawa et al (1988); Vlasova et al (1971); Labanauskas et al (2004); Tozkoparan et al (2007). For a related synthesis, see: Drutkowski et al (2002); Frohberg et al (2002).…”

Section: Related Literaturementioning

confidence: 99%

“…(2009). E65, o1015-o1016 [doi:10.1107/S160053680901263X] (Vlasova et al, 1971;Kalluraya et al, 1996), anticonvulsant (Almasirad et al, 2004;Kanazawa et al, 1988;Chai et al, 2003;Hashimoto et al, 1990), anti-inflammatory (Labanauskas et al ,2004), herbicidal, and analgesic properties (Tozkoparan et al, 2007;Amir & Shikha, 2004). Also, antifungal activity of aromatic ethers possessing a 1H-1,2,4-triazole ring has been reported (Wahbi et al, 1995).…”

Section: Data Collectionmentioning

confidence: 99%

1-[4-(Difluoromethoxy)phenyl]-N-(2,3-dimethylphenyl)-1H-1,2,4-triazole-3-carboxamide

2009

View full text Add to dashboard Cite

In the molecule of the title compound, C18H16F2N4O2, the 1,2,4-triazole ring forms dihedral angles of 3.6 (2) and 14.9 (6)° with the 4-difluoromethoxy-substituted benzene ring and the 2,3-dimethyl-substituted benzene ring, respectively. The OCHF2 group is twisted away from the plane of the benzene ring, as shown by the C—O—C—C torsion angle of 145.8 (2)°. The conformation is stabilized by an intermolecular N—H⋯N hydrogen bond. In the crystal, short C—H⋯O interactions lead to chains of molecules.

show abstract

Synthesis of hydroxymethyl compounds of 1,2,4-triazole and investigation of their antitumorigenic activity

Cited by 4 publications

References 5 publications

1-[4-(Difluoromethoxy)phenyl]-N-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-3-carboxamide

1-[4-(Difluoromethoxy)phenyl]-N-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-3-carboxamide

Study of the Addition Mechanism of 1H-Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions

1-[4-(Difluoromethoxy)phenyl]-N-(2,3-dimethylphenyl)-1H-1,2,4-triazole-3-carboxamide

Contact Info

Product

Resources

About