Synthesis and Cytotoxic Activity of 1,2,3-Triazole Derivatives in Glioma Cell Cultures

Хажиева, Инна С.; Глухарева, Т. В.; Eltsov, Oleg S.; Morzherin, Yu. Yu.; Minin, A. A.; Поздина, Варвара А.; Улитко, М. В.

doi:10.1007/s11094-015-1273-1

Cited by 8 publications

(6 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The thioamides 1a – d were prepared from the corresponding amides 4a – d by treatment with phosphorus decasulfide ( Scheme 1 ). It is worth noting that amides of 1-alkyl-1,2,3-triazole-4-carboxylic acids are poorly represented in the literature and the methods of their preparation require the addition of alkyl azides to acetylene carboxylic esters and reactions of 2-diazomalonates with aliphatic amines [ 40 , 52 ]. The first approach leads to a mixture of two regioisomers and the second method involves the use of explosive diazo compounds.…”

Section: Resultsmentioning

confidence: 99%

“…The first approach leads to a mixture of two regioisomers and the second method involves the use of explosive diazo compounds. Therefore, such compounds are better prepared by a recently found method in our laboratory which includes the reaction of 4-acetyl-1,2,3-triazole 5a-d with aniline followed by a Cornforth rearrangement of the 1,2,3-triazole ring [52]. Alkyl-(2a,b) and arylsulfonyl (2c-g) azides were prepared, respectively, from the corresponding sulfonyl chlorides and sodium azides according to published methods ( Figure 3) [53].…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

Ilkin¹,

Berseneva²,

Beryozkina³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

N-Sulfonyl amidines bearing 1,2,3-triazole, isoxazole, thiazole and pyridine substituents were successfully prepared for the first time by reactions of primary, secondary and tertiary heterocyclic thioamides with alkyl- and arylsulfonyl azides. For each type of thioamides a reliable procedure to prepare N-sulfonyl amidines in good yields was found. Reactions of 1-aryl-1,2,3-triazole-4-carbothioamides with azides were shown to be accompanied with a Dimroth rearrangement to form 1-unsubstituted 5-arylamino-1,2,3-triazole-4-N-sulfonylcarbimidamides. 2,5-Dithiocarbamoylpyridine reacts with sulfonyl azides to form a pyridine bearing two sulfonyl amidine groups.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

Ilkin¹,

Berseneva²,

Beryozkina³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…2-Diazo-3-oxo- N -phenylbutanamide ( 2a ), 2-diazo-3-oxo- N -( p -tolyl)butanamide ( 2b ) and diazocompounds 2d – 2h were synthesized using modified procedures. 2-Cyano-2-diazo- N -phenylacetamide ( 2i ), N -benzyl-2-cyano-2-diazoacetamide ( 2j ), 2-cyano-2-diazoacetamide ( 2k ), and 2-diazo-3-oxo-3-(pyrrolidin-1-yl)propanenitrile ( 2l ) were prepared according to the described procedures.…”

Section: Methodsmentioning

confidence: 99%

Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds

et al. 2022

View full text Add to dashboard Cite

A novel carbenoid-mediated approach to thioisomünchnones was developed by intermolecular copper-catalyzed reactions of diazoacetamides with aromatic and heteroaromatic thioamides bearing a pyrrolidine moiety. The direction of the reaction can be switched toward 2-amino-2-heteroarylacrylamides by replacing the pyrrolidine with an aniline group or by the use of 2-cyano-2-diazoacetamides. The proposed mechanism and DFT calculations allowed us to rationalize the effect of substituents on the reaction direction. Effective methods were found for the synthesis of previously unknown both 2-heteroarylthioisomünchones and 2-heteroarylacrylamides, based on a wide scope of available reagents with a similar structure. Some of the synthesized thioisomünchnones exhibited multicolor fluorescence in the solid state and solutions.

show abstract

“…For biological activities of 1.2.3-triazoles, see: Sathish Kumar & Kavitha (2013); Khazhieva et al (2015a). For the synthesis, see: Khazhieva et al (2015b…”

Section: Related Literaturementioning

confidence: 99%

“…The titled compound was prepared as previously reported (Khazhieva et al, 2015b). Crystals were obtained by slow evaporation of a solution in ethanol.…”

Section: S1 Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structure of 1-methoxy-5-methyl-N-phenyl-1,2,3-triazole-4-carboxamide

et al. 2015

View full text Add to dashboard Cite

The title compound, C 11H12N4O2,was prepared via the transformation of sodium 4-acetyl-1-phenyl-1H-[1.2.3]triazolate under the action of methoxyamine hydrochloride. The dihedral angle between the triazole and phenyl rings is 25.12 (16)° and the C atom of the methoxy group deviates from the triazole plane by 0.894 (4)Å. The conformation of the CONHR-group is consolodated by an intramolecular N—H⋯N hydrogen bond to an N-atom of the triazole ring, which closes an S(5) ring. In the crystal, weak N—H⋯N hydrogen bonds link the molecules into C(6) [010] chains.

show abstract

Synthesis and Cytotoxic Activity of 1,2,3-Triazole Derivatives in Glioma Cell Cultures

Cited by 8 publications

References 11 publications

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds

Crystal structure of 1-methoxy-5-methyl-N-phenyl-1,2,3-triazole-4-carboxamide

Contact Info

Product

Resources

About