l-Proline catalyzed one-step synthesis of 4,5-diaryl-2H-1,2,3-triazoles from heteroaryl cyanostilbenes via [3+2]cycloaddition of azide

Penthala, Narsimha Reddy; Madadi, Nikhil Reddy; Janganati, Venumadhav; Crooks, Peter A.

doi:10.1016/j.tetlet.2014.08.027

Cited by 16 publications

(12 citation statements)

References 26 publications

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“…The synthetic procedure has been described by Madadi et al (2014) and by Penthala et al (2014). For structure-related activity, see: Young & Chaplin (2004); Pettit et al (1995); Hsieh et al (2005); Carr et al (2010); Banimustafa et al (2013); Demchuk et al (2014 Symmetry code: (i) Àx þ 2; Ày þ 1; Àz þ 1.…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 4,5-bis(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole methanol monosolvate

et al. 2014

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The title compound, C20H23N3O6·CH3OH, was synthesized by [3 + 2] cycloaddition of (Z)-2,3-bis(3,4,5-trimethoxyphenyl)acrylonitrile with sodium azide and ammonium chloride in DMF/water. The central nitrogen of the triazole ring is protonated. The dihedral angles between the triazole ring and the 3,4,5-trimethoxyphenyl ring planes are 34.31 (4) and 45.03 (5)°, while that between the 3,4,5-trimethoxyphenyl rings is 51.87 (5)°. In the crystal, the molecules, along with two methanol solvent molecules are linked into an R 4 4(10) centrosymmetric dimer by N—H⋯O and O—H⋯N hydrogen bonds.

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Section: Related Literaturementioning

confidence: 99%

Crystal structure of 4,5-bis(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole methanol monosolvate

et al. 2014

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“…The yield was remarkably increased (96%) when a catalytic amount of L ‐proline, piperidine, or morpholine was added in the reaction system (entry 9–13) . Compared with the proline, piperidine and morpholine showed slightly lower efficiency .…”

Section: Resultsmentioning

confidence: 99%

“…III is easily transformed into the key species IV via dehydration . The electron‐deficiency of dipolarophile IV leads to lower its LUMO energy level and cause 1,3‐dipolar cycloaddition easily between IV and azide ion ,. [3+2] Cycloaddition of IV with azide ion, produces the 4,5‐disubstitute 1,2,3‐triazole product through proton transfer, and the aromatization‐promoted elimination of the pyridine ,…”

Section: Resultsmentioning

confidence: 99%

A Domino Reaction of Pyridinium Salts: Efficient Synthesis of 4,5‐Disubstituted 1,2,3‐(NH)‐Triazoles

2018

ChemistrySelect

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A one-pot mild and metal-free procedure for efficient synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles has been developed through the sequentially reaction of pyridinium salts with aldehydes and sodium azide. In the presence of L-proline, a key intermediate, an olefinic pyridinium-salt, is in situ generated via coupling of pyridinium salts with aldehydes and cyclizes with azide ion to form a triazole ring.

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“…The residue obtained was purified by flash column chromatography to afford the corresponding triazole (Scheme 1) [17]. The structure and purity of the triazole derivatives were verified by 1 H, 13 C-NMR spectroscopy, high resolution mass spectroscopy and X-ray crystallography [17–20]. …”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of novel 4,5-disubstituted 2H-1,2,3-triazoles as cis-constrained analogues of combretastatin A-4

Madadi

Penthala

Howk

et al. 2015

European Journal of Medicinal Chemistry

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A series of combretastatin A-4 (CA-4) analogues have been prepared from (Z)-substituted diarylacrylonitriles (1a–1p) obtained in a two-step synthesis from appropriate arylaldehydes and acrylonitriles. The resulting 4,5-disubstituted 2H-1,2,3-triazoles were evaluated for their anti-cancer activities against a panel of 60 human cancer cell lines. The diarylacrylonitrile analogue 2l exhibited the most potent anti-cancer activity in the screening studies, with GI50 values of <10 nM against almost all the cell lines in the human cancer cell panel and TGI values of <10nM against cancer cell lines SF-539, MDA-MB-435, OVCAR-3 and A498. Furthermore, in silico docking studies of compounds 2l, 2e and 2h within the active site of tubulin were carried out in order to rationalize the mechanism of anti-cancer properties of these compounds. From the in silico studies, compound 2e was predicted to have better affinity for the colchicine binding site on tubulin compared to compounds 2l and 2h. Analogue 2e was also evaluated for its anti-cancer activity by colony formation assay against 9LSF rat gliosarcoma cells and afforded an LD50 of 7.5 nM. A cell cycle redistribution assay using analogue 2e was conducted to further understand the mechanism of action of these CA-4 analogues. From this study, analogues 2e and 2l were the most potent anti-cancer agents in this structural class, and were considered lead compounds for further development as anti-cancer drugs.

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l-Proline catalyzed one-step synthesis of 4,5-diaryl-2H-1,2,3-triazoles from heteroaryl cyanostilbenes via [3+2]cycloaddition of azide

Cited by 16 publications

References 26 publications

Crystal structure of 4,5-bis(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole methanol monosolvate

Crystal structure of 4,5-bis(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole methanol monosolvate

A Domino Reaction of Pyridinium Salts: Efficient Synthesis of 4,5‐Disubstituted 1,2,3‐(NH)‐Triazoles

Synthesis and biological evaluation of novel 4,5-disubstituted 2H-1,2,3-triazoles as cis-constrained analogues of combretastatin A-4

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