2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma

Viswanathan, Anisha; Kute, Dinesh; Musa, Aliyu; Mani, Saravanan Konda; Sipilä, Vili; Emmert‐Streib, Frank; Zubkov, Fedor I.; Gurbanov, Atash V.; Yli‐Harja, Olli; Kandhavelu, Meenakshisundaram

doi:10.1016/j.ejmech.2019.01.021

Cited by 54 publications

(33 citation statements)

References 72 publications

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“…Due to the electrophilic nature of I we envisaged that nucleophilic partners such as enol silyl ethers of 1,3‐diketones, that have been recently investigated as coupling partners for N ‐centered radicals could be ideal traps for this intermediate. Worth noting, the thus formed azaderivatives have several applications as bioactive compounds as well as precursors of azo‐substituted heterocycles…”

Section: Methodsmentioning

confidence: 99%

Aryldiazenyl Radicals from Arylazo Sulfones: Visible Light‐Driven Diazenylation of Enol Silyl Ethers

et al. 2020

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A versatile protocol for the diazenylation of enol silyl ethers under visible light irradiation is presented herein. The reaction is based on the underused reaction of a nitrogen-based radical (the diazenyl radical) with an enol silyl ether. Arylazo sulfones were used as photoactivatable precursors of these diazenyl radicals. The resulting azaderivatives are potentially bioactive compounds as well as starting materials for the synthesis of N-containing heterocycles.

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Section: Methodsmentioning

confidence: 99%

Aryldiazenyl Radicals from Arylazo Sulfones: Visible Light‐Driven Diazenylation of Enol Silyl Ethers

et al. 2020

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“…Chemical transformations comprising carbon-carbon and carbon-heteroatom bond-formation reactions are fundamental tools in modern synthetic organic chemistry (Yadigarov et al, 2009;Abdelhamid et al, 2011;Khalilov et al, 2011;Yin et al, 2020). They are also used for the synthesis of valuable building blocks in medicinal chemistry, coordination chemistry and material science (Mahmoudi et al, 2017(Mahmoudi et al, , 2019Viswanathan et al, 2019).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 6-amino-8-(2,6-dichlorophenyl)-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbonitrile

Naghiyev¹,

Tereshina²,

Khrustalev³

et al. 2021

Acta Cryst E

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In the molecular structure of the title compound, C16H13Cl2N5, the 1,4-dihydropyridine ring of the 1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine ring system adopts a screw-boat conformation, while the 1,3-diazinane ring is puckered. In the crystal, intermolecular N—H...N and C—H...N hydrogen bonds form molecular sheets parallel to the (110) and (\overline{1}10) planes, crossing each other. Adjacent molecules are further linked by C—H...π interactions, which form zigzag chains propagating parallel to [100]. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from N...H/H...N (28.4%), H...H (24.5%), C...H/H...C (21.4%) and Cl...H/H...Cl (16.1%) contacts.

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“…N-heterocyclic compounds are of interest in the fields of synthetic organic chemistry, coordination chemistry and medicinal chemistry because of their important biological properties (Mahmoudi et al, 2016(Mahmoudi et al, , 2017a(Mahmoudi et al, ,b,c, 2018aViswanathan et al, 2019). For this reason, many approaches have been developed for their efficient and versatile synthesis (Gurbanov et al, 2017(Gurbanov et al, , 2018aMa et al, 2017a,b).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (3aR,4S,7S,7aS)-4,5,6,7,8,8-hexachloro-2-{6-[(3aR,4R,7R,7aS)-4,5,6,7,8,8-hexachloro-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl]hexyl}-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

et al. 2021

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The molecule of the title compound, C24H16Cl12N2O4, is generated by a crystallographic inversion centre at the midpoint of the central C—C bond. A kink in the molecule is defined by a torsion angle of −169.86 (15)° about this central bond of the alkyl bridge. The pyrrolidine ring is essentially planar [max. deviation = 0.014 (1) Å]. The cyclohexane ring has a boat conformation, while both cyclopentane rings adopt an envelope conformation. In the crystal structure, molecules are linked by intermolecular C—H...O, C—H...Cl and C—Cl...π interactions, and short intermolecular Cl...O and Cl...Cl contacts, forming a three-dimensional network.

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2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma

Cited by 54 publications

References 72 publications

Aryldiazenyl Radicals from Arylazo Sulfones: Visible Light‐Driven Diazenylation of Enol Silyl Ethers

Aryldiazenyl Radicals from Arylazo Sulfones: Visible Light‐Driven Diazenylation of Enol Silyl Ethers

Crystal structure and Hirshfeld surface analysis of 6-amino-8-(2,6-dichlorophenyl)-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbonitrile

Crystal structure and Hirshfeld surface analysis of (3aR,4S,7S,7aS)-4,5,6,7,8,8-hexachloro-2-{6-[(3aR,4R,7R,7aS)-4,5,6,7,8,8-hexachloro-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl]hexyl}-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

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