Fluorine containing heterocyclic compounds: synthesis of 6-substituted-2-substituted-aryl-1,2,4-triazolo[5,1-b] 1,3,5-thiadiazin-7-one derivatives

Liu, Suyou; Qian, Xuhong; Song, Gonghua; Chen, Jing; Chen, Weidong

doi:10.1016/s0022-1139(00)00287-6

Cited by 21 publications

(9 citation statements)

References 13 publications

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“…1 H and 13 C NMR spectra were recorded on a Bruker DPX-400 FT NMR spectrometer using tetramethylsilane as the internal standard DMSO-6 as a solvent (chemical shifts in , ppm). 19 F NMR spectra were determined at 84.25 MHz using hexafluorobenzene as an internal standard. Splitting patterns were designated as follows: s: singlet; m: multiplet.…”

Section: Methodsmentioning

confidence: 99%

“…In the past few years fluorine substituted heterocyclic nitrogen systems have been incorporated into drug discovery research [11][12][13][14][15][16][17][18][19][20][21][22][23] to improve the physicochemical properties of drugs. Organic fluorine is a prominent tool in the design and improvement of pharmacokinetic properties of drug molecules.…”

Section: Introductionmentioning

confidence: 99%

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Fluorine Substituted 1,2,4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitors

Makki

Abdel‐Rahman

Khan

2014

Journal of Chemistry

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Fluorine substituted 1,2,4-triazinones have been synthesized via alkylation, amination, and/or oxidation of 6-(2-amino-5-fluorophenyl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one 1 and 4-fluoro-N-(4-fluoro-2-(5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl)phenyl)benzamide 5 as possible anti-HIV-1 and CDK2 inhibitors. Alkylation on positions 2 and 4 in 1,2,4triazinone gave compounds 6-8. Further modification was performed by selective alkylation and amination on position 3 to form compounds 9-15. However oxidation of 5 yielded compounds 16-18. Structures of the target compounds have been established by spectral analysis data. Five compounds (5, 11, 14, 16, and 17) have shown very good anti-HIV activity in MT-4 cells. Similarly, five compounds (1, 3, and 14-16) have exhibited very significant CDK2 inhibition activity. Compounds 14 and 16 were found to have dual anti-HIV and anticancer activities.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorine Substituted 1,2,4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitors

Makki

Abdel‐Rahman

Khan

2014

Journal of Chemistry

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“…The reaction of carboxylic acid chlorides 1 and thiosemicarbazide gave 2, which without purification were cyclized in alkaline media to yield the corresponding 2,4-dihydro-3H--1,2,4-triazole-3-thiones 3 [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] …”

Section: Synthesis Of 24-dihydro-3h-mercapto/thione-124-triazolesmentioning

confidence: 99%

The chemistry of mercapto- and thione- substituted 1,2,4-triazoles and their utility in heterocyclic synthesis

Shaker¹

2006

Arkivoc

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“…In the past few years fluorinated heterocyclic systems have been incorporated into drug discovery research [1][2][3][4][5][6][7][8][9][10][11][12] to improve the drug physicochemical properties and the antibacterial potency.…”

Section: Introductionmentioning

confidence: 99%

Designing and Synthesis of New Fluorine Substituted Pyrimidine-Thion-5-Carbonitriles and the Related Derivatives as Photochemical Probe Agents for Inhibition of Vitiligo Disease

Makki¹,

Bakhotmah²,

Abdel‐Rahman³

et al. 2012

IJOC

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A new biocidal agents fluorine substituted-3-thioxopyrimidine-5-carbonitriles (2-9) and/or the related fluorine substituted pyrimido (4,5-d) pyrimidines (10)(11)(12)(13)(14) were synthesized by the cycloaddition of fluorinated β-arylidine malononitriles (1a-c) followed by a nucleophilic attack against α,β-bifunctional reagents in different conditions. Structures of the fluorine targets were characterized by their elemental analysis and spectral data (UV, IR, 1 H NMR, 13C NMR and mass measurements) and further evaluated as photochemical probe for inhibition of Vitiligo, it was found that compounds 5, 9, 11 and 12 exhibited high potency over the investigated compounds.

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Fluorine containing heterocyclic compounds: synthesis of 6-substituted-2-substituted-aryl-1,2,4-triazolo[5,1-b] 1,3,5-thiadiazin-7-one derivatives

Cited by 21 publications

References 13 publications

Fluorine Substituted 1,2,4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitors

Fluorine Substituted 1,2,4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitors

The chemistry of mercapto- and thione- substituted 1,2,4-triazoles and their utility in heterocyclic synthesis

Designing and Synthesis of New Fluorine Substituted Pyrimidine-Thion-5-Carbonitriles and the Related Derivatives as Photochemical Probe Agents for Inhibition of Vitiligo Disease

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