Novel Derivatives of Methyl and Ethyl 2-(4-Oxo-8-Aryl-2H-3,4,6,7-tetrahydroimidazo[2,1-c] [1,2,4]triazin-3-yl)acetates from Biologically Active 1-Aryl-2-hydrazinoimidazoles: Synthesis Crystal Structure and Antiproliferative Activity.

ChemInform ◽  
2007 ◽  
Vol 38 (16) ◽  
Author(s):  
Krzysztof Sztanke ◽  
Jolanta Rzymowska ◽  
Maciej Niemczyk ◽  
Izabela Dybala ◽  
Anna E. Koziol
Keyword(s):  
Crystal Structure ◽  
Antiproliferative Activity ◽  
Biologically Active ◽  
Derivatives Of

scholarly journals New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity

Crystals ◽  
2017 ◽  
Vol 7 (1) ◽  
pp. 15 ◽  
Author(s):  
Monika Kadela-Tomanek ◽  
Maria Jastrzębska ◽  
Ewa Bębenek ◽  
Elwira Chrobak ◽  
Małgorzata Latocha ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Antiproliferative Activity ◽  
Acetylenic Amine ◽  
Derivatives Of

Thiourea and thioether derivatives of sorafenib: synthesis, crystal structure, and antiproliferative activity

2012 ◽  
Vol 22 (8) ◽  
pp. 3959-3968 ◽  
Author(s):  
Jianwen Yao ◽  
Jing Chen ◽  
Zuopeng He ◽  
Wei Sun ◽  
Hao Fang ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Antiproliferative Activity ◽  
Derivatives Of

A new biologically active molecular scaffold: crystal structure of 7-(3-hydroxyphenyl)-4-methyl-2H-[1,2,4]triazolo[3,2-c][1,2,4]triazole and selective antiproliferative activity of three isomeric triazolo–triazoles

2019 ◽  
Vol 75 (10) ◽  
pp. 1398-1404
Author(s):  
Sandra Fusco ◽  
Domenica Capasso ◽  
Roberto Centore ◽  
Sonia Di Gaetano ◽  
Emmanuele Parisi
Keyword(s):  
Crystal Structure ◽  
Cell Lines ◽  
Antiproliferative Activity ◽  
Normal Cell ◽  
Crystal Structure Analysis ◽  
Biologically Active ◽  
Planar Geometry ◽  
Molecular Scaffold ◽  
Crystallographic Axes ◽  
Infinite Planar

A study of three isomeric compounds containing a phenolic moiety attached to the nitrogen-rich triazolo–triazole bicycle is presented. In the three isomers, the phenolic OH group is in the ortho, meta and para positions. The crystal structure analysis of the meta isomer (C10H9N5O) shows that the 2H-tautomer is present in the crystal and that the molecule adopts a substantially planar geometry. However, the conformation found in the crystal is different compared to the monoprotonated cation of the same compound previously investigated in several salts. The packing of the meta isomer is driven by the formation of strong hydrogen bonds and shows the formation of infinite planar ribbons, parallel to a, formed around 21 crystallographic axes. The three isomers were tested against some cancer cell lines and also against normal cell lines. The ortho isomer shows a weak antiproliferative activity, the meta isomer shows significant antiproliferative activity against some cancer lines and no activity against healthy cell lines, and the para isomer is active against all the tested cell lines.

SOME DIRECTIONS IN THE MODIFICATION OF AZOLES

2020 ◽  
Vol 5 (443) ◽  
pp. 85-91
Author(s):  
Ibrayev M.K., ◽  
◽  
Takibayeva A.T., ◽  
Fazylov S.D., ◽  
Rakhimberlinova Zh.B., ◽  
...  
Keyword(s):  
13C Nmr Spectroscopy ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Synthesis Conditions ◽  
Alkaloid Cytisine ◽  
Azole Ring ◽  
Cyclic Compounds ◽  
New Compounds ◽  
Derivatives Of

This article presents studies on the targeted search for new derivatives of azoles, such as benzthiazole, 3,5-dimethylpyrazole, 1,3,4-oxadiazole-2-thione, 1,3,4-thiadiazole. The possibility of combining in one molecule of the azole ring with other cyclic compounds: the alkaloid cytisine, morpholine, furan and some arenes has been studied. To obtain new compounds, the reactions of bromination, acylation, and interaction with isothiocyanates were studied. Optimal synthesis conditions were studied for all reactions. It was found that the reaction of 4-bromo-3,5-dimethylpyrazole with isothiocyanates, in contrast to the previously written derivatives of anilines, takes a longer time and requires heating the reaction mixture. The combination of a pirasol fragment with halide substituents often results in an enhanced therapeutic effect. The synthesized 2-bromine-N-(6-rodanbenzo[d]thiazole-2-yl)acetamide, due to the alkylbromide group, is an important synth in the synthesis of new benzthiazole derivatives. Its derivatives combine in one molecule the rest of rhodanbenzthiazole with alkaloid cytisine and biogenic amine morpholine and are potentially biologically active compounds, since the molecule structure contains several pharmacophoric fragments: benzthiazole and alkaloid (amine) heterocycles, rhodane and urea groups. The mechanism of formation of 1,3,4-oxadiazole-2-tyons from hydrazides under action on them by carbon disulfide was studied and assumed. It was shown that dithiocarbamates in acidic medium decompose with the release of hydrogen sulfide and the formation of highly reactive isothiocyanate group. Then, intra-molecular cyclization occurs, with the formation of end products - 1,3,4-oxadiazole-2-thions. The structures of the synthesized compounds were studied by 1H and 13C NMR spectroscopy. All synthesized substances are potentially biologically active compounds, since they contain several pharmacophore fragments in their structure.

scholarly journals Quantum-Chemical Search for Keto Tautomers of Azulenols in Vacuo and Aqueous Solution

Symmetry ◽  
2021 ◽  
Vol 13 (3) ◽  
pp. 497
Author(s):  
Ewa D. Raczyńska
Keyword(s):  
Aqueous Solution ◽  
Quantum Chemical ◽  
Biologically Active ◽  
Deprotonation Reaction ◽  
Chemical Studies ◽  
Quantum Chemical Studies ◽  
Scanty Information ◽  
Derivatives Of ◽  
Common Anion ◽  
Tautomeric Mixture

Keto-enol prototropic conversions for carbonyl compounds and phenols have been extensively studied, and many interesting review articles and even books appeared in the last 50 years. Quite a different situation takes place for derivatives of biologically active azulene, for which only scanty information on this phenomenon can be found in the literature. In this work, quantum-chemical studies have been undertaken for symmetrically and unsymmetrically substituted azulenols (constitutional isomers of naphthols). Stabilities of two enol (OH) rotamers and all possible keto (CH) tautomers have been analyzed in the gas phase {DFT(B3LYP)/6-311+G(d,p)} and also in aqueous solution {PCM(water)//DFT(B3LYP)/6-311+G(d,p)}. Contrary to naphthols, for which the keto forms can be neglected, at least one keto isomer (C1H, C2H, and/or C3H) contributes significantly to the tautomeric mixture of each azulenol to a higher degree in vacuo (non-polar environment) than in water (polar amphoteric solvent). The highest amounts of the CH forms have been found for 2- and 5-hydroxyazulenes, and the smallest ones for 1- and 6-hydroxy derivatives. The keto tautomer(s), together with the enol rotamers, can also participate in deprotonation reaction leading to a common anion and influence its acid-base properties. The strongest acidity in vacuo exhibits 6-hydroxyazulene, and the weakest one displays 1-hydroxyazulene, but all azulenols are stronger acids than phenol and naphthols. Bond length alternation in all DFT-optimized structures has been measured using the harmonic oscillator model of electron delocalization (HOMED) index. Generally, the HOMED values decrease for the keto tautomers, particularly for the ring containing the labile proton. Even for the keto tautomers possessing energetic parameters close to those of the enol isomers, the HOMED indices are low. However, some kind of parallelism exists for the keto forms between their relative energies and HOMEDs estimated for the entire molecules.

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