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Growing Science » Tags cloud » Heterocyclization

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1.

N-(5-(Dichloromethylene)-2-oxoimidazolidin-4-ylidene)sulfonamides: Small molecules with big synthetic capabilities Pages 817-830 PDF Download PDF

Authors: Svitlana A. Chumachenko, Oleh V. Shablykin, Svitlana V. Shishkina, Andrii V. Kozytskyi, Olga V. Shablykina

doi 10.5267/j.ccl.2025.8.002

๐Ÿ”‘ Keywords: 2-Amino-3, 3-dichloroacrylonitrile, Hydantoin, Heterocyclization, Alkylation, Arylation

Abstract:
A number of 5-dichloromethylidene-4-sulfonyliminohydantoins were synthesized by the reaction of 2-amino-3,3-dichloroacrylonitrile (ADAN) with aryl and alkyl isothiocyanates. These products are polyfunctional molecules that are considered as initial materials for the synthesis of bioactive compounds. The method of such derivatives multigram synthesis was optimized; also, the features of purification were described, and the main products of reaction mixture alcoholysis (acyclic carbamates) were identified for the first time. A number of modifications was carried out on the example of 5-dichloromethylidene-4-tosyliminohydantoin, namely: alkylation, hydrolysis of the amino group with subsequent arylation, substitution reaction with S-nucleophile, Suzuki โ€“ Miyaura coupling, and reduction of the dichloromethylidene fragment to the methyl group. The anticancer activity of 5-dichloromethylidene-4-tosyliminohydantoin was shown.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 4 | Views: 299

 
2.

Synthesis and evaluation of cytotoxic and antimicrobial activity of some 3-aryl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines Pages 549-556 PDF Download PDF

Authors: Abdukhakim Ziyaev, Ekaterina Terenteva, Rasul Okmanov, Sobirdjan Sasmakov, Turdibek Toshmurodov, Umida Khamidova, Muqaddas Umarova, Shakhnoz Azimova

doi 10.5267/j.ccl.2024.2.004

๐Ÿ”‘ Keywords: Heterocyclization, 5-aryl-1, 3, 4-oxadiazole-2-thiones, 3-aryl-6-phenyl-7H-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazines, Cytotoxicity, antimicrobial activity

Abstract:
3-aryl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines were obtained with good yields (81-95%) via the heterocyclization reaction of 1-phenyl-2-((5-aryl-1,3,4-oxadiazole-2-yl)thio)ethane-1-ones in acetic acid. The physicochemical characteristics of the synthesized compounds were established, the structures were confirmed by the data of IR, 1H and 13C NMR spectra, as well as the results of X-ray diffraction analysis. The cytotoxic, antibacterial and antifungal properties of these compounds were evaluated. In vitro screening results showed that compounds 8, 9 and 12 significantly inhibit (54-65%) the growth of HeLa, HBL-100 and CCRF-CEM cancer cell lines. It was found that the cytotoxicity of the synthesized compounds increases in the series of oxadiazoltiones (1-4) - S-derivatives (5-8) - triazolothiadiazines (9-12). Compounds 5-16 do not exhibit antimicrobial properties.
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Journal: CCL | Year: 2024 | Volume: 13 | Issue: 3 | Views: 876

 
3.

Interaction of two heterocyclic Schiff bases derived from 2-acetyl pyridine on mild steel in hydrochloric acid: Physicochemical and corrosion inhibition investigations Pages 19-30 PDF Download PDF

Authors: M. Paulson Binsi, Thomas K. Joby, K. Ragi, Varghese C. Sini, Johnson Reeja

doi 10.5267/j.ccl.2019.6.005

๐Ÿ”‘ Keywords: (Z)-N-(5-(Dichloromethylene)-2-oxoimidazolidin-4-ylidene)-N'-substituted sulphonamides, Heterocyclization, Anticancer Activity

Abstract:
Two heterocyclic Schiff bases namely (E)-2-(1-(2-phenylhydrazono)ethyl)pyridine (or 2-acetyl pyridine phenyl hydrazone) (2APPH) and (E)-2-(1-triazylidineethyl)pyridine (or 2-acetyl pyridine semicarbazone) (2APSC) were synthesized, characterized and their corrosion inhibition behaviour as well as mechanism of inhibition were investigated by different techniques. Structural characterization includes NMR, Mass, IR and UV-visible spectroscopy and elemental analysis. Corrosion inhibition behaviour of aforesaid compounds on mild steel in 1M hydrochloric acid was examined by electrochemical methods including potentiodynamic polarization analysis and electrochemical impedance spectroscopic techniques. The mechanism of corrosion inhibition was explored and supplemented by adsorption and surface morphological studies. Quantum mechanical investigations on corrosion behaviour of compounds were also conducted and satisfying correlation was noticed between the results of corrosion measurement methods and quantum mechanical evaluations.
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Journal: CCL | Year: 2020 | Volume: 9 | Issue: 1 | Views: 2003

 
4.

Synthesis and anticancer activity of new substituted imidazolidinone sulfonamides Pages 199-210 PDF Download PDF

Authors: Oleh V. Shablykin, Yurii Eu. Kornii, Victoriya V. Dyakonenko, Olga V. Shablykina, Volodymyr S. Brovarets

doi 10.5267/j.ccl.2019.5.003

๐Ÿ”‘ Keywords: (Z)-N-(5-(Dichloromethylene)-2-oxoimidazolidin-4-ylidene)-N'-substituted sulphonamides, Heterocyclization, Anticancer Activity

Abstract:
Obtained by the interaction of 2-amino-3,3-dichloroacrylonitrile and chlorosulphonyl isocyanate (Z)-(5-(dichloromethylene)-2-oxoimidazolidin-4-ylidene)sulfamoyl chloride reacts easily with excess of the aliphatic amine to form new (Z)-N-(5-(dichloromethylene)-2-oxoimidazolidin-4-ylidene)-N'-substituted sulfonamides. According to the National Cancer Institute (USA) examinations, two of the six synthesized sulfonamides showed a high anticancer activity.
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Journal: CCL | Year: 2019 | Volume: 8 | Issue: 4 | Views: 1988

 

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