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Tonkikh, N. N.; Strakovs, A.; Петрова, М. В.

doi:10.1023/a:1024725716147

Cited by 4 publications

(3 citation statements)

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“…The following intermediates were obtained according to methods previously described: 2-[(dimethylamino)methylene]cyclohexan-1,3-dione 7a , 2-[(dimethylamino)methylene]-5,5-dimethylcyclohexan-1,3-dione 7b , and 2-[(dimethylamino)methylene]-5-phenylcyclohexan-1,3-dione 7c ; 2-methyl-7,8-dihydroquinazolin-5(6 H )-one 8b , 2-phenyl-7,8-dihydroquinazolin-5(6 H )-one 8c ; 6-[(dimethylamino)methylene]-2-methyl-7,8-dihydroquinazolin-5(6 H )-one 9b , 6-[(dimethylamino)methylene]-2-phenyl-7,8-dihydroquinazolin-5(6 H )-one 9c ; N -(4-aminosulfonyl)phenylguanidine carbonate 10 …”

Section: Methodsmentioning

confidence: 99%

“…The 1,3-bielectrophilic reaction of 7a with nucleophilic reagents, formamidine, acetamidine, or benzamidine hydrochloride in refluxing ethanol for 15–30 h (TLC analysis) led to the pyrimidine derivatives 8a – c , that were then reacted with an excess of DMF-DMA at 100 °C for 1 h to obtain the intermediates 9a – c in very good yields. , Derivatives 9a – c were then solubilized in ethanol and reacted with a slight excess of commercial 4-hydrazinebenzenesulfonamide hydrochloride, basically according to described procedures. − The reaction mixture was heated to 80 °C for 20 h and, after cooling, the obtained crude compounds 4a – c were purified by flash chromatography (Scheme ). Similarly, the synthesis of the new bicyclic tetrahydroindazoles 5a – c and tetrahydroquinazoles 6a – c took advantage of the reactivity of derivatives 7a – c (Scheme ).…”

Section: Chemistrymentioning

confidence: 99%

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4-Substituted Benzenesulfonamides Incorporating Bi/Tricyclic Moieties Act as Potent and Isoform-Selective Carbonic Anhydrase II/IX Inhibitors

et al. 2018

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As a part of our efforts to expand chemical diversity in the carbonic anhydrases inhibitors (CAIs), three small series of polyheterocyclic compounds (4-6) featuring the primary benzenesulfonamide moiety linked to bi/tricyclic scaffolds were investigated. Highly effective inhibitors against the target tumor-associated hCA IX (low nanomolar/subnanomolar potency levels) showing significant functional selectivity profile toward hCA I, II, and IV isozymes were identified. Molecular docking studies clarified the reasons behind the activity and selectivity of the new compounds.

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Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

4-Substituted Benzenesulfonamides Incorporating Bi/Tricyclic Moieties Act as Potent and Isoform-Selective Carbonic Anhydrase II/IX Inhibitors

et al. 2018

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“…In continuation of studies on the modification of hydrogenated indazoles and quinazolines, mainly in their carbocyclic structural fragment [1][2][3][4][5], we have turned to the synthesis of 3-aryl-4-oxo-4,5,6,7-tetrahydroindazoles. Two schemes are known for their synthesis.…”

mentioning

confidence: 99%

3-Aryl- and 2,3-Diaryl-4-oxo-4,5,6,7-tetrahydroindazoles. 1. Reactions of Phenyl- and Tosylhydrazones of Dimedone and Cyclohexane-1,3-dione with Substituted Benzaldehydes

Strakova

Strakovs

Петрова

2005

Chem Heterocycl Compd

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Keywords: 3-aryl-and 2,3-diaryl-4-oxo-4,5,6,7-tetrahydroindazoles, substituted benzaldehydes, phenyland tosylhydrazones of cyclohexane-1,3-diones.In continuation of studies on the modification of hydrogenated indazoles and quinazolines, mainly in their carbocyclic structural fragment [1-5], we have turned to the synthesis of 3-aryl-4-oxo-4,5,6,7-tetrahydroindazoles. Two schemes are known for their synthesis. One is the interaction of enehydrazines, obtained from cyclohexane-1,3-diones and benzenesulfonic acid hydrazide, with aromatic aldehydes [6], and the other is the interaction of 2-benzoylcyclohexane-1,3-diones with hydrazines [7]. 2,3-Diaryl-4-oxo-4,5,6,7-tetrahydroindazoles are obtained by the interaction of phenylhydrazones of cyclohexane-1,3-diones with aromatic aldehydes [8] and by the reaction of 2,3-diphenyl-1,3,4-oxadiazolium perchlorate with dimedone [9].We selected the reaction of 3-enehydrazino-2-cyclohexen-1-ones with aromatic aldehydes for the synthesis of 3-aryl-and 2,3-diaryl-4-oxo-4,5,6,7-tetrahydroindazoles [6,8]. Such a selection was made, in spite of the extremely large number of known 2-aroylcyclohexane-1,3-diones [10-13] many of which are herbicides, because of the simplicity of the synthesis and the availability of a wide selection of aldehydes.In the present work 16 new 2,3-diaryl-4-oxo-4,5,6,7-tetrahydroindazoles 6 were synthesized by the reaction of phenylhydrazones of dimedone 2,3A and cyclohexane-1,3-dione 2,3B with substituted benzaldehydes 4.It was shown previously [8] that on boiling the reactants in alcohol for 15 min pyrazolines of type 5 are formed predominantly with only a little of their dehydrogenation products 6. However the procedure for separating these compounds is complex, and in addition pyrazolines 5 are unstable. We selected more rigid reaction conditions, heating a solution of equimolar quantities of reactants in DMSO at 100°C for 3-4 h, which leads to the formation of compounds 6 exclusively (Table 1).

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