Synthesis of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides and N-substituted sulfonamides

Kornienko, A. N.; Пильо, С. Г.; Прокопенко, В. М.; Броварец, В. С.

doi:10.1134/s1070363212110229

Cited by 8 publications

(7 citation statements)

References 8 publications

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“…4‐Cyano‐1,3‐oxazole‐5‐sulfonyl amides 19 ‐ 22 have been synthesized according to the procedure from sulfonyl chlorides 17 or 18 by refluxing with appropriate amine and excess of triethylamine (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…2‐Acylamino‐3,3‐dichloroacrylonitriles 1–4 and its synthetic procedure were described in . 4‐Cyano‐2‐(4‐methylphenyl)‐1,3‐oxazole‐5‐sulfonyl chloride ( 17 ) and 4‐cyano‐2‐phenyl‐1,3‐oxazole‐5‐sulfonyl chloride ( 18 ) were synthesized previously from appropriate enamide 1 or 2 . Methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate ( 24 ) have been synthesized by the method described in the literature …”

Section: Methodsmentioning

confidence: 99%

“…The latter were converted into the corresponding sulfonyl derivatives 12-16 by oxidation with hydrogen peroxide. [46] 4-Cyano-1,3-oxazole-5-sulfonyl amides 19-22 have been synthesized according to the procedure [35] from sulfonyl chlorides 17 or 18 [47] by refluxing with appropriate amine and excess of triethylamine (Scheme 2).…”

Section: Chemistrymentioning

confidence: 99%

“…[56] 2-Acylamino-3,3dichloroacrylonitriles 1-4 and its synthetic procedure TABLE 2 Anticancer activity of 5-amino-4-cyano-1,3-oxazoles 5, 6, its sulphonamide analogs 21, 22, 5-arylsulfanyl-(7-9), its 5-sulfonyl analogs (12)(13)(14)(15)(16) were described in. [43,44] 4-Cyano-2-(4-methylphenyl)-1,3oxazole-5-sulfonyl chloride (17) and 4-cyano-2-phenyl-1,3-oxazole-5-sulfonyl chloride (18) were synthesized previously [47] from appropriate enamide 1 or 2. Methyl 5-chlorosulfonyl-2-phenyl-1,3-oxazole-4-carboxylate (24) have been synthesized by the method described in the literature.…”

Section: Chemistrymentioning

confidence: 99%

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Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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A series of new 1,3‐oxazole derivatives, containing in position 5 both donor and acceptor substituents were synthesized. These substances were considered as potentially active anticancer pharmacophores in the human tumor cell line panel derived from nine cancer types, including lung, colon, melanoma, renal, ovarian, brain, leukemia, breast, and prostate. Primary in vitro one‐dose anticancer screening was shown that compounds with acceptor substituents (such as –C(O)OMe, –CN) in the position 5 inhibit the growth of most cell lines, and compounds with donor substituents (such as –NHR, −SR) in the position 5 do not practically inhibit the growth of cancer cell lines. It can be assumed that the pharmacological activity of 1,3‐oxazole derivatives depends on donor/acceptor nature of the substituents in position 5. It was proposed to evaluate the donor/acceptor ability of 1,3‐oxazole derivatives using the special parameter φ0, which takes into account the relative position of the boundary levels (HOMO end LUMO). The quantum‐chemical modeling was performed; the special parameter φ0 for 1,3‐oxazole derivatives correlates with the experimental results. Quantum‐chemical calculations of the special parameter φ0 allow modeling the pharmacological activity of 1,3‐oxazole derivatives by introducing donor or acceptor substituents at position 2 or 5. This work may be useful for chemists to develop a target synthesis of potential biologically active compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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“…4-Ціано-1,3-oксазол-5-сульфоніламіди 4 було синтезовано із 2 феніл-4-ціано-1,3-oк са зол-5-сульфонілхлоридів 3 [11] реакцією їх з відповідними амінами або аміаком (схема 2).…”

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Пошук Та Синтез Противірусних Агентів Серед Похідних Азотистих Гетероциклів

Качаєва¹

2021

Visn. Nac. Akad. Nauk Ukr.

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У статті йдеться про ряд нових синтезованих азотовмісних гетероциклічних сполук і дослідження їх активності проти вірусів, що спричиняють опортуністичні інфекції (цитомегаловірус людини, вірус папіломи людини, поліовірус і поліомавірус людини). Виявлено найактивніші сполуки — так звані структури-лідери, які характеризуються високим рівнем інгібування вірусної реплікації та значною селективністю дії щодо цитомегаловірусу, поліовірусу та папіломавірусу. Вивчено залежність їх активності від структури.

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In vitro activity of novel derivatives of 1,3-oxazole-4-carboxylate and 1,3-oxazole-4-carbonitrile against human cytomegalovirus

et al. 2019

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Synthesis of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides and N-substituted sulfonamides

Cited by 8 publications

References 8 publications

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Пошук Та Синтез Противірусних Агентів Серед Похідних Азотистих Гетероциклів

In vitro activity of novel derivatives of 1,3-oxazole-4-carboxylate and 1,3-oxazole-4-carbonitrile against human cytomegalovirus

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