Synthesis of functionally substituted isoxazole and isothiazole derivatives

Поткин, В. И.; Петкевич, С. К.; Клецков, А. В.; Дикусар, Е. А.; Zubenko, Yu. S.; Zhukovskaya, N. A.; Казбанов, В. В.; Pashkevich, S. G.

doi:10.1134/s1070428013100205

Cited by 25 publications

(4 citation statements)

References 7 publications

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“…Initial [(5-aryl-1,2-oxazol-3-yl)methoxy]benzaldehydes 1a-1f were synthesized by the Williamson reaction [7], and isoxazole-and isothiazolecarbonyl chlorides 3a-3d were prepared as described in [9][10][11].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of functional isoxazole and isothiazole derivatives from [(5-arylisoxazol-3-yl)methoxy]arylmethanols

et al. 2016

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A procedure has been developed for the synthesis of functional isoxazole and isothiazole derivatives by reduction of (5-aryl-1,2-oxazol-3-yl)methoxybenzaldehydes to (5-aryl-1,2-oxazol-3-yl)methoxyarylmethanols and subsequent acylation of the latter with isoxazole-and isothiazolecarbonyl chlorides.1a, 2a, 4a-4d, R 1 = H, R 2 = 2-[(5-phenyl-1,2-oxazol-3-yl)methoxy]; 1b, 2b, 5a-5d, R 1 = H, R 2 = 2-{[5-(4-methylphenyl)-1,2oxazol-3-yl]methoxy}; 1c, 2c, 6a-6d, R 1 = H, R 2 = 4-{[5-(4-methylphenyl)-1,2-oxazol-3-yl]methoxy}; 1d, 2d, 7a-7d, R 1 = 4-MeO, R 2 = 2-{[5-(4-methylphenyl)-1,2-oxazol-3-yl]methoxy}; 1e, 2e, 8a-8d, R 1 = 3-MeO, R 2 = 4-{[5-(4-methylphenyl)-1,2-oxazol-3-yl]-methoxy}; 1f, 2f, 9c, 9d, R 1 = 3-EtO, R 2 = 4-{[5-(4-methylphenyl)-1,2-oxazol-3-yl]methoxy}; 3-9, R 3 = 5-phenyl-1,2-oxazol-3yl (a), 5-(4-methylphenyl)-1,2-oxazol-3-yl (b), 5-(2,5-dimethylphenyl)-1,2-oxazol-3-yl (c), 4,5-dichloro-1,2-thiazol-3-yl (d).

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Section: Methodsmentioning

confidence: 99%

Synthesis of functional isoxazole and isothiazole derivatives from [(5-arylisoxazol-3-yl)methoxy]arylmethanols

et al. 2016

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“…4,5-Дихлор-1,2-изотиазол-3карбонилхлорид получен по методике. [4] Моно-и диаминохлорины 2, 3 получены согласно. [5] Ацильные производные хлорина е 6 6 и 7 получены согласно методике.…”

Section: экспериментальная частьunclassified

Cytotoxic Chlorin e6 Derivatives with One or Two 4,5-Dichloro-1,2-thiazole Fragments

Белых¹,

Mal’shakova²,

Клецков³

et al. 2018

MHC

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Синтезированы производные хлорина е 6 с одним и двумя фрагментами 4,5-дихлор-1,2-тиазола. Хлориновый и дихлоризотиазольный циклы конъюгированы в реакции ацилирования аминогрупп периферических заместителей хлоринового макроцикла хлорангидридом 3-карбокси-4,5-дихлор-1,2-тиазола. Новые производные вызывали темновую гибель клеток линии рака толстой кишки в микромолярных концентрациях. Ключевые слова: Хлорин е 6 , дихлор-1,2-тиазол, темновая цитотоксичность, ацилирование, аминогруппа.

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“…Ester 2 further was alkylated with 3-chloromethyl-5phenylisoxazole 3a and 4,5-dichloro-3-chloromethylisothiazole 3b in DMF in the presence of anhydrous K 2 CO 3 and corresponding methyl 4-oxo-5-((5-phenylisoxazol-3-yl)methoxy)-4H-pyran-2carboxylate 4a and methyl 5-((4,5-dichloroisothiazol-3yl)methoxy)-4-oxo-4H-pyran-2-carboxylate 4b were synthesized. Chloromethyl derivatives of isoxazole and isothiazole 3a,b were prepared by reaction of (5-phenylisoxazol-3-yl)methanol and (4,5dichloroisothiazol-3-yl)methanol [21] with thionyl chloride as we reported before [18,22]. It should be noted that the alkylation with chloromethylisoxazole proceeded more slowly than alkylation with chloromethylisothiazole and the yield of ether 4a (51%) is considerably lower than that of ether 4b (78%).…”

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confidence: 99%

Synthesis and Biological Activity of Novel Comenic Acid Derivatives Containing Isoxazole and Isothiazole Moieties

Клецков

Поткин

Kolesnik

et al. 2018

Natural Product Communications

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Methyl 5-hydroxy-4-oxo-4H-pyran-2-carboxylate was synthesized by esterification of methanol with comenic acid under acidic catalysis. The obtained ester was alkylated with 3-(chloromethyl)-5-phenylisoxazole and 4,5-dichloro-3-(chloromethyl)isothiazole to afford corresponding conjugates containing isoxazole and isothiazole moieties which then were transformed into water-soluble Li-salts. During the bioassays of synthesized isoxazole and isothiazole derivatives of comenic acid in mixtures with first-line antitumor drug Temobel (Temozolomid) used in brain tumors chemotherapy, a synergetic effect was observed.

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Synthesis of functionally substituted isoxazole and isothiazole derivatives

Cited by 25 publications

References 7 publications

Synthesis of functional isoxazole and isothiazole derivatives from [(5-arylisoxazol-3-yl)methoxy]arylmethanols

Synthesis of functional isoxazole and isothiazole derivatives from [(5-arylisoxazol-3-yl)methoxy]arylmethanols

Cytotoxic Chlorin e6 Derivatives with One or Two 4,5-Dichloro-1,2-thiazole Fragments

Synthesis and Biological Activity of Novel Comenic Acid Derivatives Containing Isoxazole and Isothiazole Moieties

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