Synthesis, properties and biological activity ylidene derivatives of 2-oxoquinoline-4-carboxylic acid hydrazide

A.N. Dubrovin; A.I. Mikhalev; S.V. Ukhov; T.M. Konshina; V.V. Novikova; R.R. Makhmudov

Synthesis, properties and biological activity ylidene derivatives of 2-oxoquinoline-4-carboxylic acid hydrazide

A.N. Dubrovin¹, A.I. Mikhalev², S.V. Ukhov³, T.M. Konshina⁴, V.V. Novikova⁵, R.R. Makhmudov⁶

research article Pages: 14-20

¹ Post-graduate Student, Department, Biological Chemistry, Perm State Pharmaceutical Academy, Russia, Perm
² Dr. Sc. (Pharm.), Perm State Pharmaceutical Academy, Russia, Perm
^3,4,5 Ph. D. (Pharm.), Perm State Pharmaceutical Academy, Russia, Perm
⁶ Ph. D. (Pharm.), Institute of Natural Sciences, Perm State National Research University, Russia, Perm

Keywords: 2-oxo-1 2-dihydroquinoline-4-carboxylic acid ethyl ester 2-dihydroquinoline-4-carboxylic acid hydrazide 2-dihyd¬roquinoline-4-carboxylic acid ylidene derivatives antiinflammatory analgetic antimicrobial activity

Abstract

The synthesis of some previously unknown 2-oxo-1,2-dihydroquinoline-4-carboxylic acid ylidene hydrazide derivatives by heating of 2-oxo-1,2-dihydroquinoline-4-carboxylic acids with aldehydes or ketones in good yields is reported. The structures of synthesized compounds have been confirmed on the basic NMR H1 spectral data. Ethyl ester and 2-oxo-1,2-dihydroquinoline-4-carboxylic acid hydrazide have been screened on animals for their acute toxicity, antiinflammatory, analgesic and antimicrobial activity, as well 2-oxo-1,2-dihydroquinoline-4-carboxylic acid ylidene hydrazide derivatives as compared to the reference substances: diclofenac sodium, acetylsalicylic acid, metamizol sodium, dioxydinum. Synthesis technique 2-oxo-1,2-dihydroquinoline-4-carboxylic acid ylidene hydrazide derivatives can be used in preparative organic chemistry for synthesis of potentially biologically active quinoline-4-carboxylic acid derivatives.

How to cite

Дубровин А.Н., Михалев А.И., Ухов С.В., Коньшина Т.М., Новикова В.В., Махмудов Р.Р. Синтез, свойства и биологическая активность илиденовых производных гидразида 2-оксо-1,2-дигидрохинолин-4-карбоновой кислоты // Вопросы биологической, медицинской и фармацевтической химии. 2014. № 4. С. 14–20.

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[3] Milyutin A.V., Amirova L.R., Kolla V.E'. i dr. Amidy' i gidrazidy' aroilpiro-vinogradny'x kislot. Sintez, protivovospalitel'naya i anal'geticheskaya aktivnost' β-aroilpiruvoilgidrazidov 2-metil(fenil)-4-xinolinkarbonovy'x kislot // Ximiko-farmaczevticheskij zhurnal. 1998. T. 32. № 8. S. 24 - 26.

[4] Mixalev A.I., Kon'shin M.E., Kon'shina T.M. i dr. Sintez, protivovospalitel'naya i anal'geticheskaya aktivnost' zameshhenny'x amidov 1,2-digidro-2-okso- i 2-tioczin-xoninovy'x kislot // Ximiko-farmaczevticheskij zhurnal. 1997. T. 31. № 3. S. 37-38.

[5] Dubrovin A.N., Mixalev A.I., Uxov S.V. i dr. Sintez i svojstva 2-zameshhenny'x amidov czinxoninovoj kisloty' // Sovremenny'e problemy' nauki i obrazovaniya. 2012. № 4. (URL: www.science-education.ru/104-6630).

[6] Toldy L., Nogradi T. Vargha L. et. al. Antituberculosus agents // I. Thiosemicarbazones and hydrazides. Acta Chim. Acad. Sci. Hung. 1954. № 4. P. 303-313.

[7] Uxov S.V., Kon'shin M.E. Sintez proizvodny'x 2-arilamino-, 2-okso- i 2-xlorczinxo-ninovy'x kislot // Dep. v VINITI 19.03.96. № 837-V96. RZhXimiya 1996. № 20. Zh194.

[8] El Sayed H. El Ashry, El Sayed Ramadan, Hamida Abdel Hamid, Mohamed Hagar. Microwave‐Assisted Synthesis of Quinoline Derivatives from Isatin, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 2005. V. 35. P. 2243-2250.

[9] Xabriev R.U. Rukovodstvo po e'ksperimental'nomu (doklinicheskomu) izucheniyu novy'x farmakologicheskix veshhestv / pod obshhej red. R.U. Xabrieva. Izd. 2-e, pererab. i dop. M.: Mediczina. 2005. S. 41-53. 515 - 531. 695-709.

[10] Belen'kij M.L. E'lementy' kolichestvennoj oczenki farmakologicheskogo e'ffekta. 2-e izd. Leningrad. Medgiz. 1963. S. 81-106.

[11] Kolla V.E'., Sy'ropyatov B.Ja. Dozy' lekarstvenny'x sredstv i ximicheskix soedinenij dlya laboratorny'x zhivotny'x. M. Mediczina. 1998. 263 s.

[12] Pavlova M.V., Mixalev A.I., Kon'shin M.E. i dr. Sintez, protivovospalitel'naya i anal'geticheskaya aktivnost' 2-zameshhenny'x amidov czinxoninovoj kisloty' // Ximiko-farmaczevticheskij zhurnal. 1999. T. 33. № 8. S. 18-19.

[13] Syubaev R.F., Mashkovskij M.D., Shvarcz G.Ja., Pokry'shkin V.I. Sravnitel'naya farmakologicheskaya aktivnost' sovremenny'x nesteroidny'x protivovospalitel'ny'x preparatov // Ximiko-farmaczevticheskij zhurnal. 1986. T. 20. № 1. S. 33-39.

[14] Padejskaya E.N. Antibakterial'ny'j preparat dioksidin: osobennosti biologicheskogo dejstviya i znachenie v terapii razlichny'x form gnojnoj infekczii // Infekcziya i antimikrobnaya terapiya. 2001. T. 3. № 5. S. 55-56.

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