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Synthesis and Biological Evaluation of Some New Hydrazone Derivatives Bearing Pyrimidine Ring as Analgesic and Anti-Inflammatory Agents

100%

Akdağ K., Ünal G., Tok F., Arıcıoğlu F., Temel H. E., Kaymakcıoğlu-Koçyiğit B.

Acta Poloniae Pharmaceutica - Drug Research

2018

vol. 75

issue 5

1147-1159

New hydrazone derivatives were synthesized from 4-chloro-2-(methylthio)pyrimidine-5-carbohydrazide. Synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR, mass spectral data and elemental analysis. All compounds were investigated for analgesic and anti-inflammatory activity with hot plate test and biochemical assay, respectively. The results of anti-inflammatory activity showed that compound 2t had maximal Lipoxygenase (LOX) inhibition (66.30%) whereas inhibitions of 2a, 2c, 2i, 2k, 2l, 2m, 2p, 2s and 2u were observed between approximately 45-15 %. Our results also indicated that 15 compounds of 21 had analgesic effect in hot plate test. Analgesic effect of 2l, 2s, 2t began earlier than others while effect of 2i began at latest time. According to the activity results, compound 2t have significant analgesic and anti-inflammatory effects.

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

63%

Gajdoš P., Pavlíková S., Bureš F., Krutošíková A.

Open Chemistry

2005

vol. 3

issue 2

311-325

The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.

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1 Acta Poloniae Pharmaceutica - Drug Research

1 Open Chemistry

1 2018

1 2005

1 Akdağ K.

1 Arıcıoğlu F.

1 Bureš F.

1 Gajdoš P.

1 Kaymakcıoğlu-Koçyiğit B.

1 Krutošíková A.

1 Pavlíková S.

1 Temel H. E.

1 Tok F.

1 Ünal G.

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Synthesis and Biological Evaluation of Some New Hydrazone Derivatives Bearing Pyrimidine Ring as Analgesic and Anti-Inflammatory Agents

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions