Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles

Abstract

Some N-(3,5-di-/1,3,5-trimethylpyrazole-4-yl)-4-substitutedbenzamide derivatives were prepared as possible antiociceptiveantimicrobial agents. New amide derivatives (3-12) were synthesized by reacting 4-amino-3,5-di and 1,3,5-trimethylpyrazoles with 4-substitutedbenzoyl chlorides. Hotplate and tail-immersion tests were used for the determination of the antinociceptive activity. Morphine, was used as a standard test drug. All compounds were administered at a dose of 100 mg/kg ip and some of them had significant antinociceptive activity in both tests. Compound 10 (N-(1,3,5-trimethylpyrazole-4-yl)-4-bromobenzamide), was the most active one in both tests among the compounds. The antinociceptive activity of the compounds 10, 11 (N-(1,3,5-trimethylpyrazole-4-yl)-4-chlorobenzamide), and 12 (N-(1,3,5-trimethylpyrazole-4-yl)-4-fluorobenzamide), started at 30 minutes and continued up to 150 minutes in the hotplate test. Also compounds were tested for their in vitro antimicrobial activity, but exhibited weak antibacterial activity.

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

“…The peaks were observed due to the specific fragmentations of compounds seen in Supporting Information Figure S2. The fragmentation patterns were compatible with the literature . For the thiourea derivatives, the bond between NH and CS was cleaved and the H atom on the nitrogen migrated to the other NH and isothiocyanate and amine were formed.…”

Anticonvulsant activity of 3,5-dimethylpyrazole derivatives in animal models

“…Target compounds 1-10 were prepared by reacting compound A with appropriate substituted carboxylic acids, benzoyl chlorides and benzaldehydes. Physicochemical and spectroscopic characterizations of the amide derivatives 1, 4 and 5 have been previously described (Kocyigit-Kaymakcioglu et al, 2008). The other pyrazole compounds, newly described here, were isolated in satisfactory yields (41-84%) and purified by recrystallisation from ethanol.…”

“…Compounds 1-10 were prepared by reacting the 4-amino-3,5-dimethylpyrazole with appropriate substituted benzoyl chlorides, carboxylic acids and benzaldehydes. Physicochemical and spectroscopic characterization of the amide derivatives 1, 4 and 5 have been previously described (Kocyigit-Kaymakcioglu et al, 2008).…”

“…ESI-MS (m/ z): 457 (MH ? ).N-(1-(4-chlorobenzoyl)-3,5-dimethylpyrazole-4-yl)-4-chlorobenzamide 4:58% yield, mp 196-198°C (Kocyi- git-Kaymakcioglu et al, 2008).N-[1-(4-methylbenzoyl)-3,5-dimethylpyrazole-4-yl]-4-methylbenzamide 5: 84% yield, mp 201°C(Kocyigit- Kaymakcioglu et al, 2008).…”

Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core

“…The structures of the obtained compounds were elucidated by spectral data. The IR spectra of 3a-f showed two separate bands resulting from the N-H and C=O streching bands of the amide function at about regions 3402-3277 and 1685-1653 cm -1 , respectively (19,20). In the spectra of 1 H-NMR of 3a-f the CH 2 and CONH of the acetylamino moiety were observed as a double singlets presumably due to the partial double bond character of the C-N bond and the bulk of the attached cyclohexyl structure which can disrupt free rotation about the cited bond (δ 3.73-3.35 and δ 10.41-10.16 ppm, respectively) (21).…”