(5R)-Ethyl 6-benzyl-8,8-dimethyl-7,9-dioxo-1-oxa-2,6-diaza­spiro­[4.4]non-2-ene-3-carboxyl­ate

In the title compound, C18H20N2O5, the pyrrolidine ring adopts an envelope conformation with the C atom bonded to the methyl groups as the flap. The dihydro­isoxazole ring is essentially planar (r.m.s. deviation = 0.041 Å) and forms a dihedral angle of 65.19 (6)° with the phenyl ring. In the crystal, neighbouring mol­ecules are linked into chains along [110] by inter­molecular C—H⋯O hydrogen bonds and weak C—H⋯π inter­actions involving the phenyl ring

(Z)-Benzyl 2-(5-methyl-2-oxoindolin-3-ylidene)hydrazinecarbodithioate

The title compound, C17H15N3OS2 was obtained from the condensation reaction of S-benzyl­dithio­carbazate and 5-methyl­isatin. In the solid-state, the mol­ecule adopts a Z configuration with the 5-methyl­isatin and di­thio­carbazate groups located on the same side of the C=N bond, involving an intra­molecular N—H⋯O hydrogen bond.Peer reviewe

Antinociceptive activity of a synthetic oxopyrrolidine-based compound, ASH21374, and determination of its possible mechanisms

This study was carried out to determine the antinociceptive activity of a novel synthetic oxopyrrolidine-based compound, (2R,3R,4S)-ethyl 4-hydroxy-1,2-dimethyl-5-oxopyrrolidine-3-carboxylate (ASH21374), and to elucidate the involvement of the opioid, vanilloid, glutamate, and nitric oxide – cyclic guanosine monophosphate (NO/cGMP) systems in modulating the observed antinociception. ASH21374, in the doses of 2, 10, and 100 mg/kg body mass, was administered orally to mice 60 mins prior to exposure to various antinociceptive assays. From the results obtained, ASH21374 exhibited significant (P< 0.05) antinociceptive activity in the abdominal constriction, hot-plate, and formalin tests that was comparable with 100 mg/kg acetylsalicylic acid or 5 mg/kg morphine, respectively. ASH21374 also attenuated capsaicin- and glutamate-induced paw licking. Pre-treatment with 5 mg/kg naloxone significantly (P< 0.05) inhibited the activity in all assays, while pretreatment with 10 mg/k-funaltraxamine, 1 mg/kg naltrindole, or 1 mg/kg nor-binaltorphimine significantly (P< 0.05) reversed the activity in the abdominal constriction test. L-Arginine,NG-nitro-L-arginine methyl esters (L-NAME), methylene blue, and their combinations, failed to inhibit the ASH21374 antinociceptive activity. In conclusion, ASH21374 demonstrated antinociceptive activities on the peripheral and central nervous systems, mediated through the activation of opioid receptors, inhibition of the glutamatergic system, and attenuation of vanilloid-mediated nociceptive transmission. Further studies have been planned to determine the pharmacological potential of ASH21374

New Access to Pyrano[2,3-<i>c</i>]pyrazole-3-carboxylates via Domino Four-Component Reaction and Their Antimicrobial Activity

A library of some novel classes of pyrano[2,3-c]pyrazole-3-carboxylates was synthesized by employing uncatalyzed domino four-component reaction using diethyloxaloacetate, hydrazine hydrate, aldehydes and malononitrile in refluxing of ethanol-acetic acid solvent systems. Series of domino reactions involving of pyrazolone formation, Michael addition, and Thorpe-Ziegler cyclization reaction managed to produce the cyclized products from moderate to excellent yield. This protocol provides a reliable, general and salient procedure for the title compound using a one-pot approach. Preliminary biological screening unveiled limited potentials of this class of compounds for antimicrobial lead compound due to its limited solubility properties

Synthesis, crystal structure and Hirshfeld surface analysis of ethyl 4-hydroxy-2-(4-hydroxyphenyl)-1-methyl-5-oxo-2,5-dihydro- 1H-pyrrole-3-carboxylate

Ethyl 4 hydroxy-2-(4-hydroxyphenyl)-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C14H15NO5 (1) was synthesized via multicomponent reaction (MCR) of sodium diethyl oxalacetate, methylamine, and 4-hydroxybenzaldehyde. The structure of 1 was elucidated by using FT-IR, NMR and GCMS. These results were further confirmed by means of single crystal X-ray crystallography. The results showed that 1 was crystallized in orthorhombic space group Pca21 where a = 17.102(4), b = 9.923(2), c = 16.037(4), Å. The quantification of intermolecular interactions in the crystal structure was obtained by Hirshfeld surface analysis and showed that the H•••H contacts were the most dominant interactions

Ethyl 4-hydroxy-1-methyl-5-oxo-2-phenylpyrrolidine-3-carboxylate 1.25-hydrate

The asymmetric unit of the title compound, C14H17NO4&#183;1.25H2O, consists of four substituted pyrrolidone molecules (two pairs of enantiomers) and five water molecules. The five-membered rings each have an envelope conformation, with the C atom bonded to the ester group as the flap. The mean planes of the five-membered rings of the four pyrrolidone molecules make dihedral angles of 60.87&#8197;(5), 64.45&#8197;(5), 62.03&#8197;(5) and 65.79&#8197;(5)&#176; with respect to the phenyl rings. In the crystal, the pyrrolidone and water molecules are connected through O&#8212;H...O hydrogen bonds, forming a layer parallel to the ab plane. The two-dimensional network is further stabilized by intermolecular C&#8212;H...O hydrogen bonds

(Z)-Benzyl 2-(5-methyl-2-oxoindolin-3-ylidene)hydrazinecarbodithioate

The title compound, C17H15N3OS2 was obtained from the condensation reaction of S-benzyl­dithio­carbazate and 5-methyl­isatin. In the solid-state, the mol­ecule adopts a Z configuration with the 5-methyl­isatin and di­thio­carbazate groups located on the same side of the C=N bond, involving an intra­molecular N—H⋯O hydrogen bond.Peer reviewe