Highly reactive zinc metal was prepared by electrolysis of a N,N-dimethylformamide (DMF) solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. This highly reactive electrogenerated zinc (EGZn/Naph) was used for transformation of ethyl 2-bromoacrylate into the corresponding organozinc compound, which can not be achieved by the use of usual zinc metals. Reaction of the organozinc compounds thus prepared with various aryl halides in the presence of 5 mol% of palladium catalyst gave the corresponding cross-coupling products in high yields. These cross-coupling reactions were successfully applied to a synthesis of the precursor of anti-inflammatory agents such as ibuprofen, naproxen, cicloprofen and suprofen.
Anti-Inflammatory Agents, Non-Steroidal/*chemical synthesis ; Catalysis ; Electrolysis ; Ibuprofen/chemical synthesis ; Naphthalenes ; Naproxen/chemical synthesis ; Prodrugs/*chemical synthesis ; Propionic Acids/chemical synthesis ; Suprofen/chemical synthesis ; Zinc/*pharmacology

Animals ; Anti-Inflammatory Agents, Non-Steroidal ; chemical synthesis ; chemistry ; pharmacology ; Antidepressive Agents ; chemical synthesis ; chemistry ; pharmacology ; Antineoplastic Agents ; chemical synthesis ; chemistry ; pharmacology ; Humans ; Indoles ; chemical synthesis ; chemistry ; pharmacology ; Molecular Structure ; Pyrroles ; chemical synthesis ; chemistry ; pharmacology

AIM(+/-) Ibuprofen sugar derivatives were prepared in order to decrease side-effects and increase bioavailability of (+/-) ibuprofen.

METHODSThe synthesis of derivatives were performed using 1,2:3, 4-di-O-isopropylidene-beta-D-galactopyranose, 1,3,4,5-tetra-O-acetyl-2-deoxy-2-amino-beta-D-gluctopyranose, 3,4 6-tri-O-acetyl-2-deoxy-2-N-acetyl-beta-D-gluctosylamine and 2,3,6,2',3',4',6'-hepta-O-acetyl-beta-D-lactosylamine as glycosyl donors, respectively. Target products (4, 7, 12a, 12b, 13) were obtained after deprotection.

RESULTSFive compounds (4, 7, 12a, 12b, 13) were synthesized as new compounds. The structures of all objective compounds were confirmed by 1HNMR, 13CNMR, HMQC, COSY, IR and MS.

CONCLUSIONIt was found that 12a showed better anti-inflammatory activity than (+/-) ibuprofen.

Animals ; Anti-Inflammatory Agents, Non-Steroidal ; chemical synthesis ; therapeutic use ; Ibuprofen ; analogs & derivatives ; chemical synthesis ; therapeutic use ; Inflammation ; drug therapy ; Male ; Mice ; Molecular Conformation ; Molecular Structure ; Random Allocation

AIMTo search for new compounds with strong anti-inflammatory activity and low gastrointestinal (GI) side effects.

METHODSA series of p-(methanesulfonyl) styrene-linked cyclic ketone derivatives were synthesized. Their anti-inflammatory activities against xylene-induced mice ear swelling and carrageenan-induced rat paw edema were evaluated, and their GI side effects in the rats were examined.

RESULTSNine target compounds (ZA(1-9)) were obtained, and their structures were determined by IR, 1HNMR, MS and elemental analysis. Compared with controls diclofenac (DC) and rofecoxib (RC) , ZA(3, 5-9) showed no significant difference in anti-inflammatory activity against xylene-induced ear swelling in mice. ZA(3, 7, 8) showed potency comparable to DC and RC (P > 0.05) and ZA6 was more potent than DC and RC (P < 0.05) in the treatment of carrageenan-induced rat paw edema. ZA(3, 5-9) showed less GI side effects than DC (P < 0.05, P < 0.01) and no significant difference compared with RC (P > 0.05).

CONCLUSIONp-(Methanesulfonyl) styrene-linked cyclic ketone derivatives showed strong anti-inflammatory activity but few GI side effects and deserve to be further investigated.

Animals ; Anti-Inflammatory Agents, Non-Steroidal ; adverse effects ; chemical synthesis ; chemistry ; Carrageenan ; Edema ; chemically induced ; drug therapy ; Ketones ; chemical synthesis ; chemistry ; Mice ; Peptic Ulcer ; drug therapy ; Rats ; Structure-Activity Relationship ; Styrenes ; chemical synthesis ; chemistry

Animals ; Anti-Inflammatory Agents, Non-Steroidal ; pharmacology ; Antineoplastic Agents, Phytogenic ; pharmacology ; Cell Line, Tumor ; drug effects ; Diterpenes ; chemical synthesis ; isolation & purification ; pharmacology ; Epoxy Compounds ; Humans ; Phenanthrenes ; chemical synthesis ; isolation & purification ; pharmacology ; Plants, Medicinal ; chemistry ; Tripterygium ; chemistry

Tepoxalin is a potent inhibitor of both the cyclooxygenase and lipoxygenase pathways of the arachidonic acid cascade, as well as a potent anti-inflammatory and control-pain (postoperation, arthritis et. al.) agent. The new method about the use of novel synthesis reagents and the first using ionic liquid as reactive solvent to synthesize tepoxalin were presented in this paper. The ionic liquid can be easily recycled and reused for several runs efficiently. The analgesic activity of tepoxalin was detected by acetic acid test on mice. The analysis of variance showed that oral administration of tepoxalin could significantly inhibit the number of writhing response within 1 hour and prolong the latent time in a dose dependent manner as compared with CMC control group (P < 0.05). At the same time, tepoxalin had the same analgesic activity as diclofenac sodium.
Administration, Oral ; Analgesics ; administration & dosage ; chemical synthesis ; pharmacology ; Animals ; Anti-Inflammatory Agents, Non-Steroidal ; administration & dosage ; chemical synthesis ; pharmacology ; Cyclooxygenase Inhibitors ; administration & dosage ; chemical synthesis ; pharmacology ; Diclofenac ; pharmacology ; Imidazoles ; chemistry ; Ionic Liquids ; chemistry ; Lipoxygenase Inhibitors ; administration & dosage ; chemical synthesis ; pharmacology ; Mice ; Pain Measurement ; drug effects ; Pyrazoles ; administration & dosage ; chemical synthesis ; pharmacology ; Random Allocation

Fluidized-bed manufactured enteric-coated diclofenac sodium pellets were compressed into tablets. The blend of two aqueous acrylic resins dispersion in different ratios, Eudragit NE30D and Eudragit L30D-55, were used to prepare enteric-coated diclofenac sodium pellets of different particle sizes and coating level. The cushioning pellets with different properties and these enteric-coated pellets were compressed into tablets in different proportions. The drug release of the tablets containing these pellets would be lower than 10% in 2 h in simulated gastric fluid, but reach (83 +/- 2.42)% in 1 h in simulated enteric fluid. The mixture of Eudragit NE30D and Eudragit L30D-55 could be used to prepare enteric pellets which are suitable for compression. The cushioning pellets which were composed of stearic acid/microcrystalline cellulose (4:1, w/w) could avoid rupture of the coating of pellets during the compression.
Acrylic Resins ; chemistry ; Anti-Inflammatory Agents, Non-Steroidal ; chemical synthesis ; Cellulose ; chemistry ; Diclofenac ; chemical synthesis ; Drug Carriers ; Drug Compounding ; methods ; Drug Delivery Systems ; Methacrylates ; chemistry ; Particle Size ; Polymers ; chemistry ; Solubility ; Tablets, Enteric-Coated ; chemistry

AIMTo provide basic data for the synthesis of new sinomenine derivatives.

METHODSThe C ring in sinomenine was modified.

RESULTSSeven compounds were prepared and screened for anti-inflammatory and analgesic activities. Compounds 2 and 5 showed better activities.

CONCLUSIONModification of the C ring in sinomenine should be worthy to be studied further.

Animals ; Anti-Inflammatory Agents, Non-Steroidal ; chemical synthesis ; pharmacology ; Edema ; pathology ; Mice ; Molecular Conformation ; Molecular Structure ; Morphinans ; chemical synthesis ; isolation & purification ; pharmacology ; Pain Measurement ; Plants, Medicinal ; chemistry ; Rats ; Sinomenium ; chemistry

AIMTo study the anti-inflammatory activity of N-(4-arylamidophenyl) methanesulfonamide derivatives.

METHODSThe target compounds were synthesized from p-nitroaniline via three steps and were evaluated for anti-inflammatory activity with the model of xylene-induced ear edema in mice.

RESULTSEleven compounds were obtained and confirmed by IR, 1HNMR and MS. Some compounds were shown to have significant anti-inflammatory activity.

CONCLUSIONN-(4-arylamidophenyl) methanesulfonamide showed appreciable anti-inflammatory activity.

Animals ; Anti-Inflammatory Agents, Non-Steroidal ; chemical synthesis ; chemistry ; pharmacology ; Ear ; pathology ; Ear Diseases ; chemically induced ; pathology ; Edema ; chemically induced ; pathology ; Male ; Mice ; Molecular Structure ; Sulfonamides ; chemical synthesis ; chemistry ; pharmacology ; Xylenes

A new pyranocoumarin as an analogue of calophyllolide, compound 6, is firstly prepared and reported to have potent anti-inflammatory activity on carrageenin-induced edema in rats.
Animals ; Anti-Inflammatory Agents, Non-Steroidal ; chemical synthesis ; chemistry ; therapeutic use ; Carrageenan ; Coumarins ; chemical synthesis ; chemistry ; pharmacology ; therapeutic use ; Edema ; chemically induced ; drug therapy ; Male ; Molecular Structure ; Rats ; Rats, Wistar