Synthesis, structural characterization, and antiinflammatory activity of triethylphosphinegold(I) sulfanylpropenoates of the type [(AuPEt3)2xspa] [H2xspa = 3-(aryl)-2-sulfanylpropenoic acid]: an (H2O)6 cluster in the lattice of the complexes [(AuPEt3)2xspa] x 3 H2O.
Gold complexes of the type [(AuPEt3)2xspa] were prepared by reacting AuPEt3Cl in basic media with the 3-(aryl)-2-sulfanylpropenoic acids H2xspa [x = p, Clp, -o-mp, -p-mp, -o-hp, -p-hp, diBr-o-hp, f, t, -o-py; p = 3-phenyl, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, diBr-o-hp = 3-(3,5- dibromo-2-hydroxyphenyl)-, f = 3-(2-furyl)-, t = 3-(2-thienyl)-, -o-py = 3-(2-pyridyl); spa = 2-sulfanylpropenoato], and 2-cyclopentylidene-2-sulfanylacetic acid (H2cpa). The complexes were characterized by spectroscopic methods (IR, (1)H, (13)C and (31)P NMR) and mass spectrometry, and the complexes [(AuPEt3)2pspa] x 3 H2O, [(AuPEt3)2-p-hpspa] x 3 H2O, [(AuPEt3)2tspa)] x 3 H2O, and [(AuPEt3)2-o-hpspa] by X-ray diffractometry. The crystals of the first three complexes contain (H2O)6 clusters hydrogen bonded to [(AuPEt3)2xspa]2 dimer units, whereas in the -o-hpspa derivative the hydrogen bonds are between the monomer [(AuPEt3)2-o-hpspa] units. The antiinflammatory activity of the complexes against plantar edema induced by carrageenan in rats is generally significant, with the values for the o-hpspa and tspa derivatives being particularly high.
Barreiro
Elena
E
Departamento de Quimica Inorganica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Galicia, Spain.
Casas
José S
JS
Couce
María D
MD
Gato
Angeles
A
Sánchez
Agustín
A
Sordo
José
J
Varela
José M
JM
Vázquez López
Ezequiel M
EM
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology*; D002351:Carrageenan / Q000633:toxicity; D004305:Dose-Response Relationship, Drug; D017612:Gold Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D007249:Inflammation / Q000139:chemically induced / Q000188:drug therapy; D008958:Models, Molecular; D015394:Molecular Structure; D051381:Rats; D013329:Structure-Activity Relationship
D000894:Anti-Inflammatory Agents, Non-Steroidal; D017612:Gold Compounds; D002351:Carrageenan