Synthesis and antioxidant properties of pulvinic acids analogues.
The synthesis of three types of pulvinic acid analogues, using a diversity-oriented strategy starting from a single compound, dimethyl l-tartrate, is described. Lacey-Dieckmann condensation, alcohol dehydration and Suzuki-Miyaura cross-couplings were employed in the course of the analogues syntheses. The evaluation of the antioxidant properties of the 28 synthesized analogues was carried out using antioxidant capacity assays (protection of thymidine and β-carotene) and free radical scavenging assays (DPPH radical and ABTS radical cation). This allowed to assess the relative influence of the groups bonded to the tetronic ring and to the exocyclic double bond on the activity, as well as the importance of this exocyclic double bond. It was shown that the presence of an electron-donating group on the 3-position of the tetronic ring had a beneficial effect. It was shown in several assays that the presence of the exocyclic bond was not crucial to the activity.
CEA Saclay, iBiTecS, Service de Chimie Bioorganique et de Marquage, Bât. 547, 91191 Gif-sur-Yvette, France.
Brice
B
Nadal
Sophie A-L
SA
Thetiot-Laurent
Serge
S
Pin
Jean-Philippe
JP
Renault
Damien
D
Cressier
Ghassoub
G
Rima
Antoine
A
Le Roux
Stéphane
S
Meunier
Alain
A
Wagner
Claude
C
Lion
Thierry
T
Le Gall
D052160:Benzothiazoles / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010851:Picrates / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry; D013644:Tartrates / Q000737:chemistry; D013936:Thymidine / Q000737:chemistry; D019207:beta Carotene / Q000737:chemistry / Q000378:metabolism
D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002264:Carboxylic Acids; D016166:Free Radical Scavengers; D007783:Lactones; D010851:Picrates; D013451:Sulfonic Acids; D013644:Tartrates; D019207:beta Carotene; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; C492654:pulvinic acid; D013936:Thymidine; C029768:tartaric acid