[Synthesis and bronchodilator action of 4-(methoxycarbonylalkylsulfinyl)-4-pyrrol carboxylic esters].
The dihydro-dimethoxyfuran carboxylic ester 3 reacts with different mercaptoalkyl carboxylates to give the carbomethoxyalkylthio-tetrahydrofuran carboxylic esters 4. Methanol elimination of 4 yields the dihydrofuran derivatives 5. 4 and 5 can be oxidized to afford the sulfoxides 6 and the sulfones 7, respectively. 4 reacts with primary amines to give the title compounds 8. Derivatives of 8 can be cyclized to afford the thienopyrroles 11 and 12 as well as the thienopyranopyrrole 14. The mercaptopyrrole carboxylic ester 10 is obtained from 8f by elimination of propenic acid. 8e shows bronchodilatoric activity in low concentration.
Eiden
F
F
Grusdt
U
U
D000818:Animals; D001993:Bronchodilator Agents / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D006168:Guinea Pigs; D066298:In Vitro Techniques; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology
D001993:Bronchodilator Agents; D002264:Carboxylic Acids; D011758:Pyrroles
Synthese und bronchodilatatorische Wirkung von 4-(Methoxycarbonylalkylsulfinyl)-3-pyrrolcarbonsäureestern.