88255-40-7

Upstream product

• 28948-58-5 7-chlorothieno<2,3-c>pyridine 
• 85517-71-1 3,4-Dimethoxybenzyl-(tri-n-butyl)-phosphoniumchlorid 
• 98-03-3 thiophene-2-carbaldehyde 
• 756477-25-5 {[(2,2-Dimethoxy-ethyl)-ethoxycarbonyl-amino]-thiophen-2-yl-methyl}-phosphonic acid dimethyl ester 
• 93582-96-8 6-Carbethoxy-7-cyano-6,7-dihydrothieno<2,3-c>pyridine 
• 272-12-8 thieno[2,3-c]-pyridine 
• 55390-18-6 (2,2-Dimethoxy-ethyl)-[1-thiophen-2-yl-meth-(Z)-ylidene]-amine 

Relevant academic research and scientific papers

Dihydroisoquinoline rearrangement, XXXV: 6,7-Dihydro-7-(3,4-dimethoxybenzyl)-6-methylthieno[2,3-c]pyridine

The title compound 4 is synthesized from the 7-chlorotheinopyridine 1 via the 7-(dimethoxybenzyl) compound 2 which is obtained by Wittig alkylation. Compound 2 is methylated by methyl iodide to give the iminium salt 3 which is reduced with LiAlH4 to yield 4. When 4 is treated with 0.1 N-HCl the disproportionation products 3 and 5 are formed. Moreover, the rearrangement product 6 is obtained in 6% yield. Compound 6 was isolated as the pseudocyanide 7.

Synthesis and radioligand binding studies of C-5- and C-8-substituted 1-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK channel blockers related to N-methyl-laudanosine and N-methyl-noscapine

The synthesis and the 125I-apamin binding studies of original C-5- and C-8-substituted 1-(3,4-dimethoxy-benzyl)-2,2-dimethyl-1,2,3,4- tetrahydroisoquinoliniums and 1-(3,4-dimethoxy-benzyl)-6,6-dimethyl-4,5,6,7- tetrahydrothieno[2,3-c]pyridiniums were performed in order to find a reversible and selective SK channel blocker structurally related to N-methyl-laudanosine and N-methyl-noscapine. A bulky alkyl substituent in the C-8 position of the tetrahydroisoquinoline produces a clear increase in the affinity for the apamin sensitive binding sites. The presence of an electron-withdrawing group in the C-5 and C-8 positions is not a suitable substitution for the affinity of drugs structurally related to N-methyl-laudanosine. Thiophenic analogues and 8-methoxy derivatives possess a poor affinity for the apamin sensitive binding sites. Electrophysiological studies performed with the most effective compound showed a blockade of the apamin sensitive afterhyperpolarization in rat dopaminergic neurons.