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In this letter, we report the synthesis of a pyrano[2,3,4- cd ]indole chemical scaffold designed through a tandem bioisostere generation/virtual screening protocol in search of 5-HT 6 R ligands. The discovered chemical scaffold resulted in the design of highly active basic and nonbasic 5-HT 6 R ligands (5-HT 6 R K  i = 1 nM for basic compound 6b and 5-HT 6 R K  i = 4 nM for its neutral analog 7b ). Additionally, molecular modeling suggested that the hydroxyl group of nonbasic ligands 7a - 7d forms hydrogen bonds with aspartic acid D 3×32 or D 7.36×35 .

Pyrano[2,3,4-cd]indole as a Scaffold for Selective Nonbasic 5-HT6R Ligands

Pyrano[2,3,4-cd]indole as a Scaffold for Selective Nonbasic 5-HT₆R Ligands