e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Design, synthesis and evaluation of bicyclic benzamides as novel 5-HT 1F receptor agonists

D Zhang, D Kohlman, J Krushinski, S Liang…

Index: Zhang, Deyi; Kohlman, Dan; Krushinski, Joseph; Liang, Sidney; Ying, Bai-Ping; Reilly, John E.; Dinn, Sean R.; Wainscott, David B.; Nutter, Suzanne; Gough, Wendy; Nelson, David L.G.; Schaus, John M.; Xu, Yao-Chang Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 24 p. 6011 - 6016

Full Text: HTML

Citation Number: 19

Abstract

Several fused bicyclic systems have been investigated to serve as the core structure of potent and selective 5-HT1F receptor agonists. Replacement of the indole nucleus in 2 with indazole and 'inverted'indazole provided more potent and selective 5-HT1F receptor ligands. Indoline and 1, 2-benzisoxazole systems also provided potent 5-HT1F receptor agonists, and the 5-HT1A receptor selectivity of the indoline-and 1, 2-benzisoxazole- ...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide Structure

1-methyl-piperi...

~53%

(5-bromo-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-bromo-2-fluo...

(5-((diphenylmethylene)amino)-2-fluorophenyl)(1-methylpiperidin-4-yl)methanone Structure

(5-((diphenylme...

~82%

(5-amino-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-amino-2-fluo...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~%

(5-amino-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-amino-2-fluo...

1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide Structure

1-methyl-piperi...

~%

(5-amino-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-amino-2-fluo...

(5-bromo-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-bromo-2-fluo...

~%

(5-amino-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-amino-2-fluo...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~%

3-(1-methylpiperidin-4-yl)-1,2-benzoxazol-5-amine Structure

3-(1-methylpipe...

1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide Structure

1-methyl-piperi...

~%

3-(1-methylpiperidin-4-yl)-1,2-benzoxazol-5-amine Structure

3-(1-methylpipe...

(5-amino-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-amino-2-fluo...

~%

3-(1-methylpiperidin-4-yl)-1,2-benzoxazol-5-amine Structure

3-(1-methylpipe...

(5-bromo-2-fluorophenyl)-(1-methylpiperidin-4-yl)methanone Structure

(5-bromo-2-fluo...

~%

3-(1-methylpiperidin-4-yl)-1,2-benzoxazol-5-amine Structure

3-(1-methylpipe...

(5-((diphenylmethylene)amino)-2-fluorophenyl)(1-methylpiperidin-4-yl)methanone Structure

(5-((diphenylme...

~%

3-(1-methylpiperidin-4-yl)-1,2-benzoxazol-5-amine Structure

3-(1-methylpipe...

2,4-Difluoro-N-[4-fluoro-3-(1-methyl-piperidine-4-carbonyl)-phenyl]-benzamide Structure

2,4-Difluoro-N-...

~%

3-(1-methylpiperidin-4-yl)-1,2-benzoxazol-5-amine Structure

3-(1-methylpipe...

N-Methyl-4-piperidone Structure

N-Methyl-4-pipe...

~%

4-(1-methylpiperidin-4-yl)-2,3-dihydro-1,4-benzoxazin-6-amine Structure

4-(1-methylpipe...

6-Nitro-3,4-dihydro-2H-1,4-benzoxazine Structure

6-Nitro-3,4-dih...

~%

4-(1-methylpiperidin-4-yl)-2,3-dihydro-1,4-benzoxazin-6-amine Structure

4-(1-methylpipe...

tert-butyl 4-(6-(4-fluorobenzamido)-1H-indazol-1-yl)piperidine-1-carboxylate Structure

tert-butyl 4-(6...

~94%

4-fluoro-N-(1-piperidin-4-ylindazol-6-yl)benzamide Structure

4-fluoro-N-(1-p...

6-Nitroindazole Structure

6-Nitroindazole

~%

4-fluoro-N-(1-piperidin-4-ylindazol-6-yl)benzamide Structure

4-fluoro-N-(1-p...

1-Piperidinecarboxylic acid, 4-(Methylsulfonyl)-, 1,1-dimethylethyl ester Structure

1-Piperidinecar...

~%

4-fluoro-N-(1-piperidin-4-ylindazol-6-yl)benzamide Structure

4-fluoro-N-(1-p...

4-FLUOROBENZOYL CHLORIDE Structure

4-FLUOROBENZOYL...

~%

4-fluoro-N-(1-piperidin-4-ylindazol-6-yl)benzamide Structure

4-fluoro-N-(1-p...

tert-butyl 4-(6-amino-1H-indazol-1-yl)piperidine-1-carboxylate Structure

tert-butyl 4-(6...

~%

4-fluoro-N-(1-piperidin-4-ylindazol-6-yl)benzamide Structure

4-fluoro-N-(1-p...