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

6-(4-Chlorophenyl)-3-substituted-thieno [3, 2-d] pyrimidin-4 (3 H)-one-Based Melanin-Concentrating Hormone Receptor 1 Antagonist

FX Tavares, KA Al-Barazanji, MJ Bishop…

Index: Tavares, Francis X.; Al-Barazanji, Kamal A.; Bishop, Michael J.; Britt, Christy S.; Carlton, David L.; Cooper, Joel P.; Feldman, Paul L.; Garrido, Dulce M.; Goetz, Aaron S.; Grizzle, Mary K.; Hertzog, Donald L.; Ignar, Diane M.; Lang, Daniel G.; McIntyre, Maggie S.; Ott, Ronda J.; Peat, Andrew J.; Zhou, Hui-Qiang Journal of Medicinal Chemistry, 2006 , vol. 49, # 24 p. 7108 - 7118

Full Text: HTML

Citation Number: 20

Abstract

Genetic manipulation studies in mice at both the MCH receptor 1 (MCHR1) as well as the MCH peptide levels have implicated MCHR1 as a key player in energy homeostasis. The phenotype exhibited by these studies, that is, increased metabolic rate, resistance to high fat diet, and subsequent weight loss, has spurred considerable efforts to develop antagonists of MCHR1. In continuation of efforts directed toward this goal, the present work capitalizes ...

Ethyl 5-Nitroindole-2-Carboxylate Structure

Ethyl 5-Nitroin...

methyl iodide Structure

~61%

ethyl 1-methyl-5-nitroindole-2-carboxylate Structure

ethyl 1-methyl-...

(5-nitro-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-nitro-1-benz...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-amino-1-benz...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-amino-1-benz...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-amino-1-benz...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-amino-1-benz...

4-Phenylpiperidine Structure

4-Phenylpiperidine

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-amino-1-benz...

2,2-dimethyl-N-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]propanamide Structure

2,2-dimethyl-N-...

~63%

6-(piperidin-1-ylmethyl)naphthalen-2-amine Structure

6-(piperidin-1-...

N-[6-(chloromethyl)naphthalen-2-yl]-2,2-dimethylpropanamide Structure

N-[6-(chloromet...

~%

6-(piperidin-1-ylmethyl)naphthalen-2-amine Structure

6-(piperidin-1-...

N-[6-(hydroxymethyl)-2-naphthalenyl]-2,2-dimethylpropanamide Structure

N-[6-(hydroxyme...

~%

6-(piperidin-1-ylmethyl)naphthalen-2-amine Structure

6-(piperidin-1-...

6-AMINO-2-NAPHTHOIC ACID METHYL ESTER Structure

6-AMINO-2-NAPHT...

~%

6-(piperidin-1-ylmethyl)naphthalen-2-amine Structure

6-(piperidin-1-...

6-AMINO-2-NAPHTHOIC ACID Structure

6-AMINO-2-NAPHT...

~%

6-(piperidin-1-ylmethyl)naphthalen-2-amine Structure

6-(piperidin-1-...

(2-AMINONAPHTHALEN-6-YL)METHANOL Structure

(2-AMINONAPHTHA...

~%

6-(piperidin-1-ylmethyl)naphthalen-2-amine Structure

6-(piperidin-1-...

(5-nitro-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-nitro-1-benz...

~%

2-[(4-phenylpiperidin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

2-[(4-phenylpiperidin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

2-[(4-phenylpiperidin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

2-[(4-phenylpiperidin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

4-Phenylpiperidine Structure

4-Phenylpiperidine

~%

2-[(4-phenylpiperidin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-amino-1-benz...

~%

2-[(4-phenylpiperidin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

1-[(5-nitro-1-benzothien-2-yl)carbonyl]-4-phenylpiperazine Structure

1-[(5-nitro-1-b...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperazin-1-yl)methanone Structure

(5-amino-1-benz...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperazin-1-yl)methanone Structure

(5-amino-1-benz...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperazin-1-yl)methanone Structure

(5-amino-1-benz...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperazin-1-yl)methanone Structure

(5-amino-1-benz...

1-Phenylpiperazine Structure

1-Phenylpiperazine

~%

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperazin-1-yl)methanone Structure

(5-amino-1-benz...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

2-(morpholin-4-ylmethyl)-1-benzothiophen-5-amine Structure

2-(morpholin-4-...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

2-(morpholin-4-ylmethyl)-1-benzothiophen-5-amine Structure

2-(morpholin-4-...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

2-(morpholin-4-ylmethyl)-1-benzothiophen-5-amine Structure

2-(morpholin-4-...

Piperidine Structure

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

(5-nitro-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-nitro-1-benz...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

(5-nitro-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-nitro-1-benz...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

(5-nitro-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-nitro-1-benz...

6-AMINO-2-NAPHTHOIC ACID METHYL ESTER Structure

6-AMINO-2-NAPHT...

~%

(2-AMINONAPHTHALEN-6-YL)METHANOL Structure

(2-AMINONAPHTHA...

1-[(5-nitro-1-benzothien-2-yl)carbonyl]-4-phenylpiperazine Structure

1-[(5-nitro-1-b...

~%

2-[(4-phenylpiperazin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

2-[(4-phenylpiperazin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

2-[(4-phenylpiperazin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

2-[(4-phenylpiperazin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

1-Phenylpiperazine Structure

1-Phenylpiperazine

~%

2-[(4-phenylpiperazin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

(5-amino-1-benzothiophen-2-yl)-(4-phenylpiperazin-1-yl)methanone Structure

(5-amino-1-benz...

~%

2-[(4-phenylpiperazin-1-yl)methyl]-1-benzothiophen-5-amine Structure

2-[(4-phenylpip...

morpholine Structure

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

morpholin-4-yl-(5-nitro-1-benzothiophen-2-yl)methanone Structure

morpholin-4-yl-...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

morpholin-4-yl-(5-nitro-1-benzothiophen-2-yl)methanone Structure

morpholin-4-yl-...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

morpholin-4-yl-(5-nitro-1-benzothiophen-2-yl)methanone Structure

morpholin-4-yl-...

(1-methyl-5-nitro-1H-indol-2-yl)methanol Structure

(1-methyl-5-nit...

~26%

2-(bromomethyl)-1-methyl-5-nitroindole Structure

2-(bromomethyl)...

Ethyl 5-Nitroindole-2-Carboxylate Structure

Ethyl 5-Nitroin...

~%

2-(bromomethyl)-1-methyl-5-nitroindole Structure

2-(bromomethyl)...

ethyl 1-methyl-5-nitroindole-2-carboxylate Structure

ethyl 1-methyl-...

~%

2-(bromomethyl)-1-methyl-5-nitroindole Structure

2-(bromomethyl)...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

2-(piperidin-1-ylmethyl)-1-benzothiophen-5-amine Structure

2-(piperidin-1-...

(5-nitro-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-nitro-1-benz...

~%

2-(piperidin-1-ylmethyl)-1-benzothiophen-5-amine Structure

2-(piperidin-1-...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

2-(piperidin-1-ylmethyl)-1-benzothiophen-5-amine Structure

2-(piperidin-1-...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

2-(piperidin-1-ylmethyl)-1-benzothiophen-5-amine Structure

2-(piperidin-1-...

Piperidine Structure

~%

2-(piperidin-1-ylmethyl)-1-benzothiophen-5-amine Structure

2-(piperidin-1-...

(5-amino-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-amino-1-benz...

~%

2-(piperidin-1-ylmethyl)-1-benzothiophen-5-amine Structure

2-(piperidin-1-...

Pyrrolidine Structure

5-nitro-1-benzofuran-2-carbonyl chloride Structure

5-nitro-1-benzo...

~%

(5-nitro-1-benzofuran-2-yl)-pyrrolidin-1-ylmethanone Structure

(5-nitro-1-benz...

5-NITROBENZOFURAN-2-CARBOXYLIC ACID Structure

5-NITROBENZOFUR...

~%

(5-nitro-1-benzofuran-2-yl)-pyrrolidin-1-ylmethanone Structure

(5-nitro-1-benz...

(5-nitro-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-nitro-1-benz...

~%

(5-amino-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-amino-1-benz...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

(5-amino-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-amino-1-benz...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

(5-amino-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-amino-1-benz...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

(5-amino-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-amino-1-benz...

Piperidine Structure

~%

(5-amino-1-benzothiophen-2-yl)-piperidin-1-ylmethanone Structure

(5-amino-1-benz...

N-[6-(hydroxymethyl)-2-naphthalenyl]-2,2-dimethylpropanamide Structure

N-[6-(hydroxyme...

~69%

N-[6-(chloromethyl)naphthalen-2-yl]-2,2-dimethylpropanamide Structure

N-[6-(chloromet...

6-AMINO-2-NAPHTHOIC ACID METHYL ESTER Structure

6-AMINO-2-NAPHT...

~%

N-[6-(chloromethyl)naphthalen-2-yl]-2,2-dimethylpropanamide Structure

N-[6-(chloromet...

6-AMINO-2-NAPHTHOIC ACID Structure

6-AMINO-2-NAPHT...

~%

N-[6-(chloromethyl)naphthalen-2-yl]-2,2-dimethylpropanamide Structure

N-[6-(chloromet...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

N-[6-(chloromethyl)naphthalen-2-yl]-2,2-dimethylpropanamide Structure

N-[6-(chloromet...

(2-AMINONAPHTHALEN-6-YL)METHANOL Structure

(2-AMINONAPHTHA...

~%

N-[6-(chloromethyl)naphthalen-2-yl]-2,2-dimethylpropanamide Structure

N-[6-(chloromet...

(2-AMINONAPHTHALEN-6-YL)METHANOL Structure

(2-AMINONAPHTHA...

~%

2,2-dimethyl-N-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]propanamide Structure

2,2-dimethyl-N-...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

(5-amino-1-benzothiophen-2-yl)-morpholin-4-ylmethanone Structure

(5-amino-1-benz...

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

(5-amino-1-benzothiophen-2-yl)-morpholin-4-ylmethanone Structure

(5-amino-1-benz...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

(5-amino-1-benzothiophen-2-yl)-morpholin-4-ylmethanone Structure

(5-amino-1-benz...

4-Phenylpiperidine Structure

4-Phenylpiperidine

5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Structure

5-NITRO-1-BENZO...

~%

(5-nitro-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-nitro-1-benz...

Methyl 5-nitrobenzo[b]thiophene-2-carboxylate Structure

Methyl 5-nitrob...

~%

(5-nitro-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-nitro-1-benz...

2-Chloro-5-nitrobenzaldehyde Structure

2-Chloro-5-nitr...

~%

(5-nitro-1-benzothiophen-2-yl)-(4-phenylpiperidin-1-yl)methanone Structure

(5-nitro-1-benz...

N-[6-(hydroxymethyl)-2-naphthalenyl]-2,2-dimethylpropanamide Structure

N-[6-(hydroxyme...

~%

2,2-dimethyl-N-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]propanamide Structure

2,2-dimethyl-N-...

6-AMINO-2-NAPHTHOIC ACID METHYL ESTER Structure

6-AMINO-2-NAPHT...

~%

2,2-dimethyl-N-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]propanamide Structure

2,2-dimethyl-N-...

6-AMINO-2-NAPHTHOIC ACID Structure

6-AMINO-2-NAPHT...

~%

2,2-dimethyl-N-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]propanamide Structure

2,2-dimethyl-N-...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

2,2-dimethyl-N-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]propanamide Structure

2,2-dimethyl-N-...

Piperidine Structure

N-[6-(chloromethyl)naphthalen-2-yl]-2,2-dimethylpropanamide Structure

N-[6-(chloromet...

~38%

2,2-dimethyl-N-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]propanamide Structure

2,2-dimethyl-N-...