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

Structure-activity relationships of a series of pyrrolo [3, 2-d] pyrimidine derivatives and related compounds as neuropeptide Y5 receptor antagonists

…, N Han, R Hurt, T Jenkins, J Kincaid, L Liu…

Index: Norman; Chen; Fotsch; Hale; Han; Hurt; Jenkins; Kincaid; Liu; Lu; Moreno; Santora; Sonnenberg; Karbon Journal of Medicinal Chemistry, 2000 , vol. 43, # 22 p. 4288 - 4312

Full Text: HTML

Citation Number: 129

Abstract

Neuropeptide Y (NPY) has been shown to play an important role in the regulation of food intake and energy balance. Pharmacological data suggests that the Y5 receptor subtype contributes to the effects of NPY on appetite, and therefore a Y5 antagonist might be a useful therapeutic agent for the treatment of obesity. In attempts to identify potential Y5 antagonists, a series of pyrrolo [3, 2-d] pyrimidine derivatives was prepared and evaluated for their ...

3-Oxo-3-phenylpropanenitrile Structure

3-Oxo-3-phenylp...

~%

ethyl 3-amino-5-phenyl-1H-pyrrole-2-carboxylate Structure

ethyl 3-amino-5...

Piperidine Structure

6-Chloro-5-nitro-2-picoline Structure

6-Chloro-5-nitr...

~86%

6-METHYL-3-NITRO-2-(1-PIPERIDINYL)PYRIDINE Structure

6-METHYL-3-NITR...

6-methyl-3-nitropyridin-2-ol Structure

6-methyl-3-nitr...

~%

6-METHYL-3-NITRO-2-(1-PIPERIDINYL)PYRIDINE Structure

6-METHYL-3-NITR...

2-methyl-6-phenylpyrrolo[3,2-d]pyrimidin-4-ol Structure

2-methyl-6-phen...

~44%

4-Chloro-2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

4-Chloro-2-meth...

2-benzoylamino-3-oxobutyric acid ethyl ester Structure

2-benzoylamino-...

~%

4-Chloro-2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

4-Chloro-2-meth...

2,6-dimethyl-4-hydroxy-5-benzamidopyrimidine Structure

2,6-dimethyl-4-...

~%

4-Chloro-2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

4-Chloro-2-meth...

BUTANOIC ACID, 2-AMINO-3-OXO-, ETHYL ESTER Structure

BUTANOIC ACID, ...

chlorocarbonylcyclohexane Structure

chlorocarbonylc...

~%

ethyl 2-(cyclohexanecarbonylamino)-3-oxobutanoate Structure

ethyl 2-(cycloh...

3-PYRIDINETHIOL, 2-AMINO-5-CHLORO- Structure

3-PYRIDINETHIOL...

~%

ethyl 2-(cyclohexanecarbonylamino)-3-oxobutanoate Structure

ethyl 2-(cycloh...

morpholine Structure

4-Chloro-2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

4-Chloro-2-meth...

~33%

4-(2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholine Structure

4-(2-methyl-6-p...

2-benzoylamino-3-oxobutyric acid ethyl ester Structure

2-benzoylamino-...

~%

4-(2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholine Structure

4-(2-methyl-6-p...

2,6-dimethyl-4-hydroxy-5-benzamidopyrimidine Structure

2,6-dimethyl-4-...

~%

4-(2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholine Structure

4-(2-methyl-6-p...

2-methyl-6-phenylpyrrolo[3,2-d]pyrimidin-4-ol Structure

2-methyl-6-phen...

~%

4-(2-methyl-6-phenyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholine Structure

4-(2-methyl-6-p...

3-Oxo-3-phenylpropanenitrile Structure

3-Oxo-3-phenylp...

Tosyl chloride Structure

~55%

[(E)-2-cyano-1-phenylethenyl] 4-methylbenzenesulfonate Structure

[(E)-2-cyano-1-...

Methylboronic acid Structure

Methylboronic acid

3-AMINO-6-BROMO-2,4-DICHLOROPYRIDINE Structure

3-AMINO-6-BROMO...

~85%

2,4-Dichloro-6-methyl-3-pyridinamine Structure

2,4-Dichloro-6-...

2,4-Dihydroxypyridine Structure

2,4-Dihydroxypy...

~%

2,4-Dichloro-6-methyl-3-pyridinamine Structure

2,4-Dichloro-6-...

3-Amino-2,4-dichloropyridine Structure

3-Amino-2,4-dic...

~%

2,4-Dichloro-6-methyl-3-pyridinamine Structure

2,4-Dichloro-6-...

2,4-Dihydroxy-3-nitropyridine Structure

2,4-Dihydroxy-3...

~%

2,4-Dichloro-6-methyl-3-pyridinamine Structure

2,4-Dichloro-6-...

2,4-Dichloro-3-nitropyridine Structure

2,4-Dichloro-3-...

~%

2,4-Dichloro-6-methyl-3-pyridinamine Structure

2,4-Dichloro-6-...

Pent-1-yne Structure

phenyl cyanate Structure

~%

2-Hexynenitrile Structure

2-Hexynenitrile

3-amino-4-chloro-6-methyl-2-(2-phenylethynyl)pyridine Structure

3-amino-4-chlor...

~49%

7-Chloro-5-methyl-2-phenyl-1H-pyrrolo[3,2-b]pyridine Structure

7-Chloro-5-meth...

Carbethoxy isothiocyanate Structure

Carbethoxy isot...

ethyl 3-amino-5-phenyl-1H-pyrrole-2-carboxylate Structure

ethyl 3-amino-5...

~%

2-MERCAPTO-6-PHENYL-5H-PYRROLO[3,2-D]PYRIMIDIN-4-OL Structure

2-MERCAPTO-6-PH...

3-Oxo-3-phenylpropanenitrile Structure

3-Oxo-3-phenylp...

~%

2-MERCAPTO-6-PHENYL-5H-PYRROLO[3,2-D]PYRIMIDIN-4-OL Structure

2-MERCAPTO-6-PH...

[(E)-2-cyano-1-phenylethenyl] 4-methylbenzenesulfonate Structure

[(E)-2-cyano-1-...

~%

2-MERCAPTO-6-PHENYL-5H-PYRROLO[3,2-D]PYRIMIDIN-4-OL Structure

2-MERCAPTO-6-PH...

N/A Structure

~60%

2-AMINO-6-PHENYL-5H-PYRROLO[3,2-D]PYRIMIDIN-4-OL Structure

2-AMINO-6-PHENY...

3-Oxo-3-phenylpropanenitrile Structure

3-Oxo-3-phenylp...

~%

2-AMINO-6-PHENYL-5H-PYRROLO[3,2-D]PYRIMIDIN-4-OL Structure

2-AMINO-6-PHENY...

ethyl 3-amino-5-phenyl-1H-pyrrole-2-carboxylate Structure

ethyl 3-amino-5...

~%

2-AMINO-6-PHENYL-5H-PYRROLO[3,2-D]PYRIMIDIN-4-OL Structure

2-AMINO-6-PHENY...

[(E)-2-cyano-1-phenylethenyl] 4-methylbenzenesulfonate Structure

[(E)-2-cyano-1-...

~%

2-AMINO-6-PHENYL-5H-PYRROLO[3,2-D]PYRIMIDIN-4-OL Structure

2-AMINO-6-PHENY...

3-PYRIDINETHIOL, 2-AMINO-5-CHLORO- Structure

3-PYRIDINETHIOL...

~%

BUTANOIC ACID, 2-AMINO-3-OXO-, ETHYL ESTER Structure

BUTANOIC ACID, ...

(Z)-β-bromocinnamonitrile Structure

(Z)-β-bromocinn...

Glycolonitrile Structure

~89%

3-amino-5-phenylfuran-2-carbonitrile Structure

3-amino-5-pheny...

3-Oxo-3-phenylpropanenitrile Structure

3-Oxo-3-phenylp...

~%

3-amino-5-phenylfuran-2-carbonitrile Structure

3-amino-5-pheny...

2-Nitroacetamide Structure

2-Nitroacetamide

N/A Structure

~24%

6-methyl-3-nitropyridin-2-ol Structure

6-methyl-3-nitr...

6-Phenyl-5H-pyrrolo[3,2-d]pyrimidine-2,4-diol Structure

6-Phenyl-5H-pyr...

~39%

2,4-Dichloro-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

2,4-Dichloro-6-...

3-Oxo-3-phenylpropanenitrile Structure

3-Oxo-3-phenylp...

~%

2,4-Dichloro-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

2,4-Dichloro-6-...

[(E)-2-cyano-1-phenylethenyl] 4-methylbenzenesulfonate Structure

[(E)-2-cyano-1-...

~%

2,4-Dichloro-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

2,4-Dichloro-6-...

ethyl 3-amino-5-phenyl-1H-pyrrole-2-carboxylate Structure

ethyl 3-amino-5...

~%

2,4-Dichloro-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine Structure

2,4-Dichloro-6-...

6-METHYL-3-NITRO-2-(1-PIPERIDINYL)PYRIDINE Structure

6-METHYL-3-NITR...

~78%

6-METHYL-2-(1-PIPERIDINYL)-3-PYRIDINAMINE Structure

6-METHYL-2-(1-P...

6-methyl-3-nitropyridin-2-ol Structure

6-methyl-3-nitr...

~%

6-METHYL-2-(1-PIPERIDINYL)-3-PYRIDINAMINE Structure

6-METHYL-2-(1-P...

6-Chloro-5-nitro-2-picoline Structure

6-Chloro-5-nitr...

~%

6-METHYL-2-(1-PIPERIDINYL)-3-PYRIDINAMINE Structure

6-METHYL-2-(1-P...

3-Amino-2,4-dichloropyridine Structure

3-Amino-2,4-dic...

~91%

3-AMINO-6-BROMO-2,4-DICHLOROPYRIDINE Structure

3-AMINO-6-BROMO...

Acetimidamide hydrochloride Structure

Acetimidamide h...

Methyl 3-amino-5-phenyl-2-thiophenecarboxylate Structure

Methyl 3-amino-...

~%

2-METHYL-6-PHENYLTHIENO[3,2-D]PYRIMIDIN-4-OL Structure

2-METHYL-6-PHEN...