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

Isocytosine H2-receptor histamine antagonists I. Oxmetidine and related compounds

…, CR Ganellin, ME Parsons, DA Rawlings…

Index: Brown; Blakemore; Durant; Emmett; Ganellin; Parsons; Rawlings; Walker European Journal of Medicinal Chemistry, 1988 , vol. 23, # 1 p. 53 - 62

Full Text: HTML

Citation Number: 45

Abstract

Abstract A series of 2-[2-(5-methyl-4-imidazolylmethylthio) ethylamino]-4-pyrimidones was prepared based on cimetidine 1. The model compound 4 has modest H 2-antagonist activity as shown by its ability to antagonise histamine-stimulated tachycardia in guinea pig right atrium in vitro and inhibit histamine-stimulated gastric acid secretion in the lumen-perfused stomach of the anaesthetised rat. Investigation of the effect of substituents in the ...

(E)-ethyl 3-(3-trifluoromethylphenyl)prop-2-enoate Structure

(E)-ethyl 3-(3-...

~%

3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID ETHYL ESTER Structure

3-(3-TRIFLUOROM...

3-(Trifluoromethyl)benzaldehyde Structure

3-(Trifluoromet...

~%

3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID ETHYL ESTER Structure

3-(3-TRIFLUOROM...

piperonal Structure

Ethanol Structure

Malonic acid Structure

~%

ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate Structure

ethyl (E)-3-(1,...

piperonal Structure

~%

1,3-Benzodioxole-5-propanoic acid, ethyl ester Structure

1,3-Benzodioxol...

Ethyl (2E)-3-(3,4,5-trimethoxyphenyl)acrylate Structure

Ethyl (2E)-3-(3...

~%

2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-6-one,dihydrochloride Structure

2-[2-[(5-methyl...

3,4,5-Trimethoxybenzaldehyde Structure

3,4,5-Trimethox...

~%

2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-6-one,dihydrochloride Structure

2-[2-[(5-methyl...

5-(3,4,5-trimethoxybenzyl)-2-methylthio-4-pyrimidone Structure

5-(3,4,5-trimet...

4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole Structure

4-[[(2-aminoeth...

~39%

2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-6-one,dihydrochloride Structure

2-[2-[(5-methyl...

ETHYL 3,4,5-TRIMETHOXYPHENYL PROPIONATE Structure

ETHYL 3,4,5-TRI...

~%

2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-6-one,dihydrochloride Structure

2-[2-[(5-methyl...

5-(3,4,5-trimethoxybenzyl)-2-thiouracil Structure

5-(3,4,5-trimet...

~%

2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-6-one,dihydrochloride Structure

2-[2-[(5-methyl...

4(1H)-Pyrimidinone, 2-(methylthio)-5-(phenylmethyl)- Structure

4(1H)-Pyrimidin...

4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole Structure

4-[[(2-aminoeth...

~62%

5-benzyl-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-benzyl-2-[2-[...

4(1H)-Pyrimidinone,2,3-dihydro-5-(phenylmethyl)-2-thioxo- Structure

4(1H)-Pyrimidin...

~%

5-benzyl-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-benzyl-2-[2-[...

ethyl 2-formyl-3-phenylpropionate Structure

ethyl 2-formyl-...

~%

5-benzyl-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-benzyl-2-[2-[...

o-Anisaldehyde Structure

~%

3-(2-METHOXY-PHENYL)-PROPIONIC ACID ETHYL ESTER Structure

3-(2-METHOXY-PH...

Cinnamic acid, p-chloro-, ethyl ester Structure

Cinnamic acid, ...

~%

5-[(4-chlorophenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Structure

5-[(4-chlorophe...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

~%

5-[(4-chlorophenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Structure

5-[(4-chlorophe...

Ethyl 3-(4-chlorophenyl)propanoate Structure

Ethyl 3-(4-chlo...

~%

5-[(4-chlorophenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Structure

5-[(4-chlorophe...

trans-1-ethoxycarbonyl-2-(3-methoxyphenyl)ethylene Structure

trans-1-ethoxyc...

~%

4(1H)-Pyrimidinone,2,3-dihydro-5-[(3-methoxyphenyl)methyl]-2-thioxo- Structure

4(1H)-Pyrimidin...

m-Anisaldehyde Structure

~%

4(1H)-Pyrimidinone,2,3-dihydro-5-[(3-methoxyphenyl)methyl]-2-thioxo- Structure

4(1H)-Pyrimidin...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

Ethyl 3-(4-methoxyphenyl)propanoate Structure

Ethyl 3-(4-meth...

N/A Structure

~%

5-[(4-fluorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(4-fluorophe...

4-Fluorobenzaldehyde Structure

4-Fluorobenzaldehyde

~%

5-[(4-fluorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(4-fluorophe...

Ethyl 3-(4-fluorophenyl)propanoate Structure

Ethyl 3-(4-fluo...

~%

5-[(4-fluorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(4-fluorophe...

5-(4-fluorobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one Structure

5-(4-fluorobenz...

~%

5-[(4-fluorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(4-fluorophe...

piperonal Structure

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one Structure

5-(1,3-benzodio...

ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate Structure

ethyl (E)-3-(1,...

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one Structure

5-(1,3-benzodio...

1,3-Benzodioxole-5-propanoic acid, ethyl ester Structure

1,3-Benzodioxol...

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one Structure

5-(1,3-benzodio...

Ethyl 3-oxohexanoate Structure

Ethyl 3-oxohexanoate

thiourea Structure

~%

Propylthiouracil Structure

Propylthiouracil

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

~%

Ethyl 3-(4-chlorophenyl)propanoate Structure

Ethyl 3-(4-chlo...

2-Propenoic acid, 3-(3-chlorophenyl)-, ethyl ester Structure

2-Propenoic aci...

~%

5-[(3-chlorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(3-chlorophe...

3-Chlorobenzaldehyde Structure

3-Chlorobenzaldehyde

~%

5-[(3-chlorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(3-chlorophe...

N/A Structure

4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole Structure

4-[[(2-aminoeth...

~57%

5-[(3-chlorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(3-chlorophe...

N/A Structure

~%

5-[(3-chlorophenyl)methyl]-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

5-[(3-chlorophe...

piperonal Structure

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-[[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]amino]-1H-pyrimidin-4-one dihydrochloride Structure

5-(1,3-benzodio...

ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate Structure

ethyl (E)-3-(1,...

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-[[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]amino]-1H-pyrimidin-4-one dihydrochloride Structure

5-(1,3-benzodio...

1,3-Benzodioxole-5-propanoic acid, ethyl ester Structure

1,3-Benzodioxol...

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-[[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]amino]-1H-pyrimidin-4-one dihydrochloride Structure

5-(1,3-benzodio...

2-methylthio-5-(3,4-methylenedioxybenzyl)pyrimid-4-one Structure

2-methylthio-5-...

4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole Structure

4-[[(2-aminoeth...

~47%

5-(1,3-benzodioxol-5-ylmethyl)-2-[[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]amino]-1H-pyrimidin-4-one dihydrochloride Structure

5-(1,3-benzodio...

N/A Structure

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-[[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]amino]-1H-pyrimidin-4-one dihydrochloride Structure

5-(1,3-benzodio...

5-(1,3-benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one Structure

5-(1,3-benzodio...

4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole Structure

4-[[(2-aminoeth...

~%

5-(1,3-benzodioxol-5-ylmethyl)-2-[[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]amino]-1H-pyrimidin-4-one dihydrochloride Structure

5-(1,3-benzodio...

3-(3-ethoxy-phenyl)-acrylic acid ethyl ester Structure

3-(3-ethoxy-phe...

~%

4(1H)-Pyrimidinone,5-[(3-ethoxyphenyl)methyl]-2,3-dihydro-2-thioxo- Structure

4(1H)-Pyrimidin...

N/A Structure

~%

4(1H)-Pyrimidinone,5-[(3-ethoxyphenyl)methyl]-2,3-dihydro-2-thioxo- Structure

4(1H)-Pyrimidin...

N/A Structure

~%

5-[(4-methylphenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Structure

5-[(4-methylphe...

p-Tolualdehyde Structure

~%

5-[(4-methylphenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Structure

5-[(4-methylphe...

ETHYL 3-(P-TOLYL)PROPANOATE Structure

ETHYL 3-(P-TOLY...

~%

5-[(4-methylphenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Structure

5-[(4-methylphe...

veratraldehyde Structure

~%

ethyl 3-(3,4-dimethoxyphenyl)propanoate Structure

ethyl 3-(3,4-di...

2-Methylthio-4-pyrimidone Structure

2-Methylthio-4-...

4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole Structure

4-[[(2-aminoeth...

~64%

2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one,dihydrochloride Structure

2-[2-[(5-methyl...

N/A Structure

~%

ETHYL 3-(P-TOLYL)PROPANOATE Structure

ETHYL 3-(P-TOLY...

p-Tolualdehyde Structure

~%

ETHYL 3-(P-TOLYL)PROPANOATE Structure

ETHYL 3-(P-TOLY...

3-arylpropanoate esters through the palladium-catalyzed reac...

[Battistuzzi, Gianfranco; Cacchi, Sandro; Fabrizi, Giancarlo; Bernini, Roberta Synlett, 2003 , # 8 p. 1133 - 1136]

Inhibition of uridine phosphorylase: synthesis and structure...

[Orr; Musso; Boswell; Kelley; Joyner; Davis; Baccanari Journal of Medicinal Chemistry, 1995 , vol. 38, # 19 p. 3850 - 3856]