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

Studies in the heterocyclic series. XVI. Open azaphenothiazines as new central nervous system depressants.

CO Okafor, ML Steenberg, JP Buckley

Index: Okafor; Steenberg; Buckley Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 1 p. 302 - 318

Full Text: HTML

Citation Number: 4

Abstract

Acid-catalyzed condensation of 2-amino-3-mercapto-6-methylpyridine and 3-amino-pyridine- 2 [1H]-thiones with 4-chloropyrimidines having free 5-carbon centers gave N-(3-mercapto-2- pyridyl)-6-pyrimidinylamines and N-(2-thioxo-3-pyridyl)-6-pyrimidinyl-amines, which we

5-Chloro-2-pyridinamine Structure

5-Chloro-2-pyri...

~%

3-((6-Amino-2-(methylthio)-4-pyrimidinyl)amino)-6-chloro-2(1H)-pyridinethione Structure

3-((6-Amino-2-(...

2-Chloro-5-nitropyridine Structure

2-Chloro-5-nitr...

~%

3-((6-Amino-2-(methylthio)-4-pyrimidinyl)amino)-6-chloro-2(1H)-pyridinethione Structure

3-((6-Amino-2-(...

5-Chloro[1,3]thiazolo[5,4-b]pyridin-2-amine Structure

5-Chloro[1,3]th...

~%

3-((6-Amino-2-(methylthio)-4-pyrimidinyl)amino)-6-chloro-2(1H)-pyridinethione Structure

3-((6-Amino-2-(...

5-Chloro-2-pyridinamine Structure

5-Chloro-2-pyri...

~%

6-chloro-3-[(2,6-diaminopyrimidin-4-yl)amino]-1H-pyridine-2-thione Structure

6-chloro-3-[(2,...

2-Chloro-5-nitropyridine Structure

2-Chloro-5-nitr...

~%

6-chloro-3-[(2,6-diaminopyrimidin-4-yl)amino]-1H-pyridine-2-thione Structure

6-chloro-3-[(2,...

5-Chloro[1,3]thiazolo[5,4-b]pyridin-2-amine Structure

5-Chloro[1,3]th...

~%

6-chloro-3-[(2,6-diaminopyrimidin-4-yl)amino]-1H-pyridine-2-thione Structure

6-chloro-3-[(2,...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

2-amino-6-methylpyridine-3-thiol Structure

2-amino-6-methy...

2-Amino-3-thiocyanato-6-picoline Structure

2-Amino-3-thioc...

~%

2-amino-6-methylpyridine-3-thiol Structure

2-amino-6-methy...

2,4,6-Trichloropyrimidine Structure

2,4,6-Trichloro...

3-amino-6-methoxy-1H-pyridine-2-thione Structure

3-amino-6-metho...

~72%

3-[(2,6-dichloropyrimidin-4-yl)amino]-6-methoxy-1H-pyridine-2-thione Structure

3-[(2,6-dichlor...

6-methoxypyridin-3-amin Structure

6-methoxypyridi...

~%

3-[(2,6-dichloropyrimidin-4-yl)amino]-6-methoxy-1H-pyridine-2-thione Structure

3-[(2,6-dichlor...

2-Methoxy-5-nitropyridine Structure

2-Methoxy-5-nit...

~%

3-[(2,6-dichloropyrimidin-4-yl)amino]-6-methoxy-1H-pyridine-2-thione Structure

3-[(2,6-dichlor...

5-methoxy-[1,3]thiazolo[5,4-b]pyridin-2-amine Structure

5-methoxy-[1,3]...

~%

3-[(2,6-dichloropyrimidin-4-yl)amino]-6-methoxy-1H-pyridine-2-thione Structure

3-[(2,6-dichlor...

2-Amino-4,6-dichloropyrimidine Structure

2-Amino-4,6-dic...

2-amino-6-methylpyridine-3-thiol Structure

2-amino-6-methy...

~53%

3-Pyridinethiol, 2-((2-amino-4-chloro-6-pyrimidinyl)amino)-6-methyl- Structure

3-Pyridinethiol...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

3-Pyridinethiol, 2-((2-amino-4-chloro-6-pyrimidinyl)amino)-6-methyl- Structure

3-Pyridinethiol...

2-Amino-3-thiocyanato-6-picoline Structure

2-Amino-3-thioc...

~%

3-Pyridinethiol, 2-((2-amino-4-chloro-6-pyrimidinyl)amino)-6-methyl- Structure

3-Pyridinethiol...

6-Chloropyrimidine-2,4-diamine Structure

6-Chloropyrimid...

2-amino-6-methylpyridine-3-thiol Structure

2-amino-6-methy...

~67%

2-[(2,6-diaminopyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(2,6-diamino...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

2-[(2,6-diaminopyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(2,6-diamino...

2-Amino-3-thiocyanato-6-picoline Structure

2-Amino-3-thioc...

~%

2-[(2,6-diaminopyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(2,6-diamino...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

2-[(6-amino-2-methylsulfanylpyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(6-amino-2-m...

2-Amino-3-thiocyanato-6-picoline Structure

2-Amino-3-thioc...

~%

2-[(6-amino-2-methylsulfanylpyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(6-amino-2-m...

4-Chloro-2,6-dimethoxypyrimidine Structure

4-Chloro-2,6-di...

2-amino-6-methylpyridine-3-thiol Structure

2-amino-6-methy...

~60%

2-[(2,6-dimethoxypyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(2,6-dimetho...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

2-[(2,6-dimethoxypyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(2,6-dimetho...

2-Amino-3-thiocyanato-6-picoline Structure

2-Amino-3-thioc...

~%

2-[(2,6-dimethoxypyrimidin-4-yl)amino]-6-methylpyridine-3-thiol Structure

2-[(2,6-dimetho...

6-Chloropyrimidine-2,4-diamine Structure

6-Chloropyrimid...

3-amino-6-methoxy-1H-pyridine-2-thione Structure

3-amino-6-metho...

~92%

2(1H)-Pyridinethione, 3-((2,6-diamino-4-pyrimidinyl)amino)-6-methoxy- Structure

2(1H)-Pyridinet...

6-methoxypyridin-3-amin Structure

6-methoxypyridi...

~%

2(1H)-Pyridinethione, 3-((2,6-diamino-4-pyrimidinyl)amino)-6-methoxy- Structure

2(1H)-Pyridinet...

2-Methoxy-5-nitropyridine Structure

2-Methoxy-5-nit...

~%

2(1H)-Pyridinethione, 3-((2,6-diamino-4-pyrimidinyl)amino)-6-methoxy- Structure

2(1H)-Pyridinet...

5-methoxy-[1,3]thiazolo[5,4-b]pyridin-2-amine Structure

5-methoxy-[1,3]...

~%

2(1H)-Pyridinethione, 3-((2,6-diamino-4-pyrimidinyl)amino)-6-methoxy- Structure

2(1H)-Pyridinet...

2,4,6-Trichloropyrimidine Structure

2,4,6-Trichloro...

2-amino-6-methylpyridine-3-thiol Structure

2-amino-6-methy...

~58%

2-(2,4-Dichloropyrimidin-6-ylamino)-6-methyl-1H-pyridinium-3-thiolate Structure

2-(2,4-Dichloro...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

2-(2,4-Dichloropyrimidin-6-ylamino)-6-methyl-1H-pyridinium-3-thiolate Structure

2-(2,4-Dichloro...

2-Amino-3-thiocyanato-6-picoline Structure

2-Amino-3-thioc...

~%

2-(2,4-Dichloropyrimidin-6-ylamino)-6-methyl-1H-pyridinium-3-thiolate Structure

2-(2,4-Dichloro...

4-Chloro-6-methyl-2-pyrimidinamine Structure

4-Chloro-6-meth...

2-amino-6-methylpyridine-3-thiol Structure

2-amino-6-methy...

~79%

2-(2-Amino-4-methylpyrimidin-6-ylamino)-6-methyl-1H-pyridinium-3-thiol ate Structure

2-(2-Amino-4-me...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

2-(2-Amino-4-methylpyrimidin-6-ylamino)-6-methyl-1H-pyridinium-3-thiol ate Structure

2-(2-Amino-4-me...

2-Amino-3-thiocyanato-6-picoline Structure

2-Amino-3-thioc...

~%

2-(2-Amino-4-methylpyrimidin-6-ylamino)-6-methyl-1H-pyridinium-3-thiol ate Structure

2-(2-Amino-4-me...