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

Synthesis and murine antineoplastic activity of bis [carbamoyloxymethyl] derivatives of pyrrolo [2, 1-a] isoquinoline

WK Anderson, HL McPherson Jr, JS New…

Index: Anderson, Wayne K.; McPherson, Howard L.; New, James S.; Rick, Arvela C. Journal of Medicinal Chemistry, 1984 , vol. 27, # 10 p. 1321 - 1325

Full Text: HTML

Citation Number: 35

Abstract

The synthesis of 4, 5-dihydropyrrolo [2, la] isoquinolines is reported. A key intermediate in the synthesis of 8-methoxy-4, 5-dihydropyrrolo [2, lu] isoquinolines, 6-hydroxy-l, 2, 3, 4- tetrahydroisoquinoline-l-carboxylic acid (6), was prepared by using a regiospecific phenolic cyclization reaction. The P388 lymphocytic activity is reported for l, 2-bis (hydroxymethy)-5, 6- dihydro-8-methoxy-3-methylpyrrolo [2, 1-a] isoquinoline bis (isopropy1carbamate)(1 la), 1, ...

cyclohexylisocyanate Structure

cyclohexylisocyanate

N/A Structure

~72%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

3-Benzyloxybenzaldehyde Structure

3-Benzyloxybenz...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

Benzene,1-(2-nitroethenyl)-3-(phenylmethoxy)- Structure

Benzene,1-(2-ni...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

2-(3-PHENOXY-PHENYL)-ETHYLAMINE Structure

2-(3-PHENOXY-PH...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

3-Hydroxyphenethylamine hydrochloride Structure

3-Hydroxyphenet...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Structure

6-Hydroxy-1,2,3...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

dimethyl 5,6-dihydro-8-hydroxy-3-methylpyrrolo(2,1-a)isoquinoline-1,2-dicarboxylate Structure

dimethyl 5,6-di...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

dimethyl 5,6-dihydro-8-methoxy-3-methylpyrrolo(2,1-a)isoquinoline-1,2-dicarboxylate Structure

dimethyl 5,6-di...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

dimethyl 8-acetoxy-5,6-dihydro-3-methylpyrrolo(2,1-a)isoquinoline-1,2-dicarboxylate Structure

dimethyl 8-acet...

~%

Carbamic acid, cyclohexyl-, (5, 6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinolne-1, 2-diyl)bis(methylene) ester Structure

Carbamic acid, ...

N/A Structure

2-Isocyanatopropane Structure

2-Isocyanatopropane

~65%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

3-Benzyloxybenzaldehyde Structure

3-Benzyloxybenz...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

2-(3-PHENOXY-PHENYL)-ETHYLAMINE Structure

2-(3-PHENOXY-PH...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

3-Hydroxyphenethylamine hydrochloride Structure

3-Hydroxyphenet...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Structure

6-Hydroxy-1,2,3...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

dimethyl 5,6-dihydro-8-hydroxy-3-methylpyrrolo(2,1-a)isoquinoline-1,2-dicarboxylate Structure

dimethyl 5,6-di...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

dimethyl 5,6-dihydro-8-methoxy-3-methylpyrrolo(2,1-a)isoquinoline-1,2-dicarboxylate Structure

dimethyl 5,6-di...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

dimethyl 8-acetoxy-5,6-dihydro-3-methylpyrrolo(2,1-a)isoquinoline-1,2-dicarboxylate Structure

dimethyl 8-acet...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester Structure

3-methyl-5,6-di...

~%

Pyrrolo[2,1-a]isoquinoline-1,2-dimethanol, 5,6-dihydro-3-methyl-, bis (methylcarbamate) (ester) Structure

Pyrrolo[2,1-a]i...

Benzene,1-(2-nitroethenyl)-3-(phenylmethoxy)- Structure

Benzene,1-(2-ni...

~%

Carbamic acid,(1-methylethyl)-,(5,6-dihydro-8-methoxy-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene)ester (9CI) Structure

Carbamic acid,(...

3-Hydroxyphenethylamine hydrochloride Structure

3-Hydroxyphenet...

Glyoxylic acid Structure

~74%

6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Structure

6-Hydroxy-1,2,3...

Methylisocyanate 1 x 500mg neat Structure

Methylisocyanat...

[1-(hydroxymethyl)-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]methanol Structure

[1-(hydroxymeth...

~32%

Pyrrolo[2,1-a]isoquinoline-1,2-dimethanol, 5,6-dihydro-3-methyl-, bis (methylcarbamate) (ester) Structure

Pyrrolo[2,1-a]i...

[1-(hydroxymethyl)-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]methanol Structure

[1-(hydroxymeth...

Ethyl isocyanate Structure

Ethyl isocyanate

~40%

Carbamic acid, ethyl-,(5,6-dihydro-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene) ester(9CI) Structure

Carbamic acid, ...

3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester Structure

3-methyl-5,6-di...

~%

Carbamic acid, ethyl-,(5,6-dihydro-3-methylpyrrolo[2,1-a]isoquinoline-1,2-diyl)bis(methylene) ester(9CI) Structure

Carbamic acid, ...

3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester Structure

3-methyl-5,6-di...

~87%

[1-(hydroxymethyl)-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]methanol Structure

[1-(hydroxymeth...

cyclohexylisocyanate Structure

cyclohexylisocyanate

[1-(hydroxymethyl)-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]methanol Structure

[1-(hydroxymeth...

~45%

[1-(cyclohexylcarbamoyloxymethyl)-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]methyl N-cyclohexylcarbamate Structure

[1-(cyclohexylc...

3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester Structure

3-methyl-5,6-di...

~%

[1-(cyclohexylcarbamoyloxymethyl)-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]methyl N-cyclohexylcarbamate Structure

[1-(cyclohexylc...

Benzene,1-(2-nitroethenyl)-3-(phenylmethoxy)- Structure

Benzene,1-(2-ni...

~98%

2-(3-PHENOXY-PHENYL)-ETHYLAMINE Structure

2-(3-PHENOXY-PH...

3-Benzyloxybenzaldehyde Structure

3-Benzyloxybenz...

~%

2-(3-PHENOXY-PHENYL)-ETHYLAMINE Structure

2-(3-PHENOXY-PH...