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

Synthesis and CNS Activity of N, N??Disubstituted 1??(Aminomethyl)??5??alkyl??3??(aryloxyacetylhydrazono) indolin??2??ones

R Agarwal, S Misra, RK Satsangi…

Index: Agarwal; Misra; Satsangi; Tiwari Archiv der Pharmazie, 1982 , vol. 315, # 2 p. 142 - 146

Full Text: HTML

Citation Number: 5

Abstract

Abstract Isatin and 5-methylisatin were condensed with various aryloxyacetylhydrazides to furnish the 3-(aryloxyacetylhydrazono)-5-alkylindolin-2-ones 1–4. When 1–4 were subjected to Mannich reaction, the N, N-disubstituted 1-(aminomethyl)-5-alkyl-3-( aryloxyacetylhydrazono) indolin-2-ones 5–8 were obtained. The compounds were CNS active and relatively non-toxic (albino mice).

Formaldehyde Structure

1-(4-Methylphenyl)piperazine Structure

1-(4-Methylphen...

3-(2-Naphthyloxyacetylhydrazono)-indolin-2-one Structure

3-(2-Naphthylox...

~65%

N-[(E)-[1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[1-[[4-(...

2-(2-NAPHTHYLOXY)ACETOHYDRAZIDE Structure

2-(2-NAPHTHYLOX...

~%

N-[(E)-[1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[1-[[4-(...

isatin Structure

~%

N-[(E)-[1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[1-[[4-(...

Pyrrolidine Structure

Formaldehyde Structure

[2]naphthyloxy-acetic acid-(5-methyl-2-oxo-indolin-3-ylidenehydrazide) Structure

[2]naphthyloxy-...

~65%

N-[[5-methyl-2-oxo-1-(pyrrolidin-1-ylmethyl)indol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[[5-methyl-2-...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

N-[[5-methyl-2-oxo-1-(pyrrolidin-1-ylmethyl)indol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[[5-methyl-2-...

2-(2-NAPHTHYLOXY)ACETOHYDRAZIDE Structure

2-(2-NAPHTHYLOX...

~%

N-[[5-methyl-2-oxo-1-(pyrrolidin-1-ylmethyl)indol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[[5-methyl-2-...

morpholine Structure

Formaldehyde Structure

[2]naphthyloxy-acetic acid-(5-methyl-2-oxo-indolin-3-ylidenehydrazide) Structure

[2]naphthyloxy-...

~68%

N-[[5-methyl-1-(morpholin-4-ylmethyl)-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[[5-methyl-1-...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

N-[[5-methyl-1-(morpholin-4-ylmethyl)-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[[5-methyl-1-...

2-(2-NAPHTHYLOXY)ACETOHYDRAZIDE Structure

2-(2-NAPHTHYLOX...

~%

N-[[5-methyl-1-(morpholin-4-ylmethyl)-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[[5-methyl-1-...

Piperidine Structure

Formaldehyde Structure

[2]naphthyloxy-acetic acid-(5-methyl-2-oxo-indolin-3-ylidenehydrazide) Structure

[2]naphthyloxy-...

~72%

N-[(E)-[5-methyl-2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[5-methy...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

N-[(E)-[5-methyl-2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[5-methy...

2-(2-NAPHTHYLOXY)ACETOHYDRAZIDE Structure

2-(2-NAPHTHYLOX...

~%

N-[(E)-[5-methyl-2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[5-methy...

Piperidine Structure

Formaldehyde Structure

3-(2-Naphthyloxyacetylhydrazono)-indolin-2-one Structure

3-(2-Naphthylox...

~69%

2-naphthalen-2-yloxy-N-[(E)-[2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]acetamide Structure

2-naphthalen-2-...

2-(2-NAPHTHYLOXY)ACETOHYDRAZIDE Structure

2-(2-NAPHTHYLOX...

~%

2-naphthalen-2-yloxy-N-[(E)-[2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]acetamide Structure

2-naphthalen-2-...

isatin Structure

~%

2-naphthalen-2-yloxy-N-[(E)-[2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]acetamide Structure

2-naphthalen-2-...

Formaldehyde Structure

1-(4-Methylphenyl)piperazine Structure

1-(4-Methylphen...

[2]naphthyloxy-acetic acid-(5-methyl-2-oxo-indolin-3-ylidenehydrazide) Structure

[2]naphthyloxy-...

~72%

N-[(E)-[5-methyl-1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[5-methy...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

N-[(E)-[5-methyl-1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[5-methy...

2-(2-NAPHTHYLOXY)ACETOHYDRAZIDE Structure

2-(2-NAPHTHYLOX...

~%

N-[(E)-[5-methyl-1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-naphthalen-2-yloxyacetamide Structure

N-[(E)-[5-methy...

morpholine Structure

Formaldehyde Structure

N/A Structure

~82%

N-[[1-(morpholin-4-ylmethyl)-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[1-(morpholi...

Acetic acid,2-(4-nitrophenoxy)-, hydrazide Structure

Acetic acid,2-(...

~%

N-[[1-(morpholin-4-ylmethyl)-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[1-(morpholi...

isatin Structure

~%

N-[[1-(morpholin-4-ylmethyl)-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[1-(morpholi...

Formaldehyde Structure

1-(4-Methylphenyl)piperazine Structure

1-(4-Methylphen...

N/A Structure

~67%

N-[(E)-[1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[(E)-[1-[[4-(...

Acetic acid,2-(4-nitrophenoxy)-, hydrazide Structure

Acetic acid,2-(...

~%

N-[(E)-[1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[(E)-[1-[[4-(...

isatin Structure

~%

N-[(E)-[1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[(E)-[1-[[4-(...

Piperidine Structure

Formaldehyde Structure

N'-(5-methyl-2-oxoindolin-3-ylidene)-2-(4-nitrophenoxy)acetohydrazide Structure

N'-(5-methyl-2-...

~65%

N-[[5-methyl-2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[5-methyl-2-...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

N-[[5-methyl-2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[5-methyl-2-...

Acetic acid,2-(4-nitrophenoxy)-, hydrazide Structure

Acetic acid,2-(...

~%

N-[[5-methyl-2-oxo-1-(piperidin-1-ylmethyl)indol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[5-methyl-2-...

Formaldehyde Structure

1-(4-Methylphenyl)piperazine Structure

1-(4-Methylphen...

N'-(5-methyl-2-oxoindolin-3-ylidene)-2-(4-nitrophenoxy)acetohydrazide Structure

N'-(5-methyl-2-...

~72%

N-[[5-methyl-1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[5-methyl-1-...

5-Methylindoline-2,3-dione Structure

5-Methylindolin...

~%

N-[[5-methyl-1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[5-methyl-1-...

Acetic acid,2-(4-nitrophenoxy)-, hydrazide Structure

Acetic acid,2-(...

~%

N-[[5-methyl-1-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2-oxoindol-3-ylidene]amino]-2-(4-nitrophenoxy)acetamide Structure

N-[[5-methyl-1-...