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

Cytotoxic and antitumoral properties in a series of new, ring D modified, olivacine analogues

…, E Raimbaud, S Léonce, L Kraus-Berthier…

Index: Guillonneau, Claude; Nault, Annette; Raimbaud, Eric; Leonce, Stephane; Kraus-Berthier, Laurence; Pierre, Alain; Goldstein, Solo Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 1 p. 175 - 184

Full Text: HTML

Citation Number: 19

Abstract

The present study describes the synthesis and pharmacological profiles of new olivacine related compounds, possessing a modified D ring. The impact of this modification has been evaluated with respect to the cytotoxic and in vivo antitumoral effects of these molecules and in comparison with parent S 16020-2 previously prepared and investigated in our laboratory. The D ring size and number of nitrogen atoms as well as the position of the aminoalkyl ...

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

7-(diacetylamino)-8,9-dimethyl-6-nitro-9H-carbazol-3-yl acetate Structure

7-(diacetylamin...

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...

Acetyl chloride Structure

Acetyl chloride

~%

2,9,10-trimethyl-6-phenylmethoxy-3H-imidazo[4,5-b]carbazole Structure

2,9,10-trimethy...

1H-Furo[3,4-b]carbazole-1,3(5H)-dione, 4,5-dimethyl- Structure

1H-Furo[3,4-b]c...

~50%

10,11-dimethyl-1H-[1,3]oxazino[4,5-b]carbazole-2,4-dione Structure

10,11-dimethyl-...

10,11-dimethyl-1H-[1,3]oxazino[4,5-b]carbazole-2,4-dione Structure

10,11-dimethyl-...

~76%

10,11-dimethyl-1H-pyrimido[4,5-b]carbazol-4-one Structure

10,11-dimethyl-...

10,11-dimethyl-1H-pyrimido[4,5-b]carbazol-4-one Structure

10,11-dimethyl-...

~93%

4-chloro-10,11-dimethylpyrimido[4,5-b]carbazole Structure

4-chloro-10,11-...

10,11-dimethyl-1H-[1,3]oxazino[4,5-b]carbazole-2,4-dione Structure

10,11-dimethyl-...

~%

4-chloro-10,11-dimethylpyrimido[4,5-b]carbazole Structure

4-chloro-10,11-...

4-chloro-10,11-dimethylpyrimido[4,5-b]carbazole Structure

4-chloro-10,11-...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

~71%

10,11-dimethylpyrimido[4,5-b]carbazole-4-carbonitrile Structure

10,11-dimethylp...

10,11-dimethyl-1H-pyrimido[4,5-b]carbazol-4-one Structure

10,11-dimethyl-...

~%

10,11-dimethylpyrimido[4,5-b]carbazole-4-carbonitrile Structure

10,11-dimethylp...

10,11-dimethyl-1H-[1,3]oxazino[4,5-b]carbazole-2,4-dione Structure

10,11-dimethyl-...

~%

10,11-dimethylpyrimido[4,5-b]carbazole-4-carbonitrile Structure

10,11-dimethylp...

10,11-dimethylpyrimido[4,5-b]carbazole-4-carbonitrile Structure

10,11-dimethylp...

~75%

10,11-dimethylpyrimido[4,5-b]carbazole-4-carboxamide Structure

10,11-dimethylp...

4-chloro-10,11-dimethylpyrimido[4,5-b]carbazole Structure

4-chloro-10,11-...

~%

10,11-dimethylpyrimido[4,5-b]carbazole-4-carboxamide Structure

10,11-dimethylp...

10,11-dimethyl-1H-pyrimido[4,5-b]carbazol-4-one Structure

10,11-dimethyl-...

~%

10,11-dimethylpyrimido[4,5-b]carbazole-4-carboxamide Structure

10,11-dimethylp...

10,11-dimethyl-1H-[1,3]oxazino[4,5-b]carbazole-2,4-dione Structure

10,11-dimethyl-...

~%

10,11-dimethylpyrimido[4,5-b]carbazole-4-carboxamide Structure

10,11-dimethylp...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~95%

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~%

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

Ethanoic anhydride Structure

Ethanoic anhydride

~63%

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

methyl iodide Structure

~62%

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

~%

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~%

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

7-(diacetylamino)-8,9-dimethyl-6-nitro-9H-carbazol-3-yl acetate Structure

7-(diacetylamin...

~98%

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

~%

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~%

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

~99%

6,7-diamino-8,9-dimethylcarbazol-3-ol Structure

6,7-diamino-8,9...

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

~%

6,7-diamino-8,9-dimethylcarbazol-3-ol Structure

6,7-diamino-8,9...

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

6,7-diamino-8,9-dimethylcarbazol-3-ol Structure

6,7-diamino-8,9...

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

6,7-diamino-8,9-dimethylcarbazol-3-ol Structure

6,7-diamino-8,9...

7-(diacetylamino)-8,9-dimethyl-6-nitro-9H-carbazol-3-yl acetate Structure

7-(diacetylamin...

~%

6,7-diamino-8,9-dimethylcarbazol-3-ol Structure

6,7-diamino-8,9...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~%

6,7-diamino-8,9-dimethylcarbazol-3-ol Structure

6,7-diamino-8,9...

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

Benzyl chloride Structure

Benzyl chloride

~80%

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

~%

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

7-(diacetylamino)-8,9-dimethyl-6-nitro-9H-carbazol-3-yl acetate Structure

7-(diacetylamin...

~%

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~%

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

1,9-dimethyl-3-nitro-6-phenylmethoxycarbazol-2-amine Structure

1,9-dimethyl-3-...

~96%

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...

7-amino-8-methyl-9H-carbazol-3-ol Structure

7-amino-8-methy...

~%

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...

7-amino-8,9-dimethyl-6-nitrocarbazol-3-ol Structure

7-amino-8,9-dim...

~%

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...

[7-(diacetylamino)-8-methyl-9H-carbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...

[7-(diacetylamino)-8,9-dimethylcarbazol-3-yl] acetate Structure

[7-(diacetylami...

~%

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...

7-(diacetylamino)-8,9-dimethyl-6-nitro-9H-carbazol-3-yl acetate Structure

7-(diacetylamin...

~%

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...

2-acetylamino-6-methoxy-1-methyl-9H-carbazole Structure

2-acetylamino-6...

~%

1,9-dimethyl-6-phenylmethoxycarbazole-2,3-diamine Structure

1,9-dimethyl-6-...