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

Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups

Y Fukuda, H Furuta, Y Kusama, H Ebisu…

Index: Fukuda, Yasumichi; Furuta, Hirosuke; Shiga, Futoshi; Asahina, Yoshikazu; Terashima, Shiro Heterocycles, 1997 , vol. 45, # 12 p. 2303 - 2308

Full Text: HTML

Citation Number: 30

Abstract

The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl-and/or (S)-10 carrying various acyl moieties at the N6-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated.

(S)-7-(7-(1-(chloromethyl)-5-hydroxy-8-methyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-3-carbonyl)-4-hydroxy-5-methoxy-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-3-carbonyl)-4-hydroxy-5-methoxy-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxamide Structure

(S)-7-(7-(1-(ch...

~44%

Rachelmycin Structure

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester Structure

(S)-1,6-dihydro...

~%

Rachelmycin Structure

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester Structure

(S)-1-(chlorome...

~%

Rachelmycin Structure

(1S)-3-[(tert-butyloxy)carbonyl]-1-(chloromethyl)-5-hydroxy-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole Structure

(1S)-3-[(tert-b...

~%

Rachelmycin Structure

(S)-6-tert-butyl 1-methyl 8-(acetoxymethyl)-4-(benzyloxy)-7,8-dihydropyrrolo[3,2-e]indole-1,6(3H)-dicarboxylate Structure

(S)-6-tert-buty...

~%

Rachelmycin Structure

N/A Structure

~%

Rachelmycin Structure

(S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrole hydrochloride Structure

(S)-1-(chlorome...

~%

Rachelmycin Structure

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester Structure

(S)-1,6-dihydro...

~%

2-Benzofurancarboxamide,N-[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)- Structure

2-Benzofurancar...

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester Structure

(S)-1-(chlorome...

~%

2-Benzofurancarboxamide,N-[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)- Structure

2-Benzofurancar...

(S)-6-tert-butyl 1-methyl 8-(acetoxymethyl)-4-(benzyloxy)-7,8-dihydropyrrolo[3,2-e]indole-1,6(3H)-dicarboxylate Structure

(S)-6-tert-buty...

~%

2-Benzofurancarboxamide,N-[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)- Structure

2-Benzofurancar...

N/A Structure

~%

2-Benzofurancarboxamide,N-[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)- Structure

2-Benzofurancar...

(1S)-3-[(tert-butyloxy)carbonyl]-1-(chloromethyl)-5-hydroxy-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole Structure

(1S)-3-[(tert-b...

~%

2-Benzofurancarboxamide,N-[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)- Structure

2-Benzofurancar...

(S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrole hydrochloride Structure

(S)-1-(chlorome...

~%

2-Benzofurancarboxamide,N-[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)- Structure

2-Benzofurancar...

Phenylisocyanate Structure

Phenylisocyanate

6-Diethylamino-benzofuran-2-carboxylic acid [2-((S)-1-chloromethyl-5-hydroxy-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide Structure

6-Diethylamino-...

~87%

2-Benzofurancarboxamide,N-[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-[[(phenylamino)carbonyl]oxy]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]-6-(diethylamino)- Structure

2-Benzofurancar...

Methyl acetoacetate Structure

Methyl acetoacetate

~%

methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate Structure

methyl (8S)-8-(...

methylpiperazine Structure

methylpiperazine

N/A Structure

~%

methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate Structure

methyl (8S)-8-(...

Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI,(.+-.)-CC-...

[Boger,D.L.; Coleman,R.S. Journal of the American Chemical Society, 1988 , vol. 110, p. 4796]

Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI,(.+-.)-CC-...

[Boger,D.L.; Coleman,R.S. Journal of the American Chemical Society, 1988 , vol. 110, p. 4796]

Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI,(.+-.)-CC-...

[Boger,D.L.; Coleman,R.S. Journal of the American Chemical Society, 1988 , vol. 110, p. 4796]

Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI,(.+-.)-CC-...

[Boger,D.L.; Coleman,R.S. Journal of the American Chemical Society, 1988 , vol. 110, p. 4796]

Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI,(.+-.)-CC-...

[Boger,D.L.; Coleman,R.S. Journal of the American Chemical Society, 1988 , vol. 110, p. 4796]