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

Journal of medicinal chemistry

Derivatives of Fluorene. XVIII. New Halogenofluorenes. I. Potential Antitumor Agents1, 2

HL Pan, TL Fletcher

Index: Pan,H.-L.; Fletcher,T.L. J. Med. Chem., 1964 , vol. 7, p. 31 - 38

Full Text: HTML

Citation Number: 13

Abstract

A number of new halogenofluorenes have been prepared and characterized. Chlorination of K-2-fluorenylacetamide and 5-2-(9-oxofluoreny1) acetamide and some of their derivatives has been studied. With excess chlorine Y-2-fluorenylacetamide and 5-2-(7-chlorofluoreny1) acetamide give N-2-(1, 3, 4 (?), 7-tetrachlorofluoren~~ l)-acetamide3 (I), whereas? J-2-(6- chlorofluorenyl)-(LVII), and N-2-(6, 7-dichlorofluorenyl) aretamide (LXJ'III) give K-2-(1, 3, 4 ...

N-(3,6-dichloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3,6-dichloro...

~%

3,6-dichlorofluoren-9-one Structure

3,6-dichloroflu...

N-(6-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(6-chloro-9-o...

~%

3,6-dichlorofluoren-9-one Structure

3,6-dichloroflu...

9H-Fluoren-9-one,2-amino-3,6-dichloro- Structure

9H-Fluoren-9-on...

~%

3,6-dichlorofluoren-9-one Structure

3,6-dichloroflu...

9H-Fluoren-2-amine,7-nitro- Structure

9H-Fluoren-2-am...

~%

9H-Fluoren-2-amine,1,3-dibromo-7-nitro- Structure

9H-Fluoren-2-am...

N-(7-fluoro-9-oxo-fluoren-2-yl)acetamide Structure

N-(7-fluoro-9-o...

~%

Acetamide,N-(3-chloro-7-fluoro-9-oxo-9H-fluoren-2-yl)- Structure

Acetamide,N-(3-...

9H-Fluoren-9-one,2-amino-7-chloro- Structure

9H-Fluoren-9-on...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

7-chloro-2-[(2-chlorophenyl)methylideneamino]fluoren-9-one Structure

7-chloro-2-[(2-...

N-(7-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(7-chloro-9-o...

~%

N-(3,7-dichloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3,7-dichloro...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

Acetamide, N- (1,3-dichloro-7-nitro-9H-fluoren-2-yl)- Structure

Acetamide, N- (...

~%

N-(7-amino-1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(7-amino-1,3-...

2-ACETAMIDO-7-NITROFLUORENE Structure

2-ACETAMIDO-7-N...

~%

N-(7-amino-1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(7-amino-1,3-...

2,3,7-Trichlor-fluoren Structure

2,3,7-Trichlor-...

~%

9H-Fluoren-9-one,2,3,7-trichloro- Structure

9H-Fluoren-9-on...

9H FLUORENE Structure

~%

9H-Fluoren-9-one,2,3,7-trichloro- Structure

9H-Fluoren-9-on...

N/A Structure

~%

9H-Fluoren-9-one,2,3,7-trichloro- Structure

9H-Fluoren-9-on...

N/A Structure

~%

9H-Fluoren-9-one,2,3,7-trichloro- Structure

9H-Fluoren-9-on...

9H-Fluoren-9-one,2-amino-3-bromo-7-fluoro- Structure

9H-Fluoren-9-on...

~%

9H-Fluoren-9-ol,2-amino-3-bromo-7-fluoro- Structure

9H-Fluoren-9-ol...

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2,3-dichloro-7-nitro-fluoren-9-one Structure

2,3-dichloro-7-...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2,3-dichloro-7-nitro-fluoren-9-one Structure

2,3-dichloro-7-...

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

~%

2,3-dichloro-7-nitro-fluoren-9-one Structure

2,3-dichloro-7-...

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

N-(3-bromo-9-oxo-fluoren-2-yl)-2,2,2-trifluoro-acetamide Structure

N-(3-bromo-9-ox...

~%

Acetamide,N-(3-bromo-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

9H-Fluoren-9-one,7-amino-2,3-dichloro- Structure

9H-Fluoren-9-on...

~%

2-amino-3-bromo-6,7-dichloro-fluoren-9-one Structure

2-amino-3-bromo...

2,3-dichloro-7-nitro-fluoren-9-one Structure

2,3-dichloro-7-...

~%

2-amino-3-bromo-6,7-dichloro-fluoren-9-one Structure

2-amino-3-bromo...

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2-amino-3-bromo-6,7-dichloro-fluoren-9-one Structure

2-amino-3-bromo...

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

~%

2-amino-3-bromo-6,7-dichloro-fluoren-9-one Structure

2-amino-3-bromo...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2-amino-3-bromo-6,7-dichloro-fluoren-9-one Structure

2-amino-3-bromo...

N-(3,6-dichloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3,6-dichloro...

~%

9H-Fluoren-9-one,2-amino-3,6-dichloro- Structure

9H-Fluoren-9-on...

N-(6-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(6-chloro-9-o...

~%

9H-Fluoren-9-one,2-amino-3,6-dichloro- Structure

9H-Fluoren-9-on...

9H-Fluorene,2-fluoro-7-nitro- Structure

9H-Fluorene,2-f...

~%

9H-Fluorene,9-bromo-2-fluoro-7-nitro- Structure

9H-Fluorene,9-b...

2-ACETAMIDO-7-NITROFLUORENE Structure

2-ACETAMIDO-7-N...

~%

Acetamide,N-(1,3,7-trichloro-9H-fluoren-2-yl)- Structure

Acetamide,N-(1,...

Acetamide, N- (1,3-dichloro-7-nitro-9H-fluoren-2-yl)- Structure

Acetamide, N- (...

~%

Acetamide,N-(1,3,7-trichloro-9H-fluoren-2-yl)- Structure

Acetamide,N-(1,...

N-(7-amino-1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(7-amino-1,3-...

~%

Acetamide,N-(1,3,7-trichloro-9H-fluoren-2-yl)- Structure

Acetamide,N-(1,...

2-ACETAMIDO-7-NITROFLUORENE Structure

2-ACETAMIDO-7-N...

~%

N-(1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(1,3-dichloro...

Acetamide, N- (1,3-dichloro-7-nitro-9H-fluoren-2-yl)- Structure

Acetamide, N- (...

~%

N-(1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(1,3-dichloro...

N-(7-amino-1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(7-amino-1,3-...

~%

N-(1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(1,3-dichloro...

2-ACETAMIDO-7-NITROFLUORENE Structure

2-ACETAMIDO-7-N...

~%

Acetamide,N-(1,3-dichloro-7-fluoro-9H-fluoren-2-yl)- Structure

Acetamide,N-(1,...

Acetamide, N- (1,3-dichloro-7-nitro-9H-fluoren-2-yl)- Structure

Acetamide, N- (...

~%

Acetamide,N-(1,3-dichloro-7-fluoro-9H-fluoren-2-yl)- Structure

Acetamide,N-(1,...

N-(7-amino-1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(7-amino-1,3-...

~%

Acetamide,N-(1,3-dichloro-7-fluoro-9H-fluoren-2-yl)- Structure

Acetamide,N-(1,...

N-(3-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-chloro-9-o...

~%

N-(4-methoxybenzoyl)-2-methyl-furan-3-carbohydrazide Structure

N-(4-methoxyben...

9H-Fluoren-9-one,2-amino-3-chloro- Structure

9H-Fluoren-9-on...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

N-(4-methoxybenzoyl)-2-methyl-furan-3-carbohydrazide Structure

N-(4-methoxyben...

9H-Fluoren-2-amine,7-chloro- Structure

9H-Fluoren-2-am...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

Fluoren-2-amine, 7-chloro-N-(o-chlorobenzylidene)- Structure

Fluoren-2-amine...

N-(3,6,7-trichloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3,6,7-trichl...

~%

2-amino-3,6,7-trichloro-fluoren-9-one Structure

2-amino-3,6,7-t...

Acetamide,N-(6,7-dichloro-9-oxo-9H-fluoren-2-yl)- Structure

Acetamide,N-(6,...

~%

2-amino-3,6,7-trichloro-fluoren-9-one Structure

2-amino-3,6,7-t...

1-Amino-9H-fluoren-9-one Structure

1-Amino-9H-fluo...

~%

9H-Fluoren-9-one,1-amino-2,4-dibromo- Structure

9H-Fluoren-9-on...

N-(3-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-chloro-9-o...

~%

9H-Fluoren-9-one,3-chloro-2-[[(3,4-dichlorophenyl)methylene]amino]- Structure

9H-Fluoren-9-on...

9H-Fluoren-9-one,2-amino-3-chloro- Structure

9H-Fluoren-9-on...

3,4-Dichlorobenzaldehyde Structure

3,4-Dichloroben...

~%

9H-Fluoren-9-one,3-chloro-2-[[(3,4-dichlorophenyl)methylene]amino]- Structure

9H-Fluoren-9-on...

2-amino-6-chloro-fluoren-9-one Structure

2-amino-6-chlor...

~%

9H-Fluoren-2-amine,6-chloro- Structure

9H-Fluoren-2-am...

6-chloro-2-nitro-fluoren-9-one Structure

6-chloro-2-nitr...

~%

9H-Fluoren-2-amine,6-chloro- Structure

9H-Fluoren-2-am...

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

9H-Fluoren-2-amine,6-chloro- Structure

9H-Fluoren-2-am...

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

~%

9H-Fluoren-2-amine,6-chloro- Structure

9H-Fluoren-2-am...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

9H-Fluoren-2-amine,6-chloro- Structure

9H-Fluoren-2-am...

Dichloroacetyl chloride Structure

Dichloroacetyl ...

9H-Fluoren-2-amine,7-nitro- Structure

9H-Fluoren-2-am...

~%

2,2-dichloro-N-(7-nitro-9H-fluoren-2-yl)acetamide Structure

2,2-dichloro-N-...

N-(6-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(6-chloro-9-o...

~%

N-(3,6-dichloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3,6-dichloro...

N-(7-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(7-chloro-9-o...

~%

N-(7-chloro-3-nitro-9-oxo-fluoren-2-yl)acetamide Structure

N-(7-chloro-3-n...

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

6-chloro-2-nitro-fluoren-9-one Structure

6-chloro-2-nitr...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

6-chloro-2-nitro-fluoren-9-one Structure

6-chloro-2-nitr...

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

~%

6-chloro-2-nitro-fluoren-9-one Structure

6-chloro-2-nitr...

N-(7-fluoro-9-oxo-fluoren-2-yl)acetamide Structure

N-(7-fluoro-9-o...

~%

N-(3-bromo-7-fluoro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-bromo-7-fl...

Acetamide,N-(3-bromo-7-fluoro-9H-fluoren-2-yl)- Structure

Acetamide,N-(3-...

~%

N-(3-bromo-7-fluoro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-bromo-7-fl...

Acetamide,N-(7-fluoro-9H-fluoren-2-yl)- Structure

Acetamide,N-(7-...

~%

N-(3-bromo-7-fluoro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-bromo-7-fl...

2-ACETAMIDO-7-NITROFLUORENE Structure

2-ACETAMIDO-7-N...

~%

1,3-dichloro-7-nitro-9H-fluorene Structure

1,3-dichloro-7-...

Acetamide, N- (1,3-dichloro-7-nitro-9H-fluoren-2-yl)- Structure

Acetamide, N- (...

~%

1,3-dichloro-7-nitro-9H-fluorene Structure

1,3-dichloro-7-...

1.3-Dichlor-7-nitro-2-fluorenamin Structure

1.3-Dichlor-7-n...

~%

1,3-dichloro-7-nitro-9H-fluorene Structure

1,3-dichloro-7-...

2-ACETAMIDO-7-NITROFLUORENE Structure

2-ACETAMIDO-7-N...

~%

Acetamide, N- (1,3-dichloro-7-nitro-9H-fluoren-2-yl)- Structure

Acetamide, N- (...

2,3-dichloro-7-nitro-fluoren-9-one Structure

2,3-dichloro-7-...

~%

9H-Fluoren-9-one,7-amino-2,3-dichloro- Structure

9H-Fluoren-9-on...

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

9H-Fluoren-9-one,7-amino-2,3-dichloro- Structure

9H-Fluoren-9-on...

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

~%

9H-Fluoren-9-one,7-amino-2,3-dichloro- Structure

9H-Fluoren-9-on...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

9H-Fluoren-9-one,7-amino-2,3-dichloro- Structure

9H-Fluoren-9-on...

Acetamide,N-(3-bromo-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2-amino-3-bromo-7-nitro-fluoren-9-one Structure

2-amino-3-bromo...

N-(3-bromo-9-oxo-fluoren-2-yl)-2,2,2-trifluoro-acetamide Structure

N-(3-bromo-9-ox...

~%

2-amino-3-bromo-7-nitro-fluoren-9-one Structure

2-amino-3-bromo...

2,7-diacetylaminofluorene Structure

2,7-diacetylami...

~%

Acetamide,N,N'-(1,3,6,8-tetrachlorofluoren-2,7-ylene)bis- (7CI,8CI) Structure

Acetamide,N,N'-...

Acetamide,N-(7-chloro-9H-fluoren-2-yl)- Structure

Acetamide,N-(7-...

~%

N-(3,7-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(3,7-dichloro...

ACETAMIDE, N-(3-CHLORO-9H-FLUOREN-2-YL)- Structure

ACETAMIDE, N-(3...

~%

N-(3,7-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(3,7-dichloro...

N-(3-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-chloro-9-o...

~%

N-(3-chloro-7-nitro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-chloro-7-n...

6-chloro-2-nitro-fluoren-9-one Structure

6-chloro-2-nitr...

~%

2-amino-6-chloro-fluoren-9-one Structure

2-amino-6-chlor...

Acetamide,N-(3-chloro-7-nitro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2-amino-6-chloro-fluoren-9-one Structure

2-amino-6-chlor...

2-amino-3-chloro-7-nitro-fluoren-9-one Structure

2-amino-3-chlor...

~%

2-amino-6-chloro-fluoren-9-one Structure

2-amino-6-chlor...

Acetamide,N-(3-chloro-9-oxo-9H-fluoren-2-yl)-2,2,2-trifluoro- Structure

Acetamide,N-(3-...

~%

2-amino-6-chloro-fluoren-9-one Structure

2-amino-6-chlor...

7-Bromo-9H-fluoren-2-amine Structure

7-Bromo-9H-fluo...

~%

1,3,7-TRIBROMO-2-FLUORENAMINE Structure

1,3,7-TRIBROMO-...

N-(3-chloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3-chloro-9-o...

~%

3-chloro-2-(3,4-dichlorophenyl)fluoren-9-one Structure

3-chloro-2-(3,4...

9H-Fluoren-9-one,2-amino-3-chloro- Structure

9H-Fluoren-9-on...

1,2-Dichlorobenzene Structure

1,2-Dichlorobenzene

~%

3-chloro-2-(3,4-dichlorophenyl)fluoren-9-one Structure

3-chloro-2-(3,4...

2-ACETAMIDO-7-NITROFLUORENE Structure

2-ACETAMIDO-7-N...

~%

Acetamide, N-(1,3-dichloro-9-oxo-9H-fluoren-2-yl)- Structure

Acetamide, N-(1...

Acetamide, N- (1,3-dichloro-7-nitro-9H-fluoren-2-yl)- Structure

Acetamide, N- (...

~%

Acetamide, N-(1,3-dichloro-9-oxo-9H-fluoren-2-yl)- Structure

Acetamide, N-(1...

N-(1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(1,3-dichloro...

~%

Acetamide, N-(1,3-dichloro-9-oxo-9H-fluoren-2-yl)- Structure

Acetamide, N-(1...

N-(7-amino-1,3-dichloro-9H-fluoren-2-yl)acetamide Structure

N-(7-amino-1,3-...

~%

Acetamide, N-(1,3-dichloro-9-oxo-9H-fluoren-2-yl)- Structure

Acetamide, N-(1...

Acetamide,N-(6,7-dichloro-9-oxo-9H-fluoren-2-yl)- Structure

Acetamide,N-(6,...

~%

N-(3,6,7-trichloro-9-oxo-fluoren-2-yl)acetamide Structure

N-(3,6,7-trichl...

A Convenient Route to 3, 6-Diaminofluoren-9-ones

[Guinot, Stephane G. R.; Hepworth, John D.; Wainwright, Mark Journal of Chemical Research, Miniprint, 1997 , # 6 p. 1252 - 1261]

The Constitution of the Isomeric Dichlorofluorenone Carboxyl...

[Huntress; Atkinson Journal of the American Chemical Society, 1936 , vol. 58, p. 1514,1516]

Dications of fluorenylidenes. The effect of substituent elec...

[Levy, Amalia; Rakowitz, Amber; Mills, Nancy S. Journal of Organic Chemistry, 2003 , vol. 68, # 10 p. 3990 - 3998]

A Convenient Route to 3, 6-Diaminofluoren-9-ones

[Guinot, Stephane G. R.; Hepworth, John D.; Wainwright, Mark Journal of Chemical Research, Miniprint, 1997 , # 6 p. 1252 - 1261]

Dications of fluorenylidenes. The effect of substituent elec...

[Levy, Amalia; Rakowitz, Amber; Mills, Nancy S. Journal of Organic Chemistry, 2003 , vol. 68, # 10 p. 3990 - 3998]