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

Ring-hydroxylated analogs of lucanthone as antitumor agents

S Archer, KJ Miller, R Rej, C Periana…

Index: Archer; Miller; Rej; Periana; Fricker Journal of Medicinal Chemistry, 1982 , vol. 25, # 3 p. 220 - 227

Full Text: HTML

Citation Number: 36

Abstract

A series of ring-alkoxylated and ringhydroxylated analogues of lucanthone was prepared and tested for antitumor activity. The most biologically interesting members of this group were the 7-hydroxylucanthone derivatives, 50 and 51, which gave T/C values in the NCI P- 388 antitumor screen of 188 and 265, respectively. The apparent association constants and AT,,, values for a number of analogueDNA complexes were determined to ascertain ...

but-2-enedioic acid; 1-(2-diethylaminoethylamino)-2-methoxy-4-methyl-thioxanthen-9-one Structure

but-2-enedioic ...

~66%

9H-Thioxanthen-9-one, 1-((2-(diethylamino)ethyl)amino)-2-hydroxy-4-methyl- Structure

9H-Thioxanthen-...

1-(2-diethylaminoethylamino)-5-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

~%

1-(2-diethylaminoethylamino)-5-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

2-Amino-3-methoxybenzoic acid Structure

2-Amino-3-metho...

~%

1-(2-diethylaminoethylamino)-5-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

N/A Structure

~%

1-(2-diethylaminoethylamino)-5-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

2-Amino-5-methoxybenzoic acid Structure

2-Amino-5-metho...

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

Benzoic acid,2-mercapto-5-methoxy- Structure

Benzoic acid,2-...

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

2,2-Dithiobis(5-methoxybenzoic acid) Structure

2,2-Dithiobis(5...

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

N/A Structure

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

N/A Structure

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

4-Chlorotoluene Structure

4-Chlorotoluene

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

N/A Structure

~%

1-(2-aminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-aminoethyl...

2-Amino-5-methoxybenzoic acid Structure

2-Amino-5-metho...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

Benzoic acid,2-mercapto-5-methoxy- Structure

Benzoic acid,2-...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

2,2-Dithiobis(5-methoxybenzoic acid) Structure

2,2-Dithiobis(5...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

N/A Structure

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

4-Chlorotoluene Structure

4-Chlorotoluene

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

N/A Structure

1,1-Dimethylethylenediamine Structure

1,1-Dimethyleth...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

4-Chlorotoluene Structure

4-Chlorotoluene

2,2-Dithiobis(5-methoxybenzoic acid) Structure

2,2-Dithiobis(5...

1,1-Dimethylethylenediamine Structure

1,1-Dimethyleth...

~%

N/A Structure

Detail

1-chloro-4-hydroxythioxanthen-9-one Structure

1-chloro-4-hydr...

~%

9H-Thioxanthen-9-one,1-[[3-(dimethylamino)propyl]amino]-4-hydroxy-, hydriodide (1:2) Structure

9H-Thioxanthen-...

4-Chlorophenol Structure

~%

9H-Thioxanthen-9-one,1-[[3-(dimethylamino)propyl]amino]-4-hydroxy-, hydriodide (1:2) Structure

9H-Thioxanthen-...

Thiosalicylic acid Structure

Thiosalicylic acid

~%

9H-Thioxanthen-9-one,1-[[3-(dimethylamino)propyl]amino]-4-hydroxy-, hydriodide (1:2) Structure

9H-Thioxanthen-...

4-(benzyloxy)-1-((3-(dimethylamino)propyl)amino)-9H-thioxanthen-9-one Structure

4-(benzyloxy)-1...

~%

9H-Thioxanthen-9-one,1-[[3-(dimethylamino)propyl]amino]-4-hydroxy-, hydriodide (1:2) Structure

9H-Thioxanthen-...

N/A Structure

~%

9H-Thioxanthen-9-one,1-[[3-(dimethylamino)propyl]amino]-4-hydroxy-, hydriodide (1:2) Structure

9H-Thioxanthen-...

4-Chlorophenol Structure

Thiosalicylic acid Structure

Thiosalicylic acid

~38%

1-chloro-4-hydroxythioxanthen-9-one Structure

1-chloro-4-hydr...

2-Amino-5-methoxybenzoic acid Structure

2-Amino-5-metho...

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

Benzoic acid,2-mercapto-5-methoxy- Structure

Benzoic acid,2-...

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

2,2-Dithiobis(5-methoxybenzoic acid) Structure

2,2-Dithiobis(5...

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

N/A Structure

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-7-methoxy-4-methyl- Structure

9H-Thioxanthen-...

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

4-Chlorotoluene Structure

4-Chlorotoluene

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

N/A Structure

~%

1-(2-dimethylaminoethylamino)-7-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

2-Chloro-5-methylphenol Structure

2-Chloro-5-meth...

~%

1-(2-dimethylaminoethylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

N/A Structure

~%

1-(2-dimethylaminoethylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

Thiosalicylic acid Structure

Thiosalicylic acid

~%

1-(2-dimethylaminoethylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

2-(benzyloxy)-1-((2-(dimethylamino)ethyl)amino)-4-methyl-9H-thioxanthen-9-one Structure

2-(benzyloxy)-1...

~%

1-(2-dimethylaminoethylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

N/A Structure

~%

1-(2-dimethylaminoethylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

2-Amino-5-methoxybenzoic acid Structure

2-Amino-5-metho...

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

Benzoic acid,2-mercapto-5-methoxy- Structure

Benzoic acid,2-...

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

2,2-Dithiobis(5-methoxybenzoic acid) Structure

2,2-Dithiobis(5...

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

N/A Structure

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

4-Chlorotoluene Structure

4-Chlorotoluene

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

N/A Structure

~%

9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-7-hydroxy-4-methyl-, monohydriodide Structure

9H-Thioxanthen-...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

6-hydroxy-1-[2-(2-hydroxyethylamino)ethylamino]-4-methyl-thioxanthen-9-one Structure

6-hydroxy-1-[2-...

2-MERCAPTO-4-METHOXYBENZOIC ACID Structure

2-MERCAPTO-4-ME...

~%

6-hydroxy-1-[2-(2-hydroxyethylamino)ethylamino]-4-methyl-thioxanthen-9-one Structure

6-hydroxy-1-[2-...

1-chloro-6-methoxy-4-methylthioxanthenone Structure

1-chloro-6-meth...

~%

6-hydroxy-1-[2-(2-hydroxyethylamino)ethylamino]-4-methyl-thioxanthen-9-one Structure

6-hydroxy-1-[2-...

N/A Structure

~%

6-hydroxy-1-[2-(2-hydroxyethylamino)ethylamino]-4-methyl-thioxanthen-9-one Structure

6-hydroxy-1-[2-...

1-chloro-6-methoxy-4-methylthioxanthenone Structure

1-chloro-6-meth...

2-(2-Aminoethylamino)ethanol Structure

2-(2-Aminoethyl...

~%

6-hydroxy-1-[2-(2-hydroxyethylamino)ethylamino]-4-methyl-thioxanthen-9-one Structure

6-hydroxy-1-[2-...

1-((2-(dimethylamino)ethyl)amino)-5-methoxy-4-methyl-9H-thioxanthen-9-one Structure

1-((2-(dimethyl...

~%

1-(2-dimethylaminoethylamino)-5-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

2-Amino-3-methoxybenzoic acid Structure

2-Amino-3-metho...

~%

1-(2-dimethylaminoethylamino)-5-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

N/A Structure

~%

1-(2-dimethylaminoethylamino)-5-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

1-chloro-4-hydroxythioxanthen-9-one Structure

1-chloro-4-hydr...

~%

1-(2-diethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-diethylami...

4-Chlorophenol Structure

~%

1-(2-diethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-diethylami...

Thiosalicylic acid Structure

Thiosalicylic acid

~%

1-(2-diethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-diethylami...

4-(benzyloxy)-1-((2-(diethylamino)ethyl)amino)-9H-thioxanthen-9-one Structure

4-(benzyloxy)-1...

~%

1-(2-diethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-diethylami...

N/A Structure

~%

1-(2-diethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-diethylami...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-6-hydroxy-4-methyl-, hydriodide (1:1) Structure

9H-Thioxanthen-...

2-MERCAPTO-4-METHOXYBENZOIC ACID Structure

2-MERCAPTO-4-ME...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-6-hydroxy-4-methyl-, hydriodide (1:1) Structure

9H-Thioxanthen-...

1-chloro-6-methoxy-4-methylthioxanthenone Structure

1-chloro-6-meth...

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-6-hydroxy-4-methyl-, hydriodide (1:1) Structure

9H-Thioxanthen-...

N/A Structure

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-6-hydroxy-4-methyl-, hydriodide (1:1) Structure

9H-Thioxanthen-...

2-Amino-5-methoxybenzoic acid Structure

2-Amino-5-metho...

~%

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

Benzoic acid,2-mercapto-5-methoxy- Structure

Benzoic acid,2-...

~%

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

2,2-Dithiobis(5-methoxybenzoic acid) Structure

2,2-Dithiobis(5...

~%

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

N/A Structure

~%

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

4-Chlorotoluene Structure

4-Chlorotoluene

~%

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

N/A Structure

2-aminoethyldiethylamine Structure

2-aminoethyldie...

~%

1-(2-diethylaminoethylamino)-7-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

N/A Structure

~%

9H-Thioxanthen-9-one,1-[[2-(dimethylamino)ethyl]amino]-6-hydroxy-4-methyl-, hydriodide (1:1) Structure

9H-Thioxanthen-...

1-Chloro-2-methoxy-4-methylbenzene Structure

1-Chloro-2-meth...

~%

1-(2-dimethylaminoethylamino)-2-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

Thiosalicylic acid Structure

Thiosalicylic acid

~%

1-(2-dimethylaminoethylamino)-2-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-dimethylam...

2-Amino-5-methoxybenzoic acid Structure

2-Amino-5-metho...

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

Toluene, 2-bromo-4-chloro- Structure

Toluene, 2-brom...

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

Benzoic acid,2-mercapto-5-methoxy- Structure

Benzoic acid,2-...

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

2,2-Dithiobis(5-methoxybenzoic acid) Structure

2,2-Dithiobis(5...

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

N/A Structure

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

4-Chlorotoluene Structure

4-Chlorotoluene

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

N/A Structure

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

2-(2-Aminoethylamino)ethanol Structure

2-(2-Aminoethyl...

N/A Structure

~%

9H-Thioxanthen-9-one, 7-hydroxy-1-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-4-methyl- Structure

9H-Thioxanthen-...

2-Amino-3-methoxybenzoic acid Structure

2-Amino-3-metho...

~%

1-(2-diethylaminoethylamino)-5-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

N/A Structure

~%

1-(2-diethylaminoethylamino)-5-methoxy-4-methyl-thioxanthen-9-one Structure

1-(2-diethylami...

N/A Structure

~%

1-(3-diethylaminopropylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(3-diethylami...

1-Chloro-2-methoxy-4-methylbenzene Structure

1-Chloro-2-meth...

~%

1-(3-diethylaminopropylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(3-diethylami...

Thiosalicylic acid Structure

Thiosalicylic acid

~%

1-(3-diethylaminopropylamino)-2-hydroxy-4-methyl-thioxanthen-9-one Structure

1-(3-diethylami...

1-chloro-4-hydroxythioxanthen-9-one Structure

1-chloro-4-hydr...

~%

1-(2-dimethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-dimethylam...

4-Chlorophenol Structure

~%

1-(2-dimethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-dimethylam...

Thiosalicylic acid Structure

Thiosalicylic acid

~%

1-(2-dimethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-dimethylam...

4-(benzyloxy)-1-((2-(dimethylamino)ethyl)amino)-9H-thioxanthen-9-one Structure

4-(benzyloxy)-1...

~34%

1-(2-dimethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-dimethylam...

N/A Structure

~%

1-(2-dimethylaminoethylamino)-4-hydroxy-thioxanthen-9-one Structure

1-(2-dimethylam...