Synthesis and antitumor activity of 4-hydroxycoumarin derivatives

JC Jung, JH Lee, S Oh, JG Lee, OS Park

Index: Jung, Jae-Chul; Lee, Ji-Ho; Oh, Seikwan; Lee, Jae-Gon; Park, Oee-Sook Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 22 p. 5527 - 5531

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Citation Number: 63

Abstract

A series of 4-hydroxycoumarin derivatives was prepared and evaluated for antitumor activity. The key fragments were 2a–c, 5c, 12b, 13b, 17, and 18 which were prepared via dianion ring cyclization, Friedel–Crafts acylation, and Reformatsky reaction. Compound 20b showed the most potent antitumor activity among the total 12 derivatives and compounds 19a and 19b exhibited efficacy comparable to etoposide in vitro antitumor activity.

 Related Synthetic Route
4-Bromobiphenyl Structure

92-66-0

4-Bromobiphenyl

~%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

70942-04-0

1-bromo-3-[4'-b...

1-(4'-Bromo(1,1'-biphenyl)-4-yl)-2-phenylethan-1-one Structure

60312-95-0

1-(4'-Bromo(1,1...

~%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

70942-04-0

1-bromo-3-[4'-b...

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

60313-01-1

3-(4'-bromo[1,1...

~%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

70942-04-0

1-bromo-3-[4'-b...

Phenylacetyl chloride Structure

103-80-0

Phenylacetyl ch...

~%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

70942-04-0

1-bromo-3-[4'-b...

ethyl 3-(4'-bromo-[1,1'-biphenyl]-4-yl)-4-phenylbutanoate Structure

124325-90-2

ethyl 3-(4'-bro...

~%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

70942-04-0

1-bromo-3-[4'-b...

3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyric acid Structure

124325-89-9

3-(4'-Bromo-bip...

~%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

70942-04-0

1-bromo-3-[4'-b...

N/A Structure

124325-88-8

N/A

~%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

70942-04-0

1-bromo-3-[4'-b...

3-(4-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one Structure

61696-79-5

3-(4-methoxyphe...

~93%

3-(4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one Structure

90035-32-8

3-(4-hydroxyphe...

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1023-17-2

1-(4-Methoxyphe...

~%

3-(4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one Structure

90035-32-8

3-(4-hydroxyphe...

Anisole Structure

100-66-3

Anisole

~%

3-(4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one Structure

90035-32-8

3-(4-hydroxyphe...

Phenylacetyl chloride Structure

103-80-0

Phenylacetyl ch...

~%

3-(4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one Structure

90035-32-8

3-(4-hydroxyphe...

ethyl 3-hydroxy-3-(4-methoxyphenyl)-4-phenylbutanoate Structure

171818-87-4

ethyl 3-hydroxy...

~%

3-(4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one Structure

90035-32-8

3-(4-hydroxyphe...

3-(4-methoxyphenyl)-4-phenylbutanoic acid Structure

118806-78-3

3-(4-methoxyphe...

~%

3-(4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one Structure

90035-32-8

3-(4-hydroxyphe...

ethyl 3-(4-methoxyphenyl)-4-phenylbutanoate Structure

171818-88-5

ethyl 3-(4-meth...

~%

3-(4-hydroxyphenyl)-3,4-dihydro-2H-naphthalen-1-one Structure

90035-32-8

3-(4-hydroxyphe...

3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyric acid Structure

124325-89-9

3-(4'-Bromo-bip...

~78%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

60313-01-1

3-(4'-bromo[1,1...

1-(4'-Bromo(1,1'-biphenyl)-4-yl)-2-phenylethan-1-one Structure

60312-95-0

1-(4'-Bromo(1,1...

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

60313-01-1

3-(4'-bromo[1,1...

Phenylacetyl chloride Structure

103-80-0

Phenylacetyl ch...

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

60313-01-1

3-(4'-bromo[1,1...

4-Bromobiphenyl Structure

92-66-0

4-Bromobiphenyl

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

60313-01-1

3-(4'-bromo[1,1...

N/A Structure

124325-88-8

N/A

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

60313-01-1

3-(4'-bromo[1,1...

Bromo(propyl)magnesium Structure

927-77-5

Bromo(propyl)ma...

3-Phenylpropanoyl chloride Structure

645-45-4

3-Phenylpropano...

~61%

1-phenylhexan-3-one Structure

29898-25-7

1-phenylhexan-3-one

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

60313-01-1

3-(4'-bromo[1,1...

~85%

3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol Structure

56181-82-9

3-(4'-Bromo[1,1...

3-(4-methoxyphenyl)-4-phenylbutanoic acid Structure

118806-78-3

3-(4-methoxyphe...

~87%

3-(4-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one Structure

61696-79-5

3-(4-methoxyphe...

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1023-17-2

1-(4-Methoxyphe...

~%

3-(4-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one Structure

61696-79-5

3-(4-methoxyphe...

Anisole Structure

100-66-3

Anisole

~%

3-(4-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one Structure

61696-79-5

3-(4-methoxyphe...

Phenylacetyl chloride Structure

103-80-0

Phenylacetyl ch...

~%

3-(4-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one Structure

61696-79-5

3-(4-methoxyphe...

ethyl 3-hydroxy-3-(4-methoxyphenyl)-4-phenylbutanoate Structure

171818-87-4

ethyl 3-hydroxy...

~%

3-(4-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one Structure

61696-79-5

3-(4-methoxyphe...

ethyl 3-(4-methoxyphenyl)-4-phenylbutanoate Structure

171818-88-5

ethyl 3-(4-meth...

~%

3-(4-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one Structure

61696-79-5

3-(4-methoxyphe...


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