Structural modifications of anguidin and antitumor activities of its analogs

…, FA O'Herron, S Nachfolger, J Huftalen…

Index: Kaneko; Schmitz; Essery; Rose; Howell; O'Herron; Nachfolger; Huftalen; Bradner; Partyka; Doyle; Davies; Cundliffe Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 579 - 589

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Citation Number: 38

Abstract

Approximately 60 derivatives of anguidin were prepared for evaluation of antitumor activities. Positions 3, 4, 8-10, and 15 were modified, and the resultant derivatives were screened against P-388 leukemia. It was found that introduction of the C3-keto and C3, Cgdiketo groups markedly improved the antileukemic activity, whereas epoxidation of the CW 1 0 double bond or oxidation of the C15 position diminished its activity. Selected ...

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12-epi-3α-<(tetrahydropyranyl)oxy>-12,13-epoxytrichothec-9-ene-4β,15-diol Structure

77620-41-8

12-epi-3α-<(tet...

Methacryloyl chloride Structure

920-46-7

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4β-(methacryloyloxy)scirpene-3α,15-diol Structure

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4β-acetoxy-3α-O-(2-tetrahydropyranyl)scirpene-15-carboxaldehyde Structure

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4β-acetoxy-3α-hydroxyscirpene-15-carboxaldehyde Structure

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Diacetoxyscirpenol Structure

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4β-acetoxy-3α-hydroxyscirpene-15-carboxaldehyde Structure

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4β-hydroxy-3α-O-(2-tetrahydropyranyl)scirpene-15-carboxaldehyde Structure

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4β-acetoxy-3α-hydroxyscirpene-15-carboxaldehyde Structure

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12-epi-3α-<(tetrahydropyranyl)oxy>-12,13-epoxytrichothec-9-ene-4β,15-diol Structure

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4β-acetoxy-3α-hydroxyscirpene-15-carboxaldehyde Structure

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12,13-epoxytrichothec-9-ene-3α,4β,15-triol 4β,15-diacetate 3α-tetrahydropyranyl acetal Structure

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Diacetoxyscirpenol Structure

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4β-hydroxy-3α-O-(2-tetrahydropyranyl)scirpene-15-carboxaldehyde Structure

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12-epi-3α-<(tetrahydropyranyl)oxy>-12,13-epoxytrichothec-9-ene-4β,15-diol Structure

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~%

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12,13-epoxytrichothec-9-ene-3α,4β,15-triol 4β,15-diacetate 3α-tetrahydropyranyl acetal Structure

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12,13-epoxytric...

~%

Trichothec-9-en-15-oic acid, 12,13-epoxy-3,4-dihydroxy Structure

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Trichothec-9-ene-3,4,15-triol,12,13-epoxy-, (3a,4b) Structure

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Chloroacetic an...

~2%

Trichothec-9-ene-3,4,15-triol, 12,13-epoxy-, 4-(chloroacetate), (3.alpha.,4.beta.) Structure

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Trichothec-9-ene-3,4,15-triol, 12,13-epoxy-, 15- (chloroacetate), (3.alpha.,4.beta.) Structure

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4β,15-bis(methacryloyloxy)scirpene-3α,8β-diol Structure

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~78%

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Diacetoxyscirpenol Structure

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4β,15-bis(methacryloyloxy)scirpene-3,8-dione Structure

77620-59-8

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3α,8β-bis-O-(2-tetrahydropyranyl)scirpene-4β,15-diol Structure

81331-40-0

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4β,15-bis(methacryloyloxy)scirpene-3,8-dione Structure

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4,15-Bis(acetyloxy)-12,13-epoxy-3-hydroxytrichothec-9-en-8-one (3alpha,4beta) Structure

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4β,15-bis(methacryloyloxy)scirpene-3,8-dione Structure

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Neosolaniol Structure

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4β,15-bis(methacryloyloxy)scirpene-3,8-dione Structure

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4β,15-diacetoxy-8α-bromoscirpen-3α-ol Structure

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4β,15-bis(methacryloyloxy)scirpene-3,8-dione Structure

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15-acetoxy-4β-(methacryloyloxy)-3α,8β-bis-O-(2-tetrahydropyranyl)scirpene Structure

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~54%

15-acetoxy-4β-(methacryloyloxy)scirpene-3α,8β-diol Structure

81331-42-2

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Diacetoxyscirpenol Structure

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15-acetoxy-4β-(methacryloyloxy)scirpene-3α,8β-diol Structure

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3α,8β-bis-O-(2-tetrahydropyranyl)scirpene-4β,15-diol Structure

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15-acetoxy-4β-(methacryloyloxy)scirpene-3α,8β-diol Structure

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4,15-Bis(acetyloxy)-12,13-epoxy-3-hydroxytrichothec-9-en-8-one (3alpha,4beta) Structure

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15-acetoxy-4β-(methacryloyloxy)scirpene-3α,8β-diol Structure

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Neosolaniol Structure

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15-acetoxy-4β-(methacryloyloxy)scirpene-3α,8β-diol Structure

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3α,8β-bis-O-(2-tetrahydropyranyl)scirpene-4β,15-diol Structure

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4,15-Bis(acetyloxy)-12,13-epoxy-3-hydroxytrichothec-9-en-8-one (3alpha,4beta) Structure

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Diacetoxyscirpenol Structure

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81331-40-0

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4,15-Bis(acetyloxy)-12,13-epoxy-3-hydroxytrichothec-9-en-8-one (3alpha,4beta) Structure

77620-47-4

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3α,8β-bis-O-(2-tetrahydropyranyl)scirpene-4β,15-diol Structure

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Neosolaniol Structure

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3α,8β-bis-O-(2-tetrahydropyranyl)scirpene-4β,15-diol Structure

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4β,15-diacetoxy-8α-bromoscirpen-3α-ol Structure

81331-38-6

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3α,8β-bis-O-(2-tetrahydropyranyl)scirpene-4β,15-diol Structure

81331-40-0

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4β-acetoxy-3-O-(2-tetrahydropyranyl)scirpene-15-carboxaldehyde semicarbazone Structure

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4β-acetoxy-3α-hydroxyscirpene-15-carboxaldehyde semicarbazone Structure

81331-36-4

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4β-hydroxy-3α-O-(2-tetrahydropyranyl)scirpene-15-carboxaldehyde Structure

81331-31-9

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81331-32-0

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81331-32-0

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12-epi-3α-<(tetrahydropyranyl)oxy>-12,13-epoxytrichothec-9-ene-4β,15-diol Structure

77620-41-8

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81331-32-0

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77620-40-7

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3α,4β-dihydroxyscirpene-15-carboxaldehyde Structure

81331-32-0

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80178-16-1

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81331-27-3

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2270-41-9

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81331-27-3

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12-epi-3α-<(tetrahydropyranyl)oxy>-12,13-epoxytrichothec-9-ene-4β,15-diol Structure

77620-41-8

12-epi-3α-<(tet...

Methacryloyl chloride Structure

920-46-7

Methacryloyl ch...

~%

4β-(methacryloyloxy)scirpene-3α,15-diol Structure

77620-62-3

4β-(methacryloy...

Trichothec-9-ene-3,4,15-triol, 12,13-epoxy-, 15-(2-methyl-2-propenoate), (3.alpha.,4.beta.) Structure

77620-50-9

Trichothec-9-en...

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15-acetoxy-4β-(methacryloyloxy)scirpene-3α,8β-diol Structure

81331-42-2

15-acetoxy-4β-(...

~78%

Trichothec-9-ene-3,8-dione,15-(acetyloxy)-12,13-epoxy-4-[(2-methyl-1-oxo-2-propenyl)oxy]-, (4b)- (9CI) Structure

77620-58-7

Trichothec-9-en...

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Diacetoxyscirpenol Structure

2270-40-8

Diacetoxyscirpenol

~%

Trichothec-9-ene-3,8-dione,15-(acetyloxy)-12,13-epoxy-4-[(2-methyl-1-oxo-2-propenyl)oxy]-, (4b)- (9CI) Structure

77620-58-7

Trichothec-9-en...

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3α,8β-bis-O-(2-tetrahydropyranyl)scirpene-4β,15-diol Structure

81331-40-0

3α,8β-bis-O-(2-...

~%

Trichothec-9-ene-3,8-dione,15-(acetyloxy)-12,13-epoxy-4-[(2-methyl-1-oxo-2-propenyl)oxy]-, (4b)- (9CI) Structure

77620-58-7

Trichothec-9-en...

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15-acetoxy-4β-(methacryloyloxy)-3α,8β-bis-O-(2-tetrahydropyranyl)scirpene Structure

81331-41-1

15-acetoxy-4β-(...

~%

Trichothec-9-ene-3,8-dione,15-(acetyloxy)-12,13-epoxy-4-[(2-methyl-1-oxo-2-propenyl)oxy]-, (4b)- (9CI) Structure

77620-58-7

Trichothec-9-en...

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4,15-Bis(acetyloxy)-12,13-epoxy-3-hydroxytrichothec-9-en-8-one (3alpha,4beta) Structure

77620-47-4

4,15-Bis(acetyl...

~%

Trichothec-9-ene-3,8-dione,15-(acetyloxy)-12,13-epoxy-4-[(2-methyl-1-oxo-2-propenyl)oxy]-, (4b)- (9CI) Structure

77620-58-7

Trichothec-9-en...

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Neosolaniol Structure

36519-25-2

Neosolaniol

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Trichothec-9-ene-3,8-dione,15-(acetyloxy)-12,13-epoxy-4-[(2-methyl-1-oxo-2-propenyl)oxy]-, (4b)- (9CI) Structure

77620-58-7

Trichothec-9-en...

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4β,15-diacetoxy-8α-bromoscirpen-3α-ol Structure

81331-38-6

4β,15-diacetoxy...

~%

Trichothec-9-ene-3,8-dione,15-(acetyloxy)-12,13-epoxy-4-[(2-methyl-1-oxo-2-propenyl)oxy]-, (4b)- (9CI) Structure

77620-58-7

Trichothec-9-en...

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4β,15-diacetoxy-9β,10β, 12,13-diepoxytrichothecan-3α-ol Structure

81331-28-4

4β,15-diacetoxy...

~91%

4β,15-diacetoxy-9β,10β-epoxyscirpen-3-one Structure

81331-30-8

4β,15-diacetoxy...

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Diacetoxyscirpenol Structure

2270-40-8

Diacetoxyscirpenol

~%

4β,15-diacetoxy-9β,10β-epoxyscirpen-3-one Structure

81331-30-8

4β,15-diacetoxy...

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