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

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

Full Text: HTML

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 ...

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

12-epi-3α-<(tet...

Methacryloyl chloride Structure

Methacryloyl ch...

~%

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

4β-(methacryloy...

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

Trichothec-9-en...

Detail

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

4β-acetoxy-3α-O...

~45%

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

4β-acetoxy-3α-h...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

4β-acetoxy-3α-h...

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

4β-hydroxy-3α-O...

~%

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

4β-acetoxy-3α-h...

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

12-epi-3α-<(tet...

~%

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

4β-acetoxy-3α-h...

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

12,13-epoxytric...

~%

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

4β-acetoxy-3α-h...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

Trichothec-9-en...

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

4β-hydroxy-3α-O...

~%

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

Trichothec-9-en...

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

12-epi-3α-<(tet...

~%

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

Trichothec-9-en...

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

12,13-epoxytric...

~%

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

Trichothec-9-en...

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

Trichothec-9-en...

Chloroacetic anhydride Structure

Chloroacetic an...

~2%

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

Trichothec-9-en...

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

Trichothec-9-en...

Detail

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

4β,15-bis(metha...

~78%

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

4β,15-bis(metha...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

4β,15-bis(metha...

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

3α,8β-bis-O-(2-...

~%

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

4β,15-bis(metha...

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

4,15-Bis(acetyl...

~%

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

4β,15-bis(metha...

Neosolaniol Structure

~%

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

4β,15-bis(metha...

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

4β,15-diacetoxy...

~%

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

4β,15-bis(metha...

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

15-acetoxy-4β-(...

~54%

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

15-acetoxy-4β-(...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

15-acetoxy-4β-(...

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

3α,8β-bis-O-(2-...

~%

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

15-acetoxy-4β-(...

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

4,15-Bis(acetyl...

~%

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

15-acetoxy-4β-(...

Neosolaniol Structure

~%

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

15-acetoxy-4β-(...

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

4β,15-diacetoxy...

~%

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

15-acetoxy-4β-(...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

4β,15-bis(metha...

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

3α,8β-bis-O-(2-...

~%

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

4β,15-bis(metha...

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

4,15-Bis(acetyl...

~%

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

4β,15-bis(metha...

Neosolaniol Structure

~%

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

4β,15-bis(metha...

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

4β,15-diacetoxy...

~%

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

4β,15-bis(metha...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

3α,8β-bis-O-(2-...

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

4,15-Bis(acetyl...

~%

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

3α,8β-bis-O-(2-...

Neosolaniol Structure

~%

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

3α,8β-bis-O-(2-...

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

4β,15-diacetoxy...

~%

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

3α,8β-bis-O-(2-...

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

4β-acetoxy-3-O-...

~73%

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

4β-acetoxy-3α-h...

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

4β-hydroxy-3α-O...

~77%

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

3α,4β-dihydroxy...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

3α,4β-dihydroxy...

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

12-epi-3α-<(tet...

~%

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

3α,4β-dihydroxy...

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

12,13-epoxytric...

~%

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

3α,4β-dihydroxy...

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

Trichothec-9-en...

~22%

3α,15-bis(chloroacetoxy)scirpen-4-one Structure

3α,15-bis(chlor...

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

Trichothec-9-en...

~%

3α,15-bis(chloroacetoxy)scirpen-4-one Structure

3α,15-bis(chlor...

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

12-epi-3α-<(tet...

Methacryloyl chloride Structure

Methacryloyl ch...

~%

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

4β-(methacryloy...

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

Trichothec-9-en...

Detail

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

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

Trichothec-9-en...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

Trichothec-9-en...

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

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

Trichothec-9-en...

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

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

Trichothec-9-en...

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

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

Trichothec-9-en...

Neosolaniol Structure

~%

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

Trichothec-9-en...

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

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

Trichothec-9-en...

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

4β,15-diacetoxy...

~91%

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

4β,15-diacetoxy...

Diacetoxyscirpenol Structure

Diacetoxyscirpenol

~%

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

4β,15-diacetoxy...