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

Conformationally restricted retinoids

MI Dawson, PD Hobbs, K Derdzinski…

Index: Dawson, Marcia I.; Hobbs, Peter D.; Derdzinski, Krzysztof; Chan, Rebecca L.-S.; Gruber, John; et al. Journal of Medicinal Chemistry, 1984 , vol. 27, # 11 p. 1516 - 1531

Full Text: HTML

Citation Number: 56

Abstract

A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter. These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic ...

2H-1-Benzopyran,3,4-dihydro-4,4-dimethyl- Structure

2H-1-Benzopyran...

Acetyl chloride Structure

Acetyl chloride

~87%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

ISOPRENOL Structure

~%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

~%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

4,4-dimethyl-2-oxo-chroman Structure

4,4-dimethyl-2-...

~%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

diphenyl 3-methyl-3-buten-1-yl phosphate Structure

diphenyl 3-meth...

~%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

3-(2'-Hydroxyphenyl)-3,3-dimethylpropanol Structure

3-(2'-Hydroxyph...

~%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

phenyl 3-methylbut-2-enoate Structure

phenyl 3-methyl...

~%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

Phenol Structure

~%

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

4,4-dimethyl-3H-thiochromen-2-one Structure

4,4-dimethyl-3H...

~45%

4,4-DIMETHYL-THIOCHROMAN Structure

4,4-DIMETHYL-TH...

N/A Structure

Thiophenol Structure

~%

4,4-DIMETHYL-THIOCHROMAN Structure

4,4-DIMETHYL-TH...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

~%

4,4-DIMETHYL-THIOCHROMAN Structure

4,4-DIMETHYL-TH...

2-Butenethioic acid,3-methyl-, S-phenyl ester Structure

2-Butenethioic ...

~%

4,4-DIMETHYL-THIOCHROMAN Structure

4,4-DIMETHYL-TH...

ethyl 4-(diethoxyphosphorylmethyl)benzoate Structure

ethyl 4-(dietho...

1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone Structure

1-(4,4-dimethyl...

~57%

N/A Structure

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

ISOPRENOL Structure

~%

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

~%

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

4,4-dimethyl-2-oxo-chroman Structure

4,4-dimethyl-2-...

~%

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

diphenyl 3-methyl-3-buten-1-yl phosphate Structure

diphenyl 3-meth...

~%

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

ethyl 4-((1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl)benzoate Structure

ethyl 4-((1E,3E...

~64%

4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]benzoic acid Structure

4-[(1E,3E,5E)-4...

(7E,9E)-β-Ionylidene Acetaldehyde Structure

(7E,9E)-β-Ionyl...

~%

4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]benzoic acid Structure

4-[(1E,3E,5E)-4...

(7E,9E)-β-Ionylidene Acetaldehyde Structure

(7E,9E)-β-Ionyl...

ethyl 4-(diethoxyphosphorylmethyl)benzoate Structure

ethyl 4-(dietho...

~%

4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]benzoic acid Structure

4-[(1E,3E,5E)-4...

ethyl 4-((1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl)benzoate Structure

ethyl 4-((1E,3E...

4,4-dimethyl-2-oxo-chroman Structure

4,4-dimethyl-2-...

~%

2H-1-Benzopyran,3,4-dihydro-4,4-dimethyl- Structure

2H-1-Benzopyran...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

~%

2H-1-Benzopyran,3,4-dihydro-4,4-dimethyl- Structure

2H-1-Benzopyran...

phenyl 3-methylbut-2-enoate Structure

phenyl 3-methyl...

~%

2H-1-Benzopyran,3,4-dihydro-4,4-dimethyl- Structure

2H-1-Benzopyran...

Phenol Structure

~%

2H-1-Benzopyran,3,4-dihydro-4,4-dimethyl- Structure

2H-1-Benzopyran...

diphenyl 3-methyl-3-buten-1-yl phosphate Structure

diphenyl 3-meth...

Phenol Structure

~%

2H-1-Benzopyran,3,4-dihydro-4,4-dimethyl- Structure

2H-1-Benzopyran...

4,4-DIMETHYL-THIOCHROMAN Structure

4,4-DIMETHYL-TH...

Acetyl chloride Structure

Acetyl chloride

~85%

6-Acetyl-4,4-dimethylthio-chroman Structure

6-Acetyl-4,4-di...

3-(bromomethyl)benzoic acid ethyl ester Structure

3-(bromomethyl)...

Triethyl phosphite Structure

Triethyl phosphite

~64%

ethyl 3-(diethoxyphosphorylmethyl)benzoate Structure

ethyl 3-(dietho...

3-(2'-Hydroxyphenyl)-3,3-dimethylpropanol Structure

3-(2'-Hydroxyph...

~%

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

phenyl 3-methylbut-2-enoate Structure

phenyl 3-methyl...

~%

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

Phenol Structure

~%

ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate Structure

ethyl 4-(2-(3,4...

ethyl 4-(diethoxyphosphorylmethyl)benzoate Structure

ethyl 4-(dietho...

6-Acetyl-4,4-dimethylthio-chroman Structure

6-Acetyl-4,4-di...

~61%

ethyl 4-[(Z)-2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)prop-1-enyl]benzoate Structure

ethyl 4-[(Z)-2-...

Thiophenol Structure

~%

ethyl 4-[(Z)-2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)prop-1-enyl]benzoate Structure

ethyl 4-[(Z)-2-...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

~%

ethyl 4-[(Z)-2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)prop-1-enyl]benzoate Structure

ethyl 4-[(Z)-2-...

2-Butenethioic acid,3-methyl-, S-phenyl ester Structure

2-Butenethioic ...

~%

ethyl 4-[(Z)-2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)prop-1-enyl]benzoate Structure

ethyl 4-[(Z)-2-...

4,4-dimethyl-3H-thiochromen-2-one Structure

4,4-dimethyl-3H...

~%

ethyl 4-[(Z)-2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)prop-1-enyl]benzoate Structure

ethyl 4-[(Z)-2-...

4-Bromo-2-methylbenzoic acid Structure

4-Bromo-2-methy...

~%

2-(4-bromo-2-methylphenyl)-1,3-dioxolane Structure

2-(4-bromo-2-me...

(4-Bromo-2-methylphenyl)methanol Structure

(4-Bromo-2-meth...

~%

2-(4-bromo-2-methylphenyl)-1,3-dioxolane Structure

2-(4-bromo-2-me...

2-Bromo-4-methylbenzaldehyde Structure

2-Bromo-4-methy...

Ethylene glycol Structure

Ethylene glycol

~%

2-(4-bromo-2-methylphenyl)-1,3-dioxolane Structure

2-(4-bromo-2-me...

4-Bromo-4'-methylbiphenyl Structure

4-Bromo-4'-meth...

~%

4'-bromo-4-bromomethyl-biphenyl Structure

4'-bromo-4-brom...

… A deficient hamster tracheal organ cultures. Single-crysta...

[Waugh, Kristy M.; Berlin, K. Darrell; Ford, Warren T.; Holt, Elizabeth M.; Carrol, John P.; et al. Journal of Medicinal Chemistry, 1985 , vol. 28, # 1 p. 116 - 124]

… A deficient hamster tracheal organ cultures. Single-crysta...

[Waugh, Kristy M.; Berlin, K. Darrell; Ford, Warren T.; Holt, Elizabeth M.; Carrol, John P.; et al. Journal of Medicinal Chemistry, 1985 , vol. 28, # 1 p. 116 - 124]

… A deficient hamster tracheal organ cultures. Single-crysta...

[Waugh, Kristy M.; Berlin, K. Darrell; Ford, Warren T.; Holt, Elizabeth M.; Carrol, John P.; et al. Journal of Medicinal Chemistry, 1985 , vol. 28, # 1 p. 116 - 124]