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

A cannabinoid derived prototypical analgesic

LS Melvin, MR Johnson, CA Harbert…

Index: Melvin, Lawrence S.; Johnson, M. Ross; Harbert, Charles A.; Milne, George M.; Weissman, Albert Journal of Medicinal Chemistry, 1984 , vol. 27, # 1 p. 67 - 71

Full Text: HTML

Citation Number: 94

Abstract

Figure 1. Allinger's MMI calculation for 1 in 5'increments of rotation about the aryl-cyclohexyl ring bond. The 240 Newman projection overlaps the calculated least-energy conformation of HHC. and alcohol functionalities. Examination of Dreiding models of 1 relative to the conformationally rigid HHC molecule, however, revealed that structure 1 could readily adopt the orientation of the phenol and alcohol existing in HHC. Furthermore, a more detailed ...

α,α-Dimethyl-3-(phenylmethoxy)benzeneacetaldehyde Structure

α,α-Dimethyl-3-...

~%

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

α,α-dimethyl-3-(phenylmethoxy)benzeneacetonitrile Structure

α,α-dimethyl-3-...

~%

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~%

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

~%

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

~%

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

~%

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

Pentyltriphenylphosphonium bromide Structure

Pentyltriphenyl...

~%

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

~63%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

cyclohexenone Structure

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

α,α-Dimethyl-3-(phenylmethoxy)benzeneacetaldehyde Structure

α,α-Dimethyl-3-...

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

α,α-dimethyl-3-(phenylmethoxy)benzeneacetonitrile Structure

α,α-dimethyl-3-...

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

Pentyltriphenylphosphonium bromide Structure

Pentyltriphenyl...

~%

3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Structure

3-[2-hydroxy-4-...

cis-3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]-cyclohexanol Structure

cis-3-[4-(1,1-D...

~74%

(+)-CP 47,497 Structure

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

~%

(+)-CP 47,497 Structure

3-[4-(1,1-Dimethylheptyl)-2-(phenylmethoxy)phenyl]cyclohexanone Structure

3-[4-(1,1-Dimet...

~%

(+)-CP 47,497 Structure

cyclohexenone Structure

~%

(+)-CP 47,497 Structure

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

~%

(+)-CP 47,497 Structure

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

~%

(+)-CP 47,497 Structure

α,α-Dimethyl-3-(phenylmethoxy)benzeneacetaldehyde Structure

α,α-Dimethyl-3-...

~%

(+)-CP 47,497 Structure

α,α-dimethyl-3-(phenylmethoxy)benzeneacetonitrile Structure

α,α-dimethyl-3-...

~%

(+)-CP 47,497 Structure

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~%

(+)-CP 47,497 Structure

Pentyltriphenylphosphonium bromide Structure

Pentyltriphenyl...

~%

(+)-CP 47,497 Structure

α,α-Dimethyl-3-(phenylmethoxy)benzeneacetaldehyde Structure

α,α-Dimethyl-3-...

~%

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

α,α-dimethyl-3-(phenylmethoxy)benzeneacetonitrile Structure

α,α-dimethyl-3-...

~%

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~%

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

Pentyltriphenylphosphonium bromide Structure

Pentyltriphenyl...

~%

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

~%

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

~%

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

~%

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~80%

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

4-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]pentan-2-one Structure

4-[4-(2-methylo...

~35%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

~%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

~%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

~%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

α,α-Dimethyl-3-(phenylmethoxy)benzeneacetaldehyde Structure

α,α-Dimethyl-3-...

~%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

α,α-dimethyl-3-(phenylmethoxy)benzeneacetonitrile Structure

α,α-dimethyl-3-...

~%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

Pentyltriphenylphosphonium bromide Structure

Pentyltriphenyl...

~%

4-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]pentan-2-one Structure

4-[2-hydroxy-4-...

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

~99%

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~%

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

2-Bromo-5-(1,1-dimethylheptyl)phenol Structure

2-Bromo-5-(1,1-...

Benzyl bromide Structure

~%

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

α,α-Dimethyl-3-(phenylmethoxy)benzeneacetaldehyde Structure

α,α-Dimethyl-3-...

~%

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

α,α-dimethyl-3-(phenylmethoxy)benzeneacetonitrile Structure

α,α-dimethyl-3-...

~%

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

(Z)-1-(1,1-Dimethyl-2-heptenyl)-3-(phenylmethoxy)benzene Structure

(Z)-1-(1,1-Dime...

~%

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

Pentyltriphenylphosphonium bromide Structure

Pentyltriphenyl...

~%

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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

3-(1,1-Dimethylheptyl)phenol Structure

3-(1,1-Dimethyl...

~%

1-Bromo-4-(1,1-dimethylheptyl)-2-(phenylmethoxy)-benzene Structure

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