Julie Ann Dohm

US Patent:

8420692, Apr 16, 2013

Filed:

Apr 6, 2010

Appl. No.:

12/755077

Inventors:

Ru Chih C. Huang - Baltimore MD, US
Apostolos Gittis - Baltimore MD, US
Evangelos Moudrianakis - Baltimore MD, US
Julie A. Dohm - Oak Lawn IL, US
Jih Ru Hwu - Hsinchu, TW
Ming-Hua Hsu - Hsinchu, TW

Assignee:

The Johns Hopkins University - Baltimore MD

International Classification:

A01N 43/36
A61K 31/40

US Classification:

514408, 5142312, 514315

Abstract:

Reaction of nordihydroguaiaretic acid with various alkyl chlorides, 1-piperidinecarbonyl chloride, methyl chloroformate, or 1,1′-carbonyldiimidazole under alkaline conditions produced the corresponding phenol ethers, carbamates and carbonates, respectively, in 67-83% yields (Scheme 1 and Scheme 2). Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found to be stable in aqueous solution. These new compounds exerted potent activities against HIV Tat-regulated transactivation in cos-7 cells. The most active transcription inhibitor compound of this series 5b (PN, Tetrapiperidino NDGA, meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperidino)ethoxypehnyl])butane tetrakishydrochloride salt) has an ICof 0. 88 μ.

US Patent:

7741357, Jun 22, 2010

Filed:

Apr 13, 2007

Appl. No.:

11/783970

Inventors:

Ru Chih C. Huang - Baltimore MD, US
Apostolos Gittis - Baltimore MD, US
Evangelos Moudrianakis - Baltimore MD, US
Julie A. Dohm - Oak Lawn IL, US
Jih Ru Hwu - Hsinchu, TW
Ming-Hua Hsu - Hsinchu, TW

Assignee:

Johns Hopkins University - Baltimore MD

International Classification:

A01N 43/36

US Classification:

514408, 5142312, 514315, 548400, 548560, 544106, 546184

Abstract:

Reaction of nordihydroguaiaretic acid with various alkyl chlorides, 1-piperidinecarbonyl chloride, methyl chloroformate, or 1,1′-carbonyldiimidazole under alkaline conditions produced the corresponding phenol ethers, carbamates and carbonates, respectively, in 67-83% yields (Scheme 1 and Scheme 2). Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found to be stable in aqueous solution. These new compounds exerted potent activities against HIV Tat-regulated transactivation in cos-7 cells. The most active transcription inhibitor compound of this series 5b (PN, Tetrapiperidino NDGA, meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperidino)ethoxyphenyl])butane tetrakishydrochloride salt) has an ICof 0. 88 μ.