Heterocyclic and carbonate derivatives of NDGA and their use...

Details Heterocyclic and carbonate derivatives of NDGA and their use... Heterocyclic and carbonate derivatives of NDGA and their use...

2007-04-13

2010-06-22

Saeed, Kamal A (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S231200, C514S315000, C548S400000, C548S560000, C544S106000, C546S184000

Reexamination Certificate

active

07741357

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 (P4N, Tetrapiperidino NDGA, meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperidino)ethoxyphenyl])butane tetrakishydrochloride salt) has an IC50of 0.88 μM.

REFERENCES:
patent: EP 0541112 (1993-12-01), None
patent: WO 8801509 (1988-03-01), None
Wolff, Manfred, “Burger's Medicinal Chemistry”, 4thEd., Part I, John Wiley, NY (1980).
Dohm et al. (J. Mol. Biol. 2005; 349(4): p. 731-744).

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