Abstract
Reaction of nordihydroguaiaretic acid with various alkyl chloride, 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. Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found stable in aqueous solution. These new compounds exerted appealing activity against HIV Tat-regulated transactivation in human epithelial cells. The most potent compound meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperdino)ethoxyphenyl])butane tetrakishydrochloride salt (5b) showed IC50 value of 0.88 μM.
| Original language | English |
|---|---|
| Pages (from-to) | 1884-1888 |
| Number of pages | 5 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 18 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2008 Mar 15 |
Fingerprint
All Science Journal Classification (ASJC) codes
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
Cite this
}
New nordihydroguaiaretic acid derivatives as anti-HIV agents. / Hwu, Jih Ru; Hsu, Ming-Hua; Huang, Ru Chih C.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 18, No. 6, 15.03.2008, p. 1884-1888.Research output: Contribution to journal › Article
TY - JOUR
T1 - New nordihydroguaiaretic acid derivatives as anti-HIV agents
AU - Hwu, Jih Ru
AU - Hsu, Ming-Hua
AU - Huang, Ru Chih C.
PY - 2008/3/15
Y1 - 2008/3/15
N2 - Reaction of nordihydroguaiaretic acid with various alkyl chloride, 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. Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found stable in aqueous solution. These new compounds exerted appealing activity against HIV Tat-regulated transactivation in human epithelial cells. The most potent compound meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperdino)ethoxyphenyl])butane tetrakishydrochloride salt (5b) showed IC50 value of 0.88 μM.
AB - Reaction of nordihydroguaiaretic acid with various alkyl chloride, 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. Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found stable in aqueous solution. These new compounds exerted appealing activity against HIV Tat-regulated transactivation in human epithelial cells. The most potent compound meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperdino)ethoxyphenyl])butane tetrakishydrochloride salt (5b) showed IC50 value of 0.88 μM.
UR - http://www.scopus.com/inward/record.url?scp=40749139875&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=40749139875&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2008.02.018
DO - 10.1016/j.bmcl.2008.02.018
M3 - Article
C2 - 18321703
AN - SCOPUS:40749139875
VL - 18
SP - 1884
EP - 1888
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 6
ER -