The University of North Carolina at Chapel Hill

Biotech Research Laboratories

Other

Mark Cosentino

Kuo-Hsiung Lee

Lan Xie

Yoshiki Kashiwada

Mark Manak

Li Huang

Thomas Tung-Ying Lee

Jim Snider

Mark Manax

The present invention is directed to compounds that are analogs of the natural product suksdorfin. Compounds of the present invention include those having Formula IV:

Suksdorfin analogs, compositions thereof, and methods for making and using thereof

Disclosed are compounds of Formula I: ##STR1## wherein R.sup.1 through R.sup.6 are defined herein. Also disclosed are pharmaceutical compositions and methods of using these compositions for treating retroviral infections. Finally, a stereoselective method for synthesizing compounds of Formula I is described.

Suksdorfin analogs, compositions thereof, and methods for making and

The present invention is directed to compounds that are analogs of the natural product suksdorfin. Compounds of the present invention include those having Formula I: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined herein. The invention is also directed to methods of making these compounds, pharmaceutical compositions including these compounds and methods of using the compounds to inhibit retroviral infections in cells and tissues of animals. A method for stereoselectively preparing compounds within the scope of the invention by catalytic asymmetric dihydroxylation is also disclosed.

Compounds, including compositions and methods of making and using these compounds for treating retroviral infections, are provided according to formula (G-1): ##STR1## wherein M is O or NH; Z is O, NH or S; R.sup.240, and R.sup.250 are each H, C.sub.1-10 alkyl, C.sub.1-10 aryl, alkyl, amide, or CH.sub.2 COOR.sup.260, where R.sup.260 is C.sub.1-10 alkyl or acyl; R.sup.200, R.sup.210, R.sup.220 and R.sup.230 are each H, halogen, hydroxyl, NH.sub.2, NH-alkyl, N-(alkyl).sub.2, O-alkyl, O-acyl, COCF.sub.3, OCF.sub.3 or CH.sub.2 COO NH-alkyl; or R.sup.200 and R.sup.210 form C.sub.5 -C.sub.10 cyclo or heterocyclo optionally substituted with one or more of halogen, hydroxyl, NH.sub.2, NH-alkyl, N-(alkyl).sup.2, O-acyl, O-alkyl, CO, CF.sub.3, OCF.sub.3 or CH.sub.2 COONH-alkyl; wherein C3 and C4 can be bound by a single or double bond; configurations at 3' or 4' can be (R) or (S); and R.sup.240 and R.sup.250 are either cis-.beta. or cis.alpha., or trans-3'-.alpha. or trans-3'-.beta. oriented. Stereoselectivity can be enhanced by preparing these compounds by catalytic asymmetric dihyroxylation.

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Springfield, VA, United States of America

Mark Cosentino