5'-Deoxy-5'-(isobutylthio)-3-deazaadenosine, method of making sa

Drug – bio-affecting and body treating compositions – Conjugate or complex of monoclonal or polyclonal antibody,... – Conjugated via claimed linking group – bond – chelating agent,...

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536 26, 536 24, A61K 3170, C07H 1916, C07H 1700

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042106397

ABSTRACT:
5'-Deoxy-5'-(isobutylthio)-3-deazaadenosine and a method for preparation of same. In the preparation, 3-deazaadenosine is utilized as a starting material and is chlorinated at the 5' position. Subsequently, the chloro group is converted to isobutylthio by reaction with isobutyl mercaptan in ethanol containing sodium methoxide giving the desired compound.
A most preferred starting material, i.e., 3-deazaadenosine, was prepared according to the method of Montgomery et al, J. Heterocyclic Chem., 14:195 (1977). The key fusion of this process is 4,6-dichloroimidazo[4,5-c]pyridine with 1,2,3,5-tetra-O-acetyl-.beta.-D-ribofuranose, which, after removal of protective groups and reductive dechlorination of the chlorine at 6, gives 3-deazaadenosine.
This new compound has good activity as an adenosylhomocysteine (AdoHcy) hydrolase inhibitor and has shown activity against Rous sarcoma virus (RSV) in chick embryo cells and Gross murine leukemia virus (Gross MLV) in mouse embryo cells, where the activity is as a non-competitive inhibitor of AdoHcy hydrolase showing A K.sub.i of 0.4 mM.

REFERENCES:
Montgomery, J., et al., J. Heterocyclic Chem., 14, 195 (1977).
Chiang, P., et al., Biochem. Biophys. Research Communications, 82 (2), 417 (1978).
Chiang, P., et al., Molecular Pharmacology, 13, 939 (1977).
Rowe, W., et al., Virology, 42, 1136 (1970).
Shannon, W., et al., Journal of the National Cancer Institute, 52 (1), 199 (1974).

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