Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1978-11-20
1980-07-01
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 24, 424180, C07H 1916, C07H 1700
Patent
active
042107458
ABSTRACT:
The present invention is an improved multi-step process for the production of 9-.beta.-D-arabinofuranosyl-2-fluoroadenine (2-F-AraA) and an improvement over the process of Montgomery and Hewson, J. Med. Chem., 12:498 (1969). This compound is an important tool in antitumor therapy and has shown activity against leukemia L1210 and P388 in animals as well as being a potent antiviral agent. Its therapeutic effectiveness occurs because 2-F-AraA is not a substrate for adenosine deaminase which vitiated against the activity of the parent compound 9-.beta.-D-arabinofuranosyladenine (araA) as indicated in experimental animal cancers.
An advantage of making 2-F-AraA by the present process is that there is a sharply increased yield based on the chlorosugar up to about 400 percent. In the present improved process the differences lie in utilizing as a reactant 2,4,5,6-tetraaminopyrimidine; the acetylation of 2-aminoadenine in acetic acid and pyridine; the reaction of 2,6-diacetamidopurine with chlorosugar in ethylene chloride in the presence of a molecular sieve and subsequent deacetylation with methanolic sodium methoxide. Further, the diazotization step is carried out in a homogenous mixture of tetrahydrofuran and fluoboric acids. Finally, the O-benzyl groups are removed by the use of boron trichloride in ether.
REFERENCES:
patent: 3956277 (1976-05-01), Elion et al.
Montgomery, J., and Hewson, K., J. Med. Chem., 12:498, (1969).
Keller, F., et al., J. Org. Chem., 32:1644, (1967).
Robins et al., J. Am. Chem. Soc., 75:263, (1953).
Brookman, et al., Biochem. Pharmacol., 26:2193, (1977).
Brown Johnnie R.
Hazel Blondel
Roberts Jr., John S.
The United States of America as represented by the Department of
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