A simple method for synthesis of spongosine, azaspongosine, and their antiplatelet effects

Article abstract of DOI:10.1080/15257779508010711

Reaction of 2-ethylthioadenine (1) with protected ribose (2) in the presence of stannic chloride gave 2-ethylthioadenosine (4). Oxidation of 5 with potassium permanganate yielded the corresponding sulfone (6) which furnished spongosine (7) after treatment with sodium methoxide. Similarly, reactions of 7-amino-5-ethylthio-1,2,3 triazolo[4,5-d]pyrimidine (8) with the ribose (2) gave 8-azaspongosine (13). The compounds (4) and 7 demonstrated potent antiaggregatory effects both in human platelet-rich plasma and whole blood, whereas, the aza analog (13) showed no inhibitory activity on platelet aggregation. Both (4) and (7) inhibit platelet aggregation in the presence of adenosine deaminase, whereas, adenosine is non-inhibitory, suggesting that analogs (4) and (7) are poor substrates for adenosine deaminase.

Full text of DOI:10.1080/15257779508010711

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A Simple Method for Synthesis of
Spongosine, Azaspongosine, and Their
Antiplatelet Effects
Lalit M. Ojha a , Deepa Gulati a , Neena Seth a , Diwan S.
Bhakuni a , Ram Pratap a & Kailash C. Agarwal b
a Central Drug Research Institute, Lucknow, India
b Department of Molecular Pharmacology and Biotechnology,
Division of Biology and Medicine, Brown University, Providence,
RI, 02912, U.S.A.
Published online: 24 Sep 2006.
To cite this article: Lalit M. Ojha , Deepa Gulati , Neena Seth , Diwan S. Bhakuni , Ram Pratap &
Kailash C. Agarwal (1995): A Simple Method for Synthesis of Spongosine, Azaspongosine, and Their
Antiplatelet Effects, Nucleosides and Nucleotides, 14:9-10, 1889-1900
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