Tiazofurin is a drug which acts as an

inhibitor Inhibitor or inhibition may refer to: Biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotransmi ...

of the

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

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. Tiazofurin and its analogues were under investigation for potential use in the treatment of

cancer Cancer is a group of diseases involving Cell growth#Disorders, abnormal cell growth with the potential to Invasion (cancer), invade or Metastasis, spread to other parts of the body. These contrast with benign tumors, which do not spread. Po ...

, though side effects such as pleuro

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and a flu-like syndrome precluded further development. They also show

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effects and may be reevaluated as potential options in the treatment of newly emerging viral diseases.

Synthesis

The treatment of 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose 974-32-9(1) with trimethylsilyl cyanide gives 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide 3316-67-8(2). Treatment with hydrogen sulfide led to (2R,3R,4R,5R)-2-((Benzoyloxy)methyl)-5-carbamothioyltetrahydrofuran-3,4-diyl dibenzoate, PC10907289 (3). Cyclization with Ethyl bromopyruvate

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(4) led to 2-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-4-thiazolecarboxylic Acid Ethyl Ester 0084-09-5(5). Removal of the protecting groups with sodium methoxide afforded 2-beta-D-Ribofuranosyl-4-thiazolecarboxylic Acid Ethyl Ester 5936-53-1(6). Amide-ester interchange by treatment with dry ammonia completed the synthesis of Tiazofurin (7).

References

Carboxamides Ribosides Thiazoles Experimental cancer drugs {{antineoplastic-drug-stub