A novel synthesis of antineoplastic 4'-thionucleosides using D-glucose as a chiral synthon.
We have synthesized 2'-deoxy-2'-methylene-4'-thiocytidine as a potential antineoplastic agent. Isopropylidene-3-O-benzylxylose, readily obtained from D-glucose in 5 steps, was converted to 1,4-anhydro-4-deoxy-4-thio-arabinitol. After manipulation at 2-position, unique Pummerer type glycosylation at the alpha-position of sulfoxides gave the target compound. Antineoplastic effect of this compound is also reported.
Yoshimura
Y
Y
Research and Development Division, Yamasa Corporation, Chiba, Japan.
Satoh
H
H
Watanabe
M
M
Sakata
S
S
Miura
S
S
Tanaka
M
M
Sasaki
T
T
Matsuda
A
A
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005947:Glucose / Q000737:chemistry; D006801:Humans; D008722:Methods; D015394:Molecular Structure; D013237:Stereoisomerism; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D013872:Thionucleosides; D005947:Glucose