Tiwari Kamal N, Cappellacci Loredana, Montgomery John A, Secrist John A
Southern Research Institute, Birmingham, Alabama 35255-5305, USA.
Nucleosides Nucleotides Nucleic Acids. 2003 Dec;22(12):2161-70. doi: 10.1081/ncn-120026872.
1-O-Acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-erythro-pentofuranose and 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose were coupled with 5-azacytosine to obtain alpha and beta anomers of nucleosides. All four nucleosides were reduced to the corresponding dihydro derivatives and deblocked to give target compounds. All eight target compounds were evaluated in a series of human cancer cell lines in culture. Only 2'-deoxy-4'-thio-5-azacytidine (3beta) was found to be cytotoxic in all the cell lines and was further evaluated in vivo. Details of the synthesis and biological activity are reported.
1-O-乙酰基-2-脱氧-3,5-二-O-甲苯甲酰基-4-硫代-D-赤藓戊呋喃糖和2-脱氧-1,3,5-三-O-乙酰基-4-硫代-L-苏阿戊呋喃糖与5-氮杂胞嘧啶偶联，得到核苷的α和β异头物。所有四种核苷都被还原为相应的二氢衍生物，并脱保护得到目标化合物。对所有八种目标化合物在一系列培养的人类癌细胞系中进行了评估。仅发现2'-脱氧-4'-硫代-5-氮杂胞苷（3β）在所有细胞系中均具有细胞毒性，并在体内进行了进一步评估。报道了合成和生物活性的详细信息。
