- Syntheses and antitumor activities of D- and L-2'-deoxy-4'-thio pyrimidine nucleosides
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Both enantiomers of 2'-deoxy-4'-thiouridine (9) and 15, 4'-thiothymidine (10) and 16, and 2'-deoxy-4'-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio- β-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L- enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4- thio-α,β-xylofuranoside (1) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.
- Uenishi,Takahashi,Motoyama,Akashi,Sasaki
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- The development of β-selective glycosylation reactions with benzyl substituted 2-deoxy-1,4-dithio-D-erythro-pentofuranosides: enabling practical multi-gram syntheses of 4'-Thio-2'-deoxycytidine (T-dCyd) and 5-aza-4’-thio-2’-deoxycytidine (aza-T-dCyd) to s
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The lack of effective methods to perform direct β-selective glycosylation reactions with 2-deoxy-1,4-dithio-D-erythro-pentofuranosides has long been a significant stumbling block for the multi-gram synthesis of 4’-thio-2’-deoxy nucleosides. In addition, p
- Wishka, Donn G.,Lopez, Omar D.,Rudchenko, Vladimir F.,Huang, Guangfei,Bahde, Robert,Kumar, Vineet,Denysenko, Sergiy M.,Zhang, Lianhao,Zhang, Mianji,Teicher, Beverly A.,Morris, Joel
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- SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-?-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
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A compound represented by a formula [1D] as shown below (wherein R1A, R1B, R2A, R2B, R3A and R3B represent a hydrogen atom, an optionally substituted C1-6 alkyl group, and the li
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- Practical synthesis of 2′-deoxy-4′-thioribonucleosides: Substrates for the synthesis of 4′-thioDNA
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We report herein a practical synthesis of 4′-thiothymidine (15) and appropriately protected 2′-deoxy-4′-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4′-thioDNA, from the corresponding 4′- thi
- Inoue, Naonori,Kaga, Daisuke,Minakawa, Noriaki,Matsuda, Akira
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p. 8597 - 8600
(2007/10/03)
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- 2'-deoxy-4'-thioribonucleosides and their antiviral activity
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2'-Deoxy-4'-thio-ribonucleosides, intermediates in their production, and their use as antiviral and anticancer agents are disclosed.
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- The synthesis and biological activity of certain 4'-thionucleosides
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Results are presented on the synthesis and biological activity of several types of 4'-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4'-thiothymidine are also presented.
- Secrist III,Parker,Tiwari,Messini,Shaddix,Rose,Bennett Jr.,Montgomery
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p. 675 - 686
(2007/10/02)
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- Synthesis and Biological Activity of 2'-Deoxy-4'-thio Pyrimidine Nucleosides
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2'-Deoxy-4'-thiocytidine (7β), 2'-deoxy-4'-thiouridine (9), and 4'-thiothymidine (10) have been synthesized and evaluated for cytotoxicity in vitro.All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines. 4'-Thiothymidine was also act
- Secrist, John A.,Tiwari, Kamal N.,Riordan, James M.,Montgomery, John A.
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p. 2361 - 2366
(2007/10/02)
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