15981-86-9

Basic information

• Product Name: 2,3'-ANHYDRO-1-(2'-DEOXY-5'-O-METHYLSULFONYL-BETA-D-THREO-PENTOFURANOSYL)-THYMINE
• Synonyms: 2,3'-ANHYDRO-1-(2'-DEOXY-5'-O-METHYLSULFONYL-BETA-D-THREO-PENTOFURANOSYL)-THYMINE;2,3''-ANHYDRO-1-(2''-DEOXY-5''-O-METHYLSULFONYL-SS-D-THREO-PENTOFURANOSYL)-THYMINE;5'-O-Methanesulfonyl-2'-deoxy-2,3'-anhydrothymidine
• CAS NO: 15981-86-9
• Molecular Formula: C₁₁H₁₄N₂O₆S
• Molecular Weight: 302.306
• Mol File: 15981-86-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3'-ANHYDRO-1-(2'-DEOXY-5'-O-METHYLSULFONYL-BETA-D-THREO-PENTOFURANOSYL)-THYMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3'-ANHYDRO-1-(2'-DEOXY-5'-O-METHYLSULFONYL-BETA-D-THREO-PENTOFURANOSYL)-THYMINE(15981-86-9)
• EPA Substance Registry System: 2,3'-ANHYDRO-1-(2'-DEOXY-5'-O-METHYLSULFONYL-BETA-D-THREO-PENTOFURANOSYL)-THYMINE(15981-86-9)

Safety Data

• Hazardous Substances Data: 15981-86-9(Hazardous Substances Data)

Usage

General Description

2,3'-Anhydro-1-(2'-deoxy-5'-O-methylsulfonyl-beta-D-threo-pentofuranosyl)-thymine, also known as AMT, is a synthetic derivative of thymine. It contains a modified sugar ring with a methylsulfonyl group attached to the 5' carbon of the sugar ring and lacks the 2' hydroxyl group. 2,3'-ANHYDRO-1-(2'-DEOXY-5'-O-METHYLSULFONYL-BETA-D-THREO-PENTOFURANOSYL)-THYMINE has been studied for its potential antiviral and antiparasitic properties. It has shown promising activity against certain viruses, including herpes simplex virus and varicella-zoster virus, making it a potential candidate for the development of new antiviral drugs. Additionally, its antiparasitic activity suggests potential use in the treatment of parasitic infections. Further research is needed to fully understand the therapeutic potential and mechanisms of action of 2,3'-anhydro-1-(2'-deoxy-5'-O-methylsulfonyl-beta-D-threo-pentofuranosyl)-thymine.

Upstream product

• 56822-33-4 3',5'-di-O-mesylthymidine 
• 56822-33-4 1-(2-Desoxy-3,5-di-O-mesyl-β-D-ribofuranosyl)-thymin 
• 50-89-5 thymidine 

Downstream Products

• 56822-33-4 3',5'-di-O-mesylthymidine 
• 51247-06-4 3'-deoxy-3'-fluoro-5'-O-mesylthymidine 
• 25526-93-6 alovudine 
• 183428-15-1 1-[(2R,4S,5R)-4-(4-Methoxy-benzylsulfanyl)-5-(4-methoxy-benzylsulfanylmethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 209255-51-6 5'-monomethoxytritylamino-3'-amino-2',3',5'-trideoxythymidine 
• 556826-39-2 5'-monomethoxytritylamino-3'-(N'-9-fluorenylmethoxycarbonylthiouria)-2',3',5'-trideoxythymidine 

Relevant articles and documents

Mitochondrial mode of action of a thymidine-based cisplatin analogue breaks resistance in cancer cells

Cisplatin analogue complexes with platinum(II) and palladium(II) starting from 3′,5′-diamino-3′,5′-dideoxy-thymidines were synthesized, both with the D-erythro- and D-threo configurations. Complexes of the general formula [MCl2L] were obtained and characterized. NMR spectroscopic measurements and single crystal X-ray structure analysis showed that the metal centers are coordinated to the ligands by the amino groups in 3′- and 5′-positions and not through the thymine moiety. All ligands and complexes showed no significant in vitro activities except thymiplatin (cis-dichloro(3′,5′-diamino-3′,5′-dideoxy-D-threo- thymidine)platinum(II)). Detailed in vitro studies on the apoptosis pathway in lymphoma (BJAB), leukemia (NALM-6), and melanoma cells (Mel-HO) as well as on transfected or resistant cell lines were carried out. Thymiplatin significantly induced an apoptotic response, which was found to be associated with the loss of mitochondrial membrane potential and with caspase activation. The activity was shown to be independent of Fas-associated protein with death domain (FADD), but dependent on Bcl-2 expression. As a consequence, for thymiplatin a mitochondrial mode of action could be assigned. Moreover, the compound showed activity in cells resistant to common drugs, such as daunorubicin and vincristin, and showed synergistic effects with doxorubicin, vincristin, cytarabin, and daunorubicin. Prove your metal: Cisplatin analogues with platinum(II) and palladium(II) complexes based on 3′,5′-diamino thymidines were synthesized (see figure for an example) and one was found to induce apoptosis mediated by caspase-9 and -3 processing. Thymiplatin was proven to be active on cisplatin, vincristin and daunorubicin resistant leukemia cells, and was synergistic with cytarabin, vincristin, daunorubicin, and doxorubicin in lymphoma cells. Copyright

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Mercury-Free Automated Synthesis of Guanidinium Backbone Oligonucleotides

A new method for synthesizing deoxynucleic guanidine (DNG) oligonucleotides that uses iodine as a mild and inexpensive coupling reagent is reported. This method eliminates the need for the toxic mercury salts and pungent thiophenol historically used in me