199661-18-2

Upstream product

• 146557-69-9 1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine 
• 124-63-0 methanesulfonyl chloride 
• 146557-80-4 1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine 

Downstream Products

• 195967-08-9 C₄₃H₆₀N₄O₈S₂Si₂ 
• 195967-07-8 1-[(2R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-nitro-phenyldisulfanylmethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 146557-82-6 3'-(azidomethyl)-5'-O-tert-butyldimethylsilyl-3'-deoxythymidine 
• 195967-06-7 1-[(2R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzylsulfanylmethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Rational design of 5′-thiourea-substituted α-thymidine analogues as thymidine monophosphate kinase inhibitors capable of inhibiting mycobacterial growth

Recently, thymidine monophosphate kinase (TMPK) emerged as an attractive target for developing inhibitors of Mycobacterium tuberculosis growth. The elucidation of the X-ray structure of TMPK of M. tuberculosis (TMPKmt), as well as the structure of an earlier serendipitously discovered dimeric thymidine inhibitor, laid the foundation for the design of potent and selective TMPKmt inhibitors reported here. Several hits identified within a series of 3′-C-branched thiourea-substituted β-thymidine derivatives inspired us to construct a set of 5′-thiourea-substituted α-thymidine derivatives characterized by a similar relative orientation of the thymine and arylthiourea moieties. α-Thymidine derivative 15, featuring a (3-trifluoromethyl-4-chlorophenyl)thiourea moiety, has a Ki of 0.6 μM and a selectivity index of 600 versus human TMPK. Moreover, it represents the first TMPK inhibitor showing good inhibitory activity on growing M. bovis (MIC99 = 20 μg/mL) and M. tuberculosis (MIC50 = 6.25 μg/mL) strains.

Dinucleoside monophosphate analogues containing disulfide linkages

The synthesis of two dinucleoside monophosphate analogues is described in which the 3'-O-P-O-5' phosphodiester linkage is replaced by either an isosteric 3'-C-S-S-5' or a shorter 3'-S-S-5' linkage. In both cases the -S-S- bond was formed through a disulfide exchange reaction using an activated S-nucleosidyl S-aryl disulfide and a suitably protected derivative of 5'-thiothymidine.