2'-C-Methylcytidine - CAS 20724-73-6
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
2'-C-Methylcytidine
Catalog Number:
20724-73-6
Synonyms:
4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one 2'-C-methyl-cytidine 2'-C-methylcytidine
CAS Number:
20724-73-6
Description:
2'-C-Methylcytidine, also called as NM107, inhibits the replication of HCV RNA and exerts inhibitory activity and cytotoxicity against HCV 1b replicon cells (IC50= 1.13 μM). 2'-C-Methylcytidine may be used to treat direct-acting antivirals against DENV in
Molecular Weight:
257.24
Molecular Formula:
C10H15N3O5
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC1(C(C(OC1N2C=CC(=NC2=O)N)CO)O)O
InChI:
1S/C10H15N3O5/c1-10(17)7(15)5(4-14)18-8(10)13-3-2-6(11)12-9(13)16/h2-3,5,7-8,14-15,17H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,10-/m1/s1
InChIKey:
PPUDLEUZKVJXSZ-VPCXQMTMSA-N
Targets:
HCV
Chemical Structure
CAS 20724-73-6 2'-C-Methylcytidine

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Reference Reading


1.In vitro combinations containing Tegobuvir are highly efficient in curing cells from HCV replicon and in delaying/preventing the development of drug resistance.
Vliegen I1, Paeshuyse J1, Zhong W2, Neyts J3. Antiviral Res. 2015 Aug;120:112-21. doi: 10.1016/j.antiviral.2015.05.011. Epub 2015 May 30.
Tegobuvir (GS-9190) is a non-nucleoside inhibitor of HCV RNA replication with proven antiviral activity in HCV-infected patients. The in vitro antiviral activity of Tegobuvir, when combined with one or two other direct acting antivirals (DAA) was assessed. When Tegobuvir was combined with either interferon α-2b, ribavirin, the protease inhibitor (PI) VX-950, the nucleoside polymerase inhibitor (NI) 2'-C-methylcytidine or various non-nucleoside polymerase inhibitors, an overall additive antiviral activity was observed. Adding Tegobuvir (at concentrations of 6, 30 or 150nM) to replicon-containing cells in the presence of suboptimal concentrations of the PI or of the various polymerase inhibitors either markedly delayed or completely prevented resistance development against these latter compounds. Tegobuvir (15nM), when combined with the PI, was able to cure replicon-containing cells from their replicon after a single passage, whereas either compound alone (at 2-fold higher concentration) was not.
2.The enterovirus protease inhibitor rupintrivir exerts cross-genotypic anti-norovirus activity and clears cells from the norovirus replicon.
Rocha-Pereira J1, Nascimento MS2, Ma Q3, Hilgenfeld R3, Neyts J4, Jochmans D5. Antimicrob Agents Chemother. 2014 Aug;58(8):4675-81. doi: 10.1128/AAC.02546-13. Epub 2014 Jun 2.
Potent and safe inhibitors of norovirus replication are needed for the treatment and prophylaxis of norovirus infections. We here report that the in vitro anti-norovirus activity of the protease inhibitor rupintrivir is extended to murine noroviruses and that rupintrivir clears human cells from their Norwalk replicon after only two passages of antiviral pressure. In addition, we demonstrate that rupintrivir inhibits the human norovirus (genogroup II [GII]) protease and further explain the inhibitory effect of the molecule by means of molecular modeling on the basis of the crystal structure of the Norwalk virus protease. The combination of rupintrivir with the RNA-dependent RNA polymerase inhibitors 2'-C-methylcytidine and favipiravir (T-705) resulted in a merely additive antiviral effect. The fact that rupintrivir is active against noroviruses belonging to genogroup I (Norwalk virus), genogroup V (murine norovirus), and the recombinant 3C-like protease of a GII norovirus suggests that the drug exerts cross-genotypic anti-norovirus activity and will thus most likely be effective against the clinically relevant human norovirus strains.
3.One-electron oxidation of gemcitabine and analogs: mechanism of formation of C3' and C2' sugar radicals.
Adhikary A1, Kumar A, Rayala R, Hindi RM, Adhikary A, Wnuk SF, Sevilla MD. J Am Chem Soc. 2014 Nov 5;136(44):15646-53. doi: 10.1021/ja5083156. Epub 2014 Oct 23.
Gemcitabine is a modified cytidine analog having two fluorine atoms at the 2'-position of the ribose ring. It has been proposed that gemcitabine inhibits RNR activity by producing a C3'• intermediate via direct H3'-atom abstraction followed by loss of HF to yield a C2'• with 3'-keto moiety. Direct detection of C3'• and C2'• during RNR inactivation by gemcitabine still remains elusive. To test the influence of 2'- substitution on radical site formation, electron spin resonance (ESR) studies are carried out on one-electron oxidized gemcitabine and other 2'-modified analogs, i.e., 2'-deoxy-2'-fluoro-2'-C-methylcytidine (MeFdC) and 2'-fluoro-2'-deoxycytidine (2'-FdC). ESR line components from two anisotropic β-2'-F-atom hyperfine couplings identify the C3'• formation in one-electron oxidized gemcitabine, but no further reaction to C2'• is found. One-electron oxidized 2'-FdC is unreactive toward C3'• or C2'• formation. In one-electron oxidized MeFdC, ESR studies show C2'• production presumably from a very unstable C3'• precursor.
4.Nucleoside inhibitors of tick-borne encephalitis virus.
Eyer L1, Valdés JJ2, Gil VA3, Nencka R4, Hřebabecký H4, Šála M4, Salát J1, Černý J5, Palus M5, De Clercq E6, Růžek D7. Antimicrob Agents Chemother. 2015 Sep;59(9):5483-93. doi: 10.1128/AAC.00807-15. Epub 2015 Jun 29.
Tick-borne encephalitis virus (TBEV) is a leading cause of human neuroinfections in Europe and Northeast Asia. There are no antiviral therapies for treating TBEV infection. A series of nucleoside analogues was tested for the ability to inhibit the replication of TBEV in porcine kidney cells and human neuroblastoma cells. The interactions of three nucleoside analogues with viral polymerase were simulated using advanced computational methods. The nucleoside analogues 7-deaza-2'-C-methyladenosine (7-deaza-2'-CMA), 2'-C-methyladenosine (2'-CMA), and 2'-C-methylcytidine (2'-CMC) inhibited TBEV replication. These compounds showed dose-dependent inhibition of TBEV-induced cytopathic effects, TBEV replication (50% effective concentrations [EC50]of 5.1 ± 0.4 μM for 7-deaza-2'-CMA, 7.1 ± 1.2 μM for 2'-CMA, and 14.2 ± 1.9 μM for 2'-CMC) and viral antigen production. Notably, 2'-CMC was relatively cytotoxic to porcine kidney cells (50% cytotoxic concentration [CC50] of ∼50 μM).