173602-25-0Relevant academic research and scientific papers
5-(4-ammonio-2-oxopyrimidine-1(2H)-yl)-1,3-oxathiolane-2-carboxylate (lamivudine acid) Semihydrate: The six-fold symmetry created by hydrogen bond network
Dutkiewicz, Grzegorz,Chidan Kumar,Yathirajan,Narayana,Kubicki, MacIej
, p. 214 - 218 (2011)
The title compound, C8H9N3O4S × 1/2(H2O), which is an impurity found in a drug lamivudine, crystallizes in the hexagonal space group P62 with a = 10.208(1) A and c = 18.073(2) A. Such a rare packing is constructed by the hierarchical network of hydrogen bonds, which connect the molecules into chains, then into pairs of chains, and neighboring chains, oriented at the angle of 60°, make the final packing mode. The molecule exists in the crystal as the zwitterion, with negative charged carboxylate and positive ammonio groups. The oxathiolane ring is close to an envelope conformation, and both pyrimidine and carboxylate substituent are in the equatorial positions.
4′-Modified Pyrimidine Nucleosides as Potential Anti-hepatitis C Virus (HCV) Agents
Shakya, Neeraj,Vedi, Satish,Liang, Chao,Agrawal, Babita,Kumar, Rakesh
, p. 917 - 921 (2014/07/21)
Herein, we have investigated novel pyrimidine nucleosides bearing a 4'-carboxyl functionality (6-10, 13 and 15) as anti-HCV agents. In this new class of compounds, 7, 9, 10 and 15 demonstrated in vitro anti-HCV activity similar to or better than a known anti-HCV drug, ribavirin. In this work, we also, surprisingly, identified a 3'-sulfoxide analog of 3′-thiacytidine (16), obtained as a side product during the synthesis of 15, as a potent inhibitor of HCV replication at the concentration similar to that of ribavirin. No detectable in vitro cytotoxicity was observed for the investigated compounds up to the highest concentration tested.
