1006032-31-0Relevant articles and documents
Structure-activity relationships of 2′-modified-4′- selenoarabinofuranosyl-pyrimidines as anticancer agents
Kim, Jin-Hee,Yu, Jinha,Alexander, Varughese,Choi, Jung Hee,Song, Jayoung,Lee, Hyuk Woo,Kim, Hea Ok,Choi, Jungwon,Lee, Sang Kook,Jeong, Lak Shin
, p. 208 - 225 (2014/07/08)
Based on the potent anticancer activity of the D-arabino-configured cytosine nucleoside ara-C, novel 2′-substituted-4′- selenoarabinofuranosyl pyrimidines 3a-3u, comprising azido, fluoro, and hydroxyl substituents at C-2′ were designed, synthesized, and evaluated for anticancer activity. The 2′-azido group was stereoselectively introduced by the Mitsunobu reaction using diphenylphosphoryl azide (DPPA), and the 2′-fluoro group was stereoselectively introduced through the double inversions of stereochemistry via the episelenium intermediate, which was formed by the participation of the selenium atom. Among the compounds tested, the 2′-fluoro derivative 3t (X = NH2, Y = H, R = F) was found to be the most potent anticancer agent and showed more potent anticancer activity than the control, ara-C in all tested human cancer cell lines (HCT116, A549, SNU638, T47D, and PC-3) except the leukemia cell lines (K562). The anticancer activity of the 2′-substituted-4′-selenonucleosides is in the following order: 2′-F > 2′-OH > 2′-N3.
New RNA purine building blocks, 4'-selenopurine nucleosides: First synthesis and unusual mixture of sugar puckerings
Yu, Jinha,Kim, Jin-Hee,Lee, Hyuk Woo,Alexander, Varughese,Ahn, Hee-Chul,Choi, Won Jun,Choi, Jungwon,Jeong, Lak Shin
supporting information, p. 5528 - 5532 (2013/06/04)
Writer's blocks: The first synthesis of RNA purine building blocks, 4'-selenoadenosine and 4'-selenoguanosine was achieved from D-ribose by regioisomeric rearrangement, which was confirmed by X-ray crystallography. 4'-Selenoadenosine exists in an unusual mixture of north and south conformers in the solid state.
First synthesis of 4′-selenonucleosides showing unusual southern conformation
Lak, Shin Jeong,Tosh, Dilip K.,Hea, Ok Kim,Wang, Ting,Hou, Xiyan,Ho, Seop Yun,Kwon, Youngjoo,Sang, Kook Lee,Choi, Jungwon,Long, Xuan Zhao
, p. 209 - 212 (2008/09/19)
(Chemical Equation Presented) The first synthesis of 4′- selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4′-oxonucleosides were overwhelmed by the size of selenium and steric interacti
Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides
Tosh, Dilip K.,Won, Jun Choi,Hea, Ok Kim,Lee, Yoonji,Pal, Shantanu,Hou, Xiyan,Choi, Jungwon,Choi, Sun,Lak, Shin Jeong
, p. 4259 - 4262 (2008/09/20)
(Chemical Equation Presented) Stereoselective synthesis of novel 2′,3′-didehydro-2′,3′-dideoxy-4′- selenonucleosides (4′-seleno-d4Ns) 4a-c was accomplished via 4′-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4′-Selenoribofuranosyl pyrimidi