1-(4-seleno-β-D-ribofuranosyl)cytosine | 1006032-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(4-seleno-β-D-ribofuranosyl)cytosine
• 英文别名: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)selenolan-2-yl]pyrimidin-2-one
• CAS: 1006032-36-5
• 化学式: C₉H₁₃N₃O₄Se
• 分子量: 306.18
• InChiKey: YPPWIQQLCCWDTG-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.46
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribitol 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 臭氧 、 三乙胺 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 7.92h， 生成 1-(4-seleno-β-D-ribofuranosyl)cytosine
  参考文献：
  名称：

  Practical synthesis of 4′-selenopyrimidine nucleosides using hypervalent iodine

  摘要：

  We report herein a synthesis of 4'-selenouridine 12 and 4'-selenocytidine 14, substrates for the synthesis of 4'-selenoRNA. The Pummerer-like reaction between the selenoxide 9 and a silylated uracil afforded the desired 4'-selenouridine derivative 10: however, the chemical yield of 10 was rather low. In addition, the reproducibility of this reaction was poor because of the instability of the selenoxide 9. Improvement of this Pummerer-like reaction to give 10 was achieved when the 4-selenosugar 8 was treated with TMSOTf, 2,6-lutidine and the silylated uracil in the presence of iodosylbenzene. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.020

文献信息

• Synthesis and biological evaluation of 2′-substituted-4′-selenoribofuranosyl pyrimidines as antitumor agents
  作者：Varughese Alexander、Jayoung Song、Jinha Yu、Jung Hee Choi、Jin-Hee Kim、Sang Kook Lee、Won Jun Choi、Lak Shin Jeong

  DOI：10.1007/s12272-014-0466-6

  日期：2015.6

  The 2′-substituted-4′-selenoribofuranosyl pyrimidines 3a–3j were synthesized from D-ribose and assayed for anticancer activity. The 2′-azido and 2′-fluoro groups with a ribo configuration were introduced by the regioselective opening of the O2,2′-anhydronucleosides with sodium azide and (HF)x-pyridine, respectively. Among the compounds tested, only 2′-fluoro derivative 3j was found to exhibit significant anticancer activity, but was much less potent than the corresponding 2′-arabino analogue 2c. This study will provide medicinal chemists with the insight into the identification of structural requirements for the anticancer activity for the developments of biologically active nucleosides.

  由 D-核糖合成 2'-取代-4'-硒代核糖呋喃糖基嘧啶 3a-3j，并测定其抗癌活性。具有核糖构型的2'-叠氮基和2'-氟基团是通过分别用叠氮化钠和(HF)x-吡啶对O2,2'-脱水核苷进行区域选择性打开而引入的。在测试的化合物中，只有2'-氟衍生物3j被发现表现出显着的抗癌活性，但其效力远低于相应的2'-阿拉伯类似物2c。这项研究将为药物化学家提供深入了解抗癌活性的结构要求的鉴定，以开发生物活性核苷。
• Stereoselective Synthesis and Conformational Study of Novel 2′,3′-Didehydro-2′,3′-dideoxy-4′-selenonucleosides
  作者：Dilip K. Tosh、Won Jun Choi、Hea Ok Kim、Yoonji Lee、Shantanu Pal、Xiyan Hou、Jungwon Choi、Sun Choi、Lak Shin Jeong

  DOI：10.1021/jo8003277

  日期：2008.6.1

  Stereoselective synthesis of novel 2',3'-didehydro-2',3'dideoxy-4'-selenonnucleosides (4'-seleno-d4Ns) 4a-c was accomplished via 4'-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4'-Selenoribofuranosyl pyrimidines 11a-c were efficiently synthesized from D-ribose or D-gulonic gamma-lactone using a Pummerer-type condensation as a key step. Introduction of 2',3'-double bond was achieved by treating cyclic 2',3'-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine.
• Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction
  作者：Kumarasamy Jayakanthan、Blair D. Johnston、B. Mario Pinto

  DOI：10.1016/j.carres.2008.02.014

  日期：2008.7

  The syntheses of four selenonucleosides, namely 4 '-O-selenoadenosine, -cytidine, -thymidine, and -uridine are described. Commercially available D-ribonolactone was converted to the key intermediate 1,4-anhydro-4-seleno-D-ribitol in seven steps in overall excellent yield. Oxidation of the seleno-D-ribitol with MCPBA gave a single diastereomeric selenoxide in excellent yield, which upon Pummerer reaction in the presence of silylated purine or pyrimidine bases gave stereoselectively the corresponding 4'-beta-selenonucleosides. The stereochemistry at the anomeric center was determined by means of 1D-NOE experiments. (C) 2008 Elsevier Ltd. All rights reserved.
• First Synthesis of 4‘-Selenonucleosides Showing Unusual Southern Conformation
  作者：Lak Shin Jeong、Dilip K. Tosh、Hea Ok Kim、Ting Wang、Xiyan Hou、Ho Seop Yun、Youngjoo Kwon、Sang Kook Lee、Jungwon Choi、Long Xuan Zhao

  DOI：10.1021/ol7025558

  日期：2008.1.1

  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 interactions, driving the conformation to the C2'-endol C3'-exo twist (Southern) conformation.
• Practical synthesis of 4′-selenopyrimidine nucleosides using hypervalent iodine
  作者：Hirotsugu Taniike、Yusuke Inagaki、Akira Matsuda、Noriaki Minakawa

  DOI：10.1016/j.tet.2011.08.020

  日期：2011.10

  We report herein a synthesis of 4'-selenouridine 12 and 4'-selenocytidine 14, substrates for the synthesis of 4'-selenoRNA. The Pummerer-like reaction between the selenoxide 9 and a silylated uracil afforded the desired 4'-selenouridine derivative 10: however, the chemical yield of 10 was rather low. In addition, the reproducibility of this reaction was poor because of the instability of the selenoxide 9. Improvement of this Pummerer-like reaction to give 10 was achieved when the 4-selenosugar 8 was treated with TMSOTf, 2,6-lutidine and the silylated uracil in the presence of iodosylbenzene. (C) 2011 Elsevier Ltd. All rights reserved.