1-(4-carbamoyl-5-ethynyl-[1,2,3]triazol-1-yl)-β-D-ribofuranose | 1190878-87-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 1-(4-carbamoyl-5-ethynyl-[1,2,3]triazol-1-yl)-β-D-ribofuranose
• 英文别名: 5-ethynyl-1-(β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide；ETCAR；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethynyltriazole-4-carboxamide
• CAS: 1190878-87-5
• 化学式: C₁₀H₁₂N₄O₅
• 分子量: 268.229
• InChiKey: XCTIXFNJHRWGGY-VPCXQMTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-乙酰基-L-半胱氨酸甲酯 、 1-(4-carbamoyl-5-ethynyl-[1,2,3]triazol-1-yl)-β-D-ribofuranose 在 三乙胺 作用下， 以 乙腈 为溶剂， 以45%的产率得到(Z)-5-{2-[2-(acetylamino)-2-(methoxycarbonyl)ethylthio]vinyl}-1-(β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide
  参考文献：
  名称：

  5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties

  摘要：

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.050
• 作为产物：
  描述：

  5-ethynyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1-(4-carbamoyl-5-ethynyl-[1,2,3]triazol-1-yl)-β-D-ribofuranose
  参考文献：
  名称：

  5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties

  摘要：

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.050

文献信息

• Tandem Azide-Alkyne 1,3-Dipolar Cycloaddition/Electrophilic Addition: A Concise Three-Component Route to 4,5-Disubstituted Triazolyl-Nucleosides
  作者：Rachid Benhida、Vincent Malnuit、Maria Duca、Anwar Manout、Khalid Bougrin

  DOI：10.1055/s-0029-1217560

  日期：2009.8

  A one-pot, three-component approach to a new family of 4,5-functionalized triazolyl-nucleosides is described. The method relies on the one-pot azide-alkyne 1,3-cycloaddition/electrophilic addition tandem reaction, which affords good yields of the corresponding 4,5-disubstituted nucleosides.

  本文介绍了一种单锅三组分方法来制备新的 4,5 功能化三唑基核苷家族。该方法依赖于叠氮-炔烃 1,3-环加成/亲电加成串联反应的一锅式反应，可获得相应的 4,5-二取代核苷的高产率。
• ACADESINE DERIVATIVES, PRODUCTS AND COMPOSITIONS INCLUDING SAME, THERAPUETIC USES THEREOF, AND METHODS FOR SYNTHESIZING SAME
  申请人：Benhida Rachid

  公开号：US20140179626A1

  公开（公告）日：2014-06-26

  Acadesine derivatives as a drug, as well as the derivatives for the treatment of cancer and in particular for the treatment of chronic myeloid leukemia are described. Also, product containing the derivatives and at least one second active ingredient as a combination product for simultaneous, separate or sequential administration, in the treatment of cancer, as well as a pharmaceutical composition containing the derivatives and a pharmaceutically acceptable carrier are described. Finally, a method for inhibiting the in vitro cell proliferation including the placement of an in vitro cell in contact with the derivatives and methods for synthesis of said derivatives and methods for synthesis of the derivatives are described.

  本文描述了作为药物的Acadesine衍生物，以及用于治疗癌症，特别是慢性髓细胞白血病的衍生物。此外，还描述了包含衍生物和至少一种第二活性成分的产品，作为联合产品进行同时、分离或顺序给药，用于治疗癌症，以及含有衍生物和药用可接受载体的制药组合物。最后，描述了抑制体外细胞增殖的方法，包括将体外细胞与衍生物接触，以及合成所述衍生物的方法。
• US9173892B2
  申请人：——

  公开号：US9173892B2

  公开（公告）日：2015-11-03
• 5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties
  作者：Tomasz Ostrowski、Piotr Januszczyk、Marcin Cieslak、Julia Kazmierczak-Baranska、Barbara Nawrot、Elzbieta Bartoszak-Adamska、Joanna Zeidler

  DOI：10.1016/j.bmc.2011.05.050

  日期：2011.7

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.