2'-O-(1-pentyn-5-yl)adenosine | 1005190-66-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2'-O-(1-pentyn-5-yl)adenosine
• 英文别名: (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-(pent-4-yn-1-yloxy)tetrahydrofuran-3-ol；2'-O-pent-4-ynyladenosine；(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-pent-4-ynoxyoxolan-3-ol
• CAS: 1005190-66-8
• 化学式: C₁₅H₁₉N₅O₄
• 分子量: 333.347
• InChiKey: AXSVFZQSEWOAPP-SDBHATRESA-N

物化性质

• 沸点：
  647.8±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-O-(1-pentyn-5-yl)adenosine 在 咪唑 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 、 三氯乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 45.0h， 生成 (S,E)-3-amino-N-(((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(pent-4-yn-1-yloxy)tetrahydrofuran-2-yl)methyl)-4-methylpent-1-ene-1-sulfonamide
  参考文献：
  名称：

  A chemical proteomic probe for detecting native carrier protein motifs in nonribosomal peptide synthetases

  摘要：

  一种基于活性的探针，与5'-(乙烯磺酰胺基脱氧腺苷支架耦合，具有可点击的炔烃功能，可选择性地靶向非核糖体肽合成酶中的天然载体蛋白基序。

  DOI：

  10.1039/c6cc07793e
• 作为产物：
  描述：

  5-氯戊炔 、 腺苷 在 sodium hydride 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 以31%的产率得到2'-O-(1-pentyn-5-yl)adenosine
  参考文献：
  名称：

  Site-specific conjugation of drug-like fragments to an antimiR scaffold as a strategy to target miRNAs inside RISC

  摘要：

  我们合成了一个miR-122 antimiR文库，其中引入了药物类片段，这以位置依赖的方式影响了细胞活性。

  DOI：

  10.1039/c5cc07478a

文献信息

• Conjugation of Nucleosides and Oligonucleotides by [3+2] Cycloaddition
  作者：Anup M. Jawalekar、Nico Meeuwenoord、J. (Sjef) G. O. Cremers、Herman S. Overkleeft、Gijs A. van der Marel、Floris P. J. T. Rutjes、Floris L. van Delft

  DOI：10.1021/jo702023s

  日期：2008.1.1

  presented for copper(I)-catalyzed [3+2] cycloaddition of nucleosides and nucleotides in near-quantitative yield. Azido−alkyne cycloaddition was applied for the preparation of a range of adenosine dimers and derivatives with versatile functionality, as well as for the smooth condensation of two oligonucleotide strands. The described technology may find valuable application in the synthesis of oligonucleotide

  提出了一种以接近定量的产率进行铜（I）催化的核苷和核苷酸的[3 + 2]环加成反应的方法。叠氮基炔烃环加成反应用于制备一系列具有通用功能的腺苷二聚体和衍生物，以及两条寡核苷酸链的平滑缩合。所描述的技术可以在寡核苷酸二聚体和缀合物的合成中找到有价值的应用。
• Interaction of Adenosine, Modified Using Carborane Clusters, with Ovarian Cancer Cells: A New Anticancer Approach against Chemoresistance
  作者：Katarzyna Bednarska-Szczepaniak、Ewelina Przelazły、Katarzyna Dominika Kania、Marzena Szwed、Miroslava Litecká、Bohumír Grűner、Zbigniew J. Leśnikowski

  DOI：10.3390/cancers13153855

  日期：——

  cancer cells and highly resistant cancer spheroids exposed to cisplatin, increasing cell cycle arrest, apoptosis or necrosis, and reactive oxygen species production. Moreover, it showed high cellular accumulation and did not induce cross-resistance to cisplatin, carboplatin, doxorubicin, paclitaxel, or gemcitabine in long-term cultures. The reference nido-carborane derivative (no metal ions) and unmodified

  铂化合物仍然是治疗大多数致命性妇科恶性肿瘤和卵巢癌的一线药物。获得性铂耐药仍然是妇科肿瘤学的主要挑战。考虑到金属碳硼烷修饰剂独特的理化性质以及核苷衍生物作为抗癌抗代谢物的重要作用，我们设计并合成了一组含有铁、钴或铬的金属碳硼烷的腺苷缀合物作为影响卵巢顺铂敏感性的半非生物化合物。癌细胞。使用卵巢癌细胞系和多细胞球体的贴壁培养物，从敏感到高度耐药，包括对铂类药物“无反应”的实验细胞系。含铁金属碳硼烷缀合物显示出最佳的抗癌活性，特别是针对耐药细胞。在 C2' 核苷位置修饰的化合物在暴露于顺铂的耐药癌细胞和高度耐药的癌球体中表现出最佳活性，增加细胞周期停滞、细胞凋亡或坏死以及活性氧的产生。此外，它表现出高细胞积累性，并且在长期培养中不会诱导对顺铂、卡铂、阿霉素、紫杉醇或吉西他滨的交叉耐药性。参考的硝基碳硼烷衍生物（无金属离子）和未修饰的核苷没有那么有效。这些发现表明，腺苷的金属碳硼烷修饰可能会使卵巢癌细胞在联合治疗中对顺铂敏感。
• Effect of adenosine modified with a boron cluster pharmacophore on reactive oxygen species production by human neutrophils
  作者：Katarzyna Bednarska、Agnieszka B. Olejniczak、Agnieszka Piskala、Magdalena Klink、Zofia Sulowska、Zbigniew J. Lesnikowski

  DOI：10.1016/j.bmc.2012.09.039

  日期：2012.11

  Methods for the synthesis of adenosine/boron cluster conjugates are proposed and the potential of the obtained derivatives to modulate neutrophil activity, especially reactive oxygen species (ROS) production in vitro, is described. An efficient inhibition of ROS production in activated neutrophils by adenosine modified at the 2'-C and 6-N positions with a para-carborane cluster (C2B10H11) was discovered. The high affinity of the selected compounds for adenosine receptor A(2A) was established. These results are in agreement with the possible involvement of receptor A(2A) in the biological activities of adenosine/boron cluster conjugates. This study extends the range of innovative molecules available for testing as agents affecting inflammatory processes. (C) 2012 Elsevier Ltd. All rights reserved.
• Modulation of human neutrophil activity by adenosine modified with a carborane pharmacophore
  作者：Katarzyna Bednarska、Agnieszka B. Olejniczak、Magdalena Klink、Zofia Sułowska、Zbigniew J. Leśnikowski

  DOI：10.1016/j.bmcl.2014.05.010

  日期：2014.7

  An impact of adenosine modification with electroneutral, lipophilic 1,12-dicarba-closo-dodecaborane or electronegative 7,8-dicarba-nido-undecaborane boron cluster at the 6-N, 2'-C and 2-C positions on human neutrophil oxidative burst, neutrophil adherence to fibronectin and protein kinase C activity was studied. Modification of adenosine with 1,12-dicarba-closo-dodecaborane, but not 7,8-dicarbanido-undecaborane, changes the function of adenosine from an inactive to an active state in regulating neutrophil response to PMA stimulation by reducing neutrophils' reactivity through a mechanism involving the PKC signaling pathway. Our results show that exogenously administered adenosine derivatives can be useful in regulating the oxidative burst of neutrophils in the inflammatory process. (C) 2014 Elsevier Ltd. All rights reserved.
• A chemical proteomic probe for detecting native carrier protein motifs in nonribosomal peptide synthetases
  作者：Shota Kasai、Fumihiro Ishikawa、Takehiro Suzuki、Naoshi Dohmae、Hideaki Kakeya

  DOI：10.1039/c6cc07793e

  日期：——

  An activity-based probe coupled to a 5′-(vinylsulfonylaminodeoxy)adenosine scaffold with a clickable alkyne functionality selectively targets native carrier protein motifs in nonribosomal peptide synthetases.

  一种基于活性的探针，与5'-(乙烯磺酰胺基脱氧腺苷支架耦合，具有可点击的炔烃功能，可选择性地靶向非核糖体肽合成酶中的天然载体蛋白基序。