5'-O-hexanoyladenosine | 1187056-85-4

• 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: 5'-O-hexanoyladenosine
• 英文别名: ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl hexanoate；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hexanoate
• CAS: 1187056-85-4
• 化学式: C₁₆H₂₃N₅O₅
• 分子量: 365.389
• InChiKey: PUWYZGSAWFBGOJ-RVXWVPLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5'-O-hexanoyl-2',3'-O-isopropylideneadenosine 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以64.3%的产率得到5'-O-hexanoyladenosine
  参考文献：
  名称：

  Adenosine analogs as inhibitors of tyrosyl-tRNA synthetase: Design, synthesis and antibacterial evaluation

  摘要：

  Herein we describe the synthesis and evaluation of a series of adenosine analogs for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Out of these compounds, compound c6 has much stronger antibacterial potency against Pseudomonas aeruginosa than ciprofloxacin, and was determined to target tyrosyl-tRNA synthetase with IC50 zof 0.8 +/- 0.07 mu M. Structure-activity relationship analysis suggested that introduction of a fluorine atom at the 3'-position of benzene ring of the phenylacetyl moiety significantly increased affinities to the enzyme. In comparison with isopropylidene analogs, 2',3'-deprotected compounds displayed higher inhibitory activity. Molecular dockings provided an explanation for observations in biological assays. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.018

文献信息

• Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF
  作者：Yolanda Simeó、José Vicente Sinisterra、Andrés R. Alcántara

  DOI：10.1039/b818992g

  日期：——

  1-β-Arabinofuranosyl uracil, 9-β-arabinofuranosyl adenosine, 2′-O-(2-methoxyethyl)-5-methyl uridine, adenosine and uridine were enzymatically acylated with hexanoic anhydride and vinyl esters by CALB lipase (lipase B from Candida antarctica) with excellent regioselectivity in many cases and analytical reaction yields above 90%. The influence of the stereochemistry of the hydroxyl group on C-2′ was studied. Some of these esterifications were carried out in 2-methyltetrahydrofuran (MeTHF), which is described as an excellent substitute for THF in biocatalysed processes in organic media. This application for this green solvent is a proof-of-concept opening the use of MeTHF in biotransformations.

  1-β-阿拉伯呋喃糖基尿嘧啶、9-β-阿拉伯呋喃糖基腺苷、2′-O-(2-甲氧基乙基)-5-甲基尿苷、腺苷和尿苷在南极假丝酵母酯酶B（CALB）的催化下，与己酸酐和乙烯酯进行酶法酰化反应，具有优异的区域选择性，反应产率高于90%。研究了C-2′羟基的立体化学性质对反应的影响。一些酰化反应在2-甲基四氢呋喃（MeTHF）中进行，该溶剂被认为是生物催化过程中有机介质中四氢呋喃的优良替代品。这种绿色溶剂的应用验证了其在生物转化中使用的概念，为MeTHF的应用开辟了道路。
• Identification of 8-Aminoadenosine Derivatives as a New Class of Human Concentrative Nucleoside Transporter 2 Inhibitors
  作者：Kazuya Tatani、Masahiro Hiratochi、Yoshinori Nonaka、Masayuki Isaji、Satoshi Shuto

  DOI：10.1021/ml500343r

  日期：2015.3.12

  Purine-rich foods have long been suspected as a major cause of hyperuricemia. We hypothesized that inhibition of human concentrative nucleoside transporter 2 (hCNT2) would suppress increases in serum urate levels derived from dietary purines. To test this hypothesis, the development of potent hCNT2 inhibitors was required. By modifying adenosine, an hCNT2 substrate, we successfully identified 8-aminoadenosine derivatives as a new class of hCNT2 inhibitors. Compound 12 moderately inhibited hCNT2 (IC50 = 52 +/- 3.8 mu M), and subsequent structure-activity relationship studies led to the discovery of compound 48 (IC50 = 0.64 +/- 0.19 mu M). Here we describe significant findings about structural requirements of 8-aminoadenosine derivatives for exhibiting potent hCNT2 inhibitory activity.
• Adenosine analogs as inhibitors of tyrosyl-tRNA synthetase: Design, synthesis and antibacterial evaluation
  作者：Wei Wei、Wei-Kang Shi、Peng-Fei Wang、Xiao-Tong Zeng、Pan Li、Ji-Rong Zhang、Qian Li、Zhi-Ping Tang、Jia Peng、Lang-Zhou Wu、Mei-Qun Xie、Chan Liu、Xian-Hui Li、Ying-Chun Wang、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2015.09.018

  日期：2015.10

  Herein we describe the synthesis and evaluation of a series of adenosine analogs for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Out of these compounds, compound c6 has much stronger antibacterial potency against Pseudomonas aeruginosa than ciprofloxacin, and was determined to target tyrosyl-tRNA synthetase with IC50 zof 0.8 +/- 0.07 mu M. Structure-activity relationship analysis suggested that introduction of a fluorine atom at the 3'-position of benzene ring of the phenylacetyl moiety significantly increased affinities to the enzyme. In comparison with isopropylidene analogs, 2',3'-deprotected compounds displayed higher inhibitory activity. Molecular dockings provided an explanation for observations in biological assays. (c) 2015 Elsevier Ltd. All rights reserved.