((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl butyrate | 109472-93-7

• 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: ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl butyrate
• 英文别名: adenosine 5'-monobutyrate；5'-O-butyryladenosine；O^5'-butyryl-adenosine；O^5'-Butyryl-adenosin；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl butanoate
• CAS: 109472-93-7
• 化学式: C₁₄H₁₉N₅O₅
• 分子量: 337.335
• InChiKey: RETXURAWYRMEDR-FRJWGUMJSA-N

物化性质

• 沸点：
  633.7±65.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2',3'-isopropylidene-5'-butanoyladenosine 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以57.3%的产率得到((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl butyrate
  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

• Manipulation of enzyme regioselectivity by solvent engineering: Enzymatic synthesis of 5′-O-acylribonucleosides
  作者：Haribansh K. Singh、Gregory L. Cote、Trina M. Hadfield

  DOI：10.1016/s0040-4039(00)76216-2

  日期：1994.2

  Regioselectivity of enzyme can be manipulated by solvent engineering. By this technique, a simple and convenient method was developed for the synthesis of 5′-O-acylribonucleosides in high yields by the protease-catalyzed regioselective esterification of the primary hydroxyl groups of ribonucleosides in anhydrous pyridine.

  酶的区域选择性可以通过溶剂工程来控制。通过这种技术，开发了一种简单方便的方法，用于通过无水吡啶中核糖核苷的伯羟基的蛋白酶催化的区域选择性酯化来高产率地合成5'-O-酰基核糖核苷。
• N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
  申请人：Shi Jiangong

  公开号：US20130045942A1

  公开（公告）日：2013-02-21

  The present invention provides N 6 -substituted adenosine derivatives and N 6 -substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.

  本发明提供了N6-取代腺苷衍生物和N6-取代腺嘌呤衍生物，其制备方法，包括上述化合物的药物组合物，以及这些化合物在制造治疗失眠、惊厥、癫痫和帕金森病的药物和保健产品以及预防和治疗痴呆症中的用途。
• N6-substituted adenosine derivatives and N6-substituted adenine derivatives and uses thereof
  申请人：Shi Jiangong

  公开号：US10174033B2

  公开（公告）日：2019-01-08

  The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.

  本发明提供了 N6-取代腺苷衍生物和 N6-取代腺嘌呤衍生物、其制造方法、包含上述化合物的药物组合物，以及这些化合物在制造治疗失眠、抽搐、癫痫和帕金森病以及预防和治疗痴呆症的药物和保健产品中的用途。
• Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide
  作者：Sergio. Riva、Joel. Chopineau、A. P. G. Kieboom、Alexander M. Klibanov

  DOI：10.1021/ja00210a045

  日期：1988.1
• Huber, Chemische Berichte, 1956, vol. 89, p. 2853,2857
  作者：Huber

  DOI：——

  日期：——