((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl octanoate | 145355-72-2

• 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 octanoate
• 英文别名: Adenosine octanoate；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl octanoate
• CAS: 145355-72-2
• 化学式: C₁₈H₂₇N₅O₅
• 分子量: 393.443
• InChiKey: GNYFNLGMSBCRCL-XKLVTHTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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'-octanoyladenosine 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以70.3%的产率得到((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl octanoate
  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

• 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。
• A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction
  作者：Francisco Moris、Vicente Gotor

  DOI：10.1021/jo00055a018

  日期：1993.1

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.
• [EN] USE OF ADENOSINE AND/OR OF ONE OF ITS DERIVATIVES AS AGENT FOR THE TREATMENT OF HUMAN PERSPIRATION<br/>[FR] UTILISATION D'ADÉNOSINE ET/OU D'UN DE SES DÉRIVÉS EN TANT QU'AGENT POUR LE TRAITEMENT DE LA TRANSPIRATION HUMAINE
  申请人：OREAL

  公开号：WO2011047982A2

  公开（公告）日：2011-04-28

  The invention thus relates to the use, as agent for the treatment of human perspiration in a cosmetic composition, of adenosine and/or one of its derivatives of formula (I). The invention also relates to a cosmetic method for treating human perspiration and optionally human body odours, which consists in applying, to the surface of the skin, a composition comprising, in a cosmetically acceptable medium, at least adenosine and/or one of its derivatives of formula (I) and also its salts, optical isomers and solvates as defined in any one of Claims 1 to 7.
• 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.