2',3'-O-(1-methylethylidene)-adenosyl 5'-benzoate | 93135-70-7

• 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: 2',3'-O-(1-methylethylidene)-adenosyl 5'-benzoate
• 英文别名: ((3aR,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl benzoate；5'-O-benzoyl-2',3'-O-isopropylideneadenosine；O^5'-benzoyl-O^2'_,O3'-isopropylidene-adenosine；((3AR,4R,6R,6AR)-6-(6-Amino-9H-purin-9-YL)-2,2-dimethyltetrahydrofuro[3,4-D][1,3]dioxol-4-YL)methyl benzoate；[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl benzoate
• CAS: 93135-70-7
• 化学式: C₂₀H₂₁N₅O₅
• 分子量: 411.417
• InChiKey: MMPQEWNVGKCTAX-SCFUHWHPSA-N

物化性质

• 沸点：
  630.3±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2',3'-O-(1-methylethylidene)-adenosyl 5'-benzoate 在 甲酸 作用下， 生成 ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl benzoate
  参考文献：
  名称：

  Synthesis and structure-activity relationships of adenosine analogs as inhibitors of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. Modifications at positions 5′ and 8

  摘要：

  A number of 5', N6- and C8, N6-disubstituted adenosine analogs was synthesized and tested for inhibition of trypanosomal glyceraldehyde 3-phosphate dehydrogenase. The most active compound, N6-(3-methyl-2-butenyl)-8-(2-thienyl)adenosine, had Kl of 9 microM and was marginally selective for the parasite enzyme.

  DOI：

  10.1016/s0960-894x(98)00635-0
• 作为产物：
  描述：

  腺苷 在 吡啶 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 38.5h， 生成 2',3'-O-(1-methylethylidene)-adenosyl 5'-benzoate
  参考文献：
  名称：

  由修饰腺苷形成的多重刺激响应超分子凝胶

  摘要：

  由腺苷合成的尿素衍生物1和2被设计为低分子量凝胶剂。疏水基团已被引入到1和2的亲水核糖部分的全部或部分羟基中，以控制分子及其聚集体的亲溶剂性。化合物2在氯仿和 1,2-二氯乙烷等卤代溶剂中选择性地形成超分子凝胶。2的超分子凝胶氯仿是热稳定的，其凝胶-溶胶相变温度高于氯仿的沸点。通过使用流变仪测定其粘弹性来研究超分子凝胶的物理性质。超分子凝胶实现了多种刺激响应的可逆凝胶-溶胶相变。通过伴随凝胶-溶胶转变的重复升温-冷却循环，超分子凝胶显示出可逆的相变。超分子凝胶可以经历五次重复的机械响应凝胶-溶胶转变。凝胶到溶胶的相变也可以通过向超分子凝胶中添加各种阴离子来实现，例如四丁基氟化铵。通过向含氟离子的溶胶中添加三氟化硼醚合物来实现再凝胶化。向超分子凝胶中加入甲醇也诱导了凝胶到溶胶的相变。通过向悬浮液中添加 4 Å 的分子筛来实现重新凝胶化。 全尺寸图像

  DOI：

  10.1248/cpb.c22-00134

文献信息

• Metal-free transesterification catalyzed by tetramethylammonium methyl carbonate
  作者：Manabu Hatano、Yuji Tabata、Yurika Yoshida、Kohei Toh、Kenji Yamashita、Yoshihiro Ogura、Kazuaki Ishihara

  DOI：10.1039/c7gc03858e

  日期：——

  tetramethylammonium methyl carbonate is effective as a catalyst for the chemoselective, scalable, and reusable transesterification of various esters and alcohols in common organic solvents. In situ-generated highly active species, tetramethylammonium alkoxides, can greatly avoid self-decomposition at ≤110 °C, and are reusable. In particular, chelating substrates, such as amino alcohols, diols, triols,

  不含环境的无金属碳酸四甲基铵甲酯可有效用作各种酯和醇在普通有机溶剂中的化学选择性，可扩展性和可重复使用的酯交换反应的催化剂。原位生成的高活性物质四甲基铵醇盐可大大避免在≤110°C时自分解，并可重复使用。特别地，可以使用使常规金属盐催化剂失活的螯合底物，例如氨基醇，二醇，三醇，糖衍生物，生物碱，α-氨基酸酯等。还展示了100克规模的生物柴油生产。
• Reactions of trimethylsilyl fluorosulfonyldifluoroacetate with purine and pyrimidine nucleosides
  作者：Magdalena Rapp、Xiaohong Cai、Wei Xu、William R. Dolbier、Stanislaw F. Wnuk

  DOI：10.1016/j.jfluchem.2008.12.004

  日期：2009.3

  4-hydroxyl group of the enolizable uracil ring. Reaction of the difluorocarbene with the adenosine substrates having the unprotected 6-amino group in the purine ring produced the 6-N-difluoromethyl derivative, while reaction with 6-N-benzoyl protected adenosine analogues gave the difluoromethyl ether product derived from the insertion of difluorocarbene into the enol form of the 6-benzamido group. Treatment

  由氟磺酰二氟乙酸三甲基甲硅烷基酯 (TFDA) 生成的二氟卡宾优先在尿嘧啶环的烯醇化酰胺部分和嘌呤环的 6-氨基与尿苷和腺苷底物反应。2',3'- Di - O -benzoyl-3'-deoxy-3'-methyleneuridine 与 TFDA 反应生成 4- O-二氟甲基产物，其衍生自二氟卡宾插入可烯醇化尿嘧啶环的 4-羟基。二氟卡宾与嘌呤环中具有未保护的 6-氨基的腺苷底物反应产生 6- N-二氟甲基衍生物，同时与 6 -N-苯甲酰基保护的腺苷类似物得到二氟甲基醚产物，其衍生自二氟卡宾插入6-苯甲酰胺基的烯醇形式。用TFDA处理 6- N-邻苯二甲酰基保护的腺苷类似物导致嘌呤的咪唑环出人意料地一锅法转化为相应的N-二氟甲基硫脲衍生物。用 TFDA 处理在糖环的 2'、3' 或 4' 碳上带有外亚甲基的适当保护的嘧啶和嘌呤核苷，得到相应的螺二氟环丙基类似物，但产率低。
• NOVEL ANTIBACTERIAL COMPOUNDS
  申请人：Pochet Sylvie

  公开号：US20130331351A1

  公开（公告）日：2013-12-12

  The present invention relates to compounds of formula (I): wherein Rj, R2, R3, R4, Xi, X2, X3 and Z are as defined in claim 1 . The compounds are useful in the prevention and/or treatment of bacterial infections.

  本发明涉及公式（I）的化合物：其中Rj，R2，R3，R4，Xi，X2，X3和Z如权利要求1所定义。该化合物对于预防和/或治疗细菌感染有用。
• Chemoselective Acylation of Nucleosides
  作者：Yu Tang、Rebecca L. Grange、Oliver D. Engl、Scott J. Miller

  DOI：10.1002/chem.202201661

  日期：2022.9.16

  Chemoselective functionalization of oxygen atoms versus nitrogen atoms in bifunctional and polyfunctional molecules is a long-standing challenge in both fundamental chemistry and in complex molecule synthesis. Different conditions that allow high selectivity in the derivatization of complex nucleosides that contain both O- and N-based functionalities are described. Particularly intriguing cases are

  双功能和多功能分子中氧原子与氮原子的化学选择性功能化是基础化学和复杂分子合成中长期存在的挑战。描述了允许高选择性衍生同时包含O和N官能团的复杂核苷的不同条件。还提出了特别有趣的案例，其中基于O和N的功能的反应性非常依赖于上下文，表现出模糊传统考虑的反应性，但也可以观察到选择性。
• 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.