5'-O-propargyl-2',3'-O,O-isopropylidene-6-N-benzoyladenosine | 1005190-81-7

• 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: 5'-O-propargyl-2',3'-O,O-isopropylidene-6-N-benzoyladenosine
• 英文别名: N⁶-benzoyl-2′,3′-O-isopropylidene-5′-O-propargyladenosine；N6-benzoyl-2',3'-O-isopropylidene-5'-O-propargyl-adenosine；N-[9-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(prop-2-ynoxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-yl]benzamide
• CAS: 1005190-81-7
• 化学式: C₂₃H₂₃N₅O₅
• 分子量: 449.466
• InChiKey: GUGQAZKHAKFFMQ-UVLLPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-propargyl-2',3'-O,O-isopropylidene-6-N-benzoyladenosine 在 甲醇 、 氨 作用下， 以92%的产率得到2',3'-O,O-isopropylidene-5'-O-propargyl-adenosine
  参考文献：
  名称：

  Triazole-Linked Inhibitors of Inosine Monophosphate Dehydrogenase from Human and Mycobacterium tuberculosis

  摘要：

  The modular nature of nicotinamide adenine dinucleotide (NAD)-mimicking inosine monophsophate dehydrogenase (IMPDH) inhibitors has prompted us to investigate novel mycophenolic adenine dinucleotides (MAD) in which 1,2,3-triazole linkers were incorporated as isosteric replacements of the pyrophosphate linker. Synthesis and evaluation of these inhibitors led to identification of low nanomolar inhibitors of human IMPDH and more importantly the first potent inhibitor of IMPDH from Mycobacterium tuberculosis (mtIMPDH). Computational studies of these IMPDH enzymes helped rationalize the observed structure-activity relationships. Additionally, the first cloning, expression, purification and characterization of mtIMPDH is reported.

  DOI：

  10.1021/jm100424m
• 作为产物：
  描述：

  3-溴丙炔 、 N6-苯甲酰基-2',3'-O-异丙亚基腺苷 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到5'-O-propargyl-2',3'-O,O-isopropylidene-6-N-benzoyladenosine
  参考文献：
  名称：

  [3 + 2]环加成反应偶联核苷和寡核苷酸

  摘要：

  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。

  DOI：

  10.1021/jo702023s

文献信息

• Sonogashira Reaction of Bromofluoropyridinaldoxime Nuclei: Convergent Synthesis of Functionalized 2- and 3-Fluoropyridine Scaffolds
  作者：Jagadeesh Yerri、Rachid Baati

  DOI：10.1002/ejoc.201800608

  日期：2018.8.15

  The palladium catalyzed Sonogashira cross‐coupling of bromofluoropyridinaldoxime with highly functionalized alkynes investigated in this study is fully compatible with unprotected sensitive aldoxime and affords representative underexplored new scaffolds.

  在这项研究中，钯催化的溴氟吡啶并二肟与高度官能化的炔烃的Sonogashira交叉偶联与未保护的敏感醛肟完全相容，并提供了开发不足的代表性新支架。
• 3,6-DISUBSTITUTED-2-PYRIDINALDOXIME SCAFFOLDS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：EP3696170A1

  公开（公告）日：2020-08-19

  The present invention relates to a compound of formula (I), or one of its pharmaceutically acceptable salts: wherein R1, R2 and -X-Y- have specific definitions. It also relates to the use of such a compound as reactivator of acetylcholinesterase for treating organophosphorous nerve agents poisoning; and to a process for preparing it.

  本发明涉及一种具有以下结构式（I）的化合物，或其药学上可接受的盐之一：其中R1、R2和-X-Y-具有特定定义。它还涉及将这种化合物用作乙酰胆碱酯酶再活化剂以治疗有机磷神经毒剂中毒的用途；以及制备该化合物的方法。
• 6-SUBSTITUTED 3-FLUORO-2-PYRIDINALDOXIME, 3-FLUORO-2-PYRIDINE HYDROXAMIC ACID, AND 3-FLUORO-2-PYRIDINAMIDOXIME SCAFFOLDS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：EP3473618A1

  公开（公告）日：2019-04-24

  The present invention relates to a compound of formula (I), as well as to a process for preparing the compounds of formula (I) by a chemoselective Sonogashira reaction. It also relates to a pharmaceutical composition comprising at least one compound of formula (I) and at least one pharmaceutically acceptable support. Finally, it relates to the use of such a compound as a medicine, preferably in the treatment of a nervous and/or respiratory failure due to intoxication with at least one organophosphorous nerve agent; in the treatment of neurological diseases such as Alzheimer's disease; and/or in the treatment of cancer; and/or for use as antiviral drug.

  本发明涉及一种化合物的公式(I)，以及通过化学选择性Sonogashira反应制备该化合物的方法。还涉及一种包含至少一种公式(I)化合物和至少一种药学上可接受的辅助物质的药物组合物。最后，涉及将这种化合物用作药物，优选用于治疗由至少一种有机磷神经毒剂中毒引起的神经和/或呼吸衰竭；治疗神经系统疾病，如阿尔茨海默病；和/或治疗癌症；和/或用作抗病毒药物。
• [EN] NOVEL ANTIBACTERIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIBACTÉRIENS
  申请人：PASTEUR INSTITUT

  公开号：WO2012090136A1

  公开（公告）日：2012-07-05

  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.

  本发明涉及以下化合物的公式(I)：其中R1、R2、R3、R4、X1、X2、X3和Z的定义如权利要求1所述。这些化合物在预防和/或治疗细菌感染方面具有用途。
• Diadenosine antibacterial compounds
  申请人：Institut Pasteur

  公开号：EP2471804B1

  公开（公告）日：2013-11-06