1-Chlor-2-desoxy-3,5-di-O-(4-methylbenzoyl)-β-D-ribofuranose | 69256-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Chlor-2-desoxy-3,5-di-O-(4-methylbenzoyl)-β-D-ribofuranose
• 英文别名: O³,O⁵-di-p-tolyl-2-deoxy-β-D-ribofuranosyl chloride；2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl chloride；1-β-chloro-2-deoxy-D-ribofuranosylbis(p-toluate)；2-deoxy-3,5-di-O-p-toluoyl-β-d-erythropentofuranosyl chloride；(2-deoxy-3,5-di-O-p-toluoyl)-α-D-ribofuranosyl chloride；(2R,3S,5S)-5-chloro-3-(4-methylphenoxy)-2-[(4-methylphenoxy)methyl]oxolane
• CAS: 69256-45-7
• 化学式: C₁₉H₂₁ClO₃
• 分子量: 332.827
• InChiKey: VJQUMYQNPLTFOB-IPMKNSEASA-N

物化性质

• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Chlor-2-desoxy-3,5-di-O-(4-methylbenzoyl)-β-D-ribofuranose 在 甲醇 、 4,4'-二甲基二苯甲酮 、 sodium methylate 、 1,8-双二甲氨基萘 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 6-(decylamino)-1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-imidazo[4,5-e][1,3]diazepine-4,8-dione
  参考文献：
  名称：

  含 5:7 融合咪唑并 [4,5-e][1,3] 二氮杂环系统的扩环核苷对 HCV 和 HIV 的双重抑制。体外结果和影响

  摘要：

  由一般结构1和2表示的扩环核苷 (REN) 的例子在细胞培养系统和各自的靶酶测定中表现出双重抗 HCV 和抗 HIV 活性，包括 HCV NTPase/解旋酶和人 RNA 解旋酶 DDX3 . 由于 HCV 是晚期 HIV AIDS 患者的主要合并感染，通常会导致肝硬化和死亡，因此观察到的靶核苷类似物对 HCV 和 HIV 的双重抑制对治疗感染了 HCV 的 HIV 患者具有潜在的有益意义。

  DOI：

  10.1016/j.bmcl.2013.12.121
• 作为产物：
  描述：

  1-O-methyl-3,5-di-O-(p-toluoyl)-2-deoxy-D-ribofuranoside 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 生成 1-Chlor-2-desoxy-3,5-di-O-(4-methylbenzoyl)-β-D-ribofuranose
  参考文献：
  名称：

  Process for the preparation of 9-beta-anomeric nucleoside analogs

  摘要：

  本文描述了一种显著增强9-β-异构核苷类似物的区域和立体选择性合成的过程。将糖基引入6-取代嘌呤碱基中，仅制备得到9-β-D-或L-嘌呤核苷类似物。这种区域和立体选择性引入糖基的方法允许高产率地合成核苷类似物，特别是2'-脱氧，3'-脱氧，2'-脱氧-2'-β-氟和2'，3'-二脱氧-2'-β-氟嘌呤核苷类似物，几乎不形成7-位异构体。这些化合物是药物或药物中间体。

  公开号：

  US20040039190A1

文献信息

• Synthesis and Anti-herpetic Activity of Phosphoramidate ProTides
  作者：Munmun Maiti、Leentje Persoons、Graciela Andrei、Robert Snoeck、Jan Balzarini、Piet Herdewijn

  DOI：10.1002/cmdc.201300035

  日期：2013.6

  cells, the phosphoramidate ProTide approach is one that has shown success, which has made it possible for some of the phosphoramidates to enter into clinical trials. Herein, we report the synthesis and antiviral activity of a series of phosphoramidate ProTides designed to bypass the thymidine kinase (TK) dependence of the parent nucleoside analogues. Phosphoramidate derivatives of (E)‐5‐(2‐bromovinyl)‐2′‐deoxyuridine

  在许多旨在将核苷一磷酸传递到细胞中的前药方法中，氨基磷酸酯ProTide方法是一种成功的方法，这使某些氨基磷酸酯进入临床试验成为可能。在本文中，我们报告了一系列旨在绕过母体核苷类似物对胸苷激酶（TK）的依赖性的氨基磷酸酯ProTides的合成和抗病毒活性。的磷酸酯衍生物（ë）-5-（2-溴乙烯基）-2'-脱氧尿苷（BVDU），其包含大号丙氨酸或新戊酰氧基甲基亚氨基二乙酸酯（IDA-POM）在细胞培养物中表现出抗HSV-1和抗VZV活性，但它们大大丧失了对TK缺陷病毒株的抗病毒能力。在脱氮嘌呤核苷及其氨基磷酸酯衍生物中，含7-脱氮杂腺嘌呤核苷及其氨基磷酸三酯衍生物对VZV的抗病毒活性较弱。显然，用这些氨基磷酸酯进行细胞内核苷酸递送是部分成功的。但是，没有一种化合物的前药显示出比其母药优越的活性。
• Neuroprotective potential of adenosine A ₁ receptor partial agonists in experimental models of cerebral ischemia
  作者：Alberto Martire、Catia Lambertucci、Rita Pepponi、Antonella Ferrante、Nicholas Benati、Michela Buccioni、Diego Dal Ben、Gabriella Marucci、Karl‐Norbert Klotz、Rosaria Volpini、Patrizia Popoli

  DOI：10.1111/jnc.14660

  日期：2019.4

  AbstractCerebral ischemia is the second most common cause of death and a major cause of disability worldwide. Available therapies are based only on anticoagulants or recombinant tissue plasminogen activator. Extracellular adenosine increases during ischemia and acts as a neuroprotective endogenous agent mainly by activating adenosine A1 receptors (A1Rs) which control calcium influx, glutamate release, membrane potential, and metabolism. Accordingly, in many experimental paradigms it has been already demonstrated that the stimulation of A1R with full agonists is able to reduce ischemia‐related structural and functional brain damage; unfortunately, cardiovascular side effects and desensitization of A1R induced by these compounds have strongly limited their exploitation in stroke therapy so far. Among the newly emerging compounds, A1R partial agonists could be almost free of side effects and equally effective. Therefore, we decided to evaluate the neuroprotective potential of two A1R partial agonists, namely 2′‐dCCPA and 3′‐dCCPA, in in vitro and ex vivo experimental models of cerebral ischemia. Within the experimental paradigm of oxygen‐glucose deprivation in vitro in human neuroblastoma (SH‐SY5Y) cells both A1R partial agonists increased cell viability. Considering the high level of expression of A1Rs in the hippocampus and the susceptibility of CA1 region to hypoxia, we performed electrophysiological experiments in this subfield. The application of 7 min of oxygen‐glucose deprivation constantly produces an irreversible synaptic failure in all the C57Bl/6 mice hippocampal slices evaluated; both tested compounds allowed a significant recovery of synaptic transmission. These findings demonstrate that A1R and its partial agonists are still of interest for cerebral ischemia therapy.Open Science BadgesThis article has received a badge for *Open Materials* because it provided all relevant information to reproduce the study in the manuscript. The complete Open Science Disclosure form for this article can be found at the end of the article. More information about the Open Practices badges can be found at https://cos.io/our-services/open-science-badges/. image
• Tarussowa, Natalia B.; Dyatkina, Natalia B.; Janta-Lipinski, Martin von, Zeitschrift fur Chemie, 1987, vol. 27, # 10, p. 366 - 367
  作者：Tarussowa, Natalia B.、Dyatkina, Natalia B.、Janta-Lipinski, Martin von、Langen, Peter

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• US2023/212178
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