methyl (2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(prop-2-ynylcarbamoyloxy)methyl]-3,4-dihydro-2H-pyran-6-carboxylate | 1172605-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(prop-2-ynylcarbamoyloxy)methyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1172605-56-9
• 化学式: C₃₀H₄₅N₅O₁₂
• 分子量: 667.714
• InChiKey: NSXBFMZHVOXBIL-PQZYZXGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  210
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(prop-2-ynylcarbamoyloxy)methyl]-3,4-dihydro-2H-pyran-6-carboxylate 、 5-(氨基维生素)戊胺 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以95%的产率得到
  参考文献：
  名称：

  通过结合竞争（RABC）进行耐药性评估的化学探针：奥司他韦药敏性评估

  摘要：

  OS向导（抗性）：使用神经氨酸酶抑制剂（扎那米韦与奥司他韦（OS））的结合差异来建立测定方法，以鉴定对OS耐药但仍对扎那米韦敏感的流感亚型（请参阅方案）。该测定使用扎那米韦-生物素偶联物来测定各种流感病毒和200多种临床分离株的OS敏感性。

  DOI：

  10.1002/anie.201204062
• 作为产物：
  描述：

  5-acetylamino-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-6-[((2,2-dimethyl-[1,3]dioxolan-4-yl)-(4-nitrophenoxy)carbonyloxy)methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid ethyl ester 、 炔丙胺 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 以92%的产率得到methyl (2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(prop-2-ynylcarbamoyloxy)methyl]-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Synergistic Effect of Zanamivir−Porphyrin Conjugates on Inhibition of Neuraminidase and Inactivation of Influenza Virus

  摘要：

  New anti-influenza agents of tetravalent zanamivir on a porphyrin scaffold were synthesized. These compounds are 10 to 100 times more potent in inhibiting influenza replications even though they are somewhat less potent in neuraminidase inhibition than the monomeric zanamivir. The enhanced anti-influenza activity is probably attributable to the additional viral inactivation by singlet oxygen due to sensitization of the porphyrin moiety, which is brought in close proximity of virus by the conjugated zanamivir in a manner resembling the "magic bullet" mechanism.

  DOI：

  10.1021/jm900515g

文献信息

• ZANAMIVIR PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY AND DETERMINING OSELTAMIVIR SUSCEPTIBILITY OF INFLUENZA VIRUSES
  申请人：Wong Chi-Huey

  公开号：US20130225532A1

  公开（公告）日：2013-08-29

  Methods and compositions for detection of drug resistant pathogens and treatment against infections thereof are provided. Methods for detection of oseltamivir-resistant influenza viruses by competitive binding assays utilizing non-oseltamivir influenza virus neuraminidase inhibitors and oseltamivir carboxylate are provided. Influenza virus neuraminidase inhibitors coupled to sensors and useful for employment in the methods of the invention are disclosed. Novel phosphonate compounds active as neuraminidase inhibitors against wild-type and oseltamivir-resistant influenza strains of H1N1, H5N1 and H3N2 viruses are disclosed. An enantioselective synthetic route to preparation of these phosphonate compounds via sialic acid is provided.

  本发明提供了检测耐药病原体和治疗感染的方法和组合物。本发明提供了利用非奥司他韦流感病毒神经氨酸酶抑制剂和奥司他韦羧酸盐进行竞争结合测定的检测奥司他韦耐药性流感病毒的方法。本发明还揭示了与传感器耦合并在本发明方法中使用的流感病毒神经氨酸酶抑制剂。本发明还揭示了对H1N1、H5N1和H3N2病毒的野生型和奥司他韦耐药株具有神经氨酸酶抑制剂活性的新型膦酸酯化合物。本发明还提供了通过唾液酸的对映选择性合成途径制备这些膦酸酯化合物的方法。
• ZANAMIVIR PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY AND DETERMINING OSELTAMIVIR SUSCEPTIBILITY OF INFLUENZA VIRUSES
  申请人：Academia Sinica

  公开号：EP2568976B1

  公开（公告）日：2015-09-30
• US9403855B2
  申请人：——

  公开号：US9403855B2

  公开（公告）日：2016-08-02