3-(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)benzo[d]oxazol-2(3H)-one | 1447464-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)benzo[d]oxazol-2(3H)-one
• 英文别名: 3-[6-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexyl]-1,3-benzoxazol-2-one
• CAS: 1447464-76-7
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: DUMGVUQENVZUPA-CYGHRXIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.09
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  119.3
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (6-溴己氧基)-叔丁基二甲基硅烷 在 palladium on activated charcoal 、 四丁基氟化铵 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 3-(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)benzo[d]oxazol-2(3H)-one
  参考文献：
  名称：

  Design and synthesis of N-alkyldeoxynojirimycin derivatives with improved metabolic stability as inhibitors of BVDV and Tacaribe virus

  摘要：

  Novel N-alkyldeoxynojirimycins (NADNJs) based on our previous lead 3 were designed, synthesized and tested in metabolic assays and in virus cultures. NADNJs containing terminal tertiary benzamide, sulfonamide, urea, and oxazolidinone moieties were discovered to have improved metabolic stability compared to 3, while maintaining submicromolar EC50 against BVDV and Tacaribe virus; and low cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.052

文献信息

• [EN] NOVEL ALKYLATED IMINO SUGARS EXHIBITING GLUCOSIDASE INHIBITION AND THEIR METHOD OF USE<br/>[FR] NOUVEAU IMINO SUCRES ALKYLÉS PRÉSENTANT UNE INHIBITION DE LA GLUCOSIDASE ET LEUR PROCÉDÉ D'UTILISATION
  申请人：INST HEPATITIS & VIRUS RES

  公开号：WO2013148791A1

  公开（公告）日：2013-10-03

  Pharmaceutical compositions of the invention comprise alkylated imino sugars derivatives having a disease-modifying action in the treatment of diseases associated with glucosidase activity that include viral hemorrhagic fevers, and any other diseases involving glucosidase activity. The present invention also relates to a method for treating or preventing diseases that involve infection with viral hemorrhagic fever (VHFs) viruses, including, for example, infection with arenaviruses, filoviruses, bunyaviruses, and flaviviruses, said method comprising administering to a subject an effective amount of a compound or composition according to the present invention.

  本发明的药物组合物包括烷基化亚胺糖衍生物，具有治疗与葡萄糖苷酶活性相关疾病的疾病修饰作用，包括病毒性出血热等与葡萄糖苷酶活性有关的疾病。本发明还涉及一种用于治疗或预防涉及感染病毒性出血热（VHFs）病毒的疾病的方法，例如与病原体感染有关的疾病，包括病毒性出血热、丝状病毒、布尼亚病毒和黄病毒感染，所述方法包括向受试者投予根据本发明的化合物或组合物的有效量。
• Novel Alkylated Imino Sugars Exhibiting Glucosidase Inhibition and Their Method of Use
  申请人：Baruch S. Bulumberg Institute

  公开号：US20150119366A1

  公开（公告）日：2015-04-30

  Pharmaceutical compositions of the invention comprise alkylated imino sugars derivatives having a disease-modifying action in the treatment of diseases associated with glucosidase activity that include Viral hemorrhagic fevers, and any other diseases involving glucosidase activity.

  本发明的制药组合物包括烷基化的亚胺糖衍生物，具有改变疾病进程的作用，用于治疗与葡萄糖苷酶活性相关的疾病，包括病毒性出血热和其他涉及葡萄糖苷酶活性的疾病。
• Alkylated imino sugars exhibiting glucosidase inhibition and their method of use
  申请人：Baruch S. Blumberg Institute

  公开号：US10376502B2

  公开（公告）日：2019-08-13

  Pharmaceutical compositions of the invention comprise alkylated imino sugars derivatives having a disease-modifying action in the treatment of diseases associated with glucosidase activity that include Viral hemorrhagic fevers, and any other diseases involving glucosidase activity.

  本发明的药物组合物包括在治疗与葡萄糖苷酶活性相关的疾病（包括病毒性出血热和其他任何涉及葡萄糖苷酶活性的疾病）时具有疾病调节作用的烷基化亚氨基糖衍生物。
• US9126937B2
  申请人：——

  公开号：US9126937B2

  公开（公告）日：2015-09-08
• Design and synthesis of N-alkyldeoxynojirimycin derivatives with improved metabolic stability as inhibitors of BVDV and Tacaribe virus
  作者：Yanming Du、Hong Ye、Fang Guo、Lijuan Wang、Tina Gill、Noshena Khan、Andrea Cuconati、Ju-Tao Guo、Timothy M. Block、Jinhong Chang、Xiaodong Xu

  DOI：10.1016/j.bmcl.2013.04.052

  日期：2013.7

  Novel N-alkyldeoxynojirimycins (NADNJs) based on our previous lead 3 were designed, synthesized and tested in metabolic assays and in virus cultures. NADNJs containing terminal tertiary benzamide, sulfonamide, urea, and oxazolidinone moieties were discovered to have improved metabolic stability compared to 3, while maintaining submicromolar EC50 against BVDV and Tacaribe virus; and low cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.