tert-butyl (2-methylcyclohexyl)(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)carbamate | 1428247-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (2-methylcyclohexyl)(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)carbamate
• 英文别名: US10376502, Entry 1；tert-butyl N-(2-methylcyclohexyl)-N-[6-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexyl]carbamate
• CAS: 1428247-29-3
• 化学式: C₂₄H₄₆N₂O₆
• 分子量: 458.639
• InChiKey: CSBWMHOCLXBLJJ-LMTUPJBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-methylcyclohexyl)(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)carbamate 在 盐酸 作用下， 以 水 为溶剂， 以100%的产率得到(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(6-((2-methylcyclohexyl)amino) hexyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  N-Alkyldeoxynojirimycin derivatives with novel terminal tertiary amide substitution for treatment of bovine viral diarrhea virus (BVDV), Dengue, and Tacaribe virus infections

  摘要：

  Novel N-alkyldeoxynojirimycins (NADNJs) with two hydrophobic groups attached to a nitrogen linker on the alkyl chain were designed. A novel NADNJ containing a terminal tertiary carboxamide moiety was discovered that was a potent inhibitor against BVDV. Further optimization resulted in a structurally more stable lead compound 24 with a submicromolar EC50 against BVDV, Dengue, and Tacaribe; and low cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.108
• 作为产物：
  描述：

  2-甲基环己胺 在 palladium on activated charcoal 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 tert-butyl (2-methylcyclohexyl)(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)carbamate
  参考文献：
  名称：

  N-Alkyldeoxynojirimycin derivatives with novel terminal tertiary amide substitution for treatment of bovine viral diarrhea virus (BVDV), Dengue, and Tacaribe virus infections

  摘要：

  Novel N-alkyldeoxynojirimycins (NADNJs) with two hydrophobic groups attached to a nitrogen linker on the alkyl chain were designed. A novel NADNJ containing a terminal tertiary carboxamide moiety was discovered that was a potent inhibitor against BVDV. Further optimization resulted in a structurally more stable lead compound 24 with a submicromolar EC50 against BVDV, Dengue, and Tacaribe; and low cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.108

文献信息

• 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
• N-Alkyldeoxynojirimycin derivatives with novel terminal tertiary amide substitution for treatment of bovine viral diarrhea virus (BVDV), Dengue, and Tacaribe virus infections
  作者：Yanming Du、Hong Ye、Tina Gill、Lijuan Wang、Fang Guo、Andrea Cuconati、Ju-Tao Guo、Timothy M. Block、Jinhong Chang、Xiaodong Xu

  DOI：10.1016/j.bmcl.2013.01.108

  日期：2013.4

  Novel N-alkyldeoxynojirimycins (NADNJs) with two hydrophobic groups attached to a nitrogen linker on the alkyl chain were designed. A novel NADNJ containing a terminal tertiary carboxamide moiety was discovered that was a potent inhibitor against BVDV. Further optimization resulted in a structurally more stable lead compound 24 with a submicromolar EC50 against BVDV, Dengue, and Tacaribe; and low cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.