2-amino-N-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-[[(2-amino-5-guanidino-pentanoyl)amino]methyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl]-5-guanidino-pentanamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-amino-N-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-[[(2-amino-5-guanidino-pentanoyl)amino]methyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl]-5-guanidino-pentanamide
• 英文别名: 2-amino-N-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-[[[2-amino-5-(diaminomethylideneamino)pentanoyl]amino]methyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]-5-(diaminomethylideneamino)pentanamide
• 化学式: C₂₄H₄₈N₁₀O₁₁
• 分子量: 652.706
• InChiKey: QXJLZADLDPLULO-YKOSCDRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.6
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  388
• 氢给体数：
  14
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  6,6'-二叠氮基-6,6'-二脱氧-Α,Α-D-海藻糖六乙酸酯 在 palladium on activated charcoal palladium dihydroxide 、 氢气 、 sodium methylate 、 N,N'-二环己基碳二亚胺 、 肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 2-amino-N-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-[[(2-amino-5-guanidino-pentanoyl)amino]methyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl]-5-guanidino-pentanamide
  参考文献：
  名称：

  α,α-Trehalose derivatives bearing guanidino groups as inhibitors to HIV-1 Tat–TAR RNA interaction in human cells

  摘要：

  Replication of HIV-1 requires specific interactions of Tat protein with TAR RNA. Disruption of Tat TAR RNA interaction could inhibit HIV-1 replication. Here four target compounds were designed and synthesized to bind to TAR RNA for blocking the interaction of Tat-TAR RNA. The core molecule 6,6'-diamino-6,6'-dideoxy-alpha,alpha-trehalose was obtained from selective bromination of, alpha,alpha-trehalose at C-6,6', followed by acetylation, azide displacement, deacetylation, and reduction. Coupling of the core molecule with the protected amino acid, then deprotection and guanidinylation generated the novel alpha,alpha-trehalose derivatives. Their abilities to inhibit Tat-TAR RNA interaction in human cells were determined by a Tat-dependent HIV-1 LTR-driven CAT assays. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.073

文献信息

• α,α-Trehalose derivatives bearing guanidino groups as inhibitors to HIV-1 Tat–TAR RNA interaction in human cells
  作者：Min Wang、Zhidong Xu、Pengfei Tu、Xiaolin Yu、Sulong Xiao、Ming Yang

  DOI：10.1016/j.bmcl.2004.02.073

  日期：2004.5

  Replication of HIV-1 requires specific interactions of Tat protein with TAR RNA. Disruption of Tat TAR RNA interaction could inhibit HIV-1 replication. Here four target compounds were designed and synthesized to bind to TAR RNA for blocking the interaction of Tat-TAR RNA. The core molecule 6,6'-diamino-6,6'-dideoxy-alpha,alpha-trehalose was obtained from selective bromination of, alpha,alpha-trehalose at C-6,6', followed by acetylation, azide displacement, deacetylation, and reduction. Coupling of the core molecule with the protected amino acid, then deprotection and guanidinylation generated the novel alpha,alpha-trehalose derivatives. Their abilities to inhibit Tat-TAR RNA interaction in human cells were determined by a Tat-dependent HIV-1 LTR-driven CAT assays. (C) 2004 Elsevier Ltd. All rights reserved.