4-Amino-N-((2R,3S,4S,5R,6R)-6-{(2R,3R,4S,5S,6R)-6-[(4-amino-butyrylamino)-methyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl)-butyramide | 714963-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Amino-N-((2R,3S,4S,5R,6R)-6-{(2R,3R,4S,5S,6R)-6-[(4-amino-butyrylamino)-methyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl)-butyramide
• CAS: 714963-92-5
• 化学式: C₂₀H₃₈N₄O₁₁
• 分子量: 510.542
• InChiKey: YUYHWWQJDHOHLV-RPDXMDMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.67
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  259.31
• 氢给体数：
  10.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  S-甲基异硫脲硫酸盐 、 4-Amino-N-((2R,3S,4S,5R,6R)-6-{(2R,3R,4S,5S,6R)-6-[(4-amino-butyrylamino)-methyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl)-butyramide 在 ammonium hydroxide 作用下， 反应 48.0h， 生成
  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
• 作为产物：
  描述：

  2,3,4,2',3',4'-hexa-O-acetyl-6,6'-dibromo-6,6'-dideoxy-α,α-trehalose 在 palladium on activated charcoal palladium dihydroxide 、 sodium azide 、 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 68.0h， 生成 4-Amino-N-((2R,3S,4S,5R,6R)-6-{(2R,3R,4S,5S,6R)-6-[(4-amino-butyrylamino)-methyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl)-butyramide
  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