6,6'-N,N'-didodecyldiamino-6,6'-dideoxy-α,α-D-trehalose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-N,N'-didodecyldiamino-6,6'-dideoxy-α,α-D-trehalose
• 英文别名: 6,6'-dideoxy-6,6'-bis(1-dodecylamino)-α,α-trehalose；(2R,3S,4S,5R,6R)-2-[(dodecylamino)methyl]-6-[(2R,3R,4S,5S,6R)-6-[(dodecylamino)methyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-tetrahydropyran-3,4,5-triol；(2R,3S,4S,5R,6R)-2-[(dodecylamino)methyl]-6-[(2R,3R,4S,5S,6R)-6-[(dodecylamino)methyl]-3,4,5-trihydroxyoxan-2-yl]oxyoxane-3,4,5-triol
• 化学式: C₃₆H₇₂N₂O₉
• 分子量: 676.976
• InChiKey: BVWGFCMVZSSSPH-XPMTUQOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  47
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  173
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  海藻糖 在 吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 四氯化碳 、 水 为溶剂， 反应 276.0h， 生成 6,6'-N,N'-didodecyldiamino-6,6'-dideoxy-α,α-D-trehalose
  参考文献：
  名称：

  Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6'-dideoxytrehalose, including N,N'-dialkylamino and 6,6'-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra and a panel of clinical isolates of Mycobacterium avium, 6,6'-Diamitiotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00288-9

文献信息

• Gemini Surfactants with a Disaccharide Spacer
  作者：Fredric M. Menger、Bessie N. A. Mbadugha

  DOI：10.1021/ja0033178

  日期：2001.2.1

  behavior of Series-A geminis in many ways parallels that of phospholipids and simple double-chain surfactants. It is as if the trehalose is less of a spacer than a large but conventional headgroup. In contrast, cationic Series-B geminis are water soluble and form micelles with critical micelle concentrations an order of magnitude lower than that of corresponding conventional surfactants. Molecular modeling

  双子表面活性剂是具有（按顺序）以下的两亲物：烃尾/极性基团/间隔基/极性基团/烃尾。最近，工业和学术实验室都对双子座产生了广泛的兴趣。在目前的贡献中，已经合成了两个相关的双子星家族，它们都使用海藻糖（一种二糖）作为极性间隔物。一个系列，A 系列，是非离子型的，并具有将长链与海藻糖间隔基分开的酰胺基团。另一个家族，B 系列，具有将长链连接到海藻糖间隔物的季铵离子。发现尽管有两个酰胺和多个羟基，A 系列双子座还是不溶于水的。当水合或挤压时，这些双子座在其转变温度（通过量热法确定）之上形成微观可见的囊泡和管状结构。由这些 Geminis 构建的不溶性单分子膜具有由糖间隔基主导的界面区域，尽管分子间链/链相互作用似乎稳定了膜。因此，A 系列双子座的行为在许多方面与磷脂和简单双链表面活性剂的行为相似。就好像海藻糖比大而传统的头部基团更像是一个间隔区。相比之下，阳离子 B 系列双子是水溶性的，并形成临
• Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis
  作者：Jerry D. Rose、Joseph A. Maddry、Robert N. Comber、William J. Suling、Larry N. Wilson、Robert C. Reynolds

  DOI：10.1016/s0008-6215(01)00288-9

  日期：2002.2

  Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6'-dideoxytrehalose, including N,N'-dialkylamino and 6,6'-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra and a panel of clinical isolates of Mycobacterium avium, 6,6'-Diamitiotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines. (C) 2002 Elsevier Science Ltd. All rights reserved.