NB23 | 1086092-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: NB23
• 英文别名: (1S,2R,3R,4S,6R)-3-[[(3aR,4R,6R,7R,7aR)-7-amino-4-(aminomethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-4,6-diaminocyclohexane-1,2-diol
• CAS: 1086092-33-2
• 化学式: C₁₃H₂₆N₄O₆
• 分子量: 334.373
• InChiKey: SGONQNZQLZHFTG-DPXNFZJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  NB23 在 硫酸 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Structure–toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds

  摘要：

  A new pseudo-disaccharide NB23 with a 3',4'-methylidene protection was designed and its properties were evaluated in comparison to other two structurally related pseudo-disaccharides. The basicity of the 2'-amine was found to be well correlated to acute toxicity data in mice: the increase in the basicity is associated with the toxicity increase. Based on these data, a new pseudo-trisaccharide NB45 was constructed. NB45 exhibited significant antibacterial activity while at the same time retained low acute toxicity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.053
• 作为产物：
  描述：

  C₁₃H₁₈N₁₂O₆ 在 sodium hydroxide 、 水 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到NB23
  参考文献：
  名称：

  Structure–toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds

  摘要：

  A new pseudo-disaccharide NB23 with a 3',4'-methylidene protection was designed and its properties were evaluated in comparison to other two structurally related pseudo-disaccharides. The basicity of the 2'-amine was found to be well correlated to acute toxicity data in mice: the increase in the basicity is associated with the toxicity increase. Based on these data, a new pseudo-trisaccharide NB45 was constructed. NB45 exhibited significant antibacterial activity while at the same time retained low acute toxicity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.053

文献信息

• Combined Chemical-Enzymatic Assembly of Aminoglycoside Derivatives with N-1-AHB Side Chain
  作者：Igor Nudelman、Lilach Chen、Nicholas M. Llewellyn、El-Habib Sahraoui、Marina Cherniavsky、Jonathan B. Spencer、Timor Baasov

  DOI：10.1002/adsc.200800229

  日期：2008.8.4

  A series of unprotected pseudo-disaccharides and pseudo-trisaccharides of 2-deoxystreptamine-containing aminoglycosides have been selectively acylated at the N-1 position with the valuable (S)-4-amino-2-hydroxybutanoyl (AHB) pharmacophore by using the recombinant BtrH and BtrG enzymes from butirosin biosynthesis in combination with a synthetic acyl donor. The process was optimized by performing two

  通过使用重组体，在有价值的（S）-4-氨基-2-羟基丁酰基（AHB）药效基团的N-1位选择性地酰化了一系列含2-脱氧链胺胺的氨基糖苷的一系列未保护的伪二糖和伪三糖。Butirosin生物合成中的BtrH和BtrG酶与合成的酰基供体结合。通过在不纯化中间产物的情况下依次进行两个酶促步骤来优化工艺。
• Structure–toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds
  作者：Lilach Chen、Mariana Hainrichson、Dmitry Bourdetsky、Amram Mor、Sima Yaron、Timor Baasov

  DOI：10.1016/j.bmc.2008.08.053

  日期：2008.10

  A new pseudo-disaccharide NB23 with a 3',4'-methylidene protection was designed and its properties were evaluated in comparison to other two structurally related pseudo-disaccharides. The basicity of the 2'-amine was found to be well correlated to acute toxicity data in mice: the increase in the basicity is associated with the toxicity increase. Based on these data, a new pseudo-trisaccharide NB45 was constructed. NB45 exhibited significant antibacterial activity while at the same time retained low acute toxicity. (C) 2008 Elsevier Ltd. All rights reserved.