(S)-2-hydroxy-4-(methylthio)-N-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)butanamide | 1529805-85-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-2-hydroxy-4-(methylthio)-N-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)butanamide
• 英文别名: (2S)-2-hydroxy-4-methylsulfanyl-N-[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]butanamide
• CAS: 1529805-85-3
• 化学式: C₁₅H₂₇NO₂S
• 分子量: 285.451
• InChiKey: MBQBJJYSQKNICN-ZAZJYDDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-2-羟基-4-(甲硫基)丁酸 、 exo-bornylamine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以37%的产率得到(S)-2-hydroxy-4-(methylthio)-N-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)butanamide
  参考文献：
  名称：

  新型基于樟脑的药物的合成及其抗分枝杆菌活性

  摘要：

  在樟脑支架的基础上设计并合成了一系列六种新的酰胺醇。天然氨基酸被转化成具有构型保留的α-羟基类似物，并与异冰片胺连接。评价化合物对结核分枝杆菌H37Rv的体外活性。一些新的化合物显示比传统高出25倍的活性抗-TB药物乙胺丁醇。活性取决于α-羟基酸部分而从微摩尔抑制浓度转变为纳摩尔抑制浓度。两种最有效的化合物发挥低水平的细胞毒活性。这些基于樟脑的酰胺醇为抗真菌剂的进一步开发提供了有希望的潜在先导化合物。

  DOI：

  10.1016/j.bmcl.2013.11.050

文献信息

• Design of novel camphane-based derivatives with antimycobacterial activity
  作者：Georgi Stavrakov、Violeta Valcheva、Irena Philipova、Irini Doytchinova

  DOI：10.1016/j.jmgm.2014.04.008

  日期：2014.6

  Although tuberculosis (TB) continues to be one of the leading infectious disease killers globally, it is curable and preventable. Despite the existence of safe, well tolerated and effective drugs used in the TB treatment, the interest in new entities, combinations and regimens increases during the last 10 years. Recently, we reported for a new class of anti-TB agents - camphane-based derivatives with nanomolar activity against Mycobacterium tuberculosis strains. The quantitative structure-activity relationship (QSAR) study on 12 compounds revealed several structural requirements for antimycobacterial activity: two hydrogen bond donors, two or three rings and no large branched substituents. Here, we describe the design of a set of nine novel camphane-based derivatives following these requirements. The compounds were synthesized and tested against M. tuberculosis strain H37Rv. Four of them showed activities in the nanomolar range, significantly higher than the activities in the initial set. The QSAR study based on all 21 derivatives pointed to two main structural requirements for anti-TB activity: two hydrogen bond donors and a side chain with aromatic ring.
• Synthesis and antimycobacterial activity of novel camphane-based agents
  作者：Georgi Stavrakov、Irena Philipova、Violeta Valcheva、Georgi Momekov

  DOI：10.1016/j.bmcl.2013.11.050

  日期：2014.1

  were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv. Some of the new compounds show 25 times higher activity than the classical anti-TB drug ethambutol. The activity shifts from micromolar to nanomolar inhibitory concentrations depending on the α-hydroxy acid moiety. Two of the most potent compounds exert low level of cytotoxic activity. These camphane-based amido-alcohols

  在樟脑支架的基础上设计并合成了一系列六种新的酰胺醇。天然氨基酸被转化成具有构型保留的α-羟基类似物，并与异冰片胺连接。评价化合物对结核分枝杆菌H37Rv的体外活性。一些新的化合物显示比传统高出25倍的活性抗-TB药物乙胺丁醇。活性取决于α-羟基酸部分而从微摩尔抑制浓度转变为纳摩尔抑制浓度。两种最有效的化合物发挥低水平的细胞毒活性。这些基于樟脑的酰胺醇为抗真菌剂的进一步开发提供了有希望的潜在先导化合物。