(R)-2-methylheptyl isonicotinate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-2-methylheptyl isonicotinate
• 英文别名: 2-methylheptyl isonicotinate；Isonicotinic acid 2-methyl-heptyl ester；[(2R)-2-methylheptyl] pyridine-4-carboxylate
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: SJGJCJLSSXJWOR-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-1-庚醇 在 Amberlyst A-21 、 Candida rogusa lipase 、 potassium carbonate 作用下， 以 甲醇 、 正己烷 、 乙腈 为溶剂， 反应 18.0h， 生成 (R)-2-methylheptyl isonicotinate
  参考文献：
  名称：

  Synthesis, absolute stereochemistry and molecular design of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201

  摘要：

  The absolute stereochemistry of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201 has been established by achieving the total synthesis of the product. A series of analogues have also been synthesized by changing the side chain and their bioactivity assessed against different microbial strains. Among them, le (R = C8H17) was found to be the most potent with MIC of 8 mug/mL against Mycobacterium tuberculosis, 12 mug/mL against Escherichia coli and 16 mug/mL against Bacillus subtilis 6 mug/ml against Proteus vulgaris. This was followed by 1b (R = C5H11) with MIC of 10-20 mug/mL range and Id (R = C7H15) with MIC of 14-24 g/mL, whereas la (R = C4H9) and If (R = C18H35) were found to be completely inactive. Besides, le (R = C6H13) showed certain extent of antibacterial activity in the range of 24-50 mug/mL. Mycobacterium tuberculosis was very sensitive to le (R = C8H17) with MIC of 8 mug/mL. Antifungal activity of analogues III (R = C7H15) and le, (R = C8H17) against Fusarium oxysporum and Rhizoctonia solani were found promising with MFCs in the 15-18 mug/mL range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.025

文献信息

• Synthesis and evaluation of antibacterial activity of (R)-2-methylheptyl isonicotinate, a putative naturally occurring bioactive agent
  作者：Jia Cao、Ben Adler、Patrick Perlmutter

  DOI：10.1016/j.bmcl.2015.10.045

  日期：2015.11

  A putative antibacterial and antifungal compound, (R)-2-methylheptyl isonicotinate, was synthesized via reductive lactone alkylation of (R)-4-methyldihydrofuran-2(3H)-one. Structural characterisation data as well as bioassay results (with Bacillus subtilis or Escherichia coli) contradict those previously reported. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, absolute stereochemistry and molecular design of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201
  作者：J. Boruwa、B. Kalita、N.C. Barua、J.C. Borah、S. Mazumder、D. Thakur、D.K. Gogoi、T.C. Bora

  DOI：10.1016/j.bmcl.2004.04.025

  日期：2004.7

  The absolute stereochemistry of the new antifungal and antibacterial antibiotic produced by Streptomyces sp.201 has been established by achieving the total synthesis of the product. A series of analogues have also been synthesized by changing the side chain and their bioactivity assessed against different microbial strains. Among them, le (R = C8H17) was found to be the most potent with MIC of 8 mug/mL against Mycobacterium tuberculosis, 12 mug/mL against Escherichia coli and 16 mug/mL against Bacillus subtilis 6 mug/ml against Proteus vulgaris. This was followed by 1b (R = C5H11) with MIC of 10-20 mug/mL range and Id (R = C7H15) with MIC of 14-24 g/mL, whereas la (R = C4H9) and If (R = C18H35) were found to be completely inactive. Besides, le (R = C6H13) showed certain extent of antibacterial activity in the range of 24-50 mug/mL. Mycobacterium tuberculosis was very sensitive to le (R = C8H17) with MIC of 8 mug/mL. Antifungal activity of analogues III (R = C7H15) and le, (R = C8H17) against Fusarium oxysporum and Rhizoctonia solani were found promising with MFCs in the 15-18 mug/mL range. (C) 2004 Elsevier Ltd. All rights reserved.