N-(5-(tert-butoxycarbonylamino)hexyl)-N-(hydroxy)-2(E)-octenamide | 777939-39-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(5-(tert-butoxycarbonylamino)hexyl)-N-(hydroxy)-2(E)-octenamide
• 英文别名: tert-butyl N-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexyl]carbamate
• CAS: 777939-39-6
• 化学式: C₁₉H₃₆N₂O₄
• 分子量: 356.506
• InChiKey: JJDAVGGVFVCBAH-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5-(tert-butoxycarbonylamino)hexyl)-N-(hydroxy)-2(E)-octenamide 在 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 2-hydroxy-4-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-[2-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-oxoethyl]-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Acinetoferrin Homologues for Use as Iron Transport Probes in Mycobacteria

  摘要：

  Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. H-1 NMR spectroscopy (CD3OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.

  DOI：

  10.1021/jm049805y
• 作为产物：
  描述：

  N-(6-(tert-butoxycarbonylamino)hexyl)-N-(benzyloxy)-2(E)-octenamide 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以86%的产率得到N-(5-(tert-butoxycarbonylamino)hexyl)-N-(hydroxy)-2(E)-octenamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Acinetoferrin Homologues for Use as Iron Transport Probes in Mycobacteria

  摘要：

  Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. H-1 NMR spectroscopy (CD3OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.

  DOI：

  10.1021/jm049805y

文献信息

• Synthesis and Biological Evaluation of New Acinetoferrin Homologues for Use as Iron Transport Probes in Mycobacteria
  作者：Richard A. Gardner、George Ghobrial、Saleh A. Naser、Phanstiel

  DOI：10.1021/jm049805y

  日期：2004.9.1

  Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. H-1 NMR spectroscopy (CD3OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.