(Z)-N-(tetradec-1-en-1-yl)decanehydrazide

• 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: (Z)-N-(tetradec-1-en-1-yl)decanehydrazide
• 英文别名: N-[(Z)-tetradec-1-enyl]decanehydrazide
• 化学式: C₂₄H₄₈N₂O
• 分子量: 380.658
• InChiKey: HXFPNAXMZUSUIP-LNVKXUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  27
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-(tetradec-1-en-1-yl)decanehydrazide 、 氯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到(Z)-N'-(2-chloroacetyl)-N-(tetradec-1-en-1-yl)decanehydrazide
  参考文献：
  名称：

  Synthesis and biological evaluation of hydrazidomycin analogues

  摘要：

  Hydrazidomycin A is an unusual secondary metabolite of Streptomyces atratus that features a rare enehydrazide core. To learn more about structure-activity relationships of the reported cytotoxic and antiproliferative agent several synthetic routes were explored to synthesize a variety of hydrazidomycin derivatives. Specifically, the size of the side chains, the nature of the double bond and the polar head group were altered. Overall, fourteen analogues were tested for their cytotoxic and antiproliferative effects. Re-examination of synthetic hydrazidomycin A suggests that the antiproliferative activity is attributed to a yet unknown compound that results from degradation or rearrangement. Several of the less complex analogues, however, show antiproliferative activities against individual cancer cell lines and turned out to be more potent than hydrazidomycin A. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.033
• 作为产物：
  描述：

  N'-decanoyl-N'-tetradec-1-en-1-yl-N-aminophthalimide 在 甲基肼 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以68%的产率得到(Z)-N-(tetradec-1-en-1-yl)decanehydrazide
  参考文献：
  名称：

  淡紫色链霉菌稀有肼代谢物 Hydrazidomycin A 的简明全合成

  摘要：

  Hydrazidomycins A–C 和 elaiomycins B–C 代表了一个不寻常的、天然存在的 enehydrazides 家族，由 Streptomyces sp. 产生。获得这些密集官能化肼衍生物的一般合成方法以肼基霉素 A 的首次全合成为例。模块化合成包括钌催化的炔烃和酰肼衍生的邻苯二甲酰亚胺的加氢酰胺化，主要产生 Z 型的烯酰肼。

  DOI：

  10.1002/ejoc.201300532

文献信息

• Concise Total Synthesis of Hydrazidomycin A, a Rare Hydrazide Metabolite of<i>Streptomyces atratus</i>
  作者：Florian Meyer、Nico Ueberschaar、Christian Hertweck

  DOI：10.1002/ejoc.201300532

  日期：2013.7

  Hydrazidomycins A–C and elaiomycins B–C represent a family of unusual, naturally occurring enehydrazides produced by Streptomyces sp. A general synthetic approach to access these densely functionalized hydrazine derivatives is exemplified by the first total synthesis of hydrazidomycin A. The modular synthesis involves a ruthenium-catalyzed hydroamidation of an alkyne and a hydrazide-derived phthalimide

  Hydrazidomycins A–C 和 elaiomycins B–C 代表了一个不寻常的、天然存在的 enehydrazides 家族，由 Streptomyces sp. 产生。获得这些密集官能化肼衍生物的一般合成方法以肼基霉素 A 的首次全合成为例。模块化合成包括钌催化的炔烃和酰肼衍生的邻苯二甲酰亚胺的加氢酰胺化，主要产生 Z 型的烯酰肼。
• Synthesis and biological evaluation of hydrazidomycin analogues
  作者：Florian Meyer、Nico Ueberschaar、Hans-Martin Dahse、Christian Hertweck

  DOI：10.1016/j.bmcl.2013.09.033

  日期：2013.11

  Hydrazidomycin A is an unusual secondary metabolite of Streptomyces atratus that features a rare enehydrazide core. To learn more about structure-activity relationships of the reported cytotoxic and antiproliferative agent several synthetic routes were explored to synthesize a variety of hydrazidomycin derivatives. Specifically, the size of the side chains, the nature of the double bond and the polar head group were altered. Overall, fourteen analogues were tested for their cytotoxic and antiproliferative effects. Re-examination of synthetic hydrazidomycin A suggests that the antiproliferative activity is attributed to a yet unknown compound that results from degradation or rearrangement. Several of the less complex analogues, however, show antiproliferative activities against individual cancer cell lines and turned out to be more potent than hydrazidomycin A. (c) 2013 Elsevier Ltd. All rights reserved.