2,4-十六碳二炔酸 | 101271-59-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,4-十六碳二炔酸
• 英文名称: 2,4-hexadecadiynoic acid
• 英文别名: hexadeca-2,4-diynoic acid；Hexadeca-2,4-diinsaeure；Hexadeca-2,4-diynoic acid
• CAS: 101271-59-4
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: LZOZBPHHFMJFGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-十六碳二炔酸 在 Lindlar's catalyst 、 乙酸甲酯 、 硫酸 作用下， 生成 ethyl hexadeca-2,4-dienoate
  参考文献：
  名称：

  Wailes, Australian Journal of Chemistry, 1959, vol. 12, p. 173,186

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴十一烷 在 正丁基锂 、 potassium fluoride dihydrate 、 甲基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 2,4-十六碳二炔酸
  参考文献：
  名称：

  Synthesis and biological activity of alkynoic acids derivatives against mycobacteria

  摘要：

  2-Alkynoic acids have bactericidal activity against Mycobacterium smegmatis but their activity fall sharply as the length of the carbon chain increased. In this study, derivatives of 2-alkynoic acids were synthesized and tested against fast- and slow-growing mycobacteria. Their activity was first evaluated in M. smegmatis against their parental 2-alkynoic acids, as well as isoniazid, a first-line antituberculosis drug. The introduction of additional unsaturation or heteroatoms into the carbon chain enhanced the antimycobacterial activity of longer chain alkynoic acids (more than 19 carbons long). In contrast, although the modification of the carboxylic group did not improve the antimycobacterial activity, it significantly reduced the toxicity of the compounds against eukaryotic cells. Importantly, 4-(alkylthio) but-2-ynoic acids, had better bactericidal activity than the parental 2-alkynoic acids and on a par with isoniazid against the slow-grower Mycobacterium bovis BCG. These compounds had also low toxicity against eukaryotic cells, suggesting that they could be potential therapeutic agents against other types of topical mycobacterial infections causing skin diseases including Mycobacterium abscessus, Mycobacterium ulcerans, and Mycobacterium leprae. Moreover, they provide a possible scaffold for future drug development. (C) 2015 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2015.08.001

文献信息

• Biosensors employing electrical, optical and mechanical signals
  申请人：Biocircuits Corporation

  公开号：EP0402917A2

  公开（公告）日：1990-12-19

  Biosensors are provided employing a thin surfactant polymeric electrically conducting layer to which may be bound members of specific binding pairs. Binding of an analyte or a reagent to the specific binding pair member layer may change the electrical, optical, or structural properties of the layer for measurement of analyte. The change in the polymeric layer provides for a sensitive measurement.

  生物传感器采用了一层薄的表面活性剂聚合物导电层，该层可与特定结合对成员结合。分析物或试剂与特定结合对成员层的结合可改变该层的电学、光学或结构特性，从而测量分析物。聚合物层的变化可提供灵敏的测量。
• Synthesis and biological activity of alkynoic acids derivatives against mycobacteria
  作者：Catherine Vilchèze、Lawrence W. Leung、Robert Bittman、William R. Jacobs Jr.

  DOI：10.1016/j.chemphyslip.2015.08.001

  日期：2016.1

  2-Alkynoic acids have bactericidal activity against Mycobacterium smegmatis but their activity fall sharply as the length of the carbon chain increased. In this study, derivatives of 2-alkynoic acids were synthesized and tested against fast- and slow-growing mycobacteria. Their activity was first evaluated in M. smegmatis against their parental 2-alkynoic acids, as well as isoniazid, a first-line antituberculosis drug. The introduction of additional unsaturation or heteroatoms into the carbon chain enhanced the antimycobacterial activity of longer chain alkynoic acids (more than 19 carbons long). In contrast, although the modification of the carboxylic group did not improve the antimycobacterial activity, it significantly reduced the toxicity of the compounds against eukaryotic cells. Importantly, 4-(alkylthio) but-2-ynoic acids, had better bactericidal activity than the parental 2-alkynoic acids and on a par with isoniazid against the slow-grower Mycobacterium bovis BCG. These compounds had also low toxicity against eukaryotic cells, suggesting that they could be potential therapeutic agents against other types of topical mycobacterial infections causing skin diseases including Mycobacterium abscessus, Mycobacterium ulcerans, and Mycobacterium leprae. Moreover, they provide a possible scaffold for future drug development. (C) 2015 Elsevier Ireland Ltd. All rights reserved.
• Wailes, Australian Journal of Chemistry, 1959, vol. 12, p. 173,186
  作者：Wailes

  DOI：——

  日期：——