十六碳-6-炔酸 | 676-25-5

• 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: 十六碳-6-炔酸
• 英文名称: 6-hexadecynoic acid
• 英文别名: hexadec-6-ynoic acid
• CAS: 676-25-5
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: OMEMMZJIJNUXIH-UHFFFAOYSA-N

物化性质

• 熔点：
  59.1°C (estimate)
• 沸点：
  409.64°C (rough estimate)
• 密度：
  0.9310 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	n-6-hexadecyn-1-ol	88109-71-1	C16H30O	238.414

反应信息

• 作为产物：
  描述：

  2H-吡喃,2-(6-庚炔-1-氧基)四氢 在 重铬酸吡啶 、 正丁基锂 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 十六碳-6-炔酸
  参考文献：
  名称：

  十六碳酸异构体对多药耐药金黄色葡萄球菌临床分离株的抗菌活性。

  摘要：

  在本研究中，进一步研究了赋予C 16炔属脂肪酸（aFA）抗菌活性的结构特征。四个步骤进行了在C-3，C-6，C-8，C-9，C-10和C-12处含有三键的十六碳烯酸（HDA）的合成，总产率为34- 78％。此外，还分别制备了C-4或C-5含硫原子的HDA类似物，总产率分别为69-77％。这项研究的结果表明，C-2处的三键对于2-HDA所显示的抗菌活性至关重要，而三键距羰基的位置越远，其对革兰氏阳性细菌的杀菌活性就越低，包括耐甲氧西林金黄色葡萄球菌的临床分离株（CIMRSA）菌株。还对五种对环丙沙星（Cipro）耐药的CIMRSA菌株评估了2-HDA作为抗菌剂的潜力，证明与单独使用Cipro或等摩尔组合Cipro相比，2-HDA是抑制其生长的最有效方法。和2‐HDA。此外，已证明金黄色葡萄球菌DNA促旋酶的抑制作用可能与2-HDA表现出的抗菌活性有关。最后，确定了HDA类似物形成胶束的能力可

  DOI：

  10.1002/lipd.12213

文献信息

• Solubilization and Targeted Delivery of Drugs With Self-Assembling Amphiphilic Polymers
  申请人：Diwan Anil

  公开号：US20100260743A1

  公开（公告）日：2010-10-14

  There are provided amphiphilic biodegradable copolymers comprising a hydrophilic backbone with pendant aliphatic groups as the hydrophobic component. The polymers form nanoscale molecular aggregates in aqueous environments, which have hydrophobic interiors that are capable of solubilizing insoluble organic compounds such as drugs, vitamins, dyes, and imaging agents. The polymers optionally feature reactive functional groups that provide attachment points for antibodies, ligands, and other targeting moieties useful for the targeted delivery of drugs and imaging agents.

  提供的两性可降解共聚物包括具有羟基亲水骨架和作为疏水组分的脂肪族侧链的共聚物。这些聚合物在水性环境中形成纳米级分子聚集体，具有疏水内部，能够溶解不溶于水的有机化合物，如药物、维生素、染料和成像剂。这些聚合物可选择性地具有反应性功能基团，提供与抗体、配体和其他靶向基团的结合点，有助于药物和成像剂的靶向传递。
• SELF ASSEMBLING AMPHIPHILIC POLYMERS AS ANTIVIRAL AGENTS
  申请人：Diwan Anil

  公开号：US20100008938A1

  公开（公告）日：2010-01-14

  There are provided amphiphilic biodegradable copolymers comprising a hydrophilic backbone with pendant aliphatic groups as the hydrophobic component. The polymers form nanoscale molecular aggregates in aqueous environments, which have hydrophobic interiors that are capable of solubilizing insoluble organic compounds and disrupting viral coat proteins. The polymers optionally feature reactive functional groups that provide attachment points for antibodies, ligands, and other targeting moieties which mediate adherence of the aggregate to a viral target.

  提供的两性亲水可生物降解共聚物包括具有侧链脂肪族基作为疏水成分的亲水性骨架。这些聚合物在水性环境中形成纳米级分子聚集体，具有疏水内部，能够溶解不溶性有机化合物并破坏病毒外壳蛋白。这些聚合物可选择性地具有反应性功能基团，提供抗体、配基和其他靶向基团的附着点，介导聚集体与病毒靶标的粘附。
• SELF-ASSEMBLING AMPHIPHILIC POLYMERS AS ANTI-CANCER AGENTS
  申请人：Diwan Anil R.

  公开号：US20100239659A1

  公开（公告）日：2010-09-23

  The invention provides amphiphilic biocompatible copolymers which have a hydrophilic backbone and pendant hydrophobic groups. The polymers form nanoscale molecular aggregates in aqueous environments, which have hydrophobic interiors within which anticancer drugs may be solubilized. The polymers optionally feature attached antibodies, receptor ligands, and other targeting moieties which mediate adherence of the drug-carrying aggregates to targeted cancer cells.

  本发明提供了一种两性亲水的生物相容性共聚物，其具有亲水性骨架和挂链疏水基团。这些聚合物在水性环境中形成纳米级分子聚集体，其中具有疏水性内部，可在其中溶解抗癌药物。这些聚合物可选地具有连接的抗体、受体配体和其他靶向基团，这些基团介导药物携带聚集体与靶向癌细胞的附着。
• 2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections
  作者：Deniz Tasdemir、David Sanabria、Ina L. Lauinger、Alice Tarun、Rob Herman、Remo Perozzo、Mire Zloh、Stefan H. Kappe、Reto Brun、Néstor M. Carballeira

  DOI：10.1016/j.bmc.2010.08.055

  日期：2010.11

  Acetylenic fatty acids are known to display several biological activities, but their antimalarial activity has remained unexplored. In this study, we synthesized the 2-, 5-, 6-, and 9-hexadecynoic acids (HDAs) and evaluated their in vitro activity against erythrocytic (blood) stages of Plasmodium falciparum and liver stages of Plasmodium yoelii infections. Since the type II fatty acid biosynthesis pathway (PfFAS-II) has recently been shown to be indispensable for liver stage malaria parasites, the inhibitory potential of the HDAs against multiple P. falciparum FAS-II (PfFAS-II) elongation enzymes was also evaluated. The highest antiplasmodial activity against blood stages of P. falciparum was displayed by 5-HDA (IC(50) value 6.6 mu g/ml), whereas the 2-HDA was the only acid arresting the growth of liver stage P. yoelii infection, in both flow cytometric assay (IC(50) value 2-HDA 15.3 mu g/ml, control drug atovaquone 2.5 ng/ml) and immunofluorescence analysis (IC(50) 2-HDA 4.88 mu g/ml, control drug atovaquone 0.37 ng/ml). 2-HDA showed the best inhibitory activity against the PfFAS-II enzymes PfFabI and PfFabZ with IC(50)values of 0.38 and 0.58 mu g/ml (IC(50)control drugs 14 and 30 ng/ml), respectively. Enzyme kinetics and molecular modeling studies revealed valuable insights into the binding mechanism of 2-HDA on the target enzymes. All HDAs showed in vitro activity against Trypanosoma brucei rhodesiense (IC(50) values 3.7-31.7 mu g/ml), Trypanosoma cruzi (only 2-HDA, IC(50) 20.2 mu g/ml), and Leishmania donovani (IC(50) values 4.1-13.4 mu g/ml) with generally low or no significant toxicity on mammalian cells. This is the first study to indicate therapeutic potential of HDAs against various parasitic protozoa. It also points out that the malarial liver stage growth inhibitory effect of the 2-HDA may be promoted via PfFAS-II enzymes. The lack of cytotoxicity, lipophilic nature, and calculated pharmacokinetic properties suggests that 2-HDA could be a useful compound to study the interaction of fatty acids with these key P. falciparum enzymes. (C) 2010 Elsevier Ltd. All rights reserved.
• ANTIMICROBIAL LIPIDS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0930821A1

  公开（公告）日：1999-07-28