linoleic azide | 221290-51-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: linoleic azide
• 英文别名: linoleyl azide；(6Z,9Z)-18-azidooctadeca-6,9-diene
• CAS: 221290-51-3
• 化学式: C₁₈H₃₃N₃
• 分子量: 291.48
• InChiKey: TVVXAOGOYPQZQF-HZJYTTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  linoleic azide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (9Z,12Z)-9,12-十八碳二烯-1-胺
  参考文献：
  名称：

  磺胺类酰胺基类似物的合成及药理学评价

  摘要：

  已经合成了花生四烯酸和亚油基磺酰胺衍生物，并在体外功能和结合试验中评估了它们的潜在拟大麻特性。-CH 2 NHSO 2 NH-R取代an南酰胺的乙醇酰胺部分会大大降低CB1受体的活性，只有一些化合物在结合分析中显示适度的大麻素特性。还测试了新化合物作为FAAH酶的抑制剂，但没有活性。

  DOI：

  10.1016/j.ejmech.2009.08.003
• 作为产物：
  描述：

  硬脂基溴 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 linoleic azide
  参考文献：
  名称：

  CHEMICAL MODIFICATIONS OF MONOMERS AND OLIGONUCLEOTIDES WITH CYCLOADDITION

  摘要：

  该发明涉及公式I或II的化合物：在一种实施方式中，该发明涉及化合物和用于将配体与寡核苷酸结合的过程。该发明进一步涉及治疗各种疾病和疾病的方法，例如病毒感染、细菌感染、寄生虫感染、癌症、过敏、自身免疫疾病、免疫缺陷和免疫抑制。

  公开号：

  US20120035115A1

文献信息

• Non-Nucleoside Building Blocks for Copper-Assisted and Copper-Free Click Chemistry for the Efficient Synthesis of RNA Conjugates
  作者：K. N. Jayaprakash、Chang Geng Peng、David Butler、Jos P. Varghese、Martin A. Maier、Kallanthottathil G. Rajeev、Muthiah Manoharan

  DOI：10.1021/ol102205j

  日期：2010.12.3

  Novel non-nucleoside alkyne monomers compatible with oligonucleotide synthesis were designed, synthesized, and efficiently incorporated into RNA and RNA analogues during solid-phase synthesis. These modifications allowed site-specific conjugation of ligands to the RNA oligonucleotides through copper-assisted (CuAAC) and copper-free strain-promoted azide−alkyne cycloaddition (SPAAC) reactions. The SPAAC

  设计，合成与寡核苷酸合成相容的新型非核苷炔烃单体，并在固相合成过程中将其有效地掺入RNA和RNA类似物中。这些修饰允许配体通过铜辅助（CuAAC）和无铜应变促进的叠氮化物-炔烃环加成（SPAAC）反应与RNA寡核苷酸进行位点特异性缀合。环辛炔-寡核苷酸与各种叠氮基官能化配体在溶液相和固相上的SPAAC点击反应是有效和定量的，并且在温和的反应条件下发生。SPAAC反应提供了一种合成方法，用于合成未被铜离子污染的寡核苷酸-配体结合物。
• Monomers and oligonucleotides comprising cycloaddition adduct(s)
  申请人：Manoharan Muthiah

  公开号：US09198972B2

  公开（公告）日：2015-12-01

  The invention features compounds of formula (V) or (XII). In one embodiment, the invention relates compounds and processes for conjugating ligand to oligonucleotide. The invention further relates to methods for treating various disorders and diseases such as viral infections, bacterial infections, parasitic infections, cancers, allergies, autoimmune diseases, immunodeficiencies and immunosuppression.

  这项发明涉及公式（V）或（XII）的化合物。在一个实施例中，该发明涉及将配体与寡核苷酸结合的化合物和过程。该发明还涉及治疗各种疾病和疾病的方法，如病毒感染、细菌感染、寄生虫感染、癌症、过敏、自身免疫疾病、免疫缺陷和免疫抑制。
• Versatile Site-Specific Conjugation of Small Molecules to siRNA Using Click Chemistry
  作者：Takeshi Yamada、Chang Geng Peng、Shigeo Matsuda、Haripriya Addepalli、K. Narayanannair Jayaprakash、Md. Rowshon Alam、Kathy Mills、Martin A. Maier、Klaus Charisse、Mitsuo Sekine、Muthiah Manoharan、Kallanthottathil G. Rajeev

  DOI：10.1021/jo101761g

  日期：2011.3.4

  We have previously demonstrated that conjugation of small molecule ligands to small interfering RNAs (siRNAs) and anti-microRNAs results in functional siRNAs and antagomirs in vivo. Here we report on the development of an efficient chemical strategy to make oligoribonucleotide-ligand conjugates using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) or click reaction. Three click reaction approaches were evaluated for their feasibility and suitability for high-throughput synthesis: the CuAAC reaction at the monomer level prior to oligonucleotide synthesis, the solution-phase postsynthetic "click conjugation", and the "click conjugation" on an immobilized and cornpletely protected alkyne-oligonucleotide scaffold. Nucleosides bearing 5'-alkyne moieties were used for conjugation to the 5'-end of the oligonucleotide. Previously described 2'- and 3'-O-propargylated nucleosides were prepared to introduce the alkyne moiety to the 3' and 5' termini and to the internal positions of the scaffold. Azido-functionalized ligands bearing lipophilic long chain alkyls, cholesterol, oligoamine, and carbohydrate were utilized to study the effect of physicochemical characteristics of the incoming azide on click conjugation to the alkyne-oligonucleotide scaffold in solution and on immobilized solid support. We found that microwave-assisted click conjugation of azido-functionalized ligands to a fully protected solid-support bound alkyne-oligonucleotide prior to deprotection was the most efficient "click conjugation" strategy for site-specific, high-throughput oligonucleotide conjugate synthesis tested. The siRNA conjugates synthesized using this approach effectively silenced expression of a luciferase gene in a stably transformed HeLa cell line.
• FATTY AMINE DRUG CONJUGATES
  申请人：Protarga Inc.

  公开号：EP1427407A2

  公开（公告）日：2004-06-16
• EP1427407A4
  申请人：——

  公开号：EP1427407A4

  公开（公告）日：2005-05-11