11-azidoundec-1-yne | 873421-29-5

• 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: 11-azidoundec-1-yne
• 英文别名: 11-azido-1-undecyne；11-Azidoundec-1-yne
• CAS: 873421-29-5
• 化学式: C₁₁H₁₉N₃
• 分子量: 193.292
• InChiKey: FTNLKVBBASMRBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  11-azidoundec-1-yne 在 iron(III) chloride 、 碳酸氢钠 、 sodium iodide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.42h， 生成 undec-10-yn-1-yl isocyanate
  参考文献：
  名称：

  Discovery of Potent Inhibitors of Human and Mouse Fatty Acid Amide Hydrolases

  摘要：

  Fatty acid amide hydrolase (FAAH, EC 3.5.1.99) is the main enzyme catabolizing endocannabinoid fatty acid amides. FAAH inactivation promotes beneficial effects upon pain and anxiety without the side effects accompanying agonists of type-1 cannabinoid receptors. Aiming at discovering new selective FAAH inhibitors, we developed a series of compounds (5a-u) characterized by a functionalized heteroaromatic scaffold. Particularly, 5c and 5d were identified as extremely potent, noncompetitive, and reversible FAAH inhibitors endowed with a remarkable selectivity profile and lacking interaction with the hERG channels. In vivo antinociceptive activity was demonstrated for 5c, 5d, and 5n at a dose much lower than that able to induce either striatal and limbic stereotypies or anxiolytic activity, thus outlining their potential to turn into optimum preclinical candidates. Aiming at improving pharmacokinetic properties and metabolic stability of 5d, we developed a subset of nanomolar dialyzable FAAH inhibitors (5v-z), functionalized by specific polyethereal lateral chains and fluorinated aromatic rings.

  DOI：

  10.1021/jm300689c
• 作为产物：
  描述：

  undec-10-yn-1-yl methanesulfonate 在 sodium azide 、 sodium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以555 mg的产率得到11-azidoundec-1-yne
  参考文献：
  名称：

  Advanced Strategies for Efficient Macrocyclic Cu(I)-Catalyzed Cycloaddition of Azides

  摘要：

  An advanced strategy for efficient macrocyclic Cu(I)-catalyzed cycloaddition is described. The key features include employing azide-iodoalkyne cycloadditions (CuAiAC), low catalyst loadings, relatively high concentrations (30 mM ? 300 mM), and application to continuous flow. The remarkably efficient new tool affords a variety of macrocyclic skeletons having either different alkyl, aryl, or amino acid spacers in high yields (70-97%). The macrocyclic CuAiAC process affords macrocycles having an iodotriazole moiety that can be further functionalized using standard Pd-catalyzed cross-couplings.

  DOI：

  10.1021/ol502415a

文献信息

• Versatile Methodology to Hydrate Alkynes, in the Presence of a Wide Variety of Functional Groups, with Mercury(II) <i>p</i>-Toluensulfonamidate, Under Catalytic, Mild, and Neutral Conditions
  作者：Albert Corominas、Ángel M. Montaña

  DOI：10.1080/00397911.2012.686003

  日期：2013.8.3

  Abstract A method to generate carbonylic compounds from alkynes under mild and neutral conditions, with excellent functional group compatibility and good yields, is described. Hydration takes place under catalytic conditions by using 0.1 to 0.2 equivalents of the easily available and inexpensive mercury(II) p-toluensulfonamidate in a hydroalcoholic solution. After use, the catalyst is rendered inert

  摘要 描述了一种在温和和中性条件下由炔烃制备羰基化合物的方法，该方法具有优异的官能团相容性和良好的产率。通过在水醇溶液中使用 0.1 至 0.2 当量的易得且廉价的对甲苯磺酰胺汞 (II)，在催化条件下发生水合。使用后，催化剂变为惰性和/或循环使用。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Synthesis of Acetogenin Analogs Comprising Pyrimidine Moieties Linked by Amine Bonds and Their Inhibitory Activity against Human Cancer Cell Lines
  作者：Hiroyuki Hosomi、Akinobu Akatsuka、Shingo Dan、Hiroki Iwasaki、Hisanori Nambu、Naoto Kojima

  DOI：10.1248/cpb.c22-00574

  日期：2022.11.1

  synthesized three acetogenin analogs containing pyrimidine moieties linked by amine bonds, which represent the skeleton structure of pyrimidifen, a mitochondrial complex I-inhibiting insecticide. Replacing the pyrimidine moiety linked by the amine bond remarkably enhanced growth-inhibitory activity of the analogs against several human cancer cell lines. Moreover, these analogs selectively and potently

  在这里，我们合成了三种含有通过胺键连接的嘧啶部分的乙酰苯胺类似物，它们代表了线粒体复合物 I 抑制杀虫剂嘧啶的骨架结构。取代由胺键连接的嘧啶部分显着增强了类似物对几种人类癌细胞系的生长抑制活性。此外，无论嘧啶取代基如何，这些类似物都选择性且有效地抑制这些人类癌细胞系的生长。此外，COMPARE 分析表明，这些类似物通过抑制线粒体复合物 I 来抑制癌症生长。我们的研究为将 acetogenin 类似物设计为新型抗肿瘤剂提供了见解。 全尺寸图像
• 10.1021/acs.jmedchem.4c00944
  作者：Pradhan, Balaram、Pavan, Matteo、Fisher, Courtney L.、Salmaso, Veronica、Wan, Tina C.、Keyes, Robert F.、Rollison, Noah、Suresh, R. Rama、Kumar, T. Santhosh、Gao, Zhan-Guo、Smith, Brian C.、Auchampach, John A.、Jacobson, Kenneth A.

  DOI：10.1021/acs.jmedchem.4c00944

  日期：——

  A3 adenosine receptor (A3AR) positive allosteric modulators (PAMs) (2,4-disubstituted-1H-imidazo[4,5-c]quinolin-4-amines) allosterically increase the Emax of A3AR agonists, but not potency, due to concurrent orthosteric antagonism. Following mutagenesis/homology modeling of the proposed lipid-exposed allosteric binding site on the cytosolic side, we functionalized the scaffold, including heteroatom

  A3 腺苷受体 （A3AR） 阳性变构调节剂 （PAM）（2,4-二取代-1H-咪唑[4,5-c]喹啉-4-胺）变构增加 A 3AR 激动剂的 Emax，但不增加效力，由于并发的正构拮抗作用。在胞质溶质侧提出的脂质暴露变构结合位点的诱变/同源建模之后，我们将支架功能化，包括杂原子取代和外环苯胺延伸，以增加变构结合。战略性地附加带有末端氨基/胍基的线性烷基-炔基链改善了人和小鼠 A3AR 的变构效应。改变链长、功能和连接位置以调节 A3AR PAM 活性。例如，26 （MRS8247，对炔烃连接的 8 亚甲基）和同系物增加了激动剂 Cl-IB-MECA 的 Emax 和效力 （[35S]GTPγS 结合）。推定的机制涉及一条灵活的末端阳离子链穿透脂质环境，以稳定的静电锚定到胞质磷脂头基，表明“脂质拖钓”，由活性状态模型的分子动力学模拟支持。因此，我们通过基于螺旋外脂质结合位点的合理设计提高了
• Discovery of Potent Inhibitors of Human and Mouse Fatty Acid Amide Hydrolases
  作者：Stefania Butini、Margherita Brindisi、Sandra Gemma、Patrizia Minetti、Walter Cabri、Grazia Gallo、Silvia Vincenti、Emanuela Talamonti、Franco Borsini、Antonio Caprioli、Maria Antonietta Stasi、Stefano Di Serio、Sindu Ros、Giuseppe Borrelli、Samuele Maramai、Filomena Fezza、Giuseppe Campiani、Mauro Maccarrone

  DOI：10.1021/jm300689c

  日期：2012.8.9

  Fatty acid amide hydrolase (FAAH, EC 3.5.1.99) is the main enzyme catabolizing endocannabinoid fatty acid amides. FAAH inactivation promotes beneficial effects upon pain and anxiety without the side effects accompanying agonists of type-1 cannabinoid receptors. Aiming at discovering new selective FAAH inhibitors, we developed a series of compounds (5a-u) characterized by a functionalized heteroaromatic scaffold. Particularly, 5c and 5d were identified as extremely potent, noncompetitive, and reversible FAAH inhibitors endowed with a remarkable selectivity profile and lacking interaction with the hERG channels. In vivo antinociceptive activity was demonstrated for 5c, 5d, and 5n at a dose much lower than that able to induce either striatal and limbic stereotypies or anxiolytic activity, thus outlining their potential to turn into optimum preclinical candidates. Aiming at improving pharmacokinetic properties and metabolic stability of 5d, we developed a subset of nanomolar dialyzable FAAH inhibitors (5v-z), functionalized by specific polyethereal lateral chains and fluorinated aromatic rings.
• Advanced Strategies for Efficient Macrocyclic Cu(I)-Catalyzed Cycloaddition of Azides
  作者：Anne-Catherine Bédard、Shawn K. Collins

  DOI：10.1021/ol502415a

  日期：2014.10.17

  An advanced strategy for efficient macrocyclic Cu(I)-catalyzed cycloaddition is described. The key features include employing azide-iodoalkyne cycloadditions (CuAiAC), low catalyst loadings, relatively high concentrations (30 mM ? 300 mM), and application to continuous flow. The remarkably efficient new tool affords a variety of macrocyclic skeletons having either different alkyl, aryl, or amino acid spacers in high yields (70-97%). The macrocyclic CuAiAC process affords macrocycles having an iodotriazole moiety that can be further functionalized using standard Pd-catalyzed cross-couplings.