2-(naphthalen-1-yl)acetyl azide | 1033694-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-1-yl)acetyl azide
• 英文别名: 2-Naphthalen-1-ylacetyl azide
• CAS: 1033694-58-4
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: CMZJSNSILXQMLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-1-yl)acetyl azide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  1-萘乙酸 在 氯化亚砜 、 sodium azide 作用下， 反应 16.0h， 生成 2-(naphthalen-1-yl)acetyl azide
  参考文献：
  名称：

  使用甲醇从酰基叠氮化物合成 N-甲基化胺。

  摘要：

  使用甲醇作为 C1 源，通过一锅 Curtius 重排和借氢方法，将酰基叠氮化物衍生物转化为N-甲胺。按照该协议，使用 (NNN)Ru( II ) 配合物从羧酸通过酰基叠氮化物中间体合成各种功能化的N-甲基化胺。进行了几项动力学研究和 DFT 计算以支持该机制，并确定 Ru( II ) 配合物和碱在这种转变中的作用。

  DOI：

  10.1039/d0ob01303j

文献信息

• Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties
  作者：Luca Banfi、Andrea Basso、Elisabetta Bevilacqua、Valentina Gandolfo、Giuseppe Giannini、Giuseppe Guanti、Loana Musso、Monica Paravidino、Renata Riva

  DOI：10.1016/j.bmc.2008.02.022

  日期：2008.4.1

  Lactenediynes are compounds characterized by the fusion of a beta-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Quantitative Structure−Activity Relationship of Fatty Acid Amide Hydrolase Inhibitors: Modulation at the N-Portion of Biphenyl-3-yl Alkylcarbamates
  作者：Marco Mor、Alessio Lodola、Silvia Rivara、Federica Vacondio、Andrea Duranti、Andrea Tontini、Silvano Sanchini、Giovanni Piersanti、Jason R. Clapper、Alvin R. King、Giorgio Tarzia、Daniele Piomelli

  DOI：10.1021/jm701631z

  日期：2008.6.1

  Alkylcarbamic acid biphenyl-3-yl esters are a class of fatty acid amide hydrolase (FAAH) inhibitors that comprises cyclohexylcarbamic acid 3'-carbamoylbiphenyl-3-yl ester (URB597), a compound with analgesic, anxiolytic-like and antidepressant-like properties in rat and mouse models. Here, we extended the structure-activity relationships (SARs) for this class of compounds by replacing the cyclohexyl ring of the parent compound cyclohexylcarbamic acid biphenyl-3-yl ester (URB524) (FAAH IC50 = 63 nM) with a selected set of substituents of different size, shape, flexibility, and lipophilicity. Docking experiments and linear interaction energy (LIE) calculations indicated that the N-terminal group of O-arylcarbamates fits within the lipophilic region of the substrate-binding site, mimicking the arachidonoyl chain of anandamide. Significant potency improvements were observed for the beta-naphthylmethyl derivative 4q (IC50 = 5.3 nM) and its 3'-carbamoylbiphenyl-3-yl ester 4z (URB880, IC50 = 0.63 nM), indicating that shape complementarity and hydrogen bonds are crucial to obtain highly potent inhibitors.
• Froyen, Synthetic Communications, 1996, vol. 26, # 24, p. 4549 - 4561
  作者：Froyen

  DOI：——

  日期：——