2-(2-叠氮乙氧基)萘 | 753022-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(2-叠氮乙氧基)萘
• 英文名称: 2-(2-azidoethoxy)naphthalene
• CAS: 753022-56-9
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: ZJNQZSUKEHWTEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-叠氮乙氧基)萘 在 1,3-丙二醇 一水合肼 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 50.0h， 生成 (2S)-2-[((2-(2-naphthoxy)ethyl)amino)methyl]-1,4-benzodioxane
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040
• 作为产物：
  描述：

  2-(2-mesyloxyethoxy)naphthalene 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以83%的产率得到2-(2-叠氮乙氧基)萘
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040

文献信息

• Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids
  作者：Paul Awolade、Nosipho Cele、Nagaraju Kerru、Parvesh Singh

  DOI：10.1007/s11030-020-10112-3

  日期：2021.11

  copper(I)-catalyzed azide-alkyne [3 + 2] dipolar cycloaddition reaction (CuAAC). Antimicrobial evaluation identified compound 16 as the most active hybrid in the library with a broad-spectrum antibacterial activity at an MIC80 value of 75.39 μM against methicillin-resistant S. aureus, E. coli, A. baumannii, and multidrug-resistant K. pneumoniae. The compound also showed interesting antifungal profile against C.

  摘要 抗菌素耐药性已成为对全球公共卫生的重大威胁，因此迫切需要具有改善治疗效果的新药。在这方面，分子杂交被认为是提供多靶点候选药物的可行策略。在此，我们报告了通过铜 (I) 催化的叠氮化物-炔烃 [3 + 2] 偶极环加成反应 (CuAAC) 合成的喹啉—1 H -1,2,3-三唑分子杂化物库。抗菌评估确定化合物16是文库中最活跃的杂合体，对耐甲氧西林金黄色葡萄球菌、大肠杆菌、鲍曼不动杆菌的 MIC 80值为 75.39 μM，具有广谱抗菌活性。和多重耐药肺炎克雷伯菌。该化合物还显示出有趣的抗白色念珠菌和新型念珠菌的抗真菌特性，MIC 80值分别为 37.69 和 2.36 μM，优于氟康唑。体外毒性分析显示对人红细胞 (hRBC) 无溶血活性，但对人胚胎肾细胞 (HEK293) 有部分细胞毒性。此外，计算机研究预测了优异的药物样特性以及三唑环在稳定与靶蛋白络合方面的重要性。总体而言，这些
• Synthesis and biological evaluation of 1,6-bis-triazole-2,3,4-tri-O-benzyl-α-d-glucopyranosides as a novel α-glucosidase inhibitor in the treatment of Type 2 diabetes
  作者：Suksamran Chaidam、Natthiya Saehlim、Anan Athipornchai、Uthaiwan Sirion、Rungnapha Saeeng

  DOI：10.1016/j.bmcl.2021.128331

  日期：2021.10

  A novel series of 1,6-bis-triazole-benzyl-α-glucoside derivatives (7a-7ee) were designed, synthesized and evaluated for inhibitory activity against α-glucosidase. Most of the synthesized compounds exhibited good activity with IC50 ranging from 3.73 µM to 53.34 µM and are more potent than the standard drug acarbose (IC50 = 146.25 ± 0.40 µM). SARs study showed the ester and menthol moiety play an important

  设计、合成了一系列新的 1,6-双-三唑-苄基-α-葡萄糖苷衍生物 ( 7a-7ee )，并评估了其对α-葡萄糖苷酶的抑制活性。大多数合成化合物表现出良好的活性，IC 50范围为 3.73 µM 至 53.34 µM，比标准药物阿卡波糖 (IC 50  = 146.25 ± 0.40 µM)更有效。SARs研究表明酯和薄荷醇部分在抑制活性中起重要作用。强效化合物7f、7z、7cc和7dd的分子对接模型显示出良好的结合能并与酶活性位点周围的氨基酸残基相互作用良好，这证实了体外活性结果。
• Supramolecular Cross-Linked Networks <i>via</i> Host−Guest Complexation with Cucurbit[8]uril
  作者：Eric A. Appel、Frank Biedermann、Urs Rauwald、Samuel T. Jones、Jameel M. Zayed、Oren A. Scherman

  DOI：10.1021/ja106362w

  日期：2010.10.13

  first guest for CB[8]) or naphthoxy derivatives (good second guests for CB[8]). A colorless solution of the two multivalent copolymers bearing first and second guests, respectively, can be transformed into a highly viscous, colored supramolecular hydrogel with the cross-link density being easily controlled through CB[8] addition. Moreover, the cross-links (1:1:1 supramolecular ternary complexes of C

  微调水性体系溶液粘度的能力在许多应用中至关重要，从大规模基于流体的工业过程到在再生医学、受控药物输送和“绿色”自愈材料中很重要的独立水凝胶。在此，我们展示了使用大环主体分子葫芦 [8] 脲 (CB[8]) 促进具有高结合常数 (K(a) > 10(11)-10(12) M) 的多价共聚物的可逆交联(-2)) 导致超分子水凝胶。多价共聚物是通过自由基聚合技术制备的，含有侧链甲基紫精（CB[8] 的良好第一客体）或萘氧基衍生物（CB[8] 的良好第二客体）。分别带有第一和第二客体的两种多价共聚物的无色溶液，可以转化为高粘性、有色的超分子水凝胶，交联密度可以通过添加 CB[8] 轻松控制。此外，交联（CB[8]/紫精/萘氧基的 1:1:1 超分子三元复合物）是动态和刺激响应的，材料特性可以通过温度或其他外部刺激进行调节。这些动态交联网络的散装材料特性的流变学表征提供了对 CB[8] 三元络合动力
• Supramolecular gold nanoparticle–polymer composites formed in water with cucurbit[8]uril
  作者：Roger J. Coulston、Samuel T. Jones、Tung-Chun Lee、Eric A. Appel、Oren A. Scherman

  DOI：10.1039/c0cc03250f

  日期：——

  A gold nanoparticle–polymer composite material has been prepared in water using cucurbit[8]uril as a supramolecular “handcuff” to hold together viologen-functionalised gold nanoparticles and a naphthol-functionalised acrylamide copolymer.

  利用葫芦[8]脲作为超分子 "手铐"，在水中制备了一种金纳米粒子与聚合物的复合材料，将病毒官能化的金纳米粒子和萘酚官能化的丙烯酰胺共聚物固定在一起。
• VISCOUS WELLBORE FLUIDS
  申请人：Scherman Oren A.

  公开号：US20120103615A1

  公开（公告）日：2012-05-03

  A wellbore fluid contains a viscosifying polymer in which portions of the polymer are connected through formation of an inclusion complex involving cucurbituril 8 (i.e. CB[8]) as host molecule. The fluid contains guest molecules with first and second guest groups covalently attached wherein at least one of the guest molecules comprises a polymer chain. The CB [8] host and the guest molecules attach together through reception of first and second guest groups within CB[8] host cavities, thereby connecting polymer chains together as a larger, supramolecular polymer and enhancing viscosity of the fluid. Polymer molecules may be synthetic polymers and guest groups may be attached to monomers before polymerization. Alternatively guest groups may be attached to existing polymers which may be polysaccharide.