1-(2-azidoethoxy)naphthalene | 753022-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-azidoethoxy)naphthalene
• CAS: 753022-51-4
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: QDTSZYCNCSLOGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：

  1-(2-azidoethoxy)naphthalene 在 1,3-丙二醇 一水合肼 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 37.5h， 生成 (2R)-2-[((2-(1-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-(1-萘氧基)乙醇 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-(2-azidoethoxy)naphthalene
  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。
• One-Pot Approach for the Synthesis of Bis-indole-1,4-disubstituted-1,2,3-triazoles
  作者：Natthiya Saehlim、Teerapich Kasemsuk、Uthaiwan Sirion、Rungnapha Saeeng

  DOI：10.1021/acs.joc.8b02056

  日期：2018.11.2

  A new strategy for the synthesis of bis-indoletriazoles was developed using a sequential one-pot four-step procedure via I2 and H2SO4–SiO2 catalyzed Friedel–Crafts reactions of indole with aldehyde followed by N-alkylation with propargyl bromide, azidation, and copper(I)-catalyzed azide alkyne cycloaddition (CuAAC). The reaction proceeded smoothly at room temperature in a short time, and a series of

  通过I 2和H 2 SO 4 -SiO 2催化的吲哚与醛的Friedel-Crafts反应，然后与炔丙基溴进行N-烷基化的连续一锅四步方法，开发了一种合成双吲哚三唑的新策略。，叠氮化和铜（I）催化的叠氮化物炔烃环加成（CuAAC）。反应在室温下在短时间内顺利进行，获得了一系列双吲哚三唑，收率良好至极好，证明了这种一锅法的普遍性。
• Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101
  作者：Cristiano Bolchi、Paolo Catalano、Laura Fumagalli、Marco Gobbi、Marco Pallavicini、Alessandro Pedretti、Luigi Villa、Giulio Vistoli、Ermanno Valoti

  DOI：10.1016/j.bmc.2004.06.040

  日期：2004.9

  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.