ethyl 2-[6-(methoxycarbonyl)(2-naphthyloxy)]acetate | 364372-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2-[6-(methoxycarbonyl)(2-naphthyloxy)]acetate
• 英文别名: Methyl 6-(2-ethoxy-2-oxoethoxy)naphthalene-2-carboxylate
• CAS: 364372-23-6
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: SFAXTTZIQCLPEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[6-(methoxycarbonyl)(2-naphthyloxy)]acetate 在 盐酸 、 水 、 lithium hydroxide 作用下， 生成 6-(carboxymethoxy)-2-naphthoic acid
  参考文献：
  名称：

  含半刚性6-（羧基甲氧基）-2-萘甲酸的配位聚合物的结构，结构多样性，发光和染料吸收性能

  摘要：

  半刚性6-（羧基甲氧基）-2-萘甲酸（H 2 CNA）已成功合成为含O桥原子的配体。在水热或溶剂热条件下成功合成了六种基于H 2 CNA配体和过渡金属离子的配位聚合物，分别命名为[Zn（CNA）] n（1），[Cd（CNA）（H 2 O）] n（2），[Co（HCNA）2（H 2 O）4 ]（3），[Ni（HCNA）2（H 2 O）4 ]（4），[Cu（CNA）（H 2 O）] n（5），[Ni（CNA）（H 2 O）] n（6）。单晶结构分析表明，1，2，5和6被示出为二维结构，和3 - 4个显示0D结构。所有结构通过氢键相互作用组装成3D超分子网络。详细讨论了这些配位聚合物的热稳定性，发光性能和UV-vis光谱。另外，5具有良好的选择性，对刚果红的吸附能力强。

  DOI：

  10.1016/j.jssc.2020.121773
• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 sodium hydroxide 、 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 ethyl 2-[6-(methoxycarbonyl)(2-naphthyloxy)]acetate
  参考文献：
  名称：

  Utilization of a Peptide Lead for the Discovery of a Novel PTP1B-Binding Motif

  摘要：

  Examination of the PTP1B inhibitory potency of an extensive series of phosphotyrosyl (pTyr) mimetics (Xxx) expressed in the EGFr-derived hexapeptide platform Ac-Asp-Ala-Asp-Xxx-Leu-amide previously led to the finding of high inhibitory potency when Xxx = 4-(phosphono-difluoromethyl)phenylalanyl (F(2)Pmp) (K-i = 0.2 muM) and when Xxx = 3-carboxy-4-carboxy-methyloxyphenylalanyl (K-i = 3.6 muM). In the first instance, further work led from the F(2)Pmp-containing peptide to monomeric inhibitor, 6-(phosphonodifluoromethyl)-2-naphthoic acid (Ki = 22 muM), and to the pseudo-dipeptide mimetic, N-[6-(phosphonodifluoromethyl)-2-naphthoyl]-glutamic acid (K-i = 12 muM). In the current study, a similar approach was applied to the 3-carboxy-4-carboxymethyloxyphenylalanyl-containing peptide, which led to the preparation of monomeric 5-carboxy-6-carboxymethyloxy-2-naphthoic acid (K-i = 900 muM). However, contrary to expectations based on the aforementioned F(2)Pmp work, incorporation of this putative pTyr mimetic into the pseudo-dipeptide, N-[5-carboxy-6-carboxymethyloxy-2-naphthoyl]-glutamic acid, resulted in a substantial loss of binding affinity. A reevaluation of binding orientation for 5-carboxy-6-carboxymethyloxy-2-naphthoic acid was therefore undertaken, which indicated a 180 degrees reversal of the binding orientation within the PTP1B catalytic site. In the new orientation, the naphthyl 2-carboxyl group, and not the o-carboxy carboxymethyloxy groups, mimics a phosphoryl group. Indeed, when 5-carboxy-2-naphthoic acid itself was examined at neutral pH for inhibitory potency, it was found to have K-i = 31 +/- 7 muM, which is lower than parent 5-carboxy-6-carboxymethyloxy-2-naphthoic acid. In this fashion, 5-carboxy-2-naphthoic acid (or more appropriately, 6-carboxy-1-naphthoic acid) has been identified as a novel PTP1B binding motif.

  DOI：

  10.1021/jm010020r

文献信息

• Utilization of a Peptide Lead for the Discovery of a Novel PTP1B-Binding Motif
  作者：Yang Gao、Johannes Voigt、He Zhao、Godwin C. G. Pais、Xuechun Zhang、Li Wu、Zhong-Yin Zhang、Terrence R. Burke

  DOI：10.1021/jm010020r

  日期：2001.8.1

  Examination of the PTP1B inhibitory potency of an extensive series of phosphotyrosyl (pTyr) mimetics (Xxx) expressed in the EGFr-derived hexapeptide platform Ac-Asp-Ala-Asp-Xxx-Leu-amide previously led to the finding of high inhibitory potency when Xxx = 4-(phosphono-difluoromethyl)phenylalanyl (F(2)Pmp) (K-i = 0.2 muM) and when Xxx = 3-carboxy-4-carboxy-methyloxyphenylalanyl (K-i = 3.6 muM). In the first instance, further work led from the F(2)Pmp-containing peptide to monomeric inhibitor, 6-(phosphonodifluoromethyl)-2-naphthoic acid (Ki = 22 muM), and to the pseudo-dipeptide mimetic, N-[6-(phosphonodifluoromethyl)-2-naphthoyl]-glutamic acid (K-i = 12 muM). In the current study, a similar approach was applied to the 3-carboxy-4-carboxymethyloxyphenylalanyl-containing peptide, which led to the preparation of monomeric 5-carboxy-6-carboxymethyloxy-2-naphthoic acid (K-i = 900 muM). However, contrary to expectations based on the aforementioned F(2)Pmp work, incorporation of this putative pTyr mimetic into the pseudo-dipeptide, N-[5-carboxy-6-carboxymethyloxy-2-naphthoyl]-glutamic acid, resulted in a substantial loss of binding affinity. A reevaluation of binding orientation for 5-carboxy-6-carboxymethyloxy-2-naphthoic acid was therefore undertaken, which indicated a 180 degrees reversal of the binding orientation within the PTP1B catalytic site. In the new orientation, the naphthyl 2-carboxyl group, and not the o-carboxy carboxymethyloxy groups, mimics a phosphoryl group. Indeed, when 5-carboxy-2-naphthoic acid itself was examined at neutral pH for inhibitory potency, it was found to have K-i = 31 +/- 7 muM, which is lower than parent 5-carboxy-6-carboxymethyloxy-2-naphthoic acid. In this fashion, 5-carboxy-2-naphthoic acid (or more appropriately, 6-carboxy-1-naphthoic acid) has been identified as a novel PTP1B binding motif.
• Construction, structure diversity, luminescent and dye absorption properties of coordination polymers comprising semi-rigid 6-(carboxymethoxy)-2-naphthoic acid
  作者：Shaoshao Jiao、Yaowen Zhang、Xinghao Zhang、Kang Liu、Dingxuan Ma、Bo Yang、Shaoxiang Li、Lei Wang

  DOI：10.1016/j.jssc.2020.121773

  日期：2021.1

  Semi-rigid 6-(carboxymethoxy)-2-naphthoic acid (H2CNA) was successfully synthesized as a ligand containing O-bridging atom. Six coordination polymers based on H2CNA ligand and transition metal ions were successfully synthesized under the hydrothermal or solvothermal conditions, which named [Zn(CNA)]n (1), [Cd(CNA) (H2O)]n (2), [Co(HCNA)2(H2O)4] (3), [Ni(HCNA)2(H2O)4] (4), [Cu(CNA) (H2O)]n (5), [Ni(CNA)

  半刚性6-（羧基甲氧基）-2-萘甲酸（H 2 CNA）已成功合成为含O桥原子的配体。在水热或溶剂热条件下成功合成了六种基于H 2 CNA配体和过渡金属离子的配位聚合物，分别命名为[Zn（CNA）] n（1），[Cd（CNA）（H 2 O）] n（2），[Co（HCNA）2（H 2 O）4 ]（3），[Ni（HCNA）2（H 2 O）4 ]（4），[Cu（CNA）（H 2 O）] n（5），[Ni（CNA）（H 2 O）] n（6）。单晶结构分析表明，1，2，5和6被示出为二维结构，和3 - 4个显示0D结构。所有结构通过氢键相互作用组装成3D超分子网络。详细讨论了这些配位聚合物的热稳定性，发光性能和UV-vis光谱。另外，5具有良好的选择性，对刚果红的吸附能力强。