6-[(tert-butoxycarbonyl)-amino]-2-naphthoic acid | 516465-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-[(tert-butoxycarbonyl)-amino]-2-naphthoic acid
• 英文别名: 6-(Tert-butoxycarbonylamino)-2-naphthoic acid；6-[(2-methylpropan-2-yl)oxycarbonylamino]naphthalene-2-carboxylic acid
• CAS: 516465-99-9
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: FSYAJMVNXZZMMF-UHFFFAOYSA-N

物化性质

• 沸点：
  416.7±20.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[(tert-butoxycarbonyl)-amino]-2-naphthoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 N'-[(6-amino-2-naphthyl)carbonyl]-5-nitro-2-furancarbohydrazide trifluoroacetate
  参考文献：
  名称：

  Synthesis of 5-Nitro-2-furancarbohydrazides and Their cis-Diamminedichloroplatinum Complexes as Bitopic and Irreversible Human Thioredoxin Reductase Inhibitors

  摘要：

  The human selenoprotein thioredoxin reductase is involved in antioxidant defense and DNA synthesis. As increased thioredoxin reductase levels are associated with drug sensitivity to cisplatin and drug resistance in tumor cells, this enzyme represents a promising target for the development of cytostatic agents. To optimize the potential of the widely used cisplatin to inhibit the human thioredoxin reductase and therefore to overcome cisplatin resistance, we developed and synthesized four cis-diamminedichloroplatinum complexes of the lead 5-nitro-2-furan-carbohydrazide 8 selected from high-throughput screening. Detailed kinetics revealed that the isolated fragments, 5-nitro-2-furancarbohydrazide and cisplatin itself, bind with micromolar affinities at two different subsites of the human enzyme. By tethering both fragments four nitrofuran-based cis-diamminedichloroplatinum complexes 13a-c and 20 were synthesized and identified as biligand irreversible inhibitors of the human enzyme with nanomolar affinities. Studies with mutant enzymes clearly demonstrate the penultimate selenocysteine residue as the prime target of the synthesized cis-diamminedichloroplatinum complexes.

  DOI：

  10.1021/jm050256l
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 6-氨基-2-萘酸 在 sodium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 以98%的产率得到6-[(tert-butoxycarbonyl)-amino]-2-naphthoic acid
  参考文献：
  名称：

  三苯甲氨酸文库的组合合成及其在表面增强拉曼散射（SERS）探针开发中的应用。

  摘要：

  进行了化合物三苯甲胺（TM）库的首次合成并筛选了其表面增强拉曼散射（SERS）能力，以鉴定具有高灵敏度的新型拉曼报道分子。我们确定了三种新型SERS报道分子（B2，B7和C7），其信号强度比常用的结晶紫（CV）高。这些报道者可能会在开发基于敏感SERS的生物传感器中发现潜在的应用。

  DOI：

  10.1039/b921550f

文献信息

• SURFACE ENHANCED RAMAN SPECTROSCOPY (SERS) COMPOUNDS AND METHODS OF THEIR PREPARATION
  申请人：CHANG Young-Tae

  公开号：US20120128592A1

  公开（公告）日：2012-05-24

  A compound for detecting an analyte using Surface Enhanced Raman Spectroscopy (SERS) and a method of forming the compound is provided. The compound has Formula I: wherein W is selected from the group consisting of an optionally substituted aryl group and an optionally substituted heteroaryl group; each Y independently is NR 1 R 2 , wherein R 1 and R 2 are independently selected from the group consisting of H and C 1 -C 6 alkyl, or R 1 and R 2 combine to form together with the nitrogen to which they are attached a heterocyclic group with 4 to 5 carbon atoms, is used to denote a single or a double bond, and Z is NH, NH 2 , NH—(C═O)—(CH 2 ) n —SH, wherein n=1 to 10, or or a tautomer or stereoisomer thereof, or a salt thereof. A method and device for detecting an analyte using Surface Enhanced Raman Spectroscopy (SERS) is also provided.

  提供了一种利用表面增强拉曼光谱（SERS）检测分析物的化合物以及形成该化合物的方法。该化合物具有式I：其中W从可选择的取代芳基和可选择的取代杂环基组成的组中选择；每个Y独立地为NR1R2，其中R1和R2独立地从H和C1-C6烷基组成的组中选择，或者R1和R2与它们连接的氮原子一起形成含有4到5个碳原子的杂环基，表示单键或双键，Z为NH、NH2、NH—(C═O)—(CH2)n—SH，其中n=1到10，或其异构体或立体异构体，或其盐。还提供了一种利用表面增强拉曼光谱（SERS）检测分析物的方法和装置。
• Intermolecular Dearomatization of Naphthalene Derivatives by Photoredox‐Catalyzed 1,2‐Hydroalkylation
  作者：Yuan‐Zheng Cheng、Xu‐Lun Huang、Wei‐Hui Zhuang、Qing‐Ru Zhao、Xiao Zhang、Tian‐Sheng Mei、Shu‐Li You

  DOI：10.1002/anie.202008358

  日期：2020.10.5

  visible‐light photoredox catalysis. With an organic photocatalyst, a series of multi‐substituted 1,2‐dihydronaphthalenes are obtained in good‐to‐excellent yields. Intriguingly, by tuning the substituents at the C2 position of naphthalenes, formal dearomative [3+2] cycloadditions occur exclusively via a hydroalkylative dearomatization–cyclization sequence. This overall redox‐neutral method features mild

  通过可见光光氧化还原催化可实现将萘与可商购获得的α-氨基酸进行分子间加氢脱芳香化反应。使用有机光催化剂，可以以优异的产率获得一系列多取代的1,2-二氢萘。有趣的是，通过调节萘C2位的取代基，形式上的脱芳香性[3 + 2]环加成仅通过加氢烷基化脱芳香化-环化序列发生。这种整体的氧化还原中性方法具有温和的反应条件，良好的功能耐受性和操作简便性。展示了产品的多种下游工艺。初步的力学研究表明，自由基与自由基的耦合途径参与其中。
• [EN] RED-SHIFTED LUCIFERINS AND METHODS OF USING SAME<br/>[FR] LUCIFÉRINES À ÉMISSION DÉCALÉE VERS LE ROUGE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：PROMEGA CORP

  公开号：WO2014159044A1

  公开（公告）日：2014-10-02

  Novel red-shifted luciferin derivatives and uses of those compounds are provided.

  提供了新型红移发光素衍生物及其化合物的用途。
• RED-SHIFTED LUCIFERINS AND METHODS OF USING SAME
  申请人：PROMEGA CORPORATION

  公开号：US20140304842A1

  公开（公告）日：2014-10-09

  Novel red-shifted luciferin derivatives and uses of those compounds are provided.

  本发明提供了新的红移荧光素衍生物以及这些化合物的用途。
• Surface Enhanced Raman Spectroscopy (SERS) compounds and methods of their preparation
  申请人：Chang Young-Tae

  公开号：US09006458B2

  公开（公告）日：2015-04-14

  A compound for detecting an analyte using Surface Enhanced Raman Spectroscopy (SERS) and a method of forming the compound is provided. The compound has Formula I: wherein W is selected from the group consisting of an optionally substituted aryl group and an optionally substituted heteroaryl group; each Y independently is NR1R2, wherein R1 and R2 are independently selected from the group consisting of H and C1-C6 alkyl, or R1 and R2 combine to form together with the nitrogen to which they are attached a heterocyclic group with 4 to 5 carbon atoms, is used to denote a single or a double bond, and Z is NH, NH2, NH—(C═O)—(CH2)n—SH, wherein n=1 to 10, or or a tautomer or stereoisomer thereof, or a salt thereof. A method and device for detecting an analyte using Surface Enhanced Raman Spectroscopy (SERS) is also provided.

  提供了一种用于使用表面增强拉曼光谱（SERS）检测分析物的化合物及其形成方法。该化合物具有公式I：其中W选自可选取代芳基和可选取代杂环芳基的群组；每个Y独立地是NR1R2，其中R1和R2独立地选自H和C1-C6烷基，或R1和R2与它们附着的氮一起形成有4至5个碳原子的杂环基团，表示单键或双键，Z为NH，NH2，NH—（C═O）—（CH2）n—SH，其中n=1至10，或其互变异构体或立体异构体，或其盐。还提供了一种使用表面增强拉曼光谱（SERS）检测分析物的方法和装置。