6-acetyl-2-naphthoic acid | 33627-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-acetyl-2-naphthoic acid
• 英文别名: 6-Acetoxy-2-naphthalincarbonsaeure；6-Acetoxy-2-naphthoesaeure；6-Acetyl-2-naphthoessaeure；6-acetylnaphthalene-2-carboxylic acid
• CAS: 33627-01-9
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: RENRXKAWNUMITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  6-acetyl-2-naphthoic acid 、 叔丁醇 在 二苯基膦叠氮化物 、 三乙胺 作用下， 生成 tert-butyl-6-acetylnaphthalen-2-ylcarbamate
  参考文献：
  名称：

  Hypoxia-Activated Prodrugs: Substituent Effects on the Properties of Nitro seco-1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indol-4-one (nitroCBI) Prodrugs of DNA Minor Groove Alkylating Agents

  摘要：

  Nitrochloromethylbenzindolines (nitroCBIs) are a new class of hypoxia-activated prodrugs for antitumor therapy. The recently reported prototypes undergo hypoxia-selective metabolism to form potent DNA minor groove alkylating agents and are selectively toxic to some but not all hypoxic tumor cell lines. Here we report a series of 31 analogues that bear an extra electron-withdrawing substituent that serves to raise the one-electron reduction potential of the nitroCBI. We identify a subset of compounds, those with a basic side chain and sulfonamide or carboxamide substituent, that have consistently high hypoxic selectivity. The best of these, with a 7-sulfonamide substituent, displays hypoxic cytotoxicity ratios of 275 and 330 in Skov3 and HT29 human tumor cell lines, respectively. This compound (28) is efficiently and selectively metabolized to the corresponding aminoCBI, is selectively cytotoxic tinder hypoxia in all 11 cell lines examined, and demonstrates activity against hypoxic tumor cells in a human tumor xenograft in vivo.

  DOI：

  10.1021/jm901202b
• 作为产物：
  描述：

  2,6-二异丙基萘 在 氧气 、 溶剂黄146 、 potassium bromide 作用下， 189.84 ℃ 、1.7 MPa 条件下， 反应 12.0h， 生成 2,6-萘二羧酸 、 6-acetyl-2-naphthoic acid
  参考文献：
  名称：

  Studies on calcined cow bone and pyrolyzed wood, suitable supports for immobilizing hybrid nano particles of Co-Mn as new catalysts for oxidation of 2,6-diisopropyl naphthalene

  摘要：

  Catalytic oxidation of 2,6-diisopropylnaphthalene (2,6-DIPN) to 2,6-naphthalene dicarboxylic acid (2,6-NDCA) was studied with two new catalysts prepared by immobilization of Co/Mn nano-hybrid particles over calcined cow bone, and pyrolyzed wood. The catalysts have the advantage of very cheap supports, and easy catalyst recovery. The effects of Co/Mn atomic ratio, reaction time and temperature, oxygen pressure, amount of catalyst, and the support on the conversion of 2,6-DIPN and product/intermediate yields were investigated. There was an interesting synergistic effect of cobalt and manganese catalysts. The maximum product (2,6-NDCA) yield was 100%, obtained at a Co/Mn atomic ratio of 10 supported on pyrolyzed wood. Lower cobalt concentration resulted the lower 2,6-NDCA yield, which was ascribed to the intermediate products formation. The catalysts were characterized in detail by SEM/EDS, BET surface area, and TEM measurements. Transmission electron microscopy (TEM) measurements indicated nanoparticles (diameter of about 2-5 nm) on the surface of the supports. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2013.02.013

文献信息

• MICROPOROUS COORDINATION COMPLEX AND METHOD OF MAKING THE SAME
  申请人：Matzger Adam J.

  公开号：US20140234624A1

  公开（公告）日：2014-08-21

  Disclosed herein is a three-dimensional coordination complex that includes a plurality of inorganic centers; a plurality of a first bis(bidentate) linker; and a plurality of a second bis(bidentate) linker, where the first and the second bis(bidentate) linkers are have different lengths, and the bidentate binding sites on each linker face in opposite directions on an axis.

  本文披露了一种三维配位化合物，包括多个无机中心；多个第一双(双齿)连接体；和多个第二双(双齿)连接体，其中第一和第二双(双齿)连接体具有不同的长度，并且每个连接体上的双齿结合位在轴上的相反方向。
• Formation of 2,6-Naphthalenedicarboxylic Acid by the Co–Mn–Br-Catalyzed Autoxidation of 2,6-Diethylnaphthalene in Acetic Acid
  作者：Yoshio Kamiya、Takashi Hama、Ichiro Kijima

  DOI：10.1246/bcsj.68.204

  日期：1995.1

  In order to elucidate the reaction mechanism and the optimum reaction conditions for the formation of 2,6-naphthalenedicarboxylic acid (NDCA), the Co(OAc)2–Mn(OAc)2–NaBr-catalyzed oxidation of 2,6-diethylnaphthalene by molecular oxygen was carried out in acetic acid. The oxidation of the ethyl groups to carboxyl groups proceeded mainly via acetyl groups and partly via 1-hydroxyethyl and 1-acetoxyethyl groups. A synergistic catalytic effect due to Co and Mn acetates was observed not only on the rate of oxidation but also on the selective formation of NDCA. The rate of oxidation was strongly retarded at higher concentrations of the substrate, showing that the naphthalene nucleus terminates the chain reaction step of the oxidation. A high concentration of metal catalyst resulted in an increase of acetoxyethylnaphthoic acid. At the optimum reaction conditions, a nearly 90% yield of NDCA was obtained along with small amounts of substituted naphthoic and trimellitic acids. The differences in the yield of NDCA from 2,6-dimethyl, 2,6-diethyl, and 2,6-diisopropylnaphthalenes were compared under similar reaction conditions and are discussed.

  为了阐明2,6-萘二甲酸(NDCA)形成的反应机理和最佳反应条件，Co(OAc)2-Mn(OAc)2-NaBr催化氧化2,6-二乙基萘分子氧在乙酸中进行。乙基向羧基的氧化主要通过乙酰基进行，部分通过1-羟乙基和1-乙酰氧基乙基进行。观察到 Co 和 Mn 乙酸盐的协同催化作用不仅对氧化速率而且对 NDCA 的选择性形成也有影响。在较高浓度的底物下，氧化速率被强烈抑制，表明萘核终止了氧化的链式反应步骤。高浓度的金属催化剂导致乙酰氧基乙基萘酸的增加。在最佳反应条件下，NDCA 产率接近 90%，同时还产生少量取代的萘酸和偏苯三酸。在相似的反应条件下比较并讨论了 2,6-二甲基、2,6-二乙基和 2,6-二异丙基萘的 NDCA 产率差异。
• Small molecule inhibitors of stat3 with anti-tumor activity
  申请人：Turkson James

  公开号：US20110201576A1

  公开（公告）日：2011-08-18

  The present invention concerns compounds, compositions containing these compounds, and methods of using these compounds and compositions as inhibitors of Stat3 signaling, Stat3 dimerization, Stat3-DNA binding, Stat5-DNA binding, and/or aberrant cell growth in vitro or in vivo, e.g., as anti-cancer agents for treatment of cancer, such as breast cancer. The compounds of the invention include, but are not limited to, NSC 74859 (S3I-201), NSC 42067, NSC 59263, NSC 75912, NSC 11421, NSC 91529, NSC 263435, and pharmaceutically acceptable salts and analogs of the foregoing. Other non-malignant diseases characterized by proliferation of cells that may be treated using the compounds of the invention, but are not limited to, cirrhosis of the liver; graft rejection; restenosis; and disorders characterized by a proliferation of T cells such as autoimmune diseases, e.g., type 1 diabetes, lupus and multiple sclerosis. The invention further includes an in-vitro screening test for the presence of malignant cells in a mammalian tissue; a method of identifying inhibitors of constitutive Stat3 activation, Stat3-DNA binding, Stat5-DNA binding, and/or Stat3 dimerization; and a method of identifying anti-cancer agents.

  本发明涉及化合物、含有这些化合物的组合物以及使用这些化合物和组合物作为Stat3信号、Stat3二聚化、Stat3-DNA结合、Stat5-DNA结合和/或体内或体外异常细胞增长的抑制剂的方法，例如作为治疗癌症（如乳腺癌）的抗癌剂。本发明的化合物包括但不限于NSC 74859（S3I-201）、NSC 42067、NSC 59263、NSC 75912、NSC 11421、NSC 91529、NSC 263435及其药学上可接受的盐和类似物。本发明还包括使用该化合物治疗其他非恶性疾病，这些疾病以细胞增生为特征，但不限于肝硬化、移植排斥、再狭窄和以T细胞增殖为特征的疾病，例如自身免疫性疾病，如1型糖尿病、红斑狼疮和多发性硬化症。本发明还包括一种体外筛选恶性细胞的方法；一种识别组成性Stat3激活、Stat3-DNA结合、Stat5-DNA结合和/或Stat3二聚化抑制剂的方法；以及一种识别抗癌剂的方法。
• SMALL MOLECULE INHIBITORS OF STAT3 WITH ANTI-TUMOR ACTIVITY
  申请人：H. Lee Moffitt Cancer Center And Research Institute, Inc.

  公开号：US20140329900A1

  公开（公告）日：2014-11-06

  The present invention concerns compounds, compositions containing these compounds, and methods of using these compounds and compositions as inhibitors of Stat3 signaling, Stat3 dimerization, Stat3-DNA binding, Stat5-DNA binding, and/or aberrant cell growth in vitro or in vivo, e.g., as anti-cancer agents for treatment of cancer, such as breast cancer. The compounds of the invention include, but are not limited to, NSC 74859 (S31-201), NSC 42067, NSC 59263, NSC 75912, NSC 11421, NSC 91529, NSC 263435, and pharmaceutically acceptable salts and analogs of the foregoing. Other non-malignant diseases characterized by proliferation of cells that may be treated using the compounds of the invention, but are not limited to, cirrhosis of the liver; graft rejection; restenosis; and disorders characterized by a proliferation of T cells such as autoimmune diseases, e.g., type 1 diabetes, lupus and multiple sclerosis. The invention further includes an in-vitro screening test for the presence of malignant cells in a mammalian tissue; a method of identifying inhibitors of constitutive Stat3 activation, Stat3-DNA binding, Stat5-DNA binding, and/or Stat3 dimerization; and a method of identifying anti-cancer agents.

  本发明涉及化合物、含有这些化合物的组合物以及使用这些化合物和组合物作为Stat3信号通路、Stat3二聚化、Stat3-DNA结合、Stat5-DNA结合和/或体外或体内异常细胞生长的抑制剂的方法，例如作为治疗癌症，如乳腺癌的抗癌剂。本发明的化合物包括但不限于NSC 74859（S31-201）、NSC 42067、NSC 59263、NSC 75912、NSC 11421、NSC 91529、NSC 263435以及其药学上可接受的盐和类似物。其他非恶性疾病，其特征为细胞增殖，可以使用本发明的化合物进行治疗，但不限于肝硬化、移植排斥反应、再狭窄以及T细胞增殖的疾病，例如自身免疫性疾病，如1型糖尿病、狼疮和多发性硬化等。本发明还包括一种用于检测哺乳动物组织中恶性细胞存在的体外筛选测试；一种识别组成性Stat3激活、Stat3-DNA结合、Stat5-DNA结合和/或Stat3二聚化抑制剂的方法；以及一种识别抗癌剂的方法。
• FACE-TO-FACE ORIENTED NONLINEAR OPTICAL MATERIAL AND METHOD OR ORIENTATION THEREOF
  申请人：OSAKA GAS CO., LTD.

  公开号：EP0555490A1

  公开（公告）日：1993-08-18

  An optically transparent material with nonlinear optical characteristics, comprising a highly face-to-face oriented main chain type liquid crystal polymer comprising repeating monomer units represented by the following general formula and having second-order and third-order nonlinear optical susceptibilities, X(2) and X(3): -(A)x-(B)y- wherein A represents a residue of 6-hydroxy-2-naphthoic acid of formula (I), B represents a residue of 4-hydroxybenzoic acid of formula (II), x falls within the range of 1-99 mole %; and y falls within the range of 99.1 mole %.

  一种具有非线性光学特性的光学透明材料，由高度面向定向主链型液晶聚合物组成，该聚合物由以下通式表示的重复单体单元组成，具有二阶和三阶非线性光学感度X(2)和X(3)：-(A)x-(B)y- 其中 A 代表式（I）的 6-羟基-2-萘酸的残余物，B 代表式（II）的 4-羟基苯甲酸的残余物，x 在 1-99 摩尔%的范围内；y 在 99.1 摩尔%的范围内。