5-氯-2-羟基-3-硝基苯乙酮 | 7195-78-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-氯-2-羟基-3-硝基苯乙酮
• 中文别名: 2-乙酰基-6-硝基-4-氯苯酚
• 英文名称: 5-chloro-2-hydroxy-3-nitrobenzoic acid
• 英文别名: 5-chloro-3-nitro-salicylic acid
• CAS: 7195-78-0
• 化学式: C₇H₄ClNO₅
• mdl: MFCD00463867
• 分子量: 217.565
• InChiKey: SIYGNKVPVGTIHB-UHFFFAOYSA-N

物化性质

• 熔点：
  132-135 °C(lit.)
• 沸点：
  329.3±42.0 °C(Predicted)
• 密度：
  1.751±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36

反应信息

• 作为反应物：
  描述：

  5-氯-2-羟基-3-硝基苯乙酮 在 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 生成 6-氯-3-氧代-4H-1,4-苯并恶嗪-8-羧酸
  参考文献：
  名称：

  Optimization of triazoles as novel and potent nonphlorizin SGLT2 inhibitors

  摘要：

  Previous efforts have led to the identification of a potent, selective, and nonphlorizin based SGLT2 inhibitor 1. This Letter describes efforts to further optimize the potency, microsomal stability, solubility and pharmacokinetic properties of this series of SGLT2 inhibitors. From these efforts, compounds 28 and 32 have improved solubility and pharmacokinetic properties compared to compound 1 (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.053
• 作为产物：
  描述：

  5-氯代水杨酸 在 硝酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.83h， 以62.8%的产率得到5-氯-2-羟基-3-硝基苯乙酮
  参考文献：
  名称：

  3-氨基水杨酸的制备方法

  摘要：

  本发明涉及制备3-氨基水杨酸的新方法。该方法起始原料为水杨酸类化合物Ⅰ，通式：用硝化剂生成3-硝基水杨酸类化合物Ⅱ，通式：3-硝基水杨酸类化合物Ⅱ在有效量催化剂及供氢体存在下催化氢化还原硝基、脱卤氢解得3-氨基水杨酸。

  公开号：

  CN103992238B

文献信息

• Carbapenem antibiotic compounds
  申请人：Zeneca Limited

  公开号：US05541178A1

  公开（公告）日：1996-07-30

  A carbapenem compound of the formula (I) ##STR1## wherein: R.sup.1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R.sup.2 is hydrogen or C.sub.1-4 alkyl; R.sup.3 is hydrogen or C.sub.1-4 alkyl; R.sup.4 is hydroxy or carboxy; and the phenyl ring is optionally further substituted by one or two substituents selected from halo, cyano, C.sub.1-4 alkyl, nitro, hydroxy, carboxy, C.sub.1-4 alkoxy, trifluoromethyl, C.sub.1-4 alkoxycarbonyl, carbamoyl, C.sub.1-4 alkylcarbamoyl, di-C.sub.1-4 alkylcarbamoyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino sulphonic acid, C.sub.1-4 alkylS(O).sub.n --(wherein n is 0-2), N-C.sub.1-4 alkanesulphonamido, C.sub.1-4 alkanoylamino and C.sub.1-4 alkanoyl(N-C.sub.1-4 alkyl)amino: provided that the phenyl ring is substituted by at least one carboxy; or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof.

  化合物的结构式（I）如下：其中：R.sup.1为1-羟乙基，1-氟乙基或羟甲基；R.sup.2为氢或C.sub.1-4烷基；R.sup.3为氢或C.sub.1-4烷基；R.sup.4为羟基或羧基；苯环可选择进一步由卤素、氰基、C.sub.1-4烷基、硝基、羟基、羧基、C.sub.1-4烷氧基、三氟甲基、C.sub.1-4烷氧羰基、氨基、C.sub.1-4烷基氨基、二C.sub.1-4烷基氨基磺酸、C.sub.1-4烷基S(O).sub.n--（其中n为0-2）、N-C.sub.1-4烷磺酰胺基、C.sub.1-4烷酰胺基和C.sub.1-4烷酰（N-C.sub.1-4烷基）氨基等取代基取代；前提是苯环至少被一个羧基取代；或其药学上可接受的盐或体内可水解的酯。
• Down-Regulation of Procollagen α1[I] Messenger RNA by Titanium Particles Correlates with Nuclear Factor κB (NF-κB) Activation and Increased Rel A and NF-κB1 Binding to the Collagen Promoter
  作者：Kenneth A. Roebuck、Csaba Vermes、Laura R. Carpenter、Elizabeth A. Fritz、Ramesh Narayanan、Tibor T. Glant

  DOI：10.1359/jbmr.2001.16.3.501

  日期：——

  Previously, we showed that exposure of human osteoblasts to titanium particles stimulates protein tyrosine phosphorylation (PTP), activates the transcription factor nuclear factor κB (NF‐κB), and causes an approximately 50% decrease in the steady‐state messenger RNA (mRNA) level of procollagen α1[I]. In this study, we identify three NF‐κB binding sites within the human procollagen α1[I] gene promoter, show that titanium particles stimulate their binding of the NF‐κB subunits Rel A (p65) and NF‐κB1 (p50), and find NF‐κB activation correlates with collagen gene suppression by titanium particles in osteoblasts. Protein tyrosine kinase (PTK) inhibitors, which significantly reduce the suppressive effect of titanium particles on collagen gene expression, inhibited NF‐κB binding activity showing that titanium particle stimulation of PTK signals in osteoblasts are critical for both NF‐κB activation and collagen gene expression. The antioxidant pyrrolidine dithiocarbamate (PDTC), which also inhibits the titanium particle suppression of collagen, abrogated the titanium particle activation of NF‐κB, suggesting the involvement of redox signals in NF‐κB‐mediated collagen gene expression. The RNA polymerase II inhibitor actinomycin D (Act D) decreased procollagen α1[I] mRNA expression and effectively blocked the titanium‐induced suppressive effect, suggesting that titanium particles activate a cascade of signals in osteoblasts, which result in a suppression of procollagen α1[I] mRNA. Collectively, these results show that titanium particles can activate NF‐κB signaling in osteoblasts and suggest that NF‐κB binding to the collagen gene promoter has a functional role in the down‐regulation of procollagen α1[I] gene transcription.

  之前，我们展示了人类成骨细胞接触钛颗粒后，促使蛋白酪氨酸磷酸化（PTP），激活转录因子核因子κB（NF-κB），并导致前胶原α1[I]的信使RNA（mRNA）水平约降低50%。在本研究中，我们识别了人类前胶原α1[I]基因启动子内的三个NF-κB结合位点，显示钛颗粒刺激NF-κB亚单位Rel A（p65）和NF-κB1（p50）的结合，并发现NF-κB的激活与钛颗粒在成骨细胞中抑制胶原基因表达相关。蛋白酪氨酸激酶（PTK）抑制剂显著减少钛颗粒对胶原基因表达的抑制作用，抑制了NF-κB结合活性，表明钛颗粒刺激成骨细胞中的PTK信号对NF-κB激活和胶原基因表达都至关重要。抗氧化剂吡咯烷二硫代氨基甲酸酯（PDTC），也抑制了钛颗粒对胶原的抑制，消除了钛颗粒对NF-κB的激活，这表明氧化还原信号参与NF-κB介导的胶原基因表达。RNA聚合酶II抑制剂青霉素D（Act D）降低了前胶原α1[I] mRNA表达，有效阻断了钛诱导的抑制效果，这表明钛颗粒在成骨细胞中激活了一系列信号，导致前胶原α1[I] mRNA的抑制。总体而言，这些结果表明钛颗粒可以在成骨细胞中激活NF-κB信号，并暗示NF-κB与胶原基因启动子的结合在前胶原α1[I]基因转录的下调中具有功能性作用。
• 3-氨基水杨酸的制备方法
  申请人：南京信诺泰医药有限公司

  公开号：CN103992238B

  公开（公告）日：2016-03-02

  本发明涉及制备3-氨基水杨酸的新方法。该方法起始原料为水杨酸类化合物Ⅰ，通式：用硝化剂生成3-硝基水杨酸类化合物Ⅱ，通式：3-硝基水杨酸类化合物Ⅱ在有效量催化剂及供氢体存在下催化氢化还原硝基、脱卤氢解得3-氨基水杨酸。
• Aromatic amino acid derivates and medicinal compositions
  申请人：Endo Hitoshi

  公开号：US20050119256A1

  公开（公告）日：2005-06-02

  1. An aromatic amino acid derivative represented by the formula (I) or its pharmacologically acceptable salt: wherein, R 1 is a hydrogen atom or an amino-protecting group, R 2 is a halogen atom or an alkyl, aralkyl or aryl group, R 3 is circle over (1)} a hydrogen atom, circle over (2)} an aroylamino group, circle over (3)} a phenyl group substituted with lower alkyl, phenyl, phenoxy, etc. circle over (4)} a naphthyl or tetrahydronaphthyl group optionally substituted with hydroxy, lower alkoxy or di(lower)alkylamino, circle over (5)} an unsaturated mono-cyclic heterocyclic group containing N, O and/or S substituted with lower alkyl, phenyl, naphthyl or tetrahydroquinolyl, circle over (6)} an unsaturated or partially saturated condensed heterocyclic group containing N, O and/or S, optionally substituted with oxo, carboxy, amino, lower alkyl, etc.; X is a halogen atom, an alkyl group or an alkoxy group; Y is oxygen atom or nitrogen atom; I is 0 or 1; m is 0, 1 or 2; n is an integer of 0-5. This compound can inhibit a transporter (LAT1) of essential amino acid which is one of main nutrition for cancer cells and accordingly cause drain of the essential amino acid on the cancer cells and finally can prohibit the multiplication of cancer cells.

  一种芳香族氨基酸衍生物，其化学式为（I）或其药理学上可接受的盐：其中，R1为氢原子或氨基保护基；R2为卤素原子或烷基、芳基烷基或芳基基团；R3为circle over (1)}氢原子，circle over (2)}芳基氨基基团，circle over (3)}苯基，其取代基为较低的烷基、苯基、苯氧基等，circle over (4)}萘基或四氢萘基，可选地取代羟基、较低的烷氧基或二（较低）烷基氨基，circle over (5)}含N、O和/或S的不饱和单环杂环基团，取代基为较低的烷基、苯基、萘基或四氢喹啉基团，circle over (6)}含N、O和/或S的不饱和或部分饱和的紧缩杂环基团，可选地取代为氧代、羧基、氨基、较低的烷基等；X为卤素原子、烷基或烷氧基；Y为氧原子或氮原子；I为0或1；m为0、1或2；n为0-5的整数。该化合物可以抑制癌细胞的主要营养物质之一的必需氨基酸转运体（LAT1），从而导致癌细胞必需氨基酸的流失，最终可以抑制癌细胞的增殖。
• Fungicidal compositions and methods, and compounds and methods for the preparation thereof
  申请人：Dow AgroSciences LLC

  公开号：US06297401B1

  公开（公告）日：2001-10-02

  Fungicidal compositions and methods comprising acylated aminosalicylamides (AASA) described herein. Novel cyclic amines and 3-nitrosalicylamides, and their use as pesticides and in the preparation of the antifungal AASA compounds are also disclosed.

  本文描述了包含酰化氨基水杨酰胺（AASA）的杀真菌组合物和方法。还披露了新型环状胺和3-硝基水杨酰胺，以及它们在杀虫剂和制备抗真菌AASA化合物方面的应用。