3-氯-5-乙氧基-4-羟基苯甲醛 | 70842-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氯-5-乙氧基-4-羟基苯甲醛
• 英文名称: 3-chloro-5-ethoxy-4-hydroxybenzaldehyde
• 英文别名: 5-Chlor-4-hydroxy-3-aethoxy-benzaldehyd
• CAS: 70842-33-0
• 化学式: C₉H₉ClO₃
• mdl: MFCD01169245
• 分子量: 200.622
• InChiKey: HXWPHQVLVFUYLR-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C
• 沸点：
  301.8±37.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2913000090
• 危险性防范说明：
  P264,P270,P280,P301+P312+P330,P305+P351+P338,P337+P313,P501
• 危险性描述：
  H302,H319

反应信息

• 作为反应物：
  描述：

  3-氯-5-乙氧基-4-羟基苯甲醛 在 哌啶 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 30.0h， 生成 5-((Z)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-3-methyl-4-oxothiazolidin-2-ylideneamino)-2-chlorobenzoic acid
  参考文献：
  名称：

  HL005—A new selective PPARγ antagonist specifically inhibits the proliferation of MCF-7

  摘要：

  Peroxisome proliferator-activated receptor-gamma (PPAR gamma) is a nuclear transcription factor which is involved in many diseases, such as diabetes, inflammation, dyslipidemia. hypertension, and cancer. Recently, there are many reports showing that PPAR gamma agonists have preclinical and clinical anticancer activity, with relatively few reports on anticancer effects of PPAR gamma antagonists. From our compound library, a novel 3-thiazolinone-modified benzoic acid derivative HL005 is found as PPAR gamma selective ligand through SPR analysis (K-D = 0.21 mu M), yeast two-hybrid results suggest that HL005 antagonize the potent PPAR gamma agonist rosiglitazone-induced recruitment of the coactivator for PPAR gamma (IC50 = 7.97 mu M). Different from the most reported PPAR gamma antagonist, HL005 can inhibit the proliferation of MCF-7 cell line in a concentration-dependent manner and induce cell cycle arrest at G2/M phase, other than interference with cell adhesion. In order to study the binding mode of this compound, three derivatives are synthesized to get more detail about the structure-activity relationship, molecular docking and the NMR spectra indicate that similar to most PPAR gamma ligand, the carboxylic acid group is an important moiety for HL005 and contributes strong interaction with PPAR gamma. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2011.01.019
• 作为产物：
  描述：

  乙基香兰素 在 sodium hydride 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以2.59 g的产率得到3-氯-5-乙氧基-4-羟基苯甲醛
  参考文献：
  名称：

  [EN] SPIRO AZETIDINE ISOXAZOLE DERIVATIVES AND THEIR USE AS SSTR5 ANTAGONISTS
  [FR] DÉRIVÉS DE SPIRO AZÉTIDINE ISOXAZOLE ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DE SSTR5

  摘要：

  提供一个具有SSTR5拮抗作用的化合物，该化合物由以下公式（1）或其盐表示：其中每个符号的定义与说明书中相同。

  公开号：

  WO2014142363A1

文献信息

• Efficient Co(OAc)2-catalyzed aerobic oxidation of EWG-substituted 4-cresols to access 4-hydroxybenzaldehydes
  作者：Jian-An Jiang、Jia-Lei Du、Dao-Hua Liao、Zhan-Guo Wang、Ya-Fei Ji

  DOI：10.1016/j.tetlet.2013.12.077

  日期：2014.2

  Co(OAc)2·4H2O/NaOH/O2/ethylene glycol reaction system that enables selective aerobic oxidation of a wide range of substrates covering 2,6-di-EWG-, 2,3,6-tri-EWG-, 2-EWG-, and 2-EWG-6-EDG-substituted 4-cresols into the corresponding 4-hydroxybenzaldehydes. Based on the experimental investigations and well-defined p-benzoquinone methides, a plausible reaction mechanism was proposed. Considering the simplicity of

  我们报告了一种高效的无配体Co（OAc）2 ·4H 2 O / NaOH / O 2 /乙二醇反应系统，该系统能够对包括2,6-di-EWG-，2,3在内的多种底物进行选择性好氧氧化，6-tri-EWG-，2-EWG-和2-EWG-6-EDG取代的4-甲酚变成相应的4-羟基苯甲醛。基于实验研究和明确定义的对苯醌甲基化物，提出了合理的反应机理。考虑到程序的简便性和产品的重要性，该方法有望成为相关的苄基C（sp 3）–H官能化化学中的一种有利且实用的工具。
• HETEROCYCLIC COMPOUND
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20160060273A1

  公开（公告）日：2016-03-03

  Provided is a compound represented by the following formula (1) or a salt thereof, which has an SSTR5 antagonistic action: wherein each symbol has the same definition as in the specification.

  提供的是以下式子（1）所代表的化合物或其盐，具有SSTR5拮抗作用：其中每个符号的定义与说明书中相同。
• A soil-disease-controlling agent
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0128006B1

  公开（公告）日：1991-09-18
• Piperidinyl Ureas Chemically Control Defective in Cullin Neddylation 1 (DCN1)-Mediated Cullin Neddylation
  作者：Jared T. Hammill、Daniel C. Scott、Jaeki Min、Michele C. Connelly、Gloria Holbrook、Fangyi Zhu、Amy Matheny、Lei Yang、Bhuvanesh Singh、Brenda A. Schulman、R. Kiplin Guy

  DOI：10.1021/acs.jmedchem.7b01277

  日期：2018.4.12

  We previously discovered and validated a class of piperidinyl ureas that regulate defective in cullin neddylation 1 (DCN1)-dependent neddylation of cullins. Here, we report preliminary structure-activity relationship studies aimed at advancing our high-throughput screen hit into a tractable tool compound for dissecting the effects of acute DCN1-UBE2M inhibition on the NEDD8/cullin pathway. Structure-enabled optimization led to a 100-fold increase in biochemical potency and modestly increased solubility and permeability as compared to our initial hit. The optimized compounds inhibit the DCN1- UBE2M protein-protein interaction in our TR-FRET binding assay and inhibit cullin neddylation in our pulse-chase NEDD8 transfer assay. The optimized compounds bind to DCN1 and selectively reduce steady-state levels of neddylated CUL1 and CUL3 in a squamous cell carcinoma cell line. Ultimately, we anticipate that these studies will identify early lead compounds for clinical development for the treatment of lung squamous cell carcinomas and other cancers.
• SPIRO AZETIDINE ISOXAZOLE DERIVATIVES AND THEIR USE AS SSTR5 ANTAGONISTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2970331A1

  公开（公告）日：2016-01-20