5-chloro-2-hydroxy-N-methylbenzamide | 70112-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-2-hydroxy-N-methylbenzamide
• 英文别名: N-Methyl-5-chlor-salicylamid；N-(5-chlorosalicyloyl)(methyl)amine
• CAS: 70112-20-8
• 化学式: C₈H₈ClNO₂
• mdl: MFCD11130734
• 分子量: 185.61
• InChiKey: GMFBXDUNANTIIL-UHFFFAOYSA-N

物化性质

• 沸点：
  322.2±32.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N-[(3-endo)-8-(4-chlorobenzyl)-8-azabicyclo[3.2.1]oct-3-yl]acetamide 、 5-chloro-2-hydroxy-N-methylbenzamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以16%的产率得到5-chloro-2-(2-((3-endo)-8-(4-chlorobenzyl)-8-azabicyclo[3.2.1]octan-3-ylamino)-2-oxoethoxy)-N-methylbenzamide
  参考文献：
  名称：

  WO2006/133802

  摘要：

  公开号：
• 作为产物：
  描述：

  5-氯代水杨酸 在 草酰氯 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 5-chloro-2-hydroxy-N-methylbenzamide
  参考文献：
  名称：

  金 (I) 催化水杨酰胺与炔烃的异环化反应：1,3-Benzoxazin-4-one 衍生物的合成

  摘要：

  金 (I) 催化的杂环化提供了高效且直接的杂环化合物构建。在此，我们开发了一种金 (I) 催化的水杨酸酰胺与炔烃的异环化反应，产生了广泛的 1,3-benzoxazin-4-ones。通过合成含有季碳中心的各种取代的苯并恶嗪酮，突出了该协议的实用性，显示出由此引入的反应过程的高官能团耐受性和优异的原子经济性。

  DOI：

  10.1021/acs.orglett.2c02066

文献信息

• N-amide Derivatives of 8-Azabicyclo[3.2.1]OCT-3-YL AS CCR1 Antagonists
  申请人：Terricabras Belart Emma

  公开号：US20090130090A1

  公开（公告）日：2009-05-21

  New antagonists of the interaction between the CCR1 Chemokine receptor and its ligands, including MIP-1α (CCL3), represented by formula (I) are disclosed, as well as pharmaceutical compositions comprising them and their use in therapy for the treatment of pathological conditions or diseases susceptible of being improved by antagonism of the CCR1 receptor.

  本发明揭示了与其配体（包括MIP-1α（CCL3））的CCR1趋化因子受体之间相互作用的新拮抗剂，其表示为公式（I）。此外，还揭示了包含它们的制药组合物以及它们在治疗病理情况或疾病中的使用，这些病理情况或疾病可以通过抗CCR1受体的作用得到改善。
• 10.1021/acs.joc.4c00898
  作者：Abe, Masahiro、Kawamoto, Megumu、Mizukami, Akiho、Kimachi, Tetsutaro、Inamoto, Kiyofumi

  DOI：10.1021/acs.joc.4c00898

  日期：——

  Herein, we report a palladium-catalyzed method to synthesize 1,4-benzoxazepin-5-ones using salicylamides and propargyl carbonates. The heteroannulation provides a wide range of products in good to excellent yields with broad functional group tolerance. In addition, H2O is used as a low-cost, abundant, and safe solvent, which is important in terms of sustainability.

  在此，我们报道了一种使用水杨酰胺和碳酸炔丙酯合成 1,4-苯并氮杂卓-5-酮的钯催化方法。杂环化提供了多种产品，产率良好至优异，并且具有广泛的官能团耐受性。此外，H 2 O被用作低成本、丰富且安全的溶剂，这对于可持续性而言很重要。
• Structure–activity relationship of salicylic acid derivatives on inhibition of TNF-α dependent NFκB activity: Implication on anti-inflammatory effect of N-(5-chlorosalicyloyl)phenethylamine against experimental colitis
  作者：Jihye Kim、Sookjin Kang、Sungchae Hong、Soowhan Yum、Young Mi Kim、Yunjin Jung

  DOI：10.1016/j.ejmech.2011.11.030

  日期：2012.2

  To develop a more potent NF kappa B inhibitor from salicylic acid which is known to inhibit activity of NF kappa B, a transcription factor regulating genes involved in immunity, inflammation and tumorigenesis, derivatives of salicylic acid (SA) where the 5 position, carboxyl or hydroxyl group was modified were treated in HCT116 cells transfected with an NF kappa B dependent luciferase gene and LPS-stimulated RAW264.7 cells. Amidation of the carboxylic group or substitution of chlorine at the 5 position increased the ability of SA to suppress the expression of NF kappa B dependent luciferase and inducible nitric oxide synthase, a product of an NF kappa B target gene. Moreover, simultaneous amidation and chlorination of SA (5-chlorosalicylamide; 5-CSAM) conferred an additive NF kappa B inhibitory activity on SA. To further enhance the inhibitory activity. N-modification was imposed on 5-CSAM. N-(5-chlorosalicyloyl)phenethylamine (5-CSPA), N-(5-chlorosalicyloyl)3-phenylpropylamine (5-CSPPA) and N-(5-chlorosalicyloyl)4-hydroxyphenylethylamine (5-CSHPA) showed greater potencies for inhibiting NF kappa B activity than other derivatives. Their IC(50)s' in the luciferase assay measured 15 mu M (5-CSPA), 17 mu M (5-CSPPA) and 91 mu M (5-CSHPA). Rectal administration of 5-CSPA ameliorated TNBS-induced rat colitis, which was more effective than a conventional drug, 5-aminosalicylic acid. These data may provide useful information for development of a therapeutic agent for treatment of diseases where NF kappa B plays a critical role in the pathogenic progresses. (C) 2011 Elsevier Masson SAS. All rights reserved.
• N-AMIDE DERIVATIVES OF 8-AZABICYCLO[3.2.1]OCT-3-YL AS CCR1 ANTAGONISTS
  申请人：Almirall, S.A.

  公开号：EP1891064B1

  公开（公告）日：2009-09-02
• STAT3 INHIBITOR
  申请人：Board of Regents, The University of Texas System

  公开号：US20170152260A1

  公开（公告）日：2017-06-01

  Provided are STAT3 inhibitors and methods of treating inflammation or a hyperproliferative disease such as, e.g., cancer. In some aspects, compounds may be used to treat breast cancer, a head/neck cancer, a lung cancer, a prostate cancer, or pancreatic cancer.