N-(2-氯-4-硝基苯基)-1-羟基萘-2-羧酰胺 | 65570-43-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-(2-氯-4-硝基苯基)-1-羟基萘-2-羧酰胺
• 英文名称: 1-hydroxy-N-(2-chloro-4-nitrophenyl)-2-naphthamide
• 英文别名: N-(2-chloro-4-nitrophenyl)-1-hydroxy-2-naphthamlde；1-hydroxy-naphthalene-2-carboxylic acid 2-chloro-4-nitro-anilide；N-(2-chloro-4-nitrophenyl)-1-hydroxynaphthalene-2-carboxamide
• CAS: 65570-43-6
• 化学式: C₁₇H₁₁ClN₂O₄
• 分子量: 342.738
• InChiKey: DACDOWVXWKIAAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-氯-4-硝基苯基)-1-羟基萘-2-羧酰胺 以82%的产率得到
  参考文献：
  名称：

  SINGH H.; SHARMA S.; IYER R. N., Z. NATURFORSCH., 1978, C33, NO 5-6, 447-448

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-4-硝基苯胺 、 1-羟基-2-萘甲酸 在 三氯化磷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 4.0h， 生成 N-(2-氯-4-硝基苯基)-1-羟基萘-2-羧酰胺
  参考文献：
  名称：

  氯硝柳胺及其类似物作为寨卡病毒和SARS-CoV-2感染小分子抑制剂的应用

  摘要：

  寨卡病毒已成为全球人类健康的潜在威胁。之前的药物再利用筛选确定已批准的驱虫药氯硝柳胺是寨卡病毒感染的小分子抑制剂。然而，由于抗蠕虫药物通常设计为口服时吸收率较低，氯硝柳胺非常有限的生物利用度可能会阻碍其直接重新用作抗病毒药物。在这里，我们针对氯硝柳胺的苯胺和水杨酸区域进行了 SAR 研究，以改善微粒体代谢稳定性、渗透性和溶解性等理化性质。我们发现水杨酸区域的 5-溴取代保留了效力，同时提供了更好的药物样特性。具有 2'-OMe 和 2'-H 取代的苯胺区域的其他修饰也是有利的。我们发现4'-NO 2取代基可以被4'-CN或4'-CF 3取代基取代。总之，这些修饰为优化氯硝柳胺的结构提供了基础，以改善氯硝柳胺类似物作为治疗寨卡和其他病毒感染的药物先导候选药物的全身暴露。事实上，关键的类似物也能够将细胞从 SARS-CoV-2 感染的细胞病变效应中拯救出来，这表明与针对 COVID-19 大流行的治疗策略的相关性。

  DOI：

  10.1016/j.bmcl.2021.127906

文献信息

• Chemical uncouplers for the treatment of obesity
  申请人：——

  公开号：US20040138301A1

  公开（公告）日：2004-07-15

  This invention relates to chemical uncouplers with a broader safety window making the use of them in treating obesity and, consequently, in the treatment of obesity related diseases and conditions such as atherosclerosis, hypertension, diabetes, especially type 2 diabetes (NIDDM (non-insulin dependent diabetes mellitus)), impaired glucose tolerance, dyslipidemia, coronary heart disease, gallbladder disease, osteoarthritis and various types of cancer such as endometrial, breast, prostate and colon cancers and the risk for premature death as well as other conditions, such as diseases and disorders, which conditions are improved by an increase in mitochondrial respiration, more attractive.

  这项发明涉及一种化学解偶联剂，它具有更宽的安全窗口，使其在治疗肥胖症以及因此引发的相关疾病和状况，如动脉硬化、高血压、糖尿病（尤其是2型糖尿病（非胰岛素依赖型糖尿病））、葡萄糖耐量受损、血脂异常、冠心病、胆结石病、骨关节炎以及子宫内膜、乳房、前列腺和结肠等各种癌症以及过早死亡的风险等方面更具吸引力。此外，还包括其他通过增加线粒体呼吸得到改善的条件、疾病和紊乱。
• Glutamate receptor modulators and therapeutic agents
  申请人：Wood Richard Delarey

  公开号：US20090239919A1

  公开（公告）日：2009-09-24

  The present invention discloses methods of modulating the activity of Group I mGluRs using a defined class of benzamide compounds. In one embodiment, methods of modulating the activity of mGluR1 are provided. In another embodiment, methods of modulating the activity of mGluR5 are provided. In still another embodiment, methods of simultaneously modulating the activities of both mGluR1 and mGluR5 are provided. The present invention also provides methods of treating diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of benzamide compounds. The present invention further provides methods of preventing diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of compounds. Diseases and disorders contemplated include, inter alia, diseases and disorders of the central nervous system, the peripheral nervous system, the gastrointestinal system, the circulatory system, skin, retina, brain, heart, and lungs.

  本发明公开了利用一类明确定义的苯甲酰胺化合物调节I类mGluRs活性的方法。在一个实施例中，提供了调节mGluR1活性的方法。在另一个实施例中，提供了调节mGluR5活性的方法。在另一个实施例中，提供了同时调节mGluR1和mGluR5活性的方法。本发明还提供了利用属于明确定定义的苯甲酰胺化合物类的一个或多个化合物治疗由I类mGluRs完全或部分介导的疾病或紊乱的方法。本发明还提供了利用属于明确定定义的化合物类的一个或多个化合物预防由I类mGluRs完全或部分介导的疾病或紊乱的方法。所考虑的疾病和紊乱包括中枢神经系统、外周神经系统、胃肠系统、循环系统、皮肤、视网膜、大脑、心脏和肺等疾病和紊乱。
• Methods and compositions for treating obesity, preventing weight gain, promoting weight loss, promoting slimming, or treating or preventing the development of diabetes
  申请人：NAN Global, LLC

  公开号：US10849872B2

  公开（公告）日：2020-12-01

  The present invention relates to compositions and kits including a chemical uncoupler, such as tyrphostin 9 or precursor or a salt thereof, and compositions including a chemical uncoupler, such as tyrphostin 9 in combination with one or more therapeutic agents, for example, L-carnitine, which are useful, for example, in treating obesity, preventing weight gain, promoting weight loss/slimming, and/or treating or preventing the development of diabetes.

  本发明涉及包括化学解偶联剂的组合物和试剂盒，如tyrphostin 9或其前体或盐，以及包括化学解偶联剂的组合物，如tyrphostin 9与一种或多种治疗剂（例如左旋肉碱）的组合物，这些组合物在治疗肥胖症、防止体重增加、促进减肥/瘦身和/或治疗或预防糖尿病发展等方面有用。
• <p>Reversible Small Molecule Inhibitors of MAO A and MAO B with Anilide Motifs</p>
  作者：Jens Hagenow、Stefanie Hagenow、Kathrin Grau、Mohammad Khanfar、Lena Hefke、Ewgenij Proschak、Holger Stark

  DOI：10.2147/dddt.s236586

  日期：——

  Background: Ligands consisting of two aryl moieties connected via a short spacer were shown to be potent inhibitors of monoamine oxidases (MAO) A and B, which are known as suitable targets in treatment of neurological diseases. Based on this general blueprint, we synthesized a series of 66 small aromatic amide derivatives as novel MAO A/B inhibitors.Methods: The compounds were synthesized, purified and structurally confirmed by spectroscopic methods. Fluorimetric enzymological assays were performed to determine MAO A/B inhibition properties. Mode and reversibility of inhibition was determined for the most potent MAO B inhibitor. Docking poses and pharmacophore models were generated to confirm the in vitro results.Results: N-(2,4-Dinitrophenyl)benzo [d] [1,3]dioxole-5-carboxamide (55, ST-2043) was found to be a reversible competitive moderately selective MAO B inhibitor (IC50 = 56 nM, K-i = 6.3 nM), while N-(2,4-dinitrophenyl)benzamide (7, ST-2023) showed higher preference for MAO A (IC50 = 126 nM). Computational analysis confirmed in vitro binding properties, where the anilides examined possessed high surface complementarity to MAO A/B active sites.Conclusion: The small molecule anilides with different substitution patterns were identified as potent MAO A/B inhibitors, which were active in nanomolar concentrations ranges. These small and easily accessible molecules are promising motifs, especially for newly designed multitargeted ligands taking advantage of these fragments.
• Synthesis of substituted 1-hydroxy-2-naphthanilides as potential cestodicidal agents
  作者：S. K. Dubey、A. K. Singh、H. Singh、S. Sharma、R. N. Iyer、J. C. Katiyar、P. Goel、A. B. Sen

  DOI：10.1021/jm00209a020

  日期：1978.11

  A series of substituted 1-hydroxy-2-naphthanilides 4--14 has been synthesized by treating 1-hydroxy-2-naphthoic acids 2 with substituted anilines 3. The nitronaphthanilides, on reduction and subsequent treatment with thiophosgene, gave the corresponding substituted 2-naphthanilide isothiocyanates 30--33. Substitution of the chlorine of 8 by various cyclic amines gave 3'-nitro-4'-substituted 1-hydroxy-2-naphthanilides 15--21. Various 3-aryl-4-oxo-2,3-dihydro-1,3-naphthoxazine-2-thiones 34-43 and 3 aryl-2,4-dioxo-2,3-dihydro-1,3-naphthoxazines 44--51 have been prepared by reacting the corresonding naphthanilides with thiophosgene and ethyl chloroformate, respectively. All the compounds were tested for their cestodicidal activity against Hymenolepis nana infection in rats; 30 was found to be the most active compound of the series, showing 100% clearance of infection at a single oral dose of 7.5 mg/kg.