methyl 2,4-dichloro-5-nitrobenzoate | 101495-62-9

• 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: methyl 2,4-dichloro-5-nitrobenzoate
• CAS: 101495-62-9
• 化学式: C₈H₅Cl₂NO₄
• mdl: MFCD11500792
• 分子量: 250.038
• InChiKey: VFUFURDNRHDVBS-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56 °C
• 沸点：
  342.5±37.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,4-dichloro-5-nitrobenzoate 在 potassium tert-butylate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 N1-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-carboxy-2-nitroaniline
  参考文献：
  名称：

  Design, Synthesis, and Preclinical Evaluations of Novel 4-Substituted 1,5-Diarylanilines as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor (NNRTI) Drug Candidates

  摘要：

  Twenty-one new 4-substituted diarylaniline compounds (DAANs) (series 13, 14, and 15) were designed, synthesized, and evaluated against wildtype and drug resistant HIV-1 viral strains. As a result, approximately a dozen new DAANs showed high potency with low nano- to subnanomolar EC50 values ranging from 0.2 to 10 nM. The three most promising compounds 14e, 14h, and 15h exhibited high potency against wild-type and drug-resistant viral strains with EC50 values at the subnanomolar level (0.29-0.87 nM) and were comparable to or more potent than the new NNRTI drug riplivirine (2) in the same assays. Drug like physicochemical property assessments revealed that the most active DAANs (EC50 < 10 nM) have better aqueous solubility (>1-90 mu g/mL at pH 7.4 and pH 2) and metabolic stability in vitro than 2, as well as desirable log P values (<5) and polar surface areas (PSA) (<140 A(2)). These promising results warrant further development of this novel compound class as potential potent anti-AIDS clinical trial candidates.

  DOI：

  10.1021/jm3007678
• 作为产物：
  描述：

  2,4-二氯苯甲酸 在 硫酸 、 硝酸 作用下， 反应 4.0h， 生成 methyl 2,4-dichloro-5-nitrobenzoate
  参考文献：
  名称：

  Optimization of 2,4-diarylanilines as non-nucleoside HIV-1 reverse transcriptase inhibitors

  摘要：

  The current optimization of 2,4-diarylaniline analogs (DAANs) on the central phenyl ring provided a series of new active DAAN derivatives 9a-9e, indicating an accessible modification approach that could improve anti-HIV potency against wild-type and resistant strains, aqueous solubility, and metabolic stability. A new compound 9e not only exhibited extremely high potency against wild-type virus (EC50 0.53 nM) and several resistant viral strains (EC50 0.36-3.9 nM), but also showed desirable aqueous solubility and metabolic stability, which were comparable or better than those of the anti-HIV-1 drug TMC278 (2). Thus, new compound 9e might be a potential drug candidate for further development of novel next-generation NNRTIs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.055

文献信息

• [EN] COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：AQUINNAH PHARMACEUTICALS INC

  公开号：WO2020117877A1

  公开（公告）日：2020-06-11

  Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.

  在这里，描述了用于调节与神经退行性疾病、肌肉骨骼疾病、癌症、眼科疾病和病毒感染相关的细胞中包涵体形成和应激颗粒的化合物、组合物和方法。
• [EN] BENZOTHIAZOLES AS GHRELIN RECEPTOR MODULATORS<br/>[FR] AGENTS THÉRAPEUTIQUES - 802
  申请人：ASTRAZENECA AB

  公开号：WO2009047558A1

  公开（公告）日：2009-04-16

  A compound of formula (I) or a pharmaceutically acceptable salt thereof in which R1, R2 , R3, R4 and m are as described in the specification for use in the treatment of obesity and/or diabetes.

  化合物的分子式（I）或其药用盐，其中R1、R2、R3、R4和m如说明书中所述，用于治疗肥胖和/或糖尿病。
• [EN] AGRICULTURAL CHEMICALS<br/>[FR] PRODUITS CHIMIQUES AGRICOLES
  申请人：REDAG CROP PROT LTD

  公开号：WO2018122559A1

  公开（公告）日：2018-07-05

  The present invention relates to compounds which are of use in the field of agriculture as herbicides. The invention also relates to methods of using said compounds and compositions comprising said compounds.

  本发明涉及在农业领域作为除草剂使用的化合物。该发明还涉及使用所述化合物的方法和包含所述化合物的组合物。
• META-DIARYLANILINE OR META-DIARYLPYRIDINAMINE COMPOUND, PREPARATION METHOD AND MEDICAL USES THEREOF
  申请人：INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY ACADEMY OF MILITARY MEDICAL SCIENCES P.L.A. CHINA

  公开号：US20150218088A1

  公开（公告）日：2015-08-06

  Meta-diarylaniline or meta-diarylpyridinamine compounds, methods for preparing the same and uses thereof in manufacture of a medicament. The compounds according to the present application have strong inhibitory activity (at nM level) against wild-type and various drug-resistant HIV viral strains, exhibit good druggability, and can be easily synthesized.

  元-二芳基苯胺或元-二芳基吡啶胺化合物，其制备方法以及在制造药物方面的用途。根据本申请的化合物在nM水平上对野生型和各种耐药性HIV病毒株具有强烈的抑制活性，表现出良好的药物可达性，并且可以容易地合成。
• THERAPEUTIC AGENTS
  申请人：ALLEN Jack McQueen

  公开号：US20120115845A1

  公开（公告）日：2012-05-10

  A compound of formula I or a pharmaceutically acceptable salt thereof in which R 1 , R 2 , R 3 , R 4 and m are as described in the specification for use in the treatment of obesity and/or diabetes.

  公式I的化合物或其药学上可接受的盐，其中R1、R2、R3、R4和m如说明书所述，用于治疗肥胖症和/或糖尿病。