2-(4-氯苯氧基)烟酸 | 51362-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(4-氯苯氧基)烟酸
• 中文别名: 4-氯－2－硝基苯酚
• 英文名称: Li-6
• 英文别名: 2-(4-chlorophenoxy)nicotinic acid；2-(4-Chlorphenoxy)nicotinsaeure；2-(4-chlorophenoxy)pyridine-3-carboxylic acid
• CAS: 51362-37-9
• 化学式: C₁₂H₈ClNO₃
• mdl: MFCD00052116
• 分子量: 249.653
• InChiKey: FVAZJGJEENAKRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159°C
• 沸点：
  396.6±32.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，没有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉干燥处。确保工作环境有良好的通风或排气装置。

反应信息

• 作为反应物：
  描述：

  2-(4-氯苯氧基)烟酸 在 PPA 、 吡啶盐酸盐 作用下， 反应 16.0h， 生成 8-hydroxy-5H-chromeno[2,3-b]pyridin-5-one
  参考文献：
  名称：

  Benzopyranopyridine derivatives. 1. Aminoalkyl derivatives of the azaxanthenes as bronchodilating agents

  摘要：

  The preparation of the four isomeric azaxanthones 3 and a number of their aromatic ring substituted derivatives is described. These ketones were converted into the title compounds which were examined for their biological properties. The most interesting compound in this series, the 1-methyl-4-piperidylidene derivative of 1-azaxanthene, shows the profile of an orally effective potent bronchodilating agent as well as a moderate antihistamine. Biological properties of this compound were compared to a number of antihistamines as well as known bronchodilating agents. Structure-activity relationships are also discussed.

  DOI：

  10.1021/jm00235a001
• 作为产物：
  描述：

  2-氯烟酸 、 对氯苯酚 在 铜 、 potassium carbonate 作用下， 以 正丁醇 为溶剂， 以2%的产率得到2-(4-氯苯氧基)烟酸
  参考文献：
  名称：

  ML390的开发：一种人类DHODH抑制剂，可诱导急性髓样白血病的分化

  摘要：

  同源异型框转录因子A9（HoxA9）在70％的诊断为急性髓细胞性白血病（AML）的患者中过表达，而只有一小部分AML患者对当前的分化疗法有反应。过表达HoxA9的细胞系来自溶菌酶-GFP小鼠的骨髓。以这种方式，GFP充当了分化的内生报告基因，可以针对MLPCN文库进行高通量的表型筛选。优化了两个化学支架的活性以产生化合物ML390，并且遗传抗性和测序工作确定了二氢乳清酸脱氢酶（DHODH）为目标酶。DHODH抑制剂布雷喹纳也对这些白血病细胞起作用。与DHODH结合的ML390的X射线晶体结构阐明了ML390的结合相互作用。

  DOI：

  10.1021/acsmedchemlett.6b00316

文献信息

• [EN] NOVEL QUINAZOLINE DERIVATIVES AND METHODS OF TREATMENT RELATED TO THE USE THEREOF<br/>[FR] NOUVEAUX DERIVES DE QUINAZOLINE ET LEUR UTILISATION THERAPEUTIQUE
  申请人：TAISHO PHARMA CO LTD

  公开号：WO2004087680A1

  公开（公告）日：2004-10-14

  The present invention relates to novel compounds of Formula (I): which act as MCH receptor antagonists. These compositions are useful in pharmaceutical compositions whose use includes prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and addiction.

  本发明涉及一种新型化合物，其化学式为（I），该化合物作为MCH受体拮抗剂。这些组合物在药物组合物中具有用途，包括预防或治疗改善记忆功能、睡眠和觉醒、焦虑、抑郁、情绪障碍、癫痫、肥胖、糖尿病、食欲和进食障碍、心血管疾病、高血压、血脂异常、心肌梗死、暴食障碍，包括暴食症、厌食症、精神障碍，包括躁郁症、精神分裂症、谵妄、痴呆、压力、认知障碍、注意力缺陷障碍、物质滥用障碍和运动障碍，包括帕金森病、癫痫和成瘾症。
• Activation and Inhibition of Kidney CLC-K Chloride Channels by Fenamates
  作者：Antonella Liantonio、Alessandra Picollo、Elena Babini、Giuseppe Carbonara、Giuseppe Fracchiolla、Fulvio Loiodice、Vincenzo Tortorella、Michael Pusch、Diana Conte Camerino

  DOI：10.1124/mol.105.017384

  日期：2006.1

  CLC-K Cl– channels are selectively expressed in kidney and ear, where they are pivotal for salt homeostasis, and loss-of-function mutations of CLC-Kb produce Bartter's syndrome type III. The only ligand known for CLC-K channels is a derivative of the 2- p -chlorophenoxypropionic acid (CPP), 3-phenyl-CPP, which blocks CLC-Ka, but not CLC-Kb. Here we show that in addition to this blocking site, CLC-K channels bear an activating binding site that controls channel opening. Using the voltage-clamp technique on channels expressed in Xenopus laevis oocytes, we found that niflumic acid (NFA) increases CLC-Ka and CLC-Kb currents in the 10 to 1000 μM range. Flufenamic acid (FFA) derivatives or high doses of NFA produced instead an inhibitory effect on CLC-Ka, but not on CLC-Kb, and on blocker-insensitive CLC-Ka mutants, indicating that the activating binding site is distinct from the blocker site. Evaluation of the sensitivity of CLC-Ka to derivatives of NFA and FFA together with a modeling study of these ligands allow us to conclude that one major characteristic of activating compounds is the coplanarity of the two rings of the molecules, whereas block requires a noncoplanar configuration. These molecules provide a starting point for identification of diuretics or drugs useful in the treatment of Bartter's syndrome.

  CLC-K Cl– 渠道在肾脏和耳朵中特异性表达，它们对盐的稳态至关重要，CLC-Kb 的功能缺失突变可导致 III 型巴特综合征。目前已知的 CLC-K 渠道唯一配体是 2- p -氯苯氧丙酸 (CPP) 的衍生物 3-苯基-CPP，它可以阻断 CLC-Ka，但不影响 CLC-Kb。在这里，我们展示了除了该阻断位点外，CLC-K 渠道还具有一个激活结合位点，该位点控制通道的开启。通过对表达在非洲爪蛙卵母细胞中的通道使用电压夹持技术，我们发现氟尼辛酸 (NFA) 在 10 至 1000 μM 范围内增加了 CLC-Ka 和 CLC-Kb 的电流。氟芬那酸 (FFA) 的衍生物或高剂量的 NFA 对 CLC-Ka 产生了抑制作用，而对 CLC-Kb 则没有，并且在对阻断剂不敏感的 CLC-Ka 突变体上同样显示出该作用，表明激活结合位点与阻断位点是不同的。对 CLC-Ka 对 NFA 和 FFA 衍生物的敏感性评估，以及对这些配体的建模研究，让我们得出结论：激活化合物的一个主要特征是分子两个环的共平面性，而阻断则需要非共平面构型。这些分子为识别利尿剂或在治疗巴特综合征方面有用的药物提供了起点。
• Design, Synthesis, and Herbicidal Activity of Novel Diphenyl Ether Derivatives Containing Fast Degrading Tetrahydrophthalimide
  作者：Li-Xia Zhao、Mao-Jun Jiang、Jia-Jun Hu、Yue-Li Zou、Yuan Cheng、Tao Ren、Shuang Gao、Ying Fu、Fei Ye

  DOI：10.1021/acs.jafc.0c00947

  日期：2020.3.25

  against maize PPO and similar herbicidal activities to Oxyfluorfen in weeding experiments in greenhouses and field weeding experiments. In view of the inspected bioactivities, the structure-activity relationship (SAR) of this series of compounds was also discussed. Crop selection experiments demonstrates that compound 6c is safe for soybeans, maize, rice, peanuts and cotton at a dose of 300 g ai/ha. Accumulation

  为了寻找具有更好生物活性的新型原卟啉原氧化酶（PPO）抑制剂，基于亚结构剪接和生物异构化的原理，设计了一系列新型的含有四氢邻苯二甲酰亚胺的二苯醚衍生物。PPO抑制实验显示6c是最有潜力的化合物，其半数最大抑制浓度（IC50）值为0.00667 mg / L，显示出比抗氧氟芬（IC50 = 0.0426 mg / L）高7倍的抗玉米PPO活性和类似的除草活性在温室除草实验和田间除草实验中使用Oxyfluorfen。鉴于所检查的生物活性，还讨论了该系列化合物的结构-活性关系（SAR）。作物选择实验表明，化合物6c对于大豆，玉米，大米，花生和棉花的剂量为300 g ai / ha。积累分析实验表明，某些作物（大豆，花生和棉花）中6c的积累显着低于Oxyfluorfen。当前的工作表明化合物6c可以作为田间除草剂的新候选物开发。
• Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
  申请人：Buchwald L. Stephen

  公开号：US20060173186A1

  公开（公告）日：2006-08-03

  One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition metal-catalyzed: aryl amination reactions; aryl amidation reactions; Suzuki couplings; and Sonogashira couplings. In certain embodiments, the invention relates to catalysts and methods of using them that operate in aqueous solvent systems.

  本发明的一个方面涉及过渡金属配体。本发明的第二个方面涉及在各种过渡金属催化的碳-杂原子和碳-碳键形成反应中使用包含这些配体的催化剂。本方法提供了许多过渡金属催化反应的特征改进，包括适合底物的范围、催化剂周转次数、反应条件和效率。例如，在过渡金属催化的芳基胺化反应、芳基酰胺化反应、Suzuki偶联和Sonogashira偶联中已经实现了改进。在某些实施例中，本发明涉及在水溶剂体系中操作的催化剂及其使用方法。
• Synthesis of 1-Azaxanthones and 1-Azathioxanthones by Yb(OTf)3/TfOH Co-Catalyzed Intramolecular Friedel-Crafts Reaction
  作者：Weike Su、Can Jin、Jie Li

  DOI：10.3987/com-10-12029

  日期：——

  Intramolecular Friedel-Crafts cyclization of phenoxypyridine acids (3a-3j) and phenythiopyridine acids (4a-4i) to form 1-azaxanthones (1a-1j) and 1-azathioxanthones (2a-2i), respectively, was efficiently promoted by Yb(OTf) 3 /TfOH as co-catalysts. And a number of substrates could be cyclized in moderate to good yields.

  Yb(OTf) 有效促进苯氧基吡啶酸 (3a-3j) 和苯硫代吡啶酸 (4a-4i) 的分子内 Friedel-Crafts 环化分别形成 1-氮杂蒽酮 (1a-1j) 和 1-氮杂噻吨酮 (2a-2i) ) 3 /TfOH 作为助催化剂。并且许多底物可以以中等至良好的产率进行环化。