1-(cyclohexyloxy)-4-nitrobenzene | 5493-73-2

• 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: 1-(cyclohexyloxy)-4-nitrobenzene
• 英文别名: 1-cyclohexyloxy-4-nitrobenzene
• CAS: 5493-73-2
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: JZCYGTUBVIJZOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  189-191 °C(Press: 12 Torr)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(cyclohexyloxy)-4-nitrobenzene 在 10percent Pd/C 2-甲基苯磺酸 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 dimethyl 6-cyclohexyloxyquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  Synthesis and in Vitro Pharmacology of Substituted Quinoline-2,4-dicarboxylic Acids as Inhibitors of Vesicular Glutamate Transport

  摘要：

  The vesicular glutamate transport (VGLUT) system selectively mediates the uptake of L-glutamate into synaptic vesicles. Uptake is linked to an H+-ATPase that provides coupling among ATP hydrolysis, an electrochemical proton gradient, and glutamate transport. Substituted quinoline-2,4-dicarboxylic acids (QDCs), prepared by condensation of dimethyl keto-glutaconate (DKG) with substituted anilines and subsequent hydrolysis, were investigated as potential VGLUT inhibitors in synaptic vesicles. A brief panel of substituted QDCs was previously reported (Carrigan et al. Bioorg. Med. Chem. Lett. 1999, 9, 2607-2612), and showed that certain substituents led to more potent competitive inhibitors of VGLUT. Using these compounds as leads, an expanded series of QDC analogues were prepared either by condensation of DKG with novel anilines or via aryl-coupling (Suzuki or Heck) to dimethyl 6-bromoquino-linedicarboxylate. From the panel of almost 50 substituted QDCs tested as inhibitors of the VGLUT system, the 6-PhCH=CH-QDC (K-i = 167 muM), 6-PhCH2CH2-QDC (K-i = 143 muM), 6-(4'-phenylstyryl)-QDC (K-i = 64 AM), and 6-biphenyl-4-yl-QDC (K-i = 41 muM) were found to be the most potent blockers. A preliminary assessment of the key elements needed for binding to the VGLUT protein based on the structure-activity relationships for the panel of substituted QDCs is discussed herein. The substituted QDCs represent the first synthetically derived VGLUT inhibitors and are promising templates for the development of selective transporter inhibitors.

  DOI：

  10.1021/jm010261z
• 作为产物：
  描述：

  对氟硝基苯 、 环己醇 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 1-(cyclohexyloxy)-4-nitrobenzene
  参考文献：
  名称：

  谷氨酸类似物的合成作为白三烯A4水解酶的有效抑制剂。

  摘要：

  白三烯B（4）（LTB（4））是一种有效的促炎介质，已与多种疾病的发病机制有关，包括牛皮癣，炎症性肠病，多发性硬化症和哮喘。作为降低LTB（4）水平并可能确定新疗法的方法，已探索了LTB（4）生物合成酶白三烯A（4）水解酶（LTA（4）-h）的抑制剂。在这里，我们从相应的甘氨酰胺2开始，描述了一种有效的LTA（4）-h抑制剂-谷氨酸4f的芳基酰胺的发现。然后介绍了4f的类似物，重点研究在全血中既有活性又稳定的化合物。这项工作最终确定了符合这些标准的氨基醇12a和氨基酯6b。

  DOI：

  10.1016/j.bmc.2008.03.042

文献信息

• [EN] 5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS DE 5-SULFAMOYL-2-HYDROXYBENZAMIDE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017153952A1

  公开（公告）日：2017-09-14

  The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代水杨酰胺衍生物。具体而言，本发明涉及根据公式(I)的化合物：其中R、R1和R2如本文所述，或其药用可接受的盐。本发明的化合物是CD73的抑制剂，可用于治疗癌症、前癌症综合症以及与CD73抑制相关的疾病，例如艾滋病、治疗HIV、自身免疫疾病、感染、动脉粥样硬化和缺血再灌注损伤。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制CD73活性和治疗与之相关的疾病的方法。
• A PEG₁₀₀₀-DAIL[CdCl₃]–toluene temperature-dependent biphasic system that regulates homogeneously catalyzed C–O coupling of organic halides with phenols and alcohols under ligand-free conditions
  作者：Yu Lin Hu、Xiao Yun Ma、Ming Lu

  DOI：10.1139/v10-170

  日期：2011.4

  An efficient, experimentally simple, and convenient procedure for the C–O coupling of organic halides with phenols and alcohols in a PEG₁₀₀₀-DAIL[CdCl₃]–toluene temperature-dependent biphasic system has been developed. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.

  在 PEG1000-DAIL[CdCl3]-甲苯温度依赖性双相体系中，开发了一种高效、实验简单且方便的有机卤化物与酚类和醇类的 C-O 偶联过程。通过简单的倾析就可以轻松分离出产物，而且催化系统可以循环和重复使用，不会丧失催化活性。
• Fe3O4@mesoporouspolyaniline: A Highly Efficient and Magnetically Separable Catalyst for Cross-Coupling of Aryl Chlorides and Phenols
  作者：R. Arundhathi、D. Damodara、Pravin R. Likhar、M. Lakshmi Kantam、P. Saravanan、Travis Magdaleno、Sun Hee Kwon

  DOI：10.1002/adsc.201000977

  日期：2011.6

  A high surface, magnetic Fe3O4@mesoporouspolyaniline core‐shell nanocomposite was synthesized from magnetic iron oxide (Fe3O4) nanoparticles and mesoporouspolyaniline (mPANI). The novel porous magnetic Fe3O4 was obtained by solvothermal method under sealed pressure reactor at high temperature to achieve high surface area. The mesoporouspolyaniline shell was synthesized by in situ surface polymerization

  由磁性氧化铁（Fe 3 O 4）纳米颗粒和介孔聚苯胺（mPANI）合成了高表面磁性Fe 3 O 4 @介孔聚苯胺核壳纳米复合材料。在密闭压力反应器中，在高温下通过溶剂热法获得了新型的多孔磁性Fe 3 O 4，从而获得了较大的表面积。通过在多孔磁性Fe 3 O 4上原位表面聚合合成介孔聚苯胺壳在聚乙烯吡咯烷酮（PVP）和十二烷基苯磺酸钠（SDBS）作为连接剂和结构导向剂的情况下，通过“黑莓纳米结构”组装。如各种表征技术所证实的，材料组成，化学计量比和反应条件在这些纳米结构的合成中起着至关重要的作用。中孔聚苯胺壳的作用是稳定多孔磁性Fe 3 O 4纳米颗粒，并提供直接进入核心Fe 3 O 4纳米颗粒的通道。在芳基氯和苯酚的交叉偶联中评估了磁性Fe 3 O 4 @mesoporousPANI纳米复合材料的催化活性。
• Studies on antidiabetic agents. II. Synthesis of 5-(4-(1-methylcyclohexylmethoxy)-benzyl)thiazolidine-2,4-dione (ADD-3878) and its derivatives.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、EIKO IMAMIYA、YASUO SUGIYAMA、TAKESHI FUJITA、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.30.3580

  日期：——

  More than 100 5-substituted thiazolidine-2, 4-diones were prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. The structure-activity relationship study showed that the 5-(4-oxybenzyl) moiety is essential for substantial activity. Among these compounds, 5-(4-cyclohexylmethoxy) benzylthiazolidine-2, 4-dione (47), 5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2, 4-dione (49, ADD-3878) and 5-4-[2-(3-pyridyl) ethoxy] benzyl} thiazolidine-2, 4-dione (59) exhibited the most favorable properties in terms of activity and toxicity.

  合成了100多种5-取代的噻唑烷-2,4-二酮类化合物，并通过遗传性肥胖和糖尿病小鼠（KK黄色小鼠）评估了它们的降血糖和降血脂活性。结构-活性关系研究表明，5-(4-羟基苄基)部分对于显著活性是必要的。在这些化合物中，5-(4-环己基甲氧基)苄基噻唑烷-2,4-二酮（47）、5-[4-(1-甲基环己基甲氧基)苄基]-噻唑烷-2,4-二酮（49，ADD-3878）和5-4-[2-(3-吡啶基)乙氧基]苄基}噻唑烷-2,4-二酮（59）在活性和毒性方面表现出最佳特性。
• [EN] PYRROLE AND PYRAZOLE DERIVATIVES AS POTENTIATORS OF GLUTAMATE RECEPTORS<br/>[FR] COMPOSES DE PYRROLE ET PYRAZOLE PRESENTANT UN EFFET POTENTIATEUR SUR LES RECEPTEURS DU GLUTAMATE
  申请人：LILLY CO ELI

  公开号：WO2005040110A1

  公开（公告）日：2005-05-06

  The present invention relates to pyrrole and pyrazole compounds of formula (I) and their pharmaceutically acceptable salts, and further relates to their use in treating schizophrenia, cognitive deficits associated with schizophrenia, Alzheimer's disease, dementia of the Alzheimer's type, mild cognitive impairment, or depression. The compounds act as potentiators on glutamate receptors, in particular AMPA and the GluR family.

  本发明涉及式(I)的吡咯和吡唑化合物及其药用可接受的盐，并且进一步涉及它们在治疗精神分裂症、与精神分裂症相关的认知缺陷、阿尔茨海默病、阿尔茨海默型痴呆、轻度认知障碍或抑郁症方面的应用。这些化合物作为谷氨酸受体的增强剂，特别是AMPA和GluR家族。