3-(p-methoxyphenyl)-2,4-dicaroethoxy-5-hydroxy-5-methylcyclohexanone | 79988-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(p-methoxyphenyl)-2,4-dicaroethoxy-5-hydroxy-5-methylcyclohexanone
• 英文别名: diethyl 4-hydroxy-2-(4-methoxyphenyl)-4-methyl-6-oxocyclohexane-1,3-dicarboxylate；5-hydroxy-5-methyl-3-(4-methoxyphenyl)cyclohexanone-2,4-dicarboxylic acid diethyl ester；2-<4-Methoxy-phenyl>-4-hydroxy-4-methyl-6-oxo-cyclohexan-1,3-dicarbonsaeure-diaethylester；4-hydroxy-2-(4-methoxy-phenyl)-4-methyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester；4-Hydroxy-2-(4-methoxy-phenyl)-4-methyl-6-oxo-cyclohexan-1,3-dicarbonsaeure-diaethylester
• CAS: 79988-76-4
• 化学式: C₂₀H₂₆O₇
• mdl: MFCD00717798
• 分子量: 378.422
• InChiKey: OYIOCGPIKHIYRT-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  514.7±50.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(p-methoxyphenyl)-2,4-dicaroethoxy-5-hydroxy-5-methylcyclohexanone 在 氢氧化钾 作用下， 生成 3-(4-甲氧基苯基)戊二酸
  参考文献：
  名称：

  667.分子内酰化。第一部分：一些β-取代的戊二酸的闭环

  摘要：

  DOI：

  10.1039/jr9490003177
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-甲氧基苯甲醛 在 哌啶 作用下， 生成 3-(p-methoxyphenyl)-2,4-dicaroethoxy-5-hydroxy-5-methylcyclohexanone
  参考文献：
  名称：

  罗汉松科的化学—十五：罗汉松酸的精制

  摘要：

  描述了将二萜树脂酸，罗汉果酸转化为具有5元环D的四环体系。由13-（2'-羧乙基）衍生物III（RCH 2 CH 2 CO 2 H）以合理的产率制备了在C-15 1处带有CO基团的未取代环，但尝试将具有1'的化合物环化C-13的-取代的2'-羧乙基侧链不成功。从13-丙烯酰基化合物以低收率获得C-17酮，但从13-巴豆酰基化合物根本得不到。描述了一些涉及苯甲醚衍生物的模型实验。

  DOI：

  10.1016/0040-4020(68)88118-9

文献信息

• Synthesis of highly functionalized 3,4-cyclohexane-annelated coumarins
  作者：Chao-Yue Chen、Xiao-Mei Zhang、Jian-Jun Shi、Jie He

  DOI：10.1007/s11164-013-1212-2

  日期：2015.2

  Efficient synthetic access to highly functionalized 3,4-cyclohexane-annelated coumarins has been achieved by combining two methods. First, the important intermediates multisubstituted cyclic β-keto esters were prepared conveniently by condensing a variety of benzaldehydes with ethyl acetoacetate. A series of highly functionalized 3,4-cyclohexane-annelated coumarins were then synthesized by Amberlyst-15-catalyzed

  通过结合两种方法，可以有效地合成高度官能化的3,4-环己烷退火香豆素。首先，通过将各种苯甲醛与乙酰乙酸乙酯缩合，可方便地制备重要的中间体多取代的环状β-酮酯。然后，通过Amberlyst-15催化的多取代环β-酮酯与酚的Pechmann缩合反应，合成了一系列高度官能化的3,4-环己烷-退火香豆素。该合成方法的优点是反应条件温和，对各种官能团的耐受性好，产率令人满意。
• PREPARATION OF 4-ALKOXY-7-(TETRAHYDRO-PYRAN-4-YL)-BENZOTHIAZOL-2-YLAMINE DERIVATIVES
  申请人：Spurr Paul

  公开号：US20080108826A1

  公开（公告）日：2008-05-08

  Processes for the preparation of 4-alkoxytetrahydropyrane derivatives used in the preparation of 4-alkoxy-7-(tetrahydropyran-4-yl)-benzothiazol-2-ylamine and derivatives.

  用于制备4-烷氧基四氢吡喃衍生物的方法，用于制备4-烷氧基-7-(四氢吡喃-4-基)-苯并噻唑-2-基胺及其衍生物。
• Effect of Aryl-Cyclohexanones and their Derivatives on Macrophage Polarization In Vitro
  作者：Tainá L. Lubschinski、Luiz A. E. Pollo、Eduarda T. B. Mohr、Julia S. da Rosa、Luigi A. Nardino、Louis P. Sandjo、Maique W. Biavatti、Eduardo M. Dalmarco

  DOI：10.1007/s10753-022-01646-9

  日期：2022.8

  Macrophages are critical in both tissue homeostasis and inflammation, and shifts in their polarization have been indicated as pivotal for the resolution of inflammatory processes. Inflammation is a complex and necessary component of the immune response to stimuli that are harmful to host homeostasis and is regulated by cellular and molecular events that remain a source of ongoing investigation. Among the compounds studied that have potential against autoimmune and inflammatory diseases, cannabinoids are currently highlighted. In this work, nineteen aryl-cyclohexanones diesters and their derivatives were synthesized based on the aryl-cyclohexane skeleton of phytocannabinoids, such as cannabidiol (CBD), and were evaluated for their anti-inflammatory and macrophage polarization potential. The results showed that Compound 4 inhibited the production of nitric oxide in RAW 264.7 macrophages. Furthermore, it reduced the levels of pro-inflammatory cytokines IL-12p70, TNF-α, IFN-γ, MCP-1, and IL-6 while, at the same time, was able to increase the production of anti-inflammatory cytokines IL-4, IL-10, and IL-13. Compound 4 also reduced macrophage apoptosis, increased the expression of the CD206 (mannose receptor) and at the same time, decreased the expression of CD284 (TLR-4 receptor) on the surface of these cells. Finally, it increased the phagocytic capacity and inhibited the phosphorylation of the p65 of NF-kβ. In conclusion, Compound 4, identified as diethyl-4-hydroxy-2-(4-methoxyphenyl)-4-methyl-6-oxocyclohexane-1–3-dicarboxylate, showed significant anti-inflammatory effect, while demonstrating the ability to transform phenotypically macrophages from the M1 phenotype (pro-inflammatory) to the M2 phenotype (anti-inflammatory). This led us to hypothesize that the main mechanism of anti-inflammatory effect of this molecule is linked to its immune modulation capacity.

  巨噬细胞在组织稳态和炎症过程中都起着至关重要的作用，其极化的变化被认为是解决炎症过程的关键。炎症是免疫反应的一个复杂而必要的组成部分，它针对的是对宿主稳态有害的刺激，并受到细胞和分子事件的调节，而这些事件仍是研究的一个来源。在已研究的具有抗自身免疫性和炎症性疾病潜力的化合物中，大麻素是目前研究的重点。本研究以大麻二酚（CBD）等植物大麻素的芳基环己烷骨架为基础，合成了 19 种芳基环己酮二酯及其衍生物，并对其抗炎和巨噬细胞极化潜力进行了评估。结果表明，化合物 4 能抑制 RAW 264.7 巨噬细胞产生一氧化氮。此外，它还能降低促炎细胞因子 IL-12p70、TNF-α、IFN-γ、MCP-1 和 IL-6 的水平，同时还能增加抗炎细胞因子 IL-4、IL-10 和 IL-13 的产生。化合物 4 还能减少巨噬细胞凋亡，增加这些细胞表面 CD206（甘露糖受体）的表达，同时减少 CD284（TLR-4 受体）的表达。最后，它还提高了吞噬能力，抑制了 NF-kβ 的 p65 的磷酸化。总之，被鉴定为二乙基-4-羟基-2-（4-甲氧基苯基）-4-甲基-6-氧代环己烷-1-3-二甲酸酯的化合物 4 显示出了显著的抗炎效果，同时还显示出了将巨噬细胞从 M1 表型（促炎）转化为 M2 表型（抗炎）的能力。由此我们推测，该分子抗炎作用的主要机制与其免疫调节能力有关。
• Heteroarylakanoic acids as intergrin receptor antagonists
  申请人：——

  公开号：US20040092497A1

  公开（公告）日：2004-05-13

  The present invention relates to a class of compounds represented by formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of Formula (I), and methods of selectively antagonizing the &agr;&ngr;&bgr; 3 and/or the &agr;&ngr;&bgr; 5 integrin without significantly antagonizing the IIb/IIIa integrin. 1

  本发明涉及一类由式（I）表示的化合物或其药学上可接受的盐、包含式（I）化合物的制药组合物以及选择性拮抗&agr;&ngr;&bgr;3和/或&agr;&ngr;&bgr;5整合素而不显著拮抗IIb/IIIa整合素的方法。
• Heteroarylalkanoic acids as integrin receptor antagonists
  申请人：——

  公开号：US20020133023A1

  公开（公告）日：2002-09-19

  The present invention relates to a class of compounds represented by the Formula I 1 or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively antagonizing the &agr; V &bgr; 3 and/or the &agr; V &bgr; 5 integrin without significantly antagonizing the IIb/IIIa or &agr; V &bgr; 6 integrin.

  本发明涉及一类由式I1表示的化合物或其药学上可接受的盐，包括式I的药物组合物，并且涉及一种选择性拮抗&agr;V&bgr;3和/或&agr;V&bgr;5整合素而不显著拮抗IIb/IIIa或&agr;V&bgr;6整合素的方法。