3-(3-(4-methoxyphenyl)propyl)phenol | 63144-63-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(3-(4-methoxyphenyl)propyl)phenol
• 英文别名: 3-[3-(4-Methoxyphenyl)propyl]phenol
• CAS: 63144-63-8
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: VPUVUASMODAGIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-(4-methoxyphenyl)propyl)phenol 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 1-{2-hydroxy-4-[3-(4-methoxyphenyl)propyl]benzyl}piperidinium chloride
  参考文献：
  名称：

  Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues

  摘要：

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.

  DOI：

  10.1021/acs.jnatprod.5b00114
• 作为产物：
  描述：

  1-(3-hydroxyphenyl)-3-(4-methoxyphenyl)-1-propanone 在 nickel-aluminum alloy 作用下， 以 水 为溶剂， 以66%的产率得到3-(3-(4-methoxyphenyl)propyl)phenol
  参考文献：
  名称：

  查尔酮，二氢查耳酮和1,3-二芳基丙烷类似物作为抗炎剂的合成和生物学评估。

  摘要：

  通过醛醇缩合制备二十一个查耳酮，随后将这些化合物还原，得到相应的二氢查耳酮和1，3-二苯基丙烷衍生物。检查了合成产物对LPS活化的小鼠腹膜巨噬细胞中NO抑制的影响。在测试的化合物中，1,3-二芳基丙烷类似物2-（3-（3,4-二甲氧基苯基）丙基）-5-甲氧基苯酚（3p）对NO的产生表现出最显着的抑制作用。为了研究作用机理，通过免疫印迹研究了3p对iNOS和COX-2蛋白表达的影响。结果得出结论，3p能够通过ERK，p38和JNK减弱NF-κB信号传导而抑制LPS诱导的RAW264.7细胞中的iNOS表达。

  DOI：

  10.1016/j.bmcl.2017.02.038

文献信息

• Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products
  作者：Philip H. Gilmartin、Marisa C. Kozlowski

  DOI：10.1021/acs.orglett.0c00577

  日期：2020.4.17

  A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and

  描述了一种温和有效的方法，用于钒催化的分子内偶联的游离酚的偶联。相应的苯酚-二烯酮产品直接以高收率和低催化剂负载量制备。电子多样性的束缚酚前体具有良好的耐受性，催化方法有效地用作了合成三种天然产物和可合成的吗啡烷生物碱前体的关键步骤。
• SCHWARTZ M. A.; ROSE B. F.; HOLTON R. A.; SCOTT S. W.; VISHNUVAJJALA BABU+, J. AM. CHEM. SOC., 1977, 99, NO 8, 2571-2578
  作者：SCHWARTZ M. A.、 ROSE B. F.、 HOLTON R. A.、 SCOTT S. W.、 VISHNUVAJJALA BABU+

  DOI：——

  日期：——
• [EN] AMINOALKYL SUBSTITUTED CHALCONES AND ANALOGUES AND DERIVATIVES THEREOF<br/>[FR] CHALCONES SUBSTITUÉES PAR AMINOALKYLE ET ANALOGUES ET DÉRIVÉS ASSOCIÉS
  申请人：UNIV FREE STATE ZA

  公开号：WO2011151789A2

  公开（公告）日：2011-12-08

  This invention relates to B-ring aminoalkyl substituted chalcones and analogues thereof. It also relates to processes for the synthesis of such compounds and to the use of such compounds as medicaments, in particular but not exclusively for the treatment of cancer and malaria.
• Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues
  作者：Anke Wilhelm、Pravin Kendrekar、Anwar E. M. Noreljaleel、Efrem T. Abay、Susan L. Bonnet、Lubbe Wiesner、Carmen de Kock、Kenneth J. Swart、Jan Hendrik van der Westhuizen

  DOI：10.1021/acs.jnatprod.5b00114

  日期：2015.8.28

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.
• Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents
  作者：Mopur Vijaya Bhaskar Reddy、Hsin-Yi Hung、Ping-Chung Kuo、Guan-Jhong Huang、Yu-Yi Chan、Shiow-Chyn Huang、Shwu-Jen Wu、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmcl.2017.02.038

  日期：2017.4

  Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol

  通过醛醇缩合制备二十一个查耳酮，随后将这些化合物还原，得到相应的二氢查耳酮和1，3-二苯基丙烷衍生物。检查了合成产物对LPS活化的小鼠腹膜巨噬细胞中NO抑制的影响。在测试的化合物中，1,3-二芳基丙烷类似物2-（3-（3,4-二甲氧基苯基）丙基）-5-甲氧基苯酚（3p）对NO的产生表现出最显着的抑制作用。为了研究作用机理，通过免疫印迹研究了3p对iNOS和COX-2蛋白表达的影响。结果得出结论，3p能够通过ERK，p38和JNK减弱NF-κB信号传导而抑制LPS诱导的RAW264.7细胞中的iNOS表达。