N-(4'-hydroxybiphenyl-3-yl)acetamide | 462660-26-0

• 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: N-(4'-hydroxybiphenyl-3-yl)acetamide
• 英文别名: 4-(3-Acetylaminophenyl)phenol；N-[3-(4-hydroxyphenyl)phenyl]acetamide
• CAS: 462660-26-0
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: XQOBDZNWQCBRSU-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C
• 沸点：
  474.0±28.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

SDS

N-[3-(4-hydroxyphenyl)phenyl]acetamideMSDS英文版

反应信息

• 作为反应物：
  描述：

  N-(4'-hydroxybiphenyl-3-yl)acetamide 在 potassium carbonate 作用下， 以 丙酮 、 N,N-二乙基苯胺 为溶剂， 反应 15.0h， 生成 N-(3'-allyl-4'-hydroxy-[1,1'-biphenyl]-3-yl)acetamide
  参考文献：
  名称：

  Design, Synthesis, and Anti-Proliferative Evaluation of [1,1′-biphenyl]-4-ols as Inhibitor of HUVEC Migration and Tube Formation

  摘要：

  烯丙基化联苯新木脂素包含多种化学预防实体，这些实体已被用作抗肿瘤药物的先导化合物。在此，我们评估了37种烯丙基化联苯对细胞增殖活性的抑制作用，以及它们对HUVEC迁移和管形成的抑制效应，这些效应具有抗血管生成特性。3-(2-甲基-3-丁烯-2-基)-3',5'-双(三氟甲基)-[1,1'-联苯]-4-醇（5c）对HUVEC的抑制作用强于细辛醇（IC50 = 47.0 vs. 52.6 μM），并且对C26、Hela、K562、A549和HepG2的增殖有显著阻断作用（IC50分别为15.0、25.0、21.2、29.5和13.0 μM），优于细辛醇的抑制作用（IC50分别为65.1、62.0、42.0、75.0和55.4 μM）。重要的是，化合物5c在体外抑制了HUVEC的迁移和类似毛细血管管的形成。

  DOI：

  10.3390/molecules17078091
• 作为产物：
  描述：

  4-溴苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.08h， 生成 N-(4'-hydroxybiphenyl-3-yl)acetamide
  参考文献：
  名称：

  Design, Synthesis, and Anti-Proliferative Evaluation of [1,1′-biphenyl]-4-ols as Inhibitor of HUVEC Migration and Tube Formation

  摘要：

  烯丙基化联苯新木脂素包含多种化学预防实体，这些实体已被用作抗肿瘤药物的先导化合物。在此，我们评估了37种烯丙基化联苯对细胞增殖活性的抑制作用，以及它们对HUVEC迁移和管形成的抑制效应，这些效应具有抗血管生成特性。3-(2-甲基-3-丁烯-2-基)-3',5'-双(三氟甲基)-[1,1'-联苯]-4-醇（5c）对HUVEC的抑制作用强于细辛醇（IC50 = 47.0 vs. 52.6 μM），并且对C26、Hela、K562、A549和HepG2的增殖有显著阻断作用（IC50分别为15.0、25.0、21.2、29.5和13.0 μM），优于细辛醇的抑制作用（IC50分别为65.1、62.0、42.0、75.0和55.4 μM）。重要的是，化合物5c在体外抑制了HUVEC的迁移和类似毛细血管管的形成。

  DOI：

  10.3390/molecules17078091

文献信息

• Ionic Liquid Acceleration of Solid-Phase Suzuki−Miyaura Cross-Coupling Reactions
  作者：Jefferson D. Revell、A. Ganesan

  DOI：10.1021/ol0263292

  日期：2002.9.1

  [reaction: see text] Room-temperature ionic liquids promote various transition metal-catalyzed reactions in the solution phase. Here, for the first time, we show that these effects are translatable to solid-phase reactions. The Suzuki-Miyaura cross-coupling of 4-iodophenol immobilized on polystyrene-Wang resin with various arylboronic acids was significantly accelerated by the ionic liquid 1-butyl

  [反应：见正文]室温离子液体在溶液相中促进各种过渡金属催化的反应。在这里，我们首次展示了这些作用可转化为固相反应。离子液体1-丁基-3-甲基咪唑四氟硼酸酯（[bmim] [BF（4）（-）]）显着加速了固定在聚苯乙烯-Wang树脂上的4-碘苯酚与各种芳基硼酸的Suzuki-Miyaura交叉偶联。 。
• 17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold
  作者：Marie Wetzel、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1016/j.bmc.2010.12.013

  日期：2011.1

  17 beta-Hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) catalyses the conversion of active 17 beta-hydroxysteroids into the less active 17-ketosteroids thereby controlling the availability of biologically active estrogens (E2) and androgens (T) in the tissues. The skeletal disease osteoporosis occurs mainly in post-menopausal women and in elderly men when the levels of estrogens and androgens, respectively, decrease. Since 17 beta-HSD2 is present in osteoblasts, inhibition of this enzyme may provide a new and promising approach to prevent the onset of osteoporosis, keeping a certain level in estrogens and androgens in bone cells of ageing people. Hydroxynaphthyl, hydroxyphenyl and hydroxymethylphenyl-substituted moieties were synthesised as mimetics of the steroidal substrate. Compound 8 has been identified as promising scaffold for 17 beta-HSD2 inhibitors displaying high activity and good selectivity toward 17 beta-HSD1, ER alpha and ER beta. (C) 2010 Elsevier Ltd. All rights reserved.
• Structure-Based Drug Design and Optimization of Mannoside Bacterial FimH Antagonists
  作者：Zhenfu Han、Jerome S. Pinkner、Bradley Ford、Robert Obermann、William Nolan、Scott A. Wildman、Doug Hobbs、Tom Ellenberger、Corinne K. Cusumano、Scott J. Hultgren、James W. Janetka

  DOI：10.1021/jm100438s

  日期：2010.6.24

  FimH-mediated cellular adhesion to mannosylated proteins is critical in the ability of uropathogenic E. coli (UPEC) to colonize and invade the bladder epithelium during urinary tract infection. We describe the discovery and optimization of potent small-molecule FimH bacterial adhesion antagonists based on alpha-D-mannose 1-position anomeric glycosides using X-ray structure-guided drug design. Optimized biarylmannosides display low nanomolar binding affinity for FimH in a fluorescence polarization assay and submicromolar cellular activity in a hemagglutination (HA) functional cell assay of bacterial adhesion. X-ray crystallography demonstrates that the biphenyl moiety makes several key interactions with the outer surface of FimH including pi-pi interactions with Tyr-48 and an H-bonding electrostatic interaction with the Arg-98/Glu-50 salt bridge. Dimeric analogues linked through the biaryl ring show an impressive 8-fold increase in potency relative to monomeric matched pairs and represent the most potent FimH antagonists identified to date. The FimH antagonists described herein hold great potential for development as novel therapeutics for the effective treatment of urinary tract infections.
• Design, Synthesis, and Anti-Proliferative Evaluation of [1,1′-biphenyl]-4-ols as Inhibitor of HUVEC Migration and Tube Formation
  作者：Yan Ran、Liang Ma、Xuewei Wang、Jinying Chen、Guangcheng Wang、Aihua Peng、Lijuan Chen

  DOI：10.3390/molecules17078091

  日期：——

  Allylated biphenol neolignans contain a variety of chemopreventive entities that have been used as anti-tumor drug leads. Herein, 37 allylated biphenols were evaluated for anti-proliferative activity by the MTT assay and inhibitory effect on the migration and tube formation of HUVECs featuring anti-angiogenic properties. 3-(2-Methylbut-3-en-2-yl)-3′,5′-bis(trifluoromethyl)-[1,1′-biphenyl]-4-ol (5c) exerted an inhibitory effect on HUVECs compared to honokiol (IC50 = 47.0 vs. 52.6 μM) and showed significant blocking effects on the proliferation of C26, Hela, K562, A549, and HepG2 (IC50 = 15.0, 25.0, 21.2, 29.5, and 13.0 μM, respectively), superior to those of honokiol (IC50 = 65.1, 62.0, 42.0, 75.0, and 55.4 μM, respectively). Importantly, compound 5c inhibited the migration and capillary-like tube formation of HUVECs in vitro.

  烯丙基化联苯新木脂素包含多种化学预防实体，这些实体已被用作抗肿瘤药物的先导化合物。在此，我们评估了37种烯丙基化联苯对细胞增殖活性的抑制作用，以及它们对HUVEC迁移和管形成的抑制效应，这些效应具有抗血管生成特性。3-(2-甲基-3-丁烯-2-基)-3',5'-双(三氟甲基)-[1,1'-联苯]-4-醇（5c）对HUVEC的抑制作用强于细辛醇（IC50 = 47.0 vs. 52.6 μM），并且对C26、Hela、K562、A549和HepG2的增殖有显著阻断作用（IC50分别为15.0、25.0、21.2、29.5和13.0 μM），优于细辛醇的抑制作用（IC50分别为65.1、62.0、42.0、75.0和55.4 μM）。重要的是，化合物5c在体外抑制了HUVEC的迁移和类似毛细血管管的形成。