4'-甲酰基-4-(三氟甲基)-2-联苯甲腈 | 716344-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4'-甲酰基-4-(三氟甲基)-2-联苯甲腈
• 英文名称: 3'-fluoro-4'-methoxybiphenyl-4-carbaldehyde
• 英文别名: 3’-fluoro-4’-methoxy-[1,1’-biphenyl]-4-carbaldehyde；3'-fluoro-4'-(methyloxy)-4-biphenylcarbaldehyde；4-(3-Fluoro-4-methoxyphenyl)benzaldehyde
• CAS: 716344-20-6
• 化学式: C₁₄H₁₁FO₂
• 分子量: 230.239
• InChiKey: GQGLQEUFJZBPIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-甲酰基-4-(三氟甲基)-2-联苯甲腈 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到4'-(dibromomethyl)-3-fluorobiphenyl-4-ol
  参考文献：
  名称：

  ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives

  摘要：

  A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-beta (ERbeta). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radio-liaand binding assay of between 8-35 nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERbeta selective, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.028
• 作为产物：
  描述：

  4-溴-2-氟苯甲醚 在 四(三苯基膦)钯 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 4.67h， 生成 4'-甲酰基-4-(三氟甲基)-2-联苯甲腈
  参考文献：
  名称：

  ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives

  摘要：

  A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-beta (ERbeta). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radio-liaand binding assay of between 8-35 nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERbeta selective, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.028

文献信息

• [EN] AZABENZIMIDAZOLES AS FATTY ACID SYNTHASE INHIBITORS<br/>[FR] AZABENZAMIDAZOLES COMME INHIBITEURS D'ACIDE GRAS SYNTHASE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011066211A1

  公开（公告）日：2011-06-03

  This invention relates to the use of azabenzimidazole derivatives for the modulation, notably the inhibition of the activity or function of fatty acid synthase (FAS). Suitably, the present invention relates to the use of azabenzimidazoles in the treatment of cancer.

  这项发明涉及使用吡唑苯并咪唑衍生物来调节，特别是抑制脂肪酸合成酶（FAS）的活性或功能。适当地，本发明涉及在癌症治疗中使用吡唑苯并咪唑。
• AZABENZIMIDAZOLES AS FATTY ACID SYNTHASE INHIBITORS
  申请人：Chaudhari Amita M.

  公开号：US20120295915A1

  公开（公告）日：2012-11-22

  Disclosed are compounds having Formula (I), wherein R 1 , R 2 , R 3 , R 4 , Ra, Rb, X, Y, m, and n are defined herein and methods of using the same.

  本发明涉及具有公式（I）的化合物，其中R1、R2、R3、R4、Ra、Rb、X、Y、m和n在此定义，并且使用这些化合物的方法。
• Discovery of a structurally novel, potent, and once-weekly free fatty acid receptor 1 agonist for the treatment of diabetes
  作者：Bin Wang、Zongyu Cai、Huixin Yao、Shixuan Jiao、Siliang Chen、Zhongcheng Yang、Wanqiu Huang、Qiang Ren、Zhijun Cao、Ya Chen、Luyong Zhang、Zheng Li

  DOI：10.1016/j.ejmech.2022.114883

  日期：2023.1

  Type 2 diabetes mellitus (T2DM) is a lifelong disease that requires long-term medication to control glucose levels, and thereby long-acting drug has been clinically needed for improving medical adherence. The free fatty acid receptor 1 (FFA1) was considered as a promising target for several diseases, such as T2DM, pain and fatty liver. However, no once-weekly FFA1 agonist has been reported until now

  2型糖尿病（T2DM）是一种终生性疾病，需要长期服药来控制血糖水平，因此临床上需要长效药物来提高医疗依从性。游离脂肪酸受体 1 (FFA1) 被认为是治疗多种疾病（如 T2DM、疼痛和脂肪肝）的有希望的靶标。然而，直到现在还没有报道过每周一次的 FFA1 激动剂。在此，我们报告了 ZLY50 的成功发现，这是第一个每周一次的 FFA1 激动剂，具有全新的化学类型、高度激动活性和对 FFA1 的选择性。此外，ZLY50 有足够的脑暴露来激活脑中的 FFA1，它是第一个具有镇痛活性的口服 FFA1 激动剂。值得注意的是，ZLY50（每周一次）的长期抗糖尿病和抗脂肪肝作用优于 HWL-088（每日一次），一种高效的 FFA1 激动剂，具有比 3 期临床候选药物 TAK-875 更强的降糖作用。进一步的机制研究表明，ZLY50通过调节肝脏脂质代谢、线粒体功能和氧化应激相关基因的表达来减轻脂肪肝。
• Structure‐Activity Relationship and Mode‐Of‐Action Studies Highlight 1‐(4‐Biphenylylmethyl)‐1 <i>H</i> ‐imidazole‐Derived Small Molecules as Potent CYP121 Inhibitors
  作者：Isabell Walter、Sebastian Adam、Maria Virginia Gentilini、Andreas M. Kany、Christian Brengel、Andreas Thomann、Tim Sparwasser、Jesko Köhnke、Rolf W. Hartmann

  DOI：10.1002/cmdc.202100283

  日期：2021.9.16

  AbstractCYP121 of Mycobacterium tuberculosis (Mtb) is an essential target for the development of novel potent drugs against tuberculosis (TB). Besides known antifungal azoles, further compounds of the azole class were recently identified as CYP121 inhibitors with antimycobacterial activity. Herein, we report the screening of a similarity‐oriented library based on the former hit compound, the evaluation of affinity toward CYP121, and activity against M. bovis BCG. The results enabled a comprehensive SAR study, which was extended through the synthesis of promising compounds and led to the identification of favorable features for affinity and/or activity and hit compounds with 2.7‐fold improved potency. Mode of action studies show that the hit compounds inhibit substrate conversion and highlighted CYP121 as the main antimycobacterial target of our compounds. Exemplified complex crystal structures of CYP121 with three inhibitors reveal a common binding site. Engaging in both hydrophobic interactions as well as hydrogen bonding to the sixth iron ligand, our compounds block a solvent channel leading to the active site heme. Additionally, we report the first CYP inhibitors that are able to reduce the intracellular replication of M. bovis BCG in macrophages, emphasizing their potential as future drug candidates against TB.
• Display device
  申请人：Katoh Takashi

  公开号：US20070003735A1

  公开（公告）日：2007-01-04

  A novel display device is disclosed. The display device comprises a plural of liquid crystal layers disposed between a pair of electrodes respectively, wherein each of the liquid crystal layers shows an absorption peak at a different wavelength and comprises at least one dichroic dye and at least one dual-frequency switchable liquid crystal as a host liquid crystal.