2'-fluoro-[1,1'-biphenyl]-4-carboxamide | 259252-03-4

• 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: 2'-fluoro-[1,1'-biphenyl]-4-carboxamide
• 英文别名: 4-carbamoyl-2'-fluoro-[1,1'-biphenyl]；2'-Fluoro[1,1'-biphenyl]-4-carboxamide；4-(2-fluorophenyl)benzamide
• CAS: 259252-03-4
• 化学式: C₁₃H₁₀FNO
• mdl: MFCD00662441
• 分子量: 215.227
• InChiKey: URNKHGDLIDSVJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-((R)-2-benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxy-benzaldehyde 、 2'-fluoro-[1,1'-biphenyl]-4-carboxamide 在 三乙基硅烷 、 lithium hydroxide monohydrate 、 双氧水 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 51.5h， 生成 (2R)-2-benzyl-3-[3-[[[4-(2-fluorophenyl)benzoyl]amino]methyl]-4-propoxyphenyl]propanoic acid
  参考文献：
  名称：

  Design and synthesis of a series of α-benzyl phenylpropanoic acid-type peroxisome proliferator-activated receptor (PPAR) gamma partial agonists with improved aqueous solubility

  摘要：

  In the continuing study directed toward the development of peroxisome proliferator-activated receptor gamma (hPPARγ) agonist, we attempted to improve the water solubility of our previously developed hPPARγ-selective agonist 3, which is insufficiently soluble for practical use, by employing two strategies: introducing substituents to reduce its molecular planarity and decreasing its hydrophobicity via replacement of the adamantyl group with a heteroaromatic ring. The first approach proved ineffective, but the second was productive. Here, we report the design and synthesis of a series of α-benzyl phenylpropanoic acid-type hPPARγ partial agonists with improved aqueous solubility. Among them, we selected (R)-7j, which activates hPPARγ to the extent of about 65% of the maximum observed with a full agonist, for further evaluation. The ligand-binding mode and the reason for the partial-agonistic activity are discussed based on X-ray-determined structure of the complex of hPPARγ ligand-binding domain (LBD) and (R)-7j with previously reported ligand-LDB structures. Preliminal apoptotic effect of (R)-7j against human scirrhous gastric cancer cell line OCUM-2MD3 is also described.

  DOI：

  10.1016/j.bmc.2013.02.003

文献信息

• Novel imidazoles
  申请人：Bolton Louis Gary

  公开号：US20050239857A1

  公开（公告）日：2005-10-27

  Novel imidazoles are provided. The compounds are useful as HMGCo-A Reductase Inhibitor. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.

  提供了新型咪唑类化合物。这些化合物可用作HMGCo-A还原酶抑制剂。还提供了这些化合物的药物组合物。还提供了制备这些化合物的方法和使用这些化合物的方法。
• Design and synthesis of 2‐hydroxyl‐4‐methoxyl‐3‐(3‐methylbut‐2‐en‐1‐yl)‐6‐(4‐phenylbenzoylamino)benzoic acid derivatives as antibacterial agents based on cajaninstilbene acid scaffold hopping
  作者：Chang Zheng、Wen Hou、Jun Liu、Xiao‐Fang Xu、Jing Lin、Ping‐Hua Sun、Wei‐Min Chen

  DOI：10.1002/ddr.21556

  日期：2019.9

  novel structural scaffolds. Cajaninstilbene acid (CSA), which is isolated from pigeonpea leaves, has shown potent antibacterial activity. In this study, a series of 2‐hydroxyl‐4‐methoxyl‐3‐(3‐methylbut‐2‐en‐1‐yl)‐6‐(4‐phenylbenzoylamino)benzoic acid derivatives derived from CSA were designed and synthesized, and their antibacterial activities were evaluated. Several synthesized compounds exhibit better

  在临床上具有重要意义的细菌病原体中，多药耐药性的流行表明，迫切需要开发具有新型结构支架的新型抗菌剂。从木豆叶片中分离出来的卡那斯汀二烯酸（CSA）已显示出强大的抗菌活性。在这项研究中，设计和合成了一系列从CSA衍生出来的2-羟基-4-甲氧基-3-（3-甲基丁-2-烯-1-基）-6（4-苯基苯甲酰氨基）苯甲酸衍生物，并对它们的抗菌活性进行了评估。几种合成的化合物对金黄色葡萄球菌，表皮葡萄球菌和两株耐甲氧西林金黄色葡萄球菌的抗菌活性均优于CSA 。。同时，3- [4,5-二甲基噻唑-2-基] -2-，5-二苯基溴化四氮唑测定的结果表明，活性最高的化合物6u和6v在细菌和正常细胞之间具有良好的选择性。此外，对接研究产生的与6u细菌RNA聚合酶的良好结合暗示了这些合成化合物抗菌活性的可能机制。
• Proteasome inhibitors and methods of using the same
  申请人：Bernadini Raffaella

  公开号：US20050107307A1

  公开（公告）日：2005-05-19

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以通过抑制蛋白酶体活性等方式调节细胞凋亡。这些化合物和组合物可以用于诱导细胞凋亡并治疗癌症等疾病，以及与蛋白酶体活性直接或间接相关的其他疾病。
• Novel pyrroles and imidazoles
  申请人：Bolton Louis Gary

  公开号：US20060287378A1

  公开（公告）日：2006-12-21

  Novel imidazoles and novel pyrroles are provided. Also provided are pharmaceutical compositions, methods of making and methods of using the compounds.

  本发明提供了新型咪唑和新型吡咯。同时，还提供了制药组合物、制备方法和使用该化合物的方法。
• PROTEASOME INHIBITORS AND METHODS OF USING THE SAME
  申请人：Bernardini Raffaella

  公开号：US20090291918A1

  公开（公告）日：2009-11-26

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以调节细胞凋亡，例如通过抑制蛋白酶体活性。这些化合物和组合物可以用于诱导细胞凋亡和治疗癌症及其他与蛋白酶体活性直接或间接相关的疾病。