3-fluoro-4′-methoxybiphenyl-4-amine

• 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: 3-fluoro-4′-methoxybiphenyl-4-amine
• 英文别名: 3-Fluoro-4'-methoxy[1,1'-biphenyl]-4-amine；2-fluoro-4-(4-methoxyphenyl)aniline
• 化学式: C₁₃H₁₂FNO
• 分子量: 217.243
• InChiKey: OYANDXPRTYQMHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-fluoro-4′-methoxybiphenyl-4-amine 在 三光气 作用下， 以 氯仿 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  作为新型人二氢乳清酸脱氢酶抑制剂的 4-噻唑烷酮衍生物的结构优化和构效关系

  摘要：

  人类二氢乳清酸脱氢酶（hDHODH）是开发免疫抑制药物的有吸引力的靶标之一，也是抗癌药物和抗白血病药物的潜在靶标。开发有前景的 hDHODH 抑制剂的需求量很大。基于我们之前报道的4-噻唑烷酮衍生物的独特结合模式，通过分子对接方法，设计并合成了三个新系列的4-噻唑烷酮衍生物作为hDHODH抑制剂。研究了初步的构效关系。联苯系列化合物9和酰胺系列化合物37的IC50值分别为1.32 μM和1.45 μM。该研究将为hDHODH抑制剂新结构的研究提供有价值的参考。

  DOI：

  10.3390/molecules24152780
• 作为产物：
  描述：

  2-氟-4-碘苯胺 、 4-甲氧基苯硼酸 在 potassium carbonate 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙醇 为溶剂， 生成 3-fluoro-4′-methoxybiphenyl-4-amine
  参考文献：
  名称：

  作为新型人二氢乳清酸脱氢酶抑制剂的 4-噻唑烷酮衍生物的结构优化和构效关系

  摘要：

  人类二氢乳清酸脱氢酶（hDHODH）是开发免疫抑制药物的有吸引力的靶标之一，也是抗癌药物和抗白血病药物的潜在靶标。开发有前景的 hDHODH 抑制剂的需求量很大。基于我们之前报道的4-噻唑烷酮衍生物的独特结合模式，通过分子对接方法，设计并合成了三个新系列的4-噻唑烷酮衍生物作为hDHODH抑制剂。研究了初步的构效关系。联苯系列化合物9和酰胺系列化合物37的IC50值分别为1.32 μM和1.45 μM。该研究将为hDHODH抑制剂新结构的研究提供有价值的参考。

  DOI：

  10.3390/molecules24152780

文献信息

• Discovery of a novel series of DHODH inhibitors by a docking procedure and QSAR refinement
  作者：Johann Leban、Wael Saeb、Gabriel Garcia、Roland Baumgartner、Bernd Kramer

  DOI：10.1016/j.bmcl.2003.10.021

  日期：2004.1

  A novel series of DHODH inhibitors was developed based on a lead which was obtained by a docking procedure and a medicinal chemistry exploration. The activity of the initial lead was improved by a QSAR method to yield low nanomolar inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.
• Trimethoxybenzanilide-Based P-Glycoprotein Modulators: An Interesting Case of Lipophilicity Tuning by Intramolecular Hydrogen Bonding
  作者：Piero Tardia、Angela Stefanachi、Mauro Niso、Diana Antonella Stolfa、Giuseppe Felice Mangiatordi、Domenico Alberga、Orazio Nicolotti、Gianluca Lattanzi、Angelo Carotti、Francesco Leonetti、Roberto Perrone、Francesco Berardi、Amalia Azzariti、Nicola Antonio Colabufo、Saverio Cellamare

  DOI：10.1021/jm500697c

  日期：2014.8.14

  One of the principal reasons for the chemotherapy failure is the overexpression of drug efflux pumps, ABCB1 (also known as MDR1 or P-gp) and ABCC1 (also known as MRP1), whose inhibition remains a priority to circumvent drug resistance. We have recently shown a clear trend between lipophilicity and P-glycoprotein inhibitory activity for a class of galloyl-based modulators targeting P-glycoprotein and MRP1. Herein we report a new series of polymethoxy benzamides, whose lipophilicity was modulated through the establishment of an intramolecular hydrogen bond (IMHB) which allows reaching of P-gp inhibitory activity at the submicromolar IC50 level. The present study provides a strong rationale for candidates in the presence of IMHB as a key element for a high P-gp inhibitory activity.
• Design, synthesis, and nematicidal activities of novel 1,3-thiazin(thiazol)-4-one derivatives against <i>Meloidogyne incognita</i>
  作者：Haowu Jia、Wei Guo、Wei Li、Tingfang Li、Xiulei Chen、Zhong Li、Xiaoyong Xu

  DOI：10.1177/1747519819857506

  日期：2019.5

  Four series of novel 1,3-thiazin(thiazol)-4-one derivatives were synthesized by Suzuki coupling. Preliminary bioassays showed that most of the synthesized compounds exhibited good inhibitory activity in vivo against root-knot nematodes, Meloidogyne spp. at 20 mg L⁻¹. Among the tested compounds, we found that two compounds displayed 46.4% and 41.4% inhibitory activity even at 1 mg L⁻¹, respectively.
• Structural Optimization and Structure–Activity Relationship of 4-Thiazolidinone Derivatives as Novel Inhibitors of Human Dihydroorotate Dehydrogenase
  作者：Fanxun Zeng、Lina Quan、Guantian Yang、Tiantian Qi、Letian Zhang、Shiliang Li、Honglin Li、Lili Zhu、Xiaoyong Xu

  DOI：10.3390/molecules24152780

  日期：——

  and anti-leukemic drugs. The development of promising hDHODH inhibitors is in high demand. Based on the unique binding mode of our previous reported 4-thiazolidinone derivatives, via molecular docking method, three new series 4-thiazolidinone derivatives were designed and synthesized as hDHODH inhibitors. The preliminary structure–activity relationship was investigated. Compound 9 of biphenyl series

  人类二氢乳清酸脱氢酶（hDHODH）是开发免疫抑制药物的有吸引力的靶标之一，也是抗癌药物和抗白血病药物的潜在靶标。开发有前景的 hDHODH 抑制剂的需求量很大。基于我们之前报道的4-噻唑烷酮衍生物的独特结合模式，通过分子对接方法，设计并合成了三个新系列的4-噻唑烷酮衍生物作为hDHODH抑制剂。研究了初步的构效关系。联苯系列化合物9和酰胺系列化合物37的IC50值分别为1.32 μM和1.45 μM。该研究将为hDHODH抑制剂新结构的研究提供有价值的参考。