3'-fluoro-4-hydroxy-[1,1'-biphenyl]-3-carbaldehyde | 893737-53-6

• 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-hydroxy-[1,1'-biphenyl]-3-carbaldehyde
• 英文别名: 3'-Fluoro-4-hydroxy[1,1'-biphenyl]-3-carbaldehyde；5-(3-fluorophenyl)-2-hydroxybenzaldehyde
• CAS: 893737-53-6
• 化学式: C₁₃H₉FO₂
• mdl: MFCD06802112
• 分子量: 216.212
• InChiKey: GDNZOKFSUVWUNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-fluoro-4-hydroxy-[1,1'-biphenyl]-3-carbaldehyde 在 sodium 、 三氯氧磷 作用下， 反应 3.0h， 生成 ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-(3-fluorophenyl)-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Structure–Activity Relationship (SAR) Study of Ethyl 2-Amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (CXL017) and the Potential of the Lead against Multidrug Resistance in Cancer Treatment

  摘要：

  Multidrug resistance (MDR) against standard therapies poses a serious challenge in cancer treatment, and there is a clinical need for new anticancer agents that would selectively target MDR malignancies. Our previous studies have identified a 4H-chromene system, CXL017 (4) as an example, that can preferentially kill MDR cancer cells. To further improve its potency, we have performed detailed structure-activity relationship (SAR) studies at the 3, 4, and 6 positions of the 4H-chromene system. The results reveal that the 3 and 4 positions prefer rigid and hydrophobic functional groups while the 6 position prefers a meta or para-substituted aryl functional group and the substituent should be small and hydrophilic. We have also identified and characterized nine MDR cancer cells that acquire MDR through different mechanisms and demonstrated the scope of our new lead, 9g, to selectively target different MDR cancers, which holds promise to help manage MDR in cancer treatment.

  DOI：

  10.1021/jm300515q
• 作为产物：
  描述：

  3-氟苯基硼酸 、 5-溴水杨醛 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到3'-fluoro-4-hydroxy-[1,1'-biphenyl]-3-carbaldehyde
  参考文献：
  名称：

  Structure–Activity Relationship (SAR) Study of Ethyl 2-Amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (CXL017) and the Potential of the Lead against Multidrug Resistance in Cancer Treatment

  摘要：

  Multidrug resistance (MDR) against standard therapies poses a serious challenge in cancer treatment, and there is a clinical need for new anticancer agents that would selectively target MDR malignancies. Our previous studies have identified a 4H-chromene system, CXL017 (4) as an example, that can preferentially kill MDR cancer cells. To further improve its potency, we have performed detailed structure-activity relationship (SAR) studies at the 3, 4, and 6 positions of the 4H-chromene system. The results reveal that the 3 and 4 positions prefer rigid and hydrophobic functional groups while the 6 position prefers a meta or para-substituted aryl functional group and the substituent should be small and hydrophilic. We have also identified and characterized nine MDR cancer cells that acquire MDR through different mechanisms and demonstrated the scope of our new lead, 9g, to selectively target different MDR cancers, which holds promise to help manage MDR in cancer treatment.

  DOI：

  10.1021/jm300515q

文献信息

• Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates
  作者：David Grassi、Alexandre Alexakis

  DOI：10.1002/adsc.201500495

  日期：2015.10.12

  Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%)

  已经合成了两个新的N杂环卡宾（NHC）配体，并用于由格氏试剂和铝酸镁介导的无过渡金属的不对称烯丙基烷基化（AAA）。这些配体的使用在第三和第四立体中心的形成中显示出高产率并改善了区域和对映选择性。此外，这种改进方法的低催化剂负载量（最高0.3 mol％）和高可扩展性（最高10 mmol）为生物活性化合物和合成有价值的中间体提供了便捷的途径。
• Inhibitors of protein kinase for the treatment of disease
  申请人：——

  公开号：US20030187007A1

  公开（公告）日：2003-10-02

  The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.

  本发明部分涉及使用基于酚和羟基萘的化合物调节蛋白激酶功能的方法。这些方法涉及表达蛋白激酶的细胞。此外，该发明描述了使用本发明鉴定的化合物预防和治疗生物体中与蛋白激酶相关的异常情况的方法。此外，该发明涉及基于酚和羟基萘的化合物以及包含这些化合物的药物组合物。
• INHIBITORS OF PROTEIN KINASE FOR THE TREATMENT OF DISEASE
  申请人：LG Biomedical Institute

  公开号：EP1412327A2

  公开（公告）日：2004-04-28
• [EN] INHIBITORS OF PROTEIN KINASE FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE LA PROTEINE KINASE DESTINES AU TRAITEMENT D'UNE MALADIE
  申请人：LG BIOMEDICAL INST

  公开号：WO2002096867A2

  公开（公告）日：2002-12-05

  The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.
• Structure–Activity Relationship (SAR) Study of Ethyl 2-Amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4<i>H</i>-chromene-3-carboxylate (CXL017) and the Potential of the Lead against Multidrug Resistance in Cancer Treatment
  作者：Gopalakrishnan Aridoss、Bo Zhou、David L. Hermanson、Nicholas P. Bleeker、Chengguo Xing

  DOI：10.1021/jm300515q

  日期：2012.6.14

  Multidrug resistance (MDR) against standard therapies poses a serious challenge in cancer treatment, and there is a clinical need for new anticancer agents that would selectively target MDR malignancies. Our previous studies have identified a 4H-chromene system, CXL017 (4) as an example, that can preferentially kill MDR cancer cells. To further improve its potency, we have performed detailed structure-activity relationship (SAR) studies at the 3, 4, and 6 positions of the 4H-chromene system. The results reveal that the 3 and 4 positions prefer rigid and hydrophobic functional groups while the 6 position prefers a meta or para-substituted aryl functional group and the substituent should be small and hydrophilic. We have also identified and characterized nine MDR cancer cells that acquire MDR through different mechanisms and demonstrated the scope of our new lead, 9g, to selectively target different MDR cancers, which holds promise to help manage MDR in cancer treatment.