methyl 3-(3-phenylphenyl)phenylacetate | 911497-17-1

• 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: methyl 3-(3-phenylphenyl)phenylacetate
• 英文别名: Methyl 2-[3-(3-phenylphenyl)phenyl]acetate
• CAS: 911497-17-1
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: VNUWTKKPAGVOHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(3-phenylphenyl)phenylacetate 在 sodium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.0h， 生成 2-[3-(3-Phenylphenyl)phenyl]acetyl chloride
  参考文献：
  名称：

  Activity of Nitrogen-Containing and Non-Nitrogen-Containing Bisphosphonates on Tumor Cell Lines

  摘要：

  We synthesized and tested three series of bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines: MCF-7 (breast), NCI-H460 (lung), and SF-268 (CNS). The first series of compounds consisted of 49 nitrogen-containing bisphosphonates, the most active species being a tetrakispivaloyloxymethyl (POM) ester, having an (average) IC50 of 6.8 mu M. The second series of compounds consisted of nine terphenylbisphosphonates, the most active species also being a POM ester, having an IC50 of 2.2 mu M. The third series of compounds consisted of seven halogen or cyanophenylbisphosphonates, the most active species again being a POM ester, having an IC50 of 500 nM. Taken together, these results are of interest because they show that bisphosphonate esters can have potent activity against a variety of tumor cell lines, with the most active terphenyl-and halophenyl-containing species having IC50 values similar to 10-40x lower than the most potent commercially available bisphosphonates.

  DOI：

  10.1021/jm060280e
• 作为产物：
  描述：

  3-联苯硼酸 、 2-(3-溴苯基)乙酸甲酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 生成 methyl 3-(3-phenylphenyl)phenylacetate
  参考文献：
  名称：

  Activity of Nitrogen-Containing and Non-Nitrogen-Containing Bisphosphonates on Tumor Cell Lines

  摘要：

  We synthesized and tested three series of bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines: MCF-7 (breast), NCI-H460 (lung), and SF-268 (CNS). The first series of compounds consisted of 49 nitrogen-containing bisphosphonates, the most active species being a tetrakispivaloyloxymethyl (POM) ester, having an (average) IC50 of 6.8 mu M. The second series of compounds consisted of nine terphenylbisphosphonates, the most active species also being a POM ester, having an IC50 of 2.2 mu M. The third series of compounds consisted of seven halogen or cyanophenylbisphosphonates, the most active species again being a POM ester, having an IC50 of 500 nM. Taken together, these results are of interest because they show that bisphosphonate esters can have potent activity against a variety of tumor cell lines, with the most active terphenyl-and halophenyl-containing species having IC50 values similar to 10-40x lower than the most potent commercially available bisphosphonates.

  DOI：

  10.1021/jm060280e

文献信息

• BISPHOSPHONATE COMPOUNDS AND METHODS
  申请人：Oldfield Eric

  公开号：US20070275931A1

  公开（公告）日：2007-11-29

  The invention provides, inter alia, novel bisphosphonate compounds and methods of making and using. In embodiments, the invention provides compounds and methods in connection with research and therapeutic applications, e.g., for tumor cell growth inhibition, activation of gammadelta T cells, inhibition of farnesyldiphosphate (FPPS) and/or undecaprenyldiphosphate synthase enzymes, bone resorption diseases, cancer, immune disorders, immunotherapy, and infectious diseases. In regards to certain embodiments, a surprising advance has been the recognition that certain structural features can significantly enhance the activity of the compounds. For example, the presence of particular cationic species e.g., phosphonium, sulfonium, and arsonium moieties can contribute to desirable functional activity when positioned near a bisphosphonate moiety. In other embodiments of non-nitrogen containing bisphosphonates, terphenyl and benzyl bisphosphonate compounds and methods are provided. Further variations are also provided.

  本发明提供了新型双膦酸盐化合物及其制备和使用方法。在实施例中，本发明提供了与研究和治疗应用相关的化合物和方法，例如用于抑制肿瘤细胞生长、激活γδT细胞、抑制法尼酰二磷酸合酶（FPPS）和/或十一烷基二磷酸合酶酶、骨吸收疾病、癌症、免疫失调、免疫疗法和传染病。关于某些实施例，一个令人惊讶的进展是认识到某些结构特征可以显著增强化合物的活性。例如，特定阳离子物种的存在，例如磷酸铵、磺酸盐和砷酸盐基团，当位于双膦酸盐基团附近时，可以促进理想的功能活性。在另一些非氮双膦酸盐的实施例中，提供了苯并双膦酸盐化合物和方法。还提供了进一步的变化。
• WO2007/109585
  申请人：——

  公开号：——

  公开（公告）日：——
• US7687482B2
  申请人：——

  公开号：US7687482B2

  公开（公告）日：2010-03-30
• [EN] BISPHOSPHONATE COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS DE BIPHOSPHONATES ET PROCÉDÉS
  申请人：UNIV ILLINOIS

  公开号：WO2007109585A2

  公开（公告）日：2007-09-27

  [EN] The invention provides, inter alia, novel bisphosphonate compounds and methods of making and using. In embodiments, the invention provides compounds and methods in connection with research and therapeutic applications, e.g., for tumor cell growth inhibition, activation of gammadelta T cells, inhibition of farnesyldiphosphate (FPPS) and/or undecaprenyldiphosphate synthase enzymes, bone resorption diseases, cancer, immune disorders, immunotherapy, and infectious diseases. In regards to certain embodiments, a surprising advance has been the recognition that certain structural features can significantly enhance the activity of the compounds. For example, the presence of particular cationic species e.g., phosphonium, sulfonium, and arsonium moieties can contribute to desirable functional activity when positioned near a bisphosphonate moiety. In other embodiments of non-nitrogen containing bisphosphonates, terphenyl and benzyl bisphosphonate compounds and methods are provided. Further variations are also provided.
  [FR] La présente invention concerne notamment des composés de bisphosphonate et leurs procédés de fabrication et d'utilisation. Dans certains modes de réalisation, l'invention concerne des composés et procédés en relation avec des applications de recherche et de thérapie, par exemple pour l'inhibition de la croissance des cellules tumorales, l'activation de lymphocytes T gamma-delta, l'inhibition des enzymes de synthèse de farnésyl-diphosphate (FPPS) et/ou d'undécaprenyl-diphosphate, les maladies à résorption osseuse, le cancer, les troubles immunitaires, l'immunothérapie, et les maladies infectieuses. Concernant certains modes de réalisation, une avancée surprise a été la reconnaissance que certains traits structuraux peuvent renforcer de façon notable l'activité de ces composés. Par exemple, la présence d'espèces cationiques telles que le groupes fonctionnels phosphonium, sulfonium, et arsonium peut contribuer à une activité fonctionnelle souhaitable quand ces espèces sont positionnées à proximité du groupe fonctionnel biphosphonate. Dans d'autres modes de réalisations de biphosphonates ne contenant pas d'azote, l'invention concerne des composés biphosphonate de therphényle et de benzyle et les procédés correspondants. L'invention concerne également d'autres variantes.
• Activity of Nitrogen-Containing and Non-Nitrogen-Containing Bisphosphonates on Tumor Cell Lines
  作者：Yonghui Zhang、Annette Leon、Yongcheng Song、Danielle Studer、Christa Haase、Lukasz A. Koscielski、Eric Oldfield

  DOI：10.1021/jm060280e

  日期：2006.9.1

  We synthesized and tested three series of bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines: MCF-7 (breast), NCI-H460 (lung), and SF-268 (CNS). The first series of compounds consisted of 49 nitrogen-containing bisphosphonates, the most active species being a tetrakispivaloyloxymethyl (POM) ester, having an (average) IC50 of 6.8 mu M. The second series of compounds consisted of nine terphenylbisphosphonates, the most active species also being a POM ester, having an IC50 of 2.2 mu M. The third series of compounds consisted of seven halogen or cyanophenylbisphosphonates, the most active species again being a POM ester, having an IC50 of 500 nM. Taken together, these results are of interest because they show that bisphosphonate esters can have potent activity against a variety of tumor cell lines, with the most active terphenyl-and halophenyl-containing species having IC50 values similar to 10-40x lower than the most potent commercially available bisphosphonates.