Bis(2-hydroxy-5-phenylphenyl)methanone | 1323153-40-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: Bis(2-hydroxy-5-phenylphenyl)methanone
• 英文别名: bis(2-hydroxy-5-phenylphenyl)methanone
• CAS: 1323153-40-7
• 化学式: C₂₅H₁₈O₃
• 分子量: 366.416
• InChiKey: SRCMXUXPCHTCCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Bis(2-hydroxy-5-phenylphenyl)methanone 在 盐酸羟胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.0h， 生成 3-[2'-hydroxy-4'-phenylphenyl]-5-phenyl-1,2-benzisoxazole 2-oxide
  参考文献：
  名称：

  杂环合成中的氧杂蒽酮。一种合成 C-3 邻羟基芳基取代的 1,2-苯并异恶唑及其 N-氧化物、血管紧张素 (II) 拮抗剂杂合肽的潜在支架的有效途径

  摘要：

  Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 o-hydroxyaryl substituted 1,2-benzisoxazoles or their N-oxides by cyclodehydration or oxidative cyclization of their corresponding ketoxime precursors, respectively. Molecular modeling analysis and H-1 NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom.

  DOI：

  10.3987/com-11-12162
• 作为产物：
  描述：

  2,7-diphenylxanthone 在 二甲基亚砜 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 生成 Bis(2-hydroxy-5-phenylphenyl)methanone
  参考文献：
  名称：

  2,2′-Dihydroxybenzophenones and their carbonyl N-analogues as inhibitor scaffolds for MDR-involved human glutathione transferase isoenzyme A1-1

  摘要：

  The MDR-involved human GSTA1-1, an important isoenzyme overexpressed in several tumors leading to chemotherapeutic-resistant tumour cells, has been targeted by 2,2'-dihydroxybenzophenones and some of their carbonyl N-analogues, as its potential inhibitors. A structure-based library of the latter was built-up by a nucleophilic cleavage of suitably substituted xanthones to 2,2'-dihydroxy-benzophenones (5-9) and subsequent formation of their N-derivatives (oximes 11-13 and N-acyl hydrazones 14-16). Screening against hGSTA1-1 led to benzophenones 6 and 8, and hydrazones 14 and 16, having the highest inhibition potency (IC₅₀ values in the range 0.18 ± 0.02 to 1.77 ± 0.10 μM). Enzyme inhibition kinetics, molecular modeling and docking studies showed that they interact primarily at the CDNB-binding catalytic site of the enzyme. In addition, the results from cytotoxicity studies with human colon adenocarcinoma cells showed low LC₅₀ values for benzophenone 6 and its N-acyl hydrazone analogue 14 (31.4 ± 0.4 μM and 87 ± 1.9 μM, respectively), in addition to the strong enzyme inhibition profile (IC₅₀(6)=1,77 ± 0.10 μM; IC₅₀(14)=0.33 ± 0.05 μM). These structures may serve as leads for the design of new potent mono- and bi-functional inhibitors and pro-drugs against human GTSs.

  DOI：

  10.1016/j.bmc.2014.06.007

文献信息

• Xanthones in Heterocyclic Synthesis. An Efficient and General Route for the Synthesis of Regioselectively Substituted Phthalazines
  作者：Petros G. Tsoungas、Paul Cordopatis、Yiannis Gardikis、Constantinos Potamitis、Maria Zervou、George Pairas

  DOI：10.3987/com-11-12168

  日期：——

  Xanthone undergoes regioselective substitution and nucleophically triggered ring opening to the corresponding ketone. Hydrazone of the latter oxidatively rearranges to ortho-diacylarenes, which, then, with hydrazine gives regioselectively substituted phthalazines. Molecular modeling analysis and H-1 NMR spectra indicate an intramolecular H-bonding engaging phenol OH and phthalazine N-3 atom.
• Xanthones in Heterocyclic Synthesis. An Efficient Route for the Synthesis of C-3 o-Hydroxyaryl Substituted 1,2-Benzisoxazoles and Their N-Oxides, Potential Scaffolds for Angiotensin(II) Antagonist Hybrid Peptides
  作者：Petros G. Tsoungas、Paul Cordopatis、Yiannis Gardikis、Constantinos Potamitis、Maria Zervou

  DOI：10.3987/com-11-12162

  日期：——

  Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 o-hydroxyaryl substituted 1,2-benzisoxazoles or their N-oxides by cyclodehydration or oxidative cyclization of their corresponding ketoxime precursors, respectively. Molecular modeling analysis and H-1 NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom.
• 2,2′-Dihydroxybenzophenones and their carbonyl N-analogues as inhibitor scaffolds for MDR-involved human glutathione transferase isoenzyme A1-1
  作者：Fereniki D. Perperopoulou、Petros G. Tsoungas、Trias N. Thireou、Vagelis E. Rinotas、Eleni K. Douni、Elias E. Eliopoulos、Nikolaos E. Labrou、Yannis D. Clonis

  DOI：10.1016/j.bmc.2014.06.007

  日期：2014.8

  The MDR-involved human GSTA1-1, an important isoenzyme overexpressed in several tumors leading to chemotherapeutic-resistant tumour cells, has been targeted by 2,2'-dihydroxybenzophenones and some of their carbonyl N-analogues, as its potential inhibitors. A structure-based library of the latter was built-up by a nucleophilic cleavage of suitably substituted xanthones to 2,2'-dihydroxy-benzophenones (5-9) and subsequent formation of their N-derivatives (oximes 11-13 and N-acyl hydrazones 14-16). Screening against hGSTA1-1 led to benzophenones 6 and 8, and hydrazones 14 and 16, having the highest inhibition potency (IC₅₀ values in the range 0.18 ± 0.02 to 1.77 ± 0.10 μM). Enzyme inhibition kinetics, molecular modeling and docking studies showed that they interact primarily at the CDNB-binding catalytic site of the enzyme. In addition, the results from cytotoxicity studies with human colon adenocarcinoma cells showed low LC₅₀ values for benzophenone 6 and its N-acyl hydrazone analogue 14 (31.4 ± 0.4 μM and 87 ± 1.9 μM, respectively), in addition to the strong enzyme inhibition profile (IC₅₀(6)=1,77 ± 0.10 μM; IC₅₀(14)=0.33 ± 0.05 μM). These structures may serve as leads for the design of new potent mono- and bi-functional inhibitors and pro-drugs against human GTSs.