4-(4-oxo-4H-chromen-3-ylmethyl)benzonitrile | 79530-05-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 4-(4-oxo-4H-chromen-3-ylmethyl)benzonitrile
• 英文别名: 3-(4-cyano-benzyl)-chromen-4-one；4-[(4-Oxochromen-3-yl)methyl]benzonitrile
• CAS: 79530-05-5
• 化学式: C₁₇H₁₁NO₂
• 分子量: 261.28
• InChiKey: SFKYRWANFXDKGR-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  449.1±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-oxo-4H-chromen-3-ylmethyl)benzonitrile 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 以73%的产率得到4-[bromo-(4-oxo-4H-chromen-3-yl)methyl]benzonitrile
  参考文献：
  名称：

  Enantioselective Nonsteroidal Aromatase Inhibitors Identified through a Multidisciplinary Medicinal Chemistry Approach

  摘要：

  To identify enantioselective nonsteroidal aromatase inhibitors, a multidisciplinary medicinal chemistry approach was pursued. First, our earlier CoMFA model [Bioorg. Med. Chem. 1998, 6, 377-3881 was extended taking purposely into account previously discovered enantioselective aromatase inhibitors. The 3D QSAR model was then exploited to design chiral ligands, whose configurational assignment was obtained, after HPLC separation, by means of a combination of circular dichroism measurements and time dependent density functional calculations. Finally, the new enantiomeric inhibitors were separately tested to ascertain both their potency against the cytochrome P450 aromatase (CYP19; EC1.14.14.1), and their selectivity relative to another enzyme of the P450 family. A satisfactory agreement between experimental and predicted data allowed us to assert that a properly built "enantioselective CoMFA model" might constitute a useful tool for addressing enantioselective ligands design.

  DOI：

  10.1021/jm058042r
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 在 哌啶 、 磷酸 作用下， 反应 7.0h， 生成 4-(4-oxo-4H-chromen-3-ylmethyl)benzonitrile
  参考文献：
  名称：

  Levai, A.; Dinya, Z.; Schag, J. B., Pharmazie, 1981, vol. 36, # 7, p. 465 - 466

  摘要：

  DOI：

文献信息

• Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds
  作者：Arto Valkonen、Katri Laihia、Erkki Kolehmainen、Reijo Kauppinen、Pál Perjési

  DOI：10.1007/s11224-011-9860-6

  日期：2012.2

  (E)-3-(4′-X-benzylidene)-4-chromanones (IIIa–IIIe, X = OCH3, CH3, Cl, N(CH3)2, Br), (Z)-3-(4′-X-benzylidene)4-thiochromanones (IVa–IVd, X = Cl, Br, F, OCH3), 2-benzyl-1,2,3,4-tetrahydro-1-naphthol (V), 2-benzyl- and (E)-2-benzylidene-1-tetralones (VI and VII), and (E)-2-benzylidene-1-benzosuberol (VIII). The crystal structures have been determined for the following seven compounds: derivatives of 4-chromanones

  摘要 基于 PFG 1H、13C HMQC 和 HMBC 实验对 3-(4'-X-苄基)-4-色酮 (Ia, X = CN 和 Ib, X = NO2) 确定并分配了 1H 和 13C NMR 化学位移, 3-(4'-X-benzyl)-4-thiochromenones (IIa, X = Cl and IIb, X = Br), (E)-3-(4'-X-benzylidene)-4-chromanones (IIIa– IIIe, X = OCH3, CH3, Cl, N(CH3)2, Br), (Z)-3-(4'-X-亚苄基)4-硫代色满酮 (IVa–IVd, X = Cl, Br, F, OCH3 )、2-苄基-1,2,3,4-四氢-1-萘酚 (V)、2-苄基-和 (E)-2-亚苄基-1-四氢萘酮 (VI 和 VII)，和 (E)- 2-benzylidene-1-benzosuberol
• Facile Synthesis of Tetrazolylchromonoids and Related Compounds
  作者：Tamás Patonay、Albert Lévai

  DOI：10.1002/ardp.19943270310

  日期：——

  The reaction between the appropriate nitriles and tributyltin azide (TBTA) provides an easy and efficient method for the synthesis of the title compounds. Treatment of thiocyanate 9b with TBTA affords the alkylthio‐substituted tetrazole 10b.

  合适的腈与叠氮化三丁基锡 (TBTA) 之间的反应为合成标题化合物提供了一种简单有效的方法。用 TBTA 处理硫氰酸酯 9b 得到烷硫基取代的四唑 10b。
• Structure–cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones
  作者：Bogumiła Kupcewicz、Grażyna Balcerowska-Czerniak、Magdalena Małecka、Piotr Paneth、Urszula Krajewska、Marek Rozalski

  DOI：10.1016/j.bmcl.2013.05.044

  日期：2013.7

  The E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone derivatives were tested in vitro for their cytotoxic activity against three cancer cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC). It was observed that substitution at C-3 position led to significant enhance in cytotoxicity. Isomeric configuration of 3-arylideneflavanones had an influence on the cytotoxic potential. Multiple regression analysis combined with variable selection by genetic algorithm was used to model relationships between molecular descriptors and the cytotoxic activity. The most accurate QSAR models were based on a combination between energy of LUMO, experimental value of logP and partial charge on carbonyl oxygen (delta O-2). (C) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective Nonsteroidal Aromatase Inhibitors Identified through a Multidisciplinary Medicinal Chemistry Approach
  作者：Andrea Cavalli、Alessandra Bisi、Carlo Bertucci、Carlo Rosini、Anja Paluszcak、Silvia Gobbi、Egidio Giorgio、Angela Rampa、Federica Belluti、Lorna Piazzi、Piero Valenti、Rolf W. Hartmann、Maurizio Recanatini

  DOI：10.1021/jm058042r

  日期：2005.11.1

  To identify enantioselective nonsteroidal aromatase inhibitors, a multidisciplinary medicinal chemistry approach was pursued. First, our earlier CoMFA model [Bioorg. Med. Chem. 1998, 6, 377-3881 was extended taking purposely into account previously discovered enantioselective aromatase inhibitors. The 3D QSAR model was then exploited to design chiral ligands, whose configurational assignment was obtained, after HPLC separation, by means of a combination of circular dichroism measurements and time dependent density functional calculations. Finally, the new enantiomeric inhibitors were separately tested to ascertain both their potency against the cytochrome P450 aromatase (CYP19; EC1.14.14.1), and their selectivity relative to another enzyme of the P450 family. A satisfactory agreement between experimental and predicted data allowed us to assert that a properly built "enantioselective CoMFA model" might constitute a useful tool for addressing enantioselective ligands design.
• Levai, A.; Dinya, Z.; Schag, J. B., Pharmazie, 1981, vol. 36, # 7, p. 465 - 466
  作者：Levai, A.、Dinya, Z.、Schag, J. B.、Toth, G.、Szoelloesy, A.

  DOI：——

  日期：——