6-Methoxy-2-(4-methoxyphenyl)-3-(2',3',4',5',6'-pentafluorobenzoyl)benzothiophene | 133295-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Methoxy-2-(4-methoxyphenyl)-3-(2',3',4',5',6'-pentafluorobenzoyl)benzothiophene
• 英文别名: 3-(2',3',4',5',6'-pentafluorobenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene；[6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophen-3-yl]-(2,3,4,5,6-pentafluorophenyl)methanone
• CAS: 133295-97-3
• 化学式: C₂₃H₁₃F₅O₃S
• 分子量: 464.412
• InChiKey: LSFXFEHMXHEHIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-Methoxy-2-(4-methoxyphenyl)-3-(2',3',4',5',6'-pentafluorobenzoyl)benzothiophene 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 6-Hydroxy-2-(4-hydroxyphenyl)-3-(2',3',4',5',6'-pentafluorobenzoyl)benzothiophene
  参考文献：
  名称：

  Synthesis of a tetrafluoro-substituted aryl azide and its protio analog as photoaffinity labeling reagents for the estrogen receptor

  摘要：

  A tetrafluoro-substituted aryl azide 1 and its protio analogue 2, both photoaffinity labeling reagents for the estrogen receptor, have been prepared by direct coupling of the appropriately substituted 4-azidobenzoyl chloride with the electron rich C-3 of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 3. This represents a rare example of aryl azide stability under Friedel-Crafts acylation conditions. Alternatively, the protio analogue 2 can also be prepared with the azide functionality masked as a phthaloyl-protected arylamine, and the tetrafluoro analogue 1, by direct displacement of a pentafluoroaryl derivative 20 with NaN3. Solution photolysis of tetrafluoro-substituted aryl azide (bis-methyl ether) 15 and its protio analogue 16 in toluene at 30-degrees-C results in relatively high yields of products derived from C-H insertion. Both azides 1 and 2 demonstrate favorable relative binding affinity (RBA) (1 = 10%, 2 = 66%, estradiol = 100%) and photoinactivation efficiency (1 = 43%, 2 = 55% at 30 min) for the estrogen receptor (ER). The synthesis of both azides has been modified to accommodate a palladium-catalyzed tritium gas hydrogenolysis of an iodoaryl precursor at a late stage in the synthetic sequence, as will be needed to prepare them in radiolabeled form, and this procedure has been verified by deuteration. This pair of compounds will allow a detailed evaluation of the role that fluorine substitution plays in the photochemistry and photocovalent attachment behavior of aryl azides in a complex biochemical system, the estrogen receptor. The radiosynthesis and further biochemical results will be presented elsewhere.

  DOI：

  10.1021/jo00009a037
• 作为产物：
  描述：

  五氟苯甲酰氯 、 6-甲氧基-2-(4-甲氧苯基)苯并噻吩 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 6-Methoxy-2-(4-methoxyphenyl)-3-(2',3',4',5',6'-pentafluorobenzoyl)benzothiophene
  参考文献：
  名称：

  Description anti-mitotic agents which inhibit tubulin polymerization

  摘要：

  甲基氧基和乙氧基取代的3-酰基-2-芳基苯并[b]噻吩及其类似物被描述用于抑制微管蛋白聚合。这些化合物用于治疗肿瘤细胞的方法也进行了描述。 此外，这里还描述了某些二芳基醚苯并[b]噻吩衍生物。还描述了来自二氢萘的特定类似物，这些类似物已被证明特别有效。描述了一些新的苯并呋喃类似物，以及某些硫氧化物苯并[b]噻吩类似物。 本文描述的重要化合物包括含有氮的康布雷他汀衍生物的首个例子。这些包括硝基、氨基和叠氮化物康布雷他汀衍生物。

  公开号：

  US06350777B2

文献信息

• Description anti-mitotic agents which inhibit tubulin polymerization
  申请人：Baylor University

  公开号：US06350777B2

  公开（公告）日：2002-02-26

  Methoxy and ethoxy substituted 3-aroyl-2-arylbenzo[b]thiophenes and benzo[b]thiophene analogues are described for use in inhibiting tubulin polymerization. The compounds' use for treating tumor cells is also described. Additional aspects described here are certain diaryl ether benzo[b]thiophene derivatives. Also described are particular analogs derived from dihydronaphthalene which have proven particularly effective. Certain new benzofuran analogs are described, as well as certain sulfur oxide benzo[b]thiophene analogs. Important compounds described herein include the first nitrogen-containing derivatives of combretastatin. These include nitro, amino and azide combrdtastatin derivatives.

  甲基氧基和乙氧基取代的3-酰基-2-芳基苯并[b]噻吩及其类似物被描述用于抑制微管蛋白聚合。这些化合物用于治疗肿瘤细胞的方法也进行了描述。 此外，这里还描述了某些二芳基醚苯并[b]噻吩衍生物。还描述了来自二氢萘的特定类似物，这些类似物已被证明特别有效。描述了一些新的苯并呋喃类似物，以及某些硫氧化物苯并[b]噻吩类似物。 本文描述的重要化合物包括含有氮的康布雷他汀衍生物的首个例子。这些包括硝基、氨基和叠氮化物康布雷他汀衍生物。
• Synthesis for the preparation of compounds for screening as potential tubulin binding agents
  申请人：Flynn Luke Bernard

  公开号：US20050130221A1

  公开（公告）日：2005-06-16

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物的方法，用于筛选作为潜在微管聚合抑制剂的化合物。本发明还提供具有微管聚合抑制剂活性的化学化合物。
• US6162930A
  申请人：——

  公开号：US6162930A

  公开（公告）日：2000-12-19
• US6350777B2
  申请人：——

  公开号：US6350777B2

  公开（公告）日：2002-02-26
• Synthesis of a tetrafluoro-substituted aryl azide and its protio analog as photoaffinity labeling reagents for the estrogen receptor
  作者：Kevin G. Pinney、John A. Katzenellenbogen

  DOI：10.1021/jo00009a037

  日期：1991.4

  A tetrafluoro-substituted aryl azide 1 and its protio analogue 2, both photoaffinity labeling reagents for the estrogen receptor, have been prepared by direct coupling of the appropriately substituted 4-azidobenzoyl chloride with the electron rich C-3 of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 3. This represents a rare example of aryl azide stability under Friedel-Crafts acylation conditions. Alternatively, the protio analogue 2 can also be prepared with the azide functionality masked as a phthaloyl-protected arylamine, and the tetrafluoro analogue 1, by direct displacement of a pentafluoroaryl derivative 20 with NaN3. Solution photolysis of tetrafluoro-substituted aryl azide (bis-methyl ether) 15 and its protio analogue 16 in toluene at 30-degrees-C results in relatively high yields of products derived from C-H insertion. Both azides 1 and 2 demonstrate favorable relative binding affinity (RBA) (1 = 10%, 2 = 66%, estradiol = 100%) and photoinactivation efficiency (1 = 43%, 2 = 55% at 30 min) for the estrogen receptor (ER). The synthesis of both azides has been modified to accommodate a palladium-catalyzed tritium gas hydrogenolysis of an iodoaryl precursor at a late stage in the synthetic sequence, as will be needed to prepare them in radiolabeled form, and this procedure has been verified by deuteration. This pair of compounds will allow a detailed evaluation of the role that fluorine substitution plays in the photochemistry and photocovalent attachment behavior of aryl azides in a complex biochemical system, the estrogen receptor. The radiosynthesis and further biochemical results will be presented elsewhere.