5-[3-(tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-3-(3,4,5-trimethoxyphenyl)isoxazole | 831222-67-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[3-(tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-3-(3,4,5-trimethoxyphenyl)isoxazole
• 英文别名: Tert-butyl-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-5-yl]phenoxy]-dimethylsilane
• CAS: 831222-67-4
• 化学式: C₂₅H₃₃NO₆Si
• 分子量: 471.626
• InChiKey: MXENZYFIVLDPGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[3-(tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-3-(3,4,5-trimethoxyphenyl)isoxazole 在 四丁基氟化铵 、 水 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[2-Methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-5-yl]phenoxy]acetic acid
  参考文献：
  名称：

  Amidobenzothiazoles And Process For The Preparation Thereof

  摘要：

  本发明提供了一种通式A的化合物，可作为潜在的抗人类癌细胞系的抗癌剂，并提供了其制备方法。其中R、R1、R2═H、烷基、烷氧基、卤素、卤代烷基、卤代甲氧基、硝基，G=其中R、R1、R2═H、烷基、烷氧基、卤素、卤代烷基、卤代甲氧基、硝基。

  公开号：

  US20130317231A1
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛肟 在 吡啶 、 manganese(IV) oxide 、 N-氯代丁二酰亚胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 1.33h， 生成 5-[3-(tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-3-(3,4,5-trimethoxyphenyl)isoxazole
  参考文献：
  名称：

  Heterocyclic and Phenyl Double-Bond-Locked Combretastatin Analogues Possessing Potent Apoptosis-Inducing Activity in HL60 and in MDR Cell Lines

  摘要：

  Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 < 1 muM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.

  DOI：

  10.1021/jm049622b

文献信息

• [EN] COMBRETASTATIN DERIVATIVES WITH CYTOTOXIC ACTION<br/>[FR] DERIVES DE LA COMBRETASTATINE A ACTION CYTOTOXIQUE
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2005007635A3

  公开（公告）日：2005-08-11
• Isoxazole-type derivatives related to combretastatin A-4, synthesis and biological evaluation
  作者：Julia Kaffy、Renée Pontikis、Danièle Carrez、Alain Croisy、Claude Monneret、Jean-Claude Florent

  DOI：10.1016/j.bmc.2006.02.001

  日期：2006.6

  Novel combretastatin analogues bearing various five-membered heterocycles with consecutive oxygen and nitrogen atoms, in place of the olefinic bridge of CA4, have been synthesized (isoxazole, isoxazoline, oxadiazole, etc). These compounds have been evaluated for cytotoxicity and their ability to inhibit the tubulin assembly. On the basis of the relative position of the aromatic A- and B-rings on the heterocyclic moiety, they could be split in two classes, the alpha,gamma- or alpha,beta-diaryl heterocyclic derivatives. In the first series, the 3,5-diaryloxadiazole 9a displayed comparable antitubulin activity to that of CA4, but was devoid of cytotoxic effects. Among the alpha,beta-diaryl heterocyclic derivatives, the 4,5-diarylisoxazole 35 exhibited greater antitubulin activity than that of CA4 (0.75 vs 1.2 mu M), but modest antiproliferative activity. These data showed that minor alteration in the chemical structure of the heterocyclic ring and its relative orientation with regard to the two phenyl rings of CA4 could dramatically influence the tubulin binding properties. (c) 2006 Elsevier Ltd. All rights reserved.
• Amidobenzothiazoles And Process For The Preparation Thereof
  申请人：Ahmed Kamal

  公开号：US20130317231A1

  公开（公告）日：2013-11-28

  The present invention provides a compound of general formulae A useful as potential anti-cancer agents against human cancer cell lines and a process for the preparation thereof. Where in R, R 1 , R 2 ═H, alkyl, alkoxy, halo, haloalkyl, halomethoxy, nitro and G= Where in R, R 1 , R 2 ═H, alkyl, alkoxy, halo, haloalkyl, halomethoxy, nitro and G=

  本发明提供了一种通式A的化合物，可作为潜在的抗人类癌细胞系的抗癌剂，并提供了其制备方法。其中R、R1、R2═H、烷基、烷氧基、卤素、卤代烷基、卤代甲氧基、硝基，G=其中R、R1、R2═H、烷基、烷氧基、卤素、卤代烷基、卤代甲氧基、硝基。
• Heterocyclic and Phenyl Double-Bond-Locked Combretastatin Analogues Possessing Potent Apoptosis-Inducing Activity in HL60 and in MDR Cell Lines
  作者：Daniele Simoni、Giuseppina Grisolia、Giuseppe Giannini、Marinella Roberti、Riccardo Rondanin、Laura Piccagli、Riccardo Baruchello、Marcello Rossi、Romeo Romagnoli、Francesco Paolo Invidiata、Stefania Grimaudo、M. Katherine Jung、Ernest Hamel、Nicola Gebbia、Lucia Crosta、Vincenzo Abbadessa、Antonietta Di Cristina、Luisa Dusonchet、Maria Meli、Manlio Tolomeo

  DOI：10.1021/jm049622b

  日期：2005.2.1

  Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 < 1 muM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.