3-(tert-butyldimethylsilanyloxy)-4-methoxybenzaldehyde oxime | 701954-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(tert-butyldimethylsilanyloxy)-4-methoxybenzaldehyde oxime
• 英文别名: 3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-methoxybenzaldehyde oxime；N-[[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxyphenyl]methylidene]hydroxylamine
• CAS: 701954-62-3
• 化学式: C₁₄H₂₃NO₃Si
• 分子量: 281.427
• InChiKey: OLCIOYIMIJGKLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsilanyloxy)-4-methoxybenzaldehyde oxime 在 吡啶 、 manganese(IV) oxide 、 N-氯代丁二酰亚胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 氯仿 、 苯 为溶剂， 反应 1.66h， 生成 2-methoxy-5-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol
  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
• 作为产物：
  描述：

  异香兰素 在 吡啶 、 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 25.0h， 生成 3-(tert-butyldimethylsilanyloxy)-4-methoxybenzaldehyde oxime
  参考文献：
  名称：

  1,3-Dipolar cycloaddition route to novel isoxazole-type derivatives related to combretastatin A-4

  摘要：

  A series of compounds related to combretastatin A-4, containing a five-membered heterocyclic ring interposed between the two phenyl groups have been Prepared. Synthetic approach involves 1,3-dipolar cycloaddition of various 3,4,5-trimethoxyphenyl units with an in situ generated nitrile oxide from a suitable aldoxime using sodium hypochlorite. Depending oil the nature of the dipolarophile, 3,5-diarylisoxazole derivatives obtained along with the 3,4-regioisomeric isomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.020

文献信息

• Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents
  作者：Ahmed Kamal、J. Surendranadha Reddy、M. Janaki Ramaiah、D. Dastagiri、E. Vijaya Bharathi、M. Ameruddin Azhar、Farheen Sultana、S.N.C.V.L. Pushpavalli、Manika Pal-Bhadra、Aarti Juvekar

  DOI：10.1016/j.ejmech.2010.05.047

  日期：2010.9

  A series of 3,5-diaryl-isoxazoline/isoxazole linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates were prepared. These conjugates showed potent anticancer activity with GI(50) values in the range of <0.1-3.6 mu M. Some of these PBD conjugates (6a-c) with promising anticancer activity were further investigated on the cell cycle distribution. Moreover, these PBD conjugates exhibited G0/G1 arrest, enhancement in the levels of p53 protein as well as mitochondrial-mediated intrinsic pathway, leading to release of cytochrome c, activation of caspase-3, cleavage of PARP and subsequent apoptotic cell death. Hence these PBD conjugates with 6a being the most potent one could be be taken up for preclinical studies either alone or in combination with existing therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.
• [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
• Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents
  作者：Ahmed Kamal、E. Vijaya Bharathi、J. Surendranadha Reddy、M. Janaki Ramaiah、D. Dastagiri、M. Kashi Reddy、A. Viswanath、T. Lakshminarayan Reddy、T. Basha Shaik、S.N.C.V.L. Pushpavalli、Manika Pal Bhadra

  DOI：10.1016/j.ejmech.2010.12.004

  日期：2011.2

  A series of new 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydro quinazolinone hybrids with different linker architectures have been designed and synthesized. These compounds have been evaluated for their anticancer activity. One of the compounds 4c amongst this series has shown promising anticancer activity. Further some detailed biological assays relating to the cell cycle aspects and tubulin depolymerization activity have been examined with a view to understand the mechanism of action of this conjugate. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 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.