2-methoxy-5-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol | 701954-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-methoxy-5-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol
• 英文别名: 2-methoxy-5-[5-(3,4,5-trimethoxy-phenyl)-3-isoxazolyl]-phenol；Phenol, 2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-3-isoxazolyl]-；2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-3-yl]phenol
• CAS: 701954-74-7
• 化学式: C₁₉H₁₉NO₆
• 分子量: 357.363
• InChiKey: QPMVNZHDVVLZST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-N-[4-(5-bromopentyloxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal 、 2-methoxy-5-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以85%的产率得到[(2S)-2-[bis(ethylsulfanyl)methyl]pyrrolidin-1-yl]-[5-methoxy-4-[5-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-3-yl]phenoxy]pentoxy]-2-nitrophenyl]methanone
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.05.047
• 作为产物：
  描述：

  3-叔-丁基二甲基硅氧基-4-甲氧基苯甲醛 在 吡啶 、 sodium hypochlorite 、 盐酸羟胺 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 2-methoxy-5-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol
  参考文献：
  名称：

  Isoxazole-type derivatives related to combretastatin A-4, synthesis and biological evaluation

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.02.001

文献信息

• [EN] ISOXAZOLE/ISOXAZOLINE/COMBRETASTATIN LINKED DIHYDROQUINAZOLINONE HYBRIDS AS POTENTIAL ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] HYBRIDES DIHYDROQUINAZOLINONE-ISOXAZOLE/ISOXAZOLINE/COMBRÉSTATATINE COMME AGENTS ANTICANCÉREUX POTENTIELS, ET PROCÉDÉ DE PRÉPARATION ASSOCIÉ
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010058417A1

  公开（公告）日：2010-05-27

  The present invention provides a compound of general formulae 3a-i to 6a-i, 7a-i to 10a- i, 12a-i to 15a-i, 16a-i to 19a-i, 21a-i to 24a-i, 25a-i to 28a-i, 30a-i to 33a-i, 34a-i to37a-i and 39a-i to 42a-i, 43a-i to 46a-i useful as potential antitumour agents against human cancer cell lines and a process for the preparation thereof.

  本发明提供了通式3a-i至6a-i、7a-i至10a-i、12a-i至15a-i、16a-i至19a-i、21a-i至24a-i、25a-i至28a-i、30a-i至33a-i、34a-i至37a-i和39a-i至42a-i、43a-i至46a-i的化合物，作为潜在的抗人类癌细胞系药剂，并提供了其制备方法。
• ISOXAZOLE/ISOXAZOLINE/COMBRETASTATIN LINKED DIHYDROQUINAZOLINONE HYBRIDS AS POTENTIAL ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Kamal Ahmed

  公开号：US20120283439A1

  公开（公告）日：2012-11-08

  The present invention provides a compound of general formulae 3a-i to 6a-i, 7a-i to 10a-i, 12a-i to 15a-i, 16a-i to 19a-i, 21a-i to 24a-i, 25a-i to 28a-i, 30a-i to 33a-i, 34a-i to 37a-i and 39a-i to 42a-i, 43a-i to 46a-i useful as potential antitumour agents against human cancer cell lines and a process for the preparation thereof.

  本发明提供了通式3a-i至6a-i、7a-i至10a-i、12a-i至15a-i、16a-i至19a-i、21a-i至24a-i、25a-i至28a-i、30a-i至33a-i、34a-i至37a-i和39a-i至42a-i、43a-i至46a-i的化合物，它们可用作潜在的抗人类癌细胞系肿瘤药物，并提供了其制备方法。
• Isoxazole/isoxazoline/combretastatin linked dihydroquinazolinone hybrids as potential anticancer agents and process for the preparation thereof
  申请人：Kamal Ahmed

  公开号：US08883809B2

  公开（公告）日：2014-11-11

  The present invention provides a compound of general formulae 3a-i to 6a-i, 7a-i to 10a-i, 12a-i to 15a-i, 16a-i to 19a-i, 21a-i to 24a-i, 25a-i to 28a-i, 30a-i to 33a-i, 34a-i to 37a-i and 39a-i to 42a-i, 43a-i to 46a-i useful as potential antitumour agents against human cancer cell lines and a process for the preparation thereof.

  本发明提供了一种通式3a-i至6a-i，7a-i至10a-i，12a-i至15a-i，16a-i至19a-i，21a-i至24a-i，25a-i至28a-i，30a-i至33a-i，34a-i至37a-i和39a-i至42a-i，43a-i至46a-i的化合物，可作为潜在的抗人类癌细胞系肿瘤药物，并提供了其制备方法。
• Combretastatin derivatives with cytotoxic action
  申请人：Giannini Giuseppe

  公开号：US20060160773A1

  公开（公告）日：2006-07-20

  The invention described herein relates to new combretastatin derivatives obtained by total synthesis and having the following general formula: in which the groups are as defined in the description here below. Said compounds, though chemically related to the structure of cis/trans-combretastatin, do not always bind tubulin, but nevertheless exhibit cytotoxic activity of interest in the oncological field as anticancer and/or antiangiogenic agents.

  本发明涉及通过全合成获得的具有以下通式的新的考布他丁衍生物： 其中各基团的定义见下文说明。上述化合物虽然在化学上与顺式/反式-考布他汀的结构有关，但并不总是与微管蛋白结合，而是作为抗癌和/或抗血管生成剂，在肿瘤领域表现出令人感兴趣的细胞毒性活性。
• 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.