2,6-dimethoxy-4-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol | 1227741-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-dimethoxy-4-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol
• 英文别名: 2,6-Dimethoxy-4-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol；2,6-dimethoxy-4-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-3-yl]phenol
• CAS: 1227741-04-9
• 化学式: C₂₀H₂₁NO₇
• 分子量: 387.389
• InChiKey: BAXWYVHIBTXGQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxy-4-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol 、 (2S)-N-[4-(5-bromopentyloxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以83%的产率得到[(2S)-2-[bis(ethylsulfanyl)methyl]pyrrolidin-1-yl]-[4-[5-[2,6-dimethoxy-4-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-3-yl]phenoxy]pentoxy]-5-methoxy-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-(4-(tert-butyldimethylsilyloxy)-3,5-dimethoxyphenyl)-5-(3,4,5-trimethoxy-phenyl)isoxazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到2,6-dimethoxy-4-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol
  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

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。
• US8883809B2
  申请人：——

  公开号：US8883809B2

  公开（公告）日：2014-11-11
• 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.