(3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)methanol | 1094099-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)methanol
• 英文别名: [3-(3,4,5-Trimethoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methanol
• CAS: 1094099-14-5
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: SOGDDNJDUXYIHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)methanol 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 18.5h， 生成 4-(5-phenyl-3-((4-(((3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)pyridin-2-yl)morpholine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles as potent inhibitors of tubulin polymerization

  摘要：

  Three series of compounds; pyridinyl-1H-1,2,3-triazoles, pyridinyl-1H-1,2,3-triazolylisoxazoles and pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles with TMP moiety were designed, synthesized and screened for their anti-cancer and anti-tubulin properties. By sequentially designing three series of compounds comprising of dihydroisoxazole in the linker, a small substituent like chlorine on one side (R-1) and aromatic group (R) on the pyridine ring, we have optimized the anti-cancer as well as anti-tubulin activity. Pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles 28b and 28c were found to be potent anti-cancer agents against all the cell lines tested with a concomitant accumulation of cells in the G2/M phase of the cell cycle. Molecular modeling suggests that the trimethoxyphenyl ring in 28b and 28c occupies the cholchicine binding domain of beta-tubulin, whereas, the dihydroisoxazole extends towards the interface of alpha,beta-tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.063
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 吡啶 、 N-氯代丁二酰亚胺 、 盐酸羟胺 、 碳酸氢钠 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 9.0h， 生成 (3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)methanol
  参考文献：
  名称：

  Synthesis and structure–activity relationships of pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles as potent inhibitors of tubulin polymerization

  摘要：

  Three series of compounds; pyridinyl-1H-1,2,3-triazoles, pyridinyl-1H-1,2,3-triazolylisoxazoles and pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles with TMP moiety were designed, synthesized and screened for their anti-cancer and anti-tubulin properties. By sequentially designing three series of compounds comprising of dihydroisoxazole in the linker, a small substituent like chlorine on one side (R-1) and aromatic group (R) on the pyridine ring, we have optimized the anti-cancer as well as anti-tubulin activity. Pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles 28b and 28c were found to be potent anti-cancer agents against all the cell lines tested with a concomitant accumulation of cells in the G2/M phase of the cell cycle. Molecular modeling suggests that the trimethoxyphenyl ring in 28b and 28c occupies the cholchicine binding domain of beta-tubulin, whereas, the dihydroisoxazole extends towards the interface of alpha,beta-tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.063

文献信息

• Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as anti-inflammatory and analgesic agents
  作者：B. Jayashankar、K.M. Lokanath Rai、N. Baskaran、H.S. Sathish

  DOI：10.1016/j.ejmech.2009.04.006

  日期：2009.10

  oxide with allyl alcohol followed by intramolecular 1,3-diploar cycloaddition reaction of nitrile imine with carbonyl group. All the newly synthesized compounds were screened for their anti-inflammatory and analgesic activities. Among the list of compounds (7a–k) studied, 7d, 7g, 7j, and 7k exhibited excellent activity comparable to ibuprofen and aspirin at the similar dosages.

  通过一氧化氮与烯丙醇的[3 + 2]-环加成反应，然后与腈亚胺与羰基的分子内1,3-二齿环加成反应，合成了一系列新型的醚键联双（杂环）。筛选所有新合成的化合物的抗炎和镇痛活性。在研究的化合物列表（7a - k）中，在相似的剂量下7d，7g，7j和7k表现出与布洛芬和阿司匹林相当的出色活性。
• Synthesis and structure–activity relationships of pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles as potent inhibitors of tubulin polymerization
  作者：P. Suman、T. Ramalinga Murthy、K. Rajkumar、D. Srikanth、Ch. Dayakar、Chandan Kishor、Anthony Addlagatta、Shasi V. Kalivendi、B. China Raju

  DOI：10.1016/j.ejmech.2014.11.063

  日期：2015.1

  Three series of compounds; pyridinyl-1H-1,2,3-triazoles, pyridinyl-1H-1,2,3-triazolylisoxazoles and pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles with TMP moiety were designed, synthesized and screened for their anti-cancer and anti-tubulin properties. By sequentially designing three series of compounds comprising of dihydroisoxazole in the linker, a small substituent like chlorine on one side (R-1) and aromatic group (R) on the pyridine ring, we have optimized the anti-cancer as well as anti-tubulin activity. Pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles 28b and 28c were found to be potent anti-cancer agents against all the cell lines tested with a concomitant accumulation of cells in the G2/M phase of the cell cycle. Molecular modeling suggests that the trimethoxyphenyl ring in 28b and 28c occupies the cholchicine binding domain of beta-tubulin, whereas, the dihydroisoxazole extends towards the interface of alpha,beta-tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.