4-[2-(3,4-Dimethoxyphenyl)ethyl]-3-hydroxy-7-(oxan-2-yl)-2,3-dihydropyridazino[4,5-b][1,4]oxazin-8-one | 1026630-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(3,4-Dimethoxyphenyl)ethyl]-3-hydroxy-7-(oxan-2-yl)-2,3-dihydropyridazino[4,5-b][1,4]oxazin-8-one
• CAS: 1026630-32-9
• 化学式: C₂₁H₂₇N₃O₆
• 分子量: 417.462
• InChiKey: JYAJMIBXVAPLRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[2-(3,4-Dimethoxyphenyl)ethyl]-3-hydroxy-7-(oxan-2-yl)-2,3-dihydropyridazino[4,5-b][1,4]oxazin-8-one 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-Allyl-8,9-dimethoxy-5,6,10b,11-tetrahydro-2H-12-oxa-2,3,4b-triaza-chrysen-1-one
  参考文献：
  名称：

  Synthetic Studies on Isoquinoline Derivatives with Multidrug Resistance (MDR) Modulating Activity

  摘要：

  Tetrahydropyridazino-1,4-oxazinoisoquinoline derivatives with multidrug resistance (MDR) modulating activity were designed and synthesized. A key step for cyclization of 1,4-oxazine ring was developed using K2CO3 and CH3CN in one-pot. Among prepared compounds, 2-(4-fluorobenzyl)-9,10-dimethoxy-12-methyl-6,7,11b,12-tetrahydropyridazino[4',5',5,6][1,4]oxazine[3,4,-a]isoquinolin-1(2H)-one (If) exhibited significant MDR reversing activity and low toxicity, which might be as potential MDR agent.

  DOI：

  10.3987/com-03-9918
• 作为产物：
  描述：

  4,5-二氯-2-(四氢-吡喃-2-基)-2H-吡嗪-3-酮 在 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 、 水 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 68.0h， 生成 4-[2-(3,4-Dimethoxyphenyl)ethyl]-3-hydroxy-7-(oxan-2-yl)-2,3-dihydropyridazino[4,5-b][1,4]oxazin-8-one
  参考文献：
  名称：

  Synthetic Studies on Isoquinoline Derivatives with Multidrug Resistance (MDR) Modulating Activity

  摘要：

  Tetrahydropyridazino-1,4-oxazinoisoquinoline derivatives with multidrug resistance (MDR) modulating activity were designed and synthesized. A key step for cyclization of 1,4-oxazine ring was developed using K2CO3 and CH3CN in one-pot. Among prepared compounds, 2-(4-fluorobenzyl)-9,10-dimethoxy-12-methyl-6,7,11b,12-tetrahydropyridazino[4',5',5,6][1,4]oxazine[3,4,-a]isoquinolin-1(2H)-one (If) exhibited significant MDR reversing activity and low toxicity, which might be as potential MDR agent.

  DOI：

  10.3987/com-03-9918

文献信息

• An efficient synthesis of [1,4]pyridazinooxazine[3,4-a]tetrahydro isoquinolines
  作者：Su-Dong Cho、Yong-Dae Park、Jeum-Jong Kim、Woo-Hong Joo、Motoo Shiro、Lothar Esser、J.R Falck、Chuljin Ahn、Dong-Soo Shin、Yong-Jin Yoon

  DOI：10.1016/j.tet.2004.03.011

  日期：2004.4

  A series of fused isoquinoline-pyridazinooxazine chimera were prepared in good overall yield from phenethylamide I and 4,5-dichloropyridazin-3-one 2 via Smiles rearrangement and Pictet-Spengler cyclization. (C) 2004 Elsevier Ltd. All rights reserved.