Botryllazine B | 252026-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Botryllazine B
• 英文别名: Botrillazine b；(4-hydroxyphenyl)-[6-(4-hydroxyphenyl)pyrazin-2-yl]methanone
• CAS: 252026-25-8
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: LHUSZTDRQIRIGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Botryllazine B 在 吡啶 作用下， 反应 1.0h， 以90%的产率得到6-(4-acetoxyphenyl)-2-((4-acetoxyphenyl)carbonyl)pyrazine
  参考文献：
  名称：

  Synthesis and in vitro evaluation of botryllazine B analogues as a new class of inhibitor against human aldose reductase

  摘要：

  Botryllazine B analogues of diverse substitution patterns have been prepared, and their in vitro inhibitory activities against recombinant human aldose reductase (h-ALR2) evaluated. Among the 15 compounds tested, 6-(4-aminophenyl)-2-(4-hydroxyphenyl)carbonylpyrazine (7b) proved to be the most potent inhibitor, with IC50=0.91 mu M. Kinetic analyses of 7b and botryllazine B(1) revealed that these inhibitors exhibit an unprecedented mixed-type inhibition on h-ALR2 with respect to the substrate D,L-glyceraldehyde, in the presence of NADPH at inhibitor concentrations near the IC50 values. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.020
• 作为产物：
  描述：

  (6-氯吡嗪-2-基)-(4-甲氧基苯基)甲酮 在 四(三苯基膦)钯 吡啶盐酸盐 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 9.0h， 生成 Botryllazine B
  参考文献：
  名称：

  从葡萄灰霉病菌合成吡嗪生物碱。二嗪43

  摘要：

  吡嗪的区域选择性金属化和交叉偶联反应提供了容易获得硼替拉嗪A和B以及硼替拉嗪A的异构体的优点，并且氯吡嗪的收率很高。

  DOI：

  10.1021/jo0478196
• 作为试剂：
  描述：

  DL-甘油醛 在 还原型辅酶II(NADPH)四钠盐 、 Botryllazine B 作用下， 生成 甘油
  参考文献：
  名称：

  Synthesis and in vitro evaluation of botryllazine B analogues as a new class of inhibitor against human aldose reductase

  摘要：

  Botryllazine B analogues of diverse substitution patterns have been prepared, and their in vitro inhibitory activities against recombinant human aldose reductase (h-ALR2) evaluated. Among the 15 compounds tested, 6-(4-aminophenyl)-2-(4-hydroxyphenyl)carbonylpyrazine (7b) proved to be the most potent inhibitor, with IC50=0.91 mu M. Kinetic analyses of 7b and botryllazine B(1) revealed that these inhibitors exhibit an unprecedented mixed-type inhibition on h-ALR2 with respect to the substrate D,L-glyceraldehyde, in the presence of NADPH at inhibitor concentrations near the IC50 values. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.020

文献信息

• Synthesis of Naturally Occurring Pyrazine and Imidazole Alkaloids from Botryllus LeachiRID=?a?ID=?a? Dedicated to Prof. G . Märkl on the occasion of his 75 th birthday
  作者：Siavosh Mahboobi、Andreas Sellmer、Thomas Burgemeister、Alexei Lyssenko、Dieter Schollmeyer

  DOI：10.1007/s00706-003-0085-2

  日期：2004.3.1

  The synthesis of the naturally occurring and biologically active alkaloids 1 and 2, first isolated from the red ascidian Botryllus leachi by Duran et al. [1], is described and the structure proposed for Botryllazine B (1) is confirmed. The analytical data for 2-(p-hydroxybenzoyl)-4-(p-hydroxyphenyl)imidazole (2) are discussed and compared with the literature. With special emphasis of H-1 NMR data the tautomerism of aroylimidazolemethanones is described.
• Synthesis and in vitro evaluation of botryllazine B analogues as a new class of inhibitor against human aldose reductase
  作者：Ryota Saito、Mai Tokita、Keisuke Uda、Chikako Ishikawa、Mitsutoshi Satoh

  DOI：10.1016/j.tet.2009.01.020

  日期：2009.4

  Botryllazine B analogues of diverse substitution patterns have been prepared, and their in vitro inhibitory activities against recombinant human aldose reductase (h-ALR2) evaluated. Among the 15 compounds tested, 6-(4-aminophenyl)-2-(4-hydroxyphenyl)carbonylpyrazine (7b) proved to be the most potent inhibitor, with IC50=0.91 mu M. Kinetic analyses of 7b and botryllazine B(1) revealed that these inhibitors exhibit an unprecedented mixed-type inhibition on h-ALR2 with respect to the substrate D,L-glyceraldehyde, in the presence of NADPH at inhibitor concentrations near the IC50 values. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Pyrazine Alcaloids from <i>Botryllus </i><i>leachi</i>. Diazines 43
  作者：Frédéric Buron、Nelly Plé,、Alain Turck、Guy Queguiner

  DOI：10.1021/jo0478196

  日期：2005.4.1

  Regioselective metalation of pyrazines and cross-coupling reactions provides an easy access to botryllazines A and B and to an isomer of botryllazine A with good yields from chloropyrazine.

  吡嗪的区域选择性金属化和交叉偶联反应提供了容易获得硼替拉嗪A和B以及硼替拉嗪A的异构体的优点，并且氯吡嗪的收率很高。

表征谱图