N-(2',5'-dimethoxyphenyl)-3-oxobutanamide | 131451-77-9

• 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: N-(2',5'-dimethoxyphenyl)-3-oxobutanamide
• 英文别名: N-(2,5-dimethoxyphenyl)-N-methyl-3-oxobutanamide
• CAS: 131451-77-9
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: FCUSFUFMTMOSPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2',5'-dimethoxyphenyl)-3-oxobutanamide 在 potassium dichromate 、 硫酸 、 氢溴酸 作用下， 以 氯仿 、 水 为溶剂， 反应 50.67h， 生成 1,4-dimethyl-8-trimethylsilyloxy-5,8,8a,10a-tetrahydro-2,9,10(2H)-1-azaanthracenetrione
  参考文献：
  名称：

  Regioselectivity of the Diels-Alder reactions of 2,5,8(1H)-quinolinetriones

  摘要：

  Diels-Alder reactions of 2,5,8(1H)-quinolinetriones were completely regioselective for all the unsymmetrical dienes tested, except in the case of isoprene. This corresponds to a level of regioselectivity higher than the one found by previous workers for 5,8-quinolinequinone.

  DOI：

  10.1016/s0040-4020(01)85276-5
• 作为产物：
  描述：

  2,5-二甲氧基苯胺 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 水 、 苯 为溶剂， 生成 N-(2',5'-dimethoxyphenyl)-3-oxobutanamide
  参考文献：
  名称：

  乙酸nybomycin类似物4-乙酰氧基甲基-1,6,9-三甲基-1，-9-二氮杂蒽-2,5,8,10-四酮的全合成。

  摘要：

  分十三步制备4-乙酰氧基甲基-1,6,9-三甲基-1,9-二氮杂蒽-2,5,8,10-四酮2（nybomycin的潜在代谢产物），并以杂Diels-Alder反应为关键步。

  DOI：

  10.1016/s0040-4039(00)97633-0

文献信息

• Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile
  作者：Jinlei Bian、Xiang Li、Nan Wang、Xingsen Wu、Qidong You、Xiaojin Zhang

  DOI：10.1016/j.ejmech.2017.02.004

  日期：2017.3

  In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b] furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control beta-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H... pi interactions with Trp105 and Phe178 residues compared to the control beta-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities
  作者：Arup Maiti、P. V. Narasimha Reddy、Megan Sturdy、Laura Marler、Scott D. Pegan、Andrew D. Mesecar、John M. Pezzuto、Mark Cushman

  DOI：10.1021/jm801335z

  日期：2009.4.9

  An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.
• LEE, HEESOON;ANDERSON, WAYNE K., TETRAHEDRON LETT., 31,(1990) N1, C. 4405-4408
  作者：LEE, HEESOON、ANDERSON, WAYNE K.

  DOI：——

  日期：——
• Perez Jose Maria, Vidal Luis, Grande Mercedes T., Menendez J. Carlos, Ave+, Tetrahedron, 50 (1994) N 26, S 7923-7932
  作者：Perez Jose Maria, Vidal Luis, Grande Mercedes T., Menendez J. Carlos, Ave+

  DOI：——

  日期：——