1-(4-isobutoxy-3-nitrophenyl)ethan-1-one | 217485-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-isobutoxy-3-nitrophenyl)ethan-1-one
• 英文别名: 1-(4-isobutyloxy-3-nitrophenyl)ethanone；1-[4-(2-methylpropoxy)-3-nitrophenyl]ethanone
• CAS: 217485-63-7
• 化学式: C₁₂H₁₅NO₄
• mdl: MFCD11136890
• 分子量: 237.255
• InChiKey: VDLADJYHNPRATA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-isobutoxy-3-nitrophenyl)ethan-1-one 在 盐酸肼 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 37.0h， 生成 6-(3-ntro-4-isobutoxyphenyl)-3-oxo-2,3-dihydropyridazine-4-hydrazide
  参考文献：
  名称：

  设计，合成和生物评价3-氧代-6-芳基-2,3-二氢哒嗪-4-碳酰肼衍生物作为新型黄嘌呤氧化酶抑制剂。

  摘要：

  为了扩大黄嘌呤氧化酶抑制剂的结构活性关系，通过分子对接设计合成了一系列3-氧代-6-芳基-2,3-二氢哒嗪-4-羧酰肼/羧酸衍生物。使用非布索坦和别嘌呤醇作为标准对照，评估所有目标化合物的体外XO抑制作用。大多数酰肼衍生物表现出在微摩尔范围内的效力水平。从对接研究的角度来看，酰肼衍生物通过一种新颖的相互作用方式与XO的活性位点结合，这与带有羧基的非布索坦的相互作用方式不同。最有希望的化合物8b进一步进行动力学分析，以推论其抑制方式。

  DOI：

  10.1016/j.bmc.2019.03.027
• 作为产物：
  描述：

  溴代异丁烷 、 4'-羟基-3'-硝基苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以58.4%的产率得到1-(4-isobutoxy-3-nitrophenyl)ethan-1-one
  参考文献：
  名称：

  Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors

  摘要：

  A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.

  DOI：

  10.1016/j.ejmech.2010.02.013

文献信息

• [EN] COMPOUNDS, IN PARTICULAR FOR USE IN THE TREATMENT OF A DISEASE OR CONDITION FOR WHICH A BROMODOMAIN INHIBITOR IS INDICATED<br/>[FR] COMPOSÉS, DESTINÉS PLUS PARTICULIÈREMENT À ÊTRE UTILISÉS DANS LE TRAITEMENT D'UNE MALADIE OU D'UNE PATHOLOGIE POUR LAQUELLE UN INHIBITEUR DU BROMODOMAINE EST INDIQUÉ
  申请人：UNIV ZUERICH

  公开号：WO2016001452A1

  公开（公告）日：2016-01-07

  The invention relates to a compound for use in the treatment of a disease or condition for which a bromodomain inhibitor is indicated characterized by a general formula (1) and a compound according to formula (3).

  该发明涉及一种化合物，用于治疗溴结构域抑制剂指示的疾病或症状，其具有一般式（1）和根据式（3）的化合物。
• Design, synthesis and bioevaluation of 2-mercapto-6-phenylpyrimidine-4-carboxylic acid derivatives as potent xanthine oxidase inhibitors
  作者：Ailong Shi、Lichao Zhang、He Wang、Sibo Wang、Mingzheng Yang、Qi Guan、Kai Bao、Weige Zhang

  DOI：10.1016/j.ejmech.2018.06.009

  日期：2018.7

  2-mercapto-6-phenylpyrimidine-4-carboxylic acid derivatives (7a‒c, 8a‒e, 9a‒e and 10a‒e) as novel xanthine oxidase inhibitors were designed based on molecular docking, and synthesized by a new method using ketoenol acids and thiourea as the starting materials. In vitro activity assay indicated that most of the designed compounds displayed submicromolar inhibitory potency. Specifically, compound 9b had the most

  以分子对接为基础，设计了一系列2-巯基-6-苯基嘧啶-4-羧酸衍生物（7a‒c，8a‒e，9a 10e和10a‒e）作为黄嘌呤氧化酶抑制剂。酮烯醇酸和硫脲为起始原料的方法。体外活性测定表明，大多数设计的化合物均表现出亚微摩尔抑制潜能。具体而言，化合物9b具有最强的酶抑制活性，IC 50为0.132μM。稳态酶动力学表明9b充当XO的混合型抑制剂。
• Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors
  作者：Shaojie Wang、Jufang Yan、Jian Wang、Jiarun Chen、Tingjian Zhang、Yong Zhao、Mingxing Xue

  DOI：10.1016/j.ejmech.2010.02.013

  日期：2010.6

  A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.
• Design, synthesis and bioevaluation of 3-oxo-6-aryl-2,3-dihydropyridazine-4-carbohydrazide derivatives as novel xanthine oxidase inhibitors
  作者：Lichao Zhang、Sibo Wang、Mingzheng Yang、Ailong Shi、He Wang、Qi Guan、Kai Bao、Weige Zhang

  DOI：10.1016/j.bmc.2019.03.027

  日期：2019.5

  In view of expanding the structure activity relationship of xanthine oxidase inhibitors, a series of 3-oxo-6-aryl-2,3-dihydropyridazine-4-carbohydrazide/carboxylic acid derivatives were designed by molecular docking and synthesized. All the target compounds were evaluated for their in vitro XO inhibition by using febuxostat and allopurinol as the standard controls. Most of the hydrazide derivatives

  为了扩大黄嘌呤氧化酶抑制剂的结构活性关系，通过分子对接设计合成了一系列3-氧代-6-芳基-2,3-二氢哒嗪-4-羧酰肼/羧酸衍生物。使用非布索坦和别嘌呤醇作为标准对照，评估所有目标化合物的体外XO抑制作用。大多数酰肼衍生物表现出在微摩尔范围内的效力水平。从对接研究的角度来看，酰肼衍生物通过一种新颖的相互作用方式与XO的活性位点结合，这与带有羧基的非布索坦的相互作用方式不同。最有希望的化合物8b进一步进行动力学分析，以推论其抑制方式。