ethyl 4-(4-bromophenyl)-3-methyl-2,4-dioxobutanoate lithium salt

• 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: ethyl 4-(4-bromophenyl)-3-methyl-2,4-dioxobutanoate lithium salt
• 英文别名: Lithium Ethyl 4-(4-bromophenyl)-3-methyl-4-oxido-2-oxobutenoate；4-(4-bromo-phenyl)-3-methyl-2,4-dioxo-butyric acid ethyl ester lithium salt；Lithium;ethyl 4-(4-bromophenyl)-3-methyl-2,4-dioxobutanoate
• 化学式: C₁₃H₁₂BrO₄*Li
• 分子量: 319.081
• InChiKey: PLFQKRDENKONIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-bromophenyl)-3-methyl-2,4-dioxobutanoate lithium salt 在 9-borabicyclo[3.3.1]nonane dimer 、 三甲基铝 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 189.0h， 生成 5-[4-[2-(2,4-dichlorophenyl)-4-methyl-5-(piperidin-1-ylcarbamoyl)pyrazol-3-yl]phenyl]pentyl methanesulfonate
  参考文献：
  名称：

  Synthesis of novel 5-substituted pyrazole derivatives as cannabinoid antagonists

  摘要：

  A facile seven-step sequence was developed from 4'-bromopropiophenone, utilizing a Suzuki-type coupling with an alkene, to give several novel 5-substituted pyrazole derivatives in overall yields of 11-31%. They are potent CB1 antagonists and have binding affinities similar to SR 141716A. Like SR 141716A, they may prove to be clinically useful for the treatment of obesity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.165
• 作为产物：
  描述：

  4'-溴苯丙酮 、 草酸二乙酯 在 lithium hexamethyldisilazane 作用下， 以 正己烷 、 甲基环己烷 为溶剂， 生成 ethyl 4-(4-bromophenyl)-3-methyl-2,4-dioxobutanoate lithium salt
  参考文献：
  名称：

  CB1 受体反向激动剂利莫那班的碘化类似物的平行固相合成方法

  摘要：

  已经开发了一种用于赛诺菲安万特的 1 型大麻素 (CB 1 ) 受体反向激动剂利莫那班 (acomplia)碘化类似物的平行固相合成 (SPS) 方法。该方法允许从树脂结合的 C3 酯前体合成一系列 C3 酰胺/酰肼衍生物。的C-戈键与Hypogel-200树脂是稳定的多样化条件，但是允许ipso-使用的NaI / NCS即使对于含有氧化不稳定的酰肼部分的产品iododegermylative裂解。

  DOI：

  10.1021/ol902038y

文献信息

• A Method for Parallel Solid-Phase Synthesis of Iodinated Analogues of the CB₁ Receptor Inverse Agonist Rimonabant
  作者：Alan C. Spivey、Chih-Chung Tseng、Teyrnon C. Jones、Andrew D. Kohler、George J. Ellames

  DOI：10.1021/ol902038y

  日期：2009.10.15

  A method for the parallel solid-phase synthesis (SPS) of iodinated analogues of Sanofi-Aventis’ type 1 cannabinoid (CB1) receptor inverse agonist rimonabant (acomplia) has been developed. The method allows the synthesis of a range of C3 amide/hydrazide derivatives from a resin-bound C3 ester precursor. The C−Ge linkage to the Hypogel-200 resin is stable to the diversification conditions but allows

  已经开发了一种用于赛诺菲安万特的 1 型大麻素 (CB 1 ) 受体反向激动剂利莫那班 (acomplia)碘化类似物的平行固相合成 (SPS) 方法。该方法允许从树脂结合的 C3 酯前体合成一系列 C3 酰胺/酰肼衍生物。的C-戈键与Hypogel-200树脂是稳定的多样化条件，但是允许ipso-使用的NaI / NCS即使对于含有氧化不稳定的酰肼部分的产品iododegermylative裂解。
• Derivatives of N′-(1,5-diphenyl-1H-pyrazol-3-yl) sulfonamide with CB1 receptor affinity
  申请人：Sanofi-Aventis

  公开号：US07294645B2

  公开（公告）日：2007-11-13

  The invention relates to compounds of formula (I): Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 are as defined herein. The invention also relates to the preparation method thereof and to the use of same in therapeutics.

  该发明涉及式(I)的化合物：其中R1、R2、R3、R4、R5、R6、R7、R8、R9如本文所定义。该发明还涉及其制备方法以及在治疗中的应用。
• 1,5-Diarylpyrazole and vanillin hybrids: Synthesis, biological activity and DFT studies
  作者：Eduardo Hernández-Vázquez、Romina Castañeda-Arriaga、Juan José Ramírez-Espinosa、Omar Noel Medina-Campos、Francisco Hernández-Luis、José Pedraza Chaverri、Samuel Estrada-Soto

  DOI：10.1016/j.ejmech.2015.06.010

  日期：2015.7

  Herein, we report the design and synthesis of 13 diarylpyrazole hybrids with vanillin constructed as dual compounds against oxidative stress and diabetes. Compounds were tested in two different antioxidant assays. It was found that all compounds showed an important antioxidant activity in both DPPH and ORAC models and the activity was even more remarkable than vanillin. In addition, the hypoglycemic effect of compounds 1, 2, 4 and 12 was evaluated. Interestingly, compound 1 had the most potent hypoglycemic effect with a glycemia reduction of 71%, which was higher than rimonabant. Finally, a DFT study to propose a reasonable antioxidant mechanism is detailed. Both thermodynamic and kinetic studies indicated that the most feasible mechanism consists in the HAT abstraction of the phenolic hydrogen due to the formation of an stable transition state through the most rapid and exergonic path, while the SPLET mechanism is the most significant at higher pH values. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis of novel 5-substituted pyrazole derivatives as cannabinoid antagonists
  作者：Olga O. Alekseeva、Anu Mahadevan、Jenny L. Wiley、Billy R. Martin、Raj K. Razdan

  DOI：10.1016/j.tetlet.2005.01.165

  日期：2005.3

  A facile seven-step sequence was developed from 4'-bromopropiophenone, utilizing a Suzuki-type coupling with an alkene, to give several novel 5-substituted pyrazole derivatives in overall yields of 11-31%. They are potent CB1 antagonists and have binding affinities similar to SR 141716A. Like SR 141716A, they may prove to be clinically useful for the treatment of obesity. (C) 2005 Elsevier Ltd. All rights reserved.