2-bromo-1-(3,5-di-tert-butyl-4-methoxyphenyl)ethanone | 940291-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(3,5-di-tert-butyl-4-methoxyphenyl)ethanone
• 英文别名: 2-Bromo-1-(3,5-ditert-butyl-4-methoxyphenyl)ethanone；2-bromo-1-(3,5-ditert-butyl-4-methoxyphenyl)ethanone
• CAS: 940291-86-1
• 化学式: C₁₇H₂₅BrO₂
• 分子量: 341.288
• InChiKey: HEAMXZJYASFRLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(3,5-di-tert-butyl-4-methoxyphenyl)ethanone 在 ammonium acetate 、 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 8-chloro-6-(3,5-di-tert-butyl-4-methoxyphenyl)-2-phenyl-1,2,4-triazolo[4,3-a]pyrazin-3(2H)-one
  参考文献：
  名称：

  Antioxidant-Conjugated 1,2,4-Triazolo[4,3-a]pyrazin-3-one Derivatives: Highly Potent and Selective Human A_2A Adenosine Receptor Antagonists Possessing Protective Efficacy in Neuropathic Pain

  摘要：

  New 8-amino-6-aryl-1,2,4-triazolo[4,3-a]pyrazin-3-ones were designed to obtain dual antioxidant-human A(2A) adenosine receptor (hA(2A) AR) antagonists. Two sets of compounds were synthesized, the first featuring phenol rings at the 6-position, the second bearing the lipoyl and 4-hydroxy-3,5-di-tertbut-benzoyl residues appended by different linkers on the 6-phenyl ring. Several new triazolopyrazines (1-21) were potent and selective hA(2A) AR antagonists (K-i = 0.17-54.5 nM). Compounds 11, 15, and 21, featuring antioxidant moieties, and compound 12, lacking the antioxidant functionality, reduced oxaliplatin-induced toxicity in microglia cells, the most active being the lipoyl-derivative 15 and the (4-hydroxy-3,5-di-tertbutyl)benzoyl-analogue 21 which were effective in reducing the oxygen free radical level. The lipoyl-derivative 15 was also able to revert oxaliplatin-induced neuropathy in the mouse. In vivo efficacy of 15 makes it a promising neuroprotective agent in oxidative stress-related diseases.

  DOI：

  10.1021/acs.jmedchem.9b00778
• 作为产物：
  描述：

  3',5'-di-tert-butyl-4'-methoxyacetophenone 在 copper(ll) bromide 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 2-bromo-1-(3,5-di-tert-butyl-4-methoxyphenyl)ethanone
  参考文献：
  名称：

  4-PHENYL-1,3-THIAZOLES AND 4-PHENYL-1,3-OXAZOLES DERIVATIVES AS CANNABINOID RECEPTOR LIGANDS

  摘要：

  本发明涉及具有一般式(I)的新4-苯基-1,3-唑衍生物，其中R1、R2、R3、R4、X、A、B和n是可变的，在消旋形式、对映异构体形式或任何组合中。这些化合物对大麻素受体具有亲和力，因此可用作药物治疗或预防涉及其中一个或多个这些受体的病理状态和疾病。本发明还涉及含有所述产品的药物组合物以及利用它们制备药物的用途。

  公开号：

  US20110059970A1

文献信息

• 4-PHENYL-1,3-THIAZOLES AND 4-PHENYL-1,3-OXAZOLES DERIVATIVES AS CANNABINOID RECEPTOR LIGANDS
  申请人：Harnett Jeremiah

  公开号：US20110059970A1

  公开（公告）日：2011-03-10

  The present invention relates to new 4-phenyl-1,3-azole derivatives having the general formula (I) wherein R1, R2, R3, R4, X, A, B, and n are variable, in a racemic form, an enantiomeric form or any combinations thereof. These compounds exhibit affinity for cannabinoid receptors and may therefore be used as drugs to treat or prevent pathological states and diseases in which one or more of these receptors are involved. The invention also relates to pharmaceutical compositions containing said products and to the use thereof to prepare a drug.

  本发明涉及具有一般式(I)的新4-苯基-1,3-唑衍生物，其中R1、R2、R3、R4、X、A、B和n是可变的，在消旋形式、对映异构体形式或任何组合中。这些化合物对大麻素受体具有亲和力，因此可用作药物治疗或预防涉及其中一个或多个这些受体的病理状态和疾病。本发明还涉及含有所述产品的药物组合物以及利用它们制备药物的用途。
• Selective benzimidazole inhibitors of the antigen receptor-mediated NF-κB activation pathway
  作者：Karl J. Okolotowicz、Ranxin Shi、Xueying Zheng、Mary MacDonald、John C. Reed、John R. Cashman

  DOI：10.1016/j.bmc.2010.01.039

  日期：2010.3

  Dysregulated antigen receptor-mediated NF-kappa B activation can contribute to development of autoimmunity, chronic inflammation, and malignancy. A chemical biology screening strategy has identified a substituted benzimidazole that selectively inhibits antigen receptor-mediated NF-kappa B activation without blocking other NF-kappa B activation pathways. A library of analogs was synthesized and the structure-activity relationship and metabolic stability for the series is presented. (C) 2010 Elsevier Ltd. All rights reserved.
• DERIVES DE 4-PHENYL-L, 3-THIAZOLES ET DE 4-PHENYL-1, 3-OXAZOLES COMME LIGANDS DES RECEPTEURS CANNABINOIDES
  申请人：IPSEN PHARMA S.A.S.

  公开号：EP2201007A1

  公开（公告）日：2010-06-30
• [EN] CANNABINOID RECEPTOR LIGANDS<br/>[FR] DERIVES DE 4-PHENYL-L, 3-THIAZOLES ET DE 4-PHENYL-L, 3-OXAZOLES COMME LIGANDS DES RECEPTEURS CANNABINOIDES
  申请人：IPSEN PHARMA SAS

  公开号：WO2009071753A1

  公开（公告）日：2009-06-11

  La présente invention a pour objet des nouveaux dérivés de 4-phenyl-1,3-azoles de formule générale (I) dans laquelle R1, R2, R3, R4, X, A, B, et n sont variables, sous forme racémique, d'énantiomère ou toutes combinaisons de ces formes. Ces composés présentent une affinité pour les récepteurs aux cannabinoides et sont donc susceptibles d'être utilisés comme médicaments pour traiter ou prévenir les états pathologiques et les maladies dans lesquels un ou plusieurs de ces récepteurs sont impliqués. L'invention concerne également des compositions pharmaceutiques contenant lesdits produits et leur utilisation pour la préparation d'un médicament.
• Antioxidant-Conjugated 1,2,4-Triazolo[4,3-<i>a</i>]pyrazin-3-one Derivatives: Highly Potent and Selective Human A_2A Adenosine Receptor Antagonists Possessing Protective Efficacy in Neuropathic Pain
  作者：Matteo Falsini、Daniela Catarzi、Flavia Varano、Costanza Ceni、Diego Dal Ben、Gabriella Marucci、Michela Buccioni、Rosaria Volpini、Lorenzo Di Cesare Mannelli、Elena Lucarini、Carla Ghelardini、Gianluca Bartolucci、Marta Menicatti、Vittoria Colotta

  DOI：10.1021/acs.jmedchem.9b00778

  日期：2019.9.26

  New 8-amino-6-aryl-1,2,4-triazolo[4,3-a]pyrazin-3-ones were designed to obtain dual antioxidant-human A(2A) adenosine receptor (hA(2A) AR) antagonists. Two sets of compounds were synthesized, the first featuring phenol rings at the 6-position, the second bearing the lipoyl and 4-hydroxy-3,5-di-tertbut-benzoyl residues appended by different linkers on the 6-phenyl ring. Several new triazolopyrazines (1-21) were potent and selective hA(2A) AR antagonists (K-i = 0.17-54.5 nM). Compounds 11, 15, and 21, featuring antioxidant moieties, and compound 12, lacking the antioxidant functionality, reduced oxaliplatin-induced toxicity in microglia cells, the most active being the lipoyl-derivative 15 and the (4-hydroxy-3,5-di-tertbutyl)benzoyl-analogue 21 which were effective in reducing the oxygen free radical level. The lipoyl-derivative 15 was also able to revert oxaliplatin-induced neuropathy in the mouse. In vivo efficacy of 15 makes it a promising neuroprotective agent in oxidative stress-related diseases.