3-溴-2-羟基-5-甲基苯甲酸甲酯 | 17746-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-2-羟基-5-甲基苯甲酸甲酯
• 英文名称: methyl 3-bromo-2-hydroxy-5-methylbenzoate
• CAS: 17746-77-9
• 化学式: C₉H₉BrO₃
• 分子量: 245.073
• InChiKey: ABFJFGPUBLCJSL-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  264.9±35.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴-2-羟基-5-甲基苯甲酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到2-溴-6-(羟甲基)-4-甲基苯酚
  参考文献：
  名称：

  Studies on Enzyme-Cleavable Dialkoxymethyl-cycloSaligenyl-2′,3′-dideoxy-2′,3′-didehydrothymidine Monophosphates

  摘要：

  Recently we reported on conceptually new enzymatically activated cycloSal-pronucleotides. Now, we developed this concept further with new compounds of this type. The basic idea is fast intracellular cleavage of a functionalized group at the cycloSal residue that results in a rapid delivery of the nucleotide and thus an intracellular enrichment of the nucleotide. The introduction of a higher alkylated acylal group, the di-iso-butyryloxymethyl group, to the aromatic ring led to the expected higher stability of these prodrugs against enzymatic cleavage but also entailed surprisingly a decrease in hydrolysis stabilities and solubility problems. For some compounds, a separation of the two diastereomeric forms (R-P, or S-P) was achieved. By X-ray structure analysis, the absolute configuration at the P-atom was assigned. For all separated diastereomers the (S-P) form showed better antiviral activity than the (R-P) form.

  DOI：

  10.1021/jm800853p
• 作为产物：
  描述：

  5-甲基水杨酸甲酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以62%的产率得到3-溴-2-羟基-5-甲基苯甲酸甲酯
  参考文献：
  名称：

  1,4-双（3-羟基羰基-4-羟基）苯乙烯基苯衍生物作为具有降血糖活性的PTP1B抑制剂。

  摘要：

  合成具有二苯乙烯和双苯乙烯基骨架的二水杨酸衍生物作为PTP1B抑制剂。该系列中最有效的药物表现出亚微摩尔IC（50）值。在动物模型中测试了化合物7b之一作为抗糖尿病药或抗肥胖药的功效。在向饮食诱导的肥胖小鼠饲喂化合物7b时，在药物治疗的小鼠和肥胖的对照小鼠之间未观察到体重增加和食物消耗的显着差异。然而，在肥胖诱导的糖尿病小鼠中，7b显着降低了空腹血糖水平并改善了葡萄糖耐量。

  DOI：

  10.1016/j.bmc.2008.07.090

文献信息

• WDR5 INHIBITORS AND MODULATORS
  申请人：Vanderbilt University

  公开号：US20200102288A1

  公开（公告）日：2020-04-02

  Described are imino-azacycle-benzamide compounds compounds that inhibit WDR5 and associated protein-protein interactions, pharmaceutical compositions including the compounds, and methods of using the compounds and compositions for treating disorders and conditions in a subject.

  描述了抑制WDR5和相关蛋白质-蛋白质相互作用的亚氨基-氮杂环-苯甲酰胺化合物，包括这些化合物的药物组合物，以及使用这些化合物和组合物治疗受试者疾病和状况的方法。
• Synthesis and reactions of some cyclohexadienones. Part II
  作者：J. R. Merchant、V. B. Desai

  DOI：10.1039/j39680000499

  日期：——

  The synthesis of 4-alkyl-4-trihalogenomethylcyclohexa-2,5-dienone derivatives by the application of the Zincke–Suhl reaction on p-alkyl-phenols is described. In some cases, only benzophenone derivatives were obtained. When the dienones were treated with reagents like phosphorus pentachloride and sulphuric acid, migration of the groups from the gem-C-atom occurred giving rise to halogenated benzoic

  描述了通过在对烷基苯酚上应用Zincke-Suhl反应合成4-烷基-4-三卤代甲基环己2,5-二烯酮衍生物。在某些情况下，仅获得二苯甲酮衍生物。当二烯酮用五氯化磷和硫酸之类的试剂处理时，基团从宝石-C原子发生迁移，生成卤代苯甲酸衍生物，在大多数情况下，卤代苯甲酸衍生物是通过独立途径合成的。在少数情况下，在与五氯化磷反应期间也观察到烷基的消除。
• Derivatives of 1,4-bis(3-hydroxycarbonyl-4-hydroxyl)styrylbenzene as PTP1B inhibitors with hypoglycemic activity
  作者：Suja Shrestha、Bharat Raj Bhattarai、Bhooshan Kafle、Keun-Hyeung Lee、Hyeongjin Cho

  DOI：10.1016/j.bmc.2008.07.090

  日期：2008.9

  Disalicylic acid derivatives with stilbene and bis-styrylbenzene skeleton were synthesized as PTP1B inhibitors. The most potent in this series exhibited a submicromolar IC(50) value. One of the compounds 7b was tested in an animal model for its efficacy as an anti-diabetic or an anti-obesity agent. In feeding compound 7b to diet-induced obese mice, no significant differences in weight gain and food

  合成具有二苯乙烯和双苯乙烯基骨架的二水杨酸衍生物作为PTP1B抑制剂。该系列中最有效的药物表现出亚微摩尔IC（50）值。在动物模型中测试了化合物7b之一作为抗糖尿病药或抗肥胖药的功效。在向饮食诱导的肥胖小鼠饲喂化合物7b时，在药物治疗的小鼠和肥胖的对照小鼠之间未观察到体重增加和食物消耗的显着差异。然而，在肥胖诱导的糖尿病小鼠中，7b显着降低了空腹血糖水平并改善了葡萄糖耐量。
• [EN] ALLOSTERIC CHROMENONE INHIBITORS OF PHOSPHOINOSITIDE 3-KINASE (PI3K) FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS CHROMÉNONE ALLOSTÉRIQUES DE LA PHOSPHOINOSITIDE 3-KINASE (PI3K) POUR LE TRAITEMENT DE MALADIES
  申请人：PETRA PHARMA CORP

  公开号：WO2022235574A1

  公开（公告）日：2022-11-10

  The disclosure relates to compounds of Formula (I) as allosteric chromenone inhibitors of phosphoinositide 3 -kinase (PI3K) useful in the treatment of diseases or disorders associated with PI3K modulation, Formula (I) or pharmaceutically acceptable salts thereof wherein R, R1, R2,R3, R4, R5, R6, R7, and R8, are as defined herein. The disclosure also relates to methods of making and using compounds of Formula (I) or pharmaceutically acceptable salts thereof.

  本公开涉及公式（I）的化合物，作为磷脂酰肌醇3-激酶（PI3K）的变构酶类黄酮酮抑制剂，用于治疗与PI3K调节相关的疾病或紊乱，其中公式（I）或其药学上可接受的盐，其中R，R1，R2，R3，R4，R5，R6，R7和R8如本文所定义。本公开还涉及制备和使用公式（I）或其药学上可接受的盐的方法。
• WDR5 inhibitors and modulators
  申请人：Vanderbilt University

  公开号：US10844044B2

  公开（公告）日：2020-11-24

  Described are imino-azacycle-benzamide compounds that inhibit WDR5 and associated protein-protein interactions, pharmaceutical compositions including the compounds, and methods of using the compounds and compositions for treating disorders and conditions in a subject.

  描述了抑制 WDR5 和相关蛋白-蛋白相互作用的亚氨基氮杂环苯甲酰胺化合物、包括这些化合物的药物组合物，以及使用这些化合物和组合物治疗受试者疾病和病症的方法。