5-bromoacetyl-2-hydroxy-benzoic acid | 62423-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromoacetyl-2-hydroxy-benzoic acid
• 英文别名: 5-Bromacetyl-2-hydroxy-benzoesaeure；2-hydroxy-5-(α-bromoacetyl) benzoic acid；5-(2-bromoacetyl)-2-hydroxybenzoate；5-bromoacetylsalicylic acid；5-Bromacetyl-salicylsaeure；5-(2-Bromoacetyl)-2-hydroxybenzoic acid
• CAS: 62423-71-6
• 化学式: C₉H₇BrO₄
• 分子量: 259.056
• InChiKey: AWCZHDQYNKDRCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromoacetyl-2-hydroxy-benzoic acid 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 丁酮 为溶剂， 25.0 ℃ 、98.06 kPa 条件下， 反应 110.0h， 生成 5-(2-Amino-1-hydroxyethyl)-2-hydroxybenzoic acid;hydrochloride
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008
• 作为产物：
  描述：

  阿司匹林 在 三氯化铝 、 1,4-dioxane dibromide 作用下， 以 1,4-二氧六环 、 乙醚 、 硝基苯 为溶剂， 反应 3.0h， 生成 5-bromoacetyl-2-hydroxy-benzoic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008

文献信息

• Thiazolyl benzoic acid compounds
  申请人：Science Union et Cie, Societe Francaise de Recherche Medical

  公开号：US04001420A1

  公开（公告）日：1977-01-04

  m-(thiazol-4-yl) benzoic acids substituted in 2- and optionally 5-position of the thiazol ring by lower alkyl, phenylalkyl, phenyl, halo-phenyl, lower alkylphenyl or lower alkoxyphenyl, and on the phenyl ring of the benzoic acid moiety by halogen, hydroxyl, lower alkyl or lower alkoxy. These compounds possess fibrinolytic, platelet stickiness decreasing and antiulcer properties and have an impact on the immunological processes.

  2-和（可选）5-位置被较低烷基，苯基烷基，苯基，卤苯基，较低烷基苯基或较低烷氧基取代的m-(噻唑-4-基)苯甲酸，以及苯甲酸部分的苯环上被卤素，羟基，较低烷基或较低烷氧基取代。这些化合物具有纤溶，降低血小板粘附和抗溃疡特性，并对免疫过程产生影响。
• Design, synthesis, docking and biological evaluation of 4-phenyl-thiazole derivatives as autotaxin (ATX) inhibitors
  作者：Anand Balupuri、Dae-Yon Lee、Myeong Hwi Lee、Sangeun Chae、Eunmi Jung、Yunki Kim、Jeonghee Ryu、Nam Sook Kang

  DOI：10.1016/j.bmcl.2017.07.022

  日期：2017.9

  displayed higher potency (IC50 = 14.99 nM) than the first clinical ATX inhibitor, GLPG1690 (IC50 = 242.00 nM) in the human plasma assay. Molecular docking studies were carried out to explore the binding pattern of newly synthesized compounds within active site of ATX. Docking studies suggested the putative binding mode of the novel compounds. Good ATX inhibitory activity of 21 was attributed to the hydrogen

  紫杉醇-糖原酸（ATX-LPA）信号通路涉及多种人类疾病，例如癌症，自身免疫性疾病，炎性疾病，神经退行性疾病和纤维化疾病。在此，设计并合成了一系列基于4-苯基噻唑的化合物。使用FS-3和人血浆分析法评估化合物的ATX抑制活性。在FS-3分析中，化合物20和21在低纳摩尔浓度（分别为IC 50  = 2.99和2.19 nM）下显着抑制了ATX 。发现21的抑制活性比PF-8380（IC 50  = 2.80 nM）略好，PF-8380是迄今报道的最有效的ATX抑制剂之一。此外21 在人血浆检测中显示出 比第一种临床ATX抑制剂GLPG1690（IC 50 = 242.00 nM）更高的效价（IC 50 = 14.99 nM）。进行了分子对接研究以探索新合成的化合物在ATX活性位点内的结合模式。对接研究表明了新型化合物的推定结合模式。良好的ATX抑制活性为21，这归因于与Asn230，Trp
• 2-Hydro
  申请人：Richardson-Merrell Inc.

  公开号：US04200755A1

  公开（公告）日：1980-04-29

  Derivatives of 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]ben zoic acid are prepared which are useful for their blocking action on .alpha. and .beta.-adrenergic receptors. In addition, these compounds are useful for their spasmolytic and anti-hypertensive activity.

  制备了2-羟基-5-[1-羟基-2-[4-(2-氧代-1-苯并咪唑啉基)哌啶基]乙基]苯甲酸的衍生物，这些衍生物对阻断α和β肾上腺素受体具有作用。此外，这些化合物对于其解痉和降压活性也是有用的。
• Salicylsäurederivate
  申请人：MERCK PATENT GmbH

  公开号：EP0338352A2

  公开（公告）日：1989-10-25

  Neue Salicylsäurederivate der allgemeinen Formel I worin R¹      H oder CH₃, R²      4-(4-Methyl-2-thiazolyl)-piperazino, 4-(Tetrahydro-2-furoyl)-piperazino, 4-(4-Methyl-2-thiazolyl)-homopiperazino, 4-Benzamidopiperidino, 6,7-Dimethoxy-1,2,3,4-tetrahydroisochinolino, 1-Imidazolyl, Tribrom-1-imidazolyl oder 2-(3-Indolyl)-1,1-dimethyl-ethylamino und R³      Alkoxy mit 1 - 4 C-Atomen, NH₂ oder Alkylamino mit 1 - 4 C-Atomen bedeuten, sowie deren physiologisch unbedenkliche Säureadditions­salze zeigen Wirkungen auf den Kreislauf, insbesondere blutdrucksenkende, herzentlastende und diuretische Wirkungen.

  通式 I 的新型水杨酸衍生物 其中 R¹ 是 H 或 CH₃、 R² 是 4-(4-甲基-2-噻唑基)-哌嗪基、4-(四氢-2-呋喃基)-哌嗪基、4-(4-甲基-2-噻唑基)-高哌嗪基、4-苯甲酰胺基哌嗪基、6,7-二甲氧基-1,2,3,4-四氢异喹啉基、1-咪唑基、三溴-1-咪唑基或 2-(3-吲哚基)-1,1-二甲基-乙基氨基，以及 R³ 含 1 - 4 个 C 原子的烷氧基、NH₂ 或 1 - 4 个 C 原子的烷基氨基 是指 以及它们对生理无害的酸加成盐对血液循环有影响，特别是降血压、舒缓心脏和利尿作用。
• Indolizine Derivatives as HIV-1 VIF-ElonginC Interaction Inhibitors
  作者：Wenlin Huang、Tao Zuo、Xiao Luo、Hongwei Jin、Zhenming Liu、Zhenjun Yang、Xianghui Yu、Liangren Zhang、Lihe Zhang

  DOI：10.1111/cbdd.12119

  日期：2013.6

  Compound 1 (VEC‐5) was identified as a potent small‐molecular HIV‐1 viron infectivity factor inhibitor that targets the viron infectivity factor–ElonginC interaction. A structure–activity relationship study was carried out to develop compounds with improved efficacy against HIV‐1 and 49 indolizine derivatives of three categories were designed and synthesized. We found that five compounds exhibited promising anti‐HIV‐1 activity, and the most active compound 2g had an IC50 value of 11.0 μm. These results provide new information to develop highly potent small‐molecule HIV‐1 viron infectivity factor inhibitors.