[(2-溴苯甲酰基)氨基]乙酸 | 81568-83-4

• 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: [(2-溴苯甲酰基)氨基]乙酸
• 英文名称: 2-bromobenzoylglycine
• 英文别名: o-Brom-hippursaeure；2-bromo-hippuric acid；N-(2-bromobenzoyl)glycine；N-(2-Brom-benzoyl)-glycin；2-Brom-benzaminoessigsaeure；2-Brom-hippursaeure；2-Bromohippuric acid；2-[(2-bromobenzoyl)amino]acetic acid
• CAS: 81568-83-4
• 化学式: C₉H₈BrNO₃
• mdl: MFCD00460077
• 分子量: 258.071
• InChiKey: FVCGQCONGSANIN-UHFFFAOYSA-N

物化性质

• 熔点：
  192-193 °C
• 沸点：
  461.5±30.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  [(2-溴苯甲酰基)氨基]乙酸 在 乙酸酐 作用下， 生成 2--oxazolon-(5)
  参考文献：
  名称：

  Tan,H.S. et al., Recueil des Travaux Chimiques des Pays-Bas, 1969, vol. 88, # 2, p. 209 - 219

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl N-(o-bromobenzoyl)aminoacetate 在 水 、 sodium hydroxide 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 1.0h， 生成 [(2-溴苯甲酰基)氨基]乙酸
  参考文献：
  名称：

  Substituents Effect on the Erlenmeyer−Plöchl Reaction: Understanding an Observed Process Reaction Time

  摘要：

  A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Hunig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.

  DOI：

  10.1021/op100032s

文献信息

• A Fragment-Based Method to Discover Irreversible Covalent Inhibitors of Cysteine Proteases
  作者：Stefan G. Kathman、Ziyang Xu、Alexander V. Statsyuk

  DOI：10.1021/jm500345q

  日期：2014.6.12

  reported which irreversibly tethers drug-like fragments to catalytic cysteines. We attached an electrophile to 100 fragments without significant alterations in the reactivity of the electrophile. A mass spectrometry assay discovered three nonpeptidic inhibitors of the cysteine protease papain. The identified compounds display the characteristics of irreversible inhibitors. The irreversible tethering system

  报道了一种新的基于片段的药物发现方法，该方法不可逆地将类药物片段束缚在催化半胱氨酸上。我们将亲电试剂连接到 100 个片段上，而亲电试剂的反应性没有显着改变。质谱分析发现了半胱氨酸蛋白酶木瓜蛋白酶的三种非肽抑制剂。鉴定出的化合物显示出不可逆抑制剂的特征。不可逆的束缚系统也显示出特异性：三种鉴定出的木瓜蛋白酶抑制剂不与 UbcH7、USP08 或带有 GST 标签的人类鼻病毒 3C 蛋白酶共价反应。
• Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents
  作者：Xiaoke Gu、Yinpeng Zhang、Yueting Zou、Xin Li、Mingyu Guan、Qingqing Zhou、Jingying Qiu

  DOI：10.1016/j.bmc.2020.115892

  日期：2021.1

  As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value

  作为我们先前工作的延续，设计并合成了一系列新的苯基丙烯酰胺衍生物（4Aa-g，4Ba-t，5和6a-c）作为非核苷类抗HBV剂。其中，化合物4Bs可以有效抑制野生型和拉米夫定（3TC）/恩替卡韦耐药HBV突变株中HBV DNA复制，IC 50值分别为0.19和0.18μM。值得注意的是，4Bs的选择性指数值高于526，表明安全性良好。有趣的是，不像核苷类似物3TC，4BS能显著禁止3.5kb的pgRNA表达。分子对接研究表明4B通过疏水，π-π和H键相互作用可以很好地适合HBV核心蛋白的二聚体-二聚体界面。考虑到强效的抗HBV活性，低毒性以及与核苷类抗HBV药物3TC不同的抗HBV机理，化合物4Bs有望成为开发新型非核苷类抗HBV治疗药物的有希望的线索，并值得进一步研究。
• Grimshaw, James; Hamilton, Robert; Trocha-Grimshaw, Jadwiga, Journal of the Chemical Society. Perkin transactions I, 1982, p. 229 - 234
  作者：Grimshaw, James、Hamilton, Robert、Trocha-Grimshaw, Jadwiga

  DOI：——

  日期：——
• N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure–activity relationship
  作者：Daniel J. Burdick、Ken Paris、Kenneth Weese、Mark Stanley、Maureen Beresini、Kevin Clark、Robert S. McDowell、James C. Marsters、Thomas R. Gadek

  DOI：10.1016/s0960-894x(03)00084-2

  日期：2003.3

  The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Identification of non-peptidic cysteine reactive fragments as inhibitors of cysteine protease rhodesain
  作者：Danielle McShan、Stefan Kathman、Brittiney Lowe、Ziyang Xu、Jennifer Zhan、Alexander Statsyuk、Ifedayo Victor Ogungbe

  DOI：10.1016/j.bmcl.2015.08.074

  日期：2015.10

  Rhodesain, the major cathepsin L-like cysteine protease in the protozoan Trypanosoma brucei rhodesiense, the causative agent of African sleeping sickness, is a well-validated drug target. In this work, we used a fragment-based approach to identify inhibitors of this cysteine protease, and identified inhibitors of T. brucei. To discover inhibitors active against rhodesain and T. brucei, we screened a library of covalent fragments against rhodesain and conducted preliminary SAR studies. We envision that in vitro enzymatic assays will further expand the use of the covalent tethering method, a simple fragment-based drug discovery technique to discover covalent drug leads. (C) 2015 Elsevier Ltd. All rights reserved.