2-acetoxy-5-(bromomethyl)benzoic acid methyl ester | 13339-11-2

• 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: 2-acetoxy-5-(bromomethyl)benzoic acid methyl ester
• 英文别名: 2-Acetoxy-5-brommethyl-benzoesaeure-methylester；methyl 2-acetoxy-5-(bromomethyl)benzoate；Methyl 2-acetyloxy-5-(bromomethyl)benzoate
• CAS: 13339-11-2
• 化学式: C₁₁H₁₁BrO₄
• 分子量: 287.11
• InChiKey: HYWVHCAPFUFYRR-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  345.5±37.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetoxy-5-(bromomethyl)benzoic acid methyl ester 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 14.0h， 生成 methyl 2-(3-(methoxycarbonyl)benzyloxy)-5-(tritylthiomethyl)benzoate
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Glutamate Carboxypeptidase II (GCPII) Inhibitors Based on Thioalkylbenzoic Acid Scaffolds

  摘要：

  A series of thiol-based glutamate carboxypeptidase II (GCPII) inhibitors have been synthesized with either a 3-(mercaptomethyl)benzoic acid or 2-(2-mercaptoethyl)benzoic acid scaffold. Potent inhibitors were identified from each of the two scaffolds with IC50 values in the single-digit nanomolar range, including 2-(3-carboxybenzyloxy)-5-(mercaptomethyl)benzoic acid 27c and 3-(2-mercaptoethyl)-biphenyl-2,3'-dicarboxylic acid 35c. Compound 35c was found to be metabolically stable and selective over a number of targets related to glutamate-mediated neurotransmission. Furthermore, compound 35c was found to be orally available in rats and exhibited efficacy in an animal model of neuropathic pain following oral administration.

  DOI：

  10.1021/jm300488m
• 作为产物：
  描述：

  5-甲基水杨酸甲酯 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 2-acetoxy-5-(bromomethyl)benzoic acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Glutamate Carboxypeptidase II (GCPII) Inhibitors Based on Thioalkylbenzoic Acid Scaffolds

  摘要：

  A series of thiol-based glutamate carboxypeptidase II (GCPII) inhibitors have been synthesized with either a 3-(mercaptomethyl)benzoic acid or 2-(2-mercaptoethyl)benzoic acid scaffold. Potent inhibitors were identified from each of the two scaffolds with IC50 values in the single-digit nanomolar range, including 2-(3-carboxybenzyloxy)-5-(mercaptomethyl)benzoic acid 27c and 3-(2-mercaptoethyl)-biphenyl-2,3'-dicarboxylic acid 35c. Compound 35c was found to be metabolically stable and selective over a number of targets related to glutamate-mediated neurotransmission. Furthermore, compound 35c was found to be orally available in rats and exhibited efficacy in an animal model of neuropathic pain following oral administration.

  DOI：

  10.1021/jm300488m

文献信息

• Novel Antiproliferative Agents Derived from Lavendustin A
  作者：Peter Nussbaumer、Anthony P. Winiski、Salvatore Cammisuli、Peter Hiestand、Gisbert Weckbecker、Anton Stuetz

  DOI：10.1021/jm00050a005

  日期：1994.11

  The active partial structure of the potent tyrosine kinase inhibitor lavendustin A was derivatized in the search for novel agents against cellular proliferation. The antiproliferative potential of the new derivatives was determined using the human keratinocyte cell line HaCaT as the primary test system. Whereas the lavendustin A partial structure is ineffective in inhibiting cell proliferation, esterification of its carboxylic acid function leads to measurable antiproliferative activity. Additional O-methylation of the 2,5-dihydroxyphenyl moiety yields activity in the micromolar range. Further substantial increases in activity are achieved by replacing the nitrogen with oxygen and carbon within the 2,5-dimethoxyphenyl series (but not within the 2,5-dihydroxyphenyl analogs) leading to 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid methyl ester (13) as the most potent analog identified to date. These increases in antiproliferative activity are paralleled, however, by the disappearance of activity against the epidermal growth factor receptor-associated tyrosine kinase, suggesting another mechanism of action.
• [EN] ARYL C-GLYCOSIDE COMPOUNDS AND SULFATED ESTERS THEREOF<br/>[FR] COMPOSES ARYLE C-GLYCOSIDE ET ESTERS SULFATES DE CES DERNIERS
  申请人：SANKYO COMPANY, LIMITED

  公开号：WO1998031697A1

  公开（公告）日：1998-07-23

  (EN) An aryl C-glycoside of formula (I), wherein R1 is a natural or artificial monosaccharide having an $g(a) or $g(b) bond or a disaccharide, trisaccharide or tetrasaccharide of the monosaccharide; m is 1 to 4; Ar is an aromatic or heterocyclic aromatic; R2 is hydrogen, hydroxy, amino, halogen, carboxy or a straight, branched or cyclic alkyl; k is 1 to 4; and n is 1 to 4. The aryl C-glycoside can be used in the treatment or prevention of inflammatory diseases, autoimmune diseases, infections, cancer and cancer metastasis, reperfusion disorders, thrombosis, ulcer, wounds and osteoporosis.(FR) Aryle C-glycoside de la formule (I), dans laquelle R1 est un monosaccharide naturel ou artificiel présentant une liaison $g(a) ou $g(b) ou un disaccharide, trisaccharide ou tétrasaccharide du monosaccharide; m est un nombre compris entre 1 et 4; Ar est un aromatique ou un aromatique hétérocyclique; R2 est hydrogène, hydroxy, amino, halogène, carboxy ou alkyle linéaire, ramifié ou cyclique; k est un nombre compris entre 1 et 4; et n est un nombre compris entre 1 et 4. L'aryle C-glycoside peut être utilisé dans le traitement ou la prévention des maladies inflammatoires, des maladies auto-immunes, des infections, des cancers et des métastases cancéreuses, des problèmes liés aux perfusions répétées, des thromboses, des ulcères, des plaies et de l'ostéoporose.