4,5-dihydroxy-2-fluorobenzoic acid | 158641-64-6

• 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: 4,5-dihydroxy-2-fluorobenzoic acid
• 英文别名: 2-Fluoro-4,5-dihydroxybenzoic acid
• CAS: 158641-64-6
• 化学式: C₇H₅FO₄
• 分子量: 172.113
• InChiKey: VQTABBMEZKSJRW-UHFFFAOYSA-N

物化性质

• 沸点：
  425.9±45.0 °C(Predicted)
• 密度：
  1.670±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dihydroxy-2-fluorobenzoic acid 在 ammonium hydroxide 、 氯化亚砜 、 硫酸 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 4.33h， 生成 (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-{[ethyl-(2-fluoro-4,5-dihydroxy-benzoyl)-amino]-methyl}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Pharmacokinetics of catechol cephalosporins. The effect of incorporating substituents into the catechol moiety on pharmacokinetics in a marmoset model

  摘要：

  Two series of cephalosporins A and B have been synthesized, bearing at C-3' catechols substituted with various electron withdrawing groups (Y) and differing links (X), and were evaluated for their in vitro antibacterial activity and their pharmacokinetics in marmosets. Compounds in series A, bearing an isobutyric oxime substituent, proved to be highly active against Gram-negative organisms and were especially noteworthy for showing long elimination phase (beta) half-lives in marmosets. It was established that introduction of electron withdrawing substituents greatly increased the beta-half-lives of compounds (5, X = NHCO, Y = H, t1/2 = 1.25 h, AUC = 27 mg/h per L; 11, X = NHCO, Y = 5-Cl, t1/2, = 4.5 h, AUC = 638 mg/h per L) and that the nature of the link also influenced t1/2, the highest values being obtained when X = NHCO and OCO. Acidities (pK(a) values) of the substituted catechols were measured, and relationships between the acidities and half-lives were evaluated. Thus it was established that the more acidic catechols gave the longest half-lives (12, X = NHCO, Y = 2,5-Cl2, t1/2 = 8.2 h, AUC = 461 mg/h per L). Further elaboration of the catechol to bicyclic systems maintained good pharmacokinetics when the pK(a) was sufficiently acidic.

  DOI：

  10.1021/jm00092a015
• 作为产物：
  描述：

  4-氟-1,2-二甲氧基苯 在 盐酸 、 三氯化铝 、 水 、 溴 、 三溴化硼 、 二乙胺 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 10.5h， 生成 4,5-dihydroxy-2-fluorobenzoic acid
  参考文献：
  名称：

  Stegmann, Hartmut B.; Deuschle, Gabriele; Schuler, Paul, Journal of the Chemical Society. Perkin transactions II, 1994, # 3, p. 547 - 556

  摘要：

  DOI：

文献信息

• [EN] ARYLAMIDE INHIBITOR, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF<br/>[FR] INHIBITEUR D'ARYLAMIDE, SON PROCÉDÉ DE PRÉPARATION ET SON APPLICATION<br/>[ZH] 芳基酰胺类抑制剂及其制备方法和应用
  申请人：SUZHOU ZELGEN BIOPHARMACEUTICALS CO LTD

  公开号：WO2020143385A1

  公开（公告）日：2020-07-16

  本发明公开了一种凋亡信号调节激酶1(ASK1)抑制剂，提供具有式(I)结构的芳基酰胺类化合物，其立体异构体、互变异构体或药学上可以接受的盐、水合物、溶剂合物及前药，还提供该类化合物在药学上可接受的盐的药物组合物。所述芳基酰胺类化合物可用于治疗和预防非酒精性脂肪肝炎以及相关的疾病。
• [EN] COMPOSITIONS AND METHODS FOR ANTIOXIDANT AND ANTI-INFLAMMATORY THERAPEUTICS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR DES AGENTS THÉRAPEUTIQUES ANTIOXYDANTS ET ANTI-INFLAMMATOIRES
  申请人：[en]AVANTI BIOSCIENCES INC.

  公开号：WO2023288020A1

  公开（公告）日：2023-01-19

  The present invention relates to compositions and methods for antioxidant and anti-inflammatory therapeutics.
• Pharmacokinetics of catechol cephalosporins. The effect of incorporating substituents into the catechol moiety on pharmacokinetics in a marmoset model
  作者：T. G. C. Bird、J. C. Arnould、A. Bertrandie、F. H. Jung

  DOI：10.1021/jm00092a015

  日期：1992.7

  Two series of cephalosporins A and B have been synthesized, bearing at C-3' catechols substituted with various electron withdrawing groups (Y) and differing links (X), and were evaluated for their in vitro antibacterial activity and their pharmacokinetics in marmosets. Compounds in series A, bearing an isobutyric oxime substituent, proved to be highly active against Gram-negative organisms and were especially noteworthy for showing long elimination phase (beta) half-lives in marmosets. It was established that introduction of electron withdrawing substituents greatly increased the beta-half-lives of compounds (5, X = NHCO, Y = H, t1/2 = 1.25 h, AUC = 27 mg/h per L; 11, X = NHCO, Y = 5-Cl, t1/2, = 4.5 h, AUC = 638 mg/h per L) and that the nature of the link also influenced t1/2, the highest values being obtained when X = NHCO and OCO. Acidities (pK(a) values) of the substituted catechols were measured, and relationships between the acidities and half-lives were evaluated. Thus it was established that the more acidic catechols gave the longest half-lives (12, X = NHCO, Y = 2,5-Cl2, t1/2 = 8.2 h, AUC = 461 mg/h per L). Further elaboration of the catechol to bicyclic systems maintained good pharmacokinetics when the pK(a) was sufficiently acidic.
• Stegmann, Hartmut B.; Deuschle, Gabriele; Schuler, Paul, Journal of the Chemical Society. Perkin transactions II, 1994, # 3, p. 547 - 556
  作者：Stegmann, Hartmut B.、Deuschle, Gabriele、Schuler, Paul

  DOI：——

  日期：——

表征谱图