3,4-diacetoxy-5-bromo-benzoic acid | 127450-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3,4-diacetoxy-5-bromo-benzoic acid
• 英文别名: Diacetyl-5-brom-protocatechusaeure；3,4-Diacetoxy-5-brom-benzoesaeure；3,4-Diacetyloxy-5-bromobenzoic acid
• CAS: 127450-30-0
• 化学式: C₁₁H₉BrO₆
• 分子量: 317.093
• InChiKey: LNCYHAZRXOLRHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-diacetoxy-5-bromo-benzoic acid 在 氯化亚砜 、 叠氮基三甲基硅烷 作用下， 以 甲苯 为溶剂， 反应 4.33h， 生成 3-bromo-4,5-diacetoxyphenyl isocyanate
  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：

  原儿茶酸 在 溴 、 溶剂黄146 作用下， 生成 3,4-diacetoxy-5-bromo-benzoic acid
  参考文献：
  名称：

  Zincke; Francke, Justus Liebigs Annalen der Chemie, 1896, vol. 293, p. 190

  摘要：

  DOI：

文献信息

• Cephalosporins, process for their preparation and pharmaceutical compositions
  申请人：ZENECA LIMITED

  公开号：EP0341948A2

  公开（公告）日：1989-11-15

  Cephalosporin antibiotics having a 3-position substituent of the formula: -CH₂NR¹-Y-A-Z-Q are described, wherein R¹ is hydrogen or certain optionally substituted alkyl groups; Y is -CO- or -SO₂-; A is optionally substituted phenylene or heterocyclylene; Z is a linking group and Q is a catechol or related ring system. Processes for their preparation and use are described.

  具有式中 3 位取代基的头孢菌素类抗生素： -Ch₂nr¹-y-a-z-q 其中 R¹ 是氢或某些任选取代的烷基；Y 是 -CO- 或 -SO₂-； A 是任选取代的亚苯基或杂环基； Z 是连接基团，Q 是邻苯二酚或相关环系。 描述了其制备和使用过程。
• PATHOGEN DETECTION
  申请人：University of Notre Dame Du Lac

  公开号：US20160319322A1

  公开（公告）日：2016-11-03

  A device for detecting bacteria in a sample, comprising: a substrate having a surface; and a plurality of Fe(III)-bound or Fe(III)-binding siderophores specific to the bacteria and covalently attached to the surface; wherein the siderophores are selected from the group consisting of one or more natural siderophores, siderophores having one or more of the formulas described herein, or combination thereof. Methods of detection are also provided.
• REDUCTION-TRIGGERED ANTIBACTERIAL SIDEROMYCINS
  申请人：MILLER Marvin J

  公开号：US20160368878A1

  公开（公告）日：2016-12-22

  A compound is provided, comprising: an Fe(III)-binding or an Fe(III)-bound siderophore; one or more optional linker covalently bound to the siderophore; a drug; and an Fe(III) to Fe(II) reduction triggered linker bound to the drug and the linker or, if no linker is present, then bound to the drug and the siderophore. Compositions and methods including the compound are also provided.
• US5055462A
  申请人：——

  公开号：US5055462A

  公开（公告）日：1991-10-08
• US5149803A
  申请人：——

  公开号：US5149803A

  公开（公告）日：1992-09-22