dibenzoyl diester of 1,4-dihydro-6,7-dihydroxy-1-ethyl-4-oxocinnoline-3-carboxylic acid | 141555-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: dibenzoyl diester of 1,4-dihydro-6,7-dihydroxy-1-ethyl-4-oxocinnoline-3-carboxylic acid
• CAS: 141555-22-8
• 化学式: C₂₅H₁₈N₂O₇
• 分子量: 458.427
• InChiKey: BDUYTCBAOKBEFR-UHFFFAOYSA-N

物化性质

• 沸点：
  726.2±70.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  dibenzoyl diester of 1,4-dihydro-6,7-dihydroxy-1-ethyl-4-oxocinnoline-3-carboxylic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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