(-)-AA 2414 | 103196-89-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: (-)-AA 2414
• 英文别名: (S)-Serabenast；(7S)-7-phenyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)heptanoic acid
• CAS: 103196-89-0
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: ZBVKEHDGYSLCCC-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

Seratrodast 已知的人类代谢物包括 4'-羟基-Seratrodast 和 5-羟基-Seratrodast。

Seratrodast has known human metabolites that include 4'-hydroxy-seratrodast and 5-hydroxy-seratrodast.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  6-(氯甲酸基)己炔羧酸乙酯 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氯化铝 、 三氟化硼乙醚 、 三氯化铁 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 8.0h， 生成 (-)-AA 2414
  参考文献：
  名称：

  Quinones. 4. Novel eicosanoid antagonists: synthesis and pharmacological evaluation

  摘要：

  A new series of omega-phenyl-omega-quinonylalkanoic acids and related compounds was synthesized. The compounds were tested for their inhibitory effects on U-44069-induced contraction of the rabbit aorta. (+/- )-7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (4d) (AA-2414) with pA2 value of 8.28 was one of the most potent compounds. Compound 4d inhibited U-46619-induced contraction of the guinea pig lung (pA2 = 8.29) and U-44069-induced aggregation of the guinea pig platelet (IC50 = 3.5 x 10(-7) M). Compound 4d displaced the binding of [3H]U-46619 to guinea pig platelets (IC50 = 7.4 x 10(-9) M). Compound 4d also showed very potent inhibitory effects with an MED of 0.3 mg/kg (po) on U-46619-, LTD4-, PAF-, or IgG1-induced bronchoconstriction in guinea pigs. The enantiomers of 4d were prepared. The R-(+) isomer 8a was active in both in vitro and in vivo tests, but the S-(-) isomer 8b was much less active. We concluded that the antiasthmatic effects of 4d were based mainly on the TXA2 receptor antagonistic action. In addition, compound 4d showed potent inhibitory effects on PGD2-, PGF2 alpha-, and 11-epi-PGF2 alpha-induced contraction of the guinea pig tracheal strips. The diverse inhibitory effects might be expressed in terms of eicosanoid-antagonistic activity.

  DOI：

  10.1021/jm00129a030