6-(4-Propionyl-3-hydroxy-2-propylphenoxy)hexanoic acid | 92518-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4-Propionyl-3-hydroxy-2-propylphenoxy)hexanoic acid
• 英文别名: 6-(3-Hydroxy-4-propanoyl-2-propylphenoxy)hexanoic acid
• CAS: 92518-45-1
• 化学式: C₁₈H₂₆O₅
• 分子量: 322.401
• InChiKey: WMEQXGSCLTWZSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-溴己酸 在 三乙基硅烷 、 甲酸 、 三氟化硼乙醚 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 96.0h， 生成 6-(4-Propionyl-3-hydroxy-2-propylphenoxy)hexanoic acid
  参考文献：
  名称：

  Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives

  摘要：

  A series of derivatives of 2,4-dihydroxy-3-propylacetophenone(1) were prepared and examined for their ability to block leukotriene D4 (LTD4) induced contraction of guinea pig ileum. Straight-chain carboxylic acids where the carboxyl group was separated from the acetophenone moiety by varying numbers of methylenes were evaluated, and maximum activity was obtained with the pentamethylene acid (6). Examination of ring substitution showed that the 2-propyl-3-hydroxy-4-acetyl substitution pattern was required for maximum LTD4 antagonist activity. Additional chain terminal groups were examined, and the acidic 5-tetrazolyl group separated from the acetophenone moiety by four to seven methylenes (26, 23, 27, 28) gave excellent in vitro and in vivo activities. Compound 26 (LY171883) had the best balance of in vitro and in vivo activity. It lacked bronchospastic activity at the doses administered and has been chosen for clinical evaluation.

  DOI：

  10.1021/jm00387a018

文献信息

• Leukotriene antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0108592A1

  公开（公告）日：1984-05-16

  Novel alkane derivatives of the formula (I) or a pharmaceutically acceptable salt thereof, wherein: R, is hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, or phenyl; R2 is hydrogen, C1-C6 alkyl, or C2-C6 alkenyl; R3 is hydrogen, C1-C10 alkyl, phenyl, C1-C10 alkyl-substituted phenyl, biphenyl, or benzylphenyl; R4 is -COOR7, -CONRaR9, -CONHOH, -NR8R9, -SC(=NH)NH2, cyano, cyanothio, where R7 is hydrogen or C1-C4 alkyl, R8 and R9 are each independently hydrogen, C1-C3 alkyl, or when taken together with the nitrogen atom form a : morpholine or N-methyl piperazine ring, R is hydrogen, C1-C4 alkyl, or-CH2COOR7, and p is 0,1, or 2; R5 and R6 are each independently hydrogen or C1-C3 alkyl; and n is 0-10 are leukotriene antagonists.

  式 (I) 的新型烷烃衍生物 或其药学上可接受的盐，其中 R，是氢、C1-C6 烷基、C3-C8 环烷基或苯基； R2 是氢、C1-C6 烷基或 C2-C6 烯基 R3 是氢、C1-C10 烷基、苯基、C1-C10 烷基取代的苯基、联苯或苄基苯基； R4 是-COOR7、-CONRaR9、-CONHOH、-NR8R9、-SC(=NH)NH2、氰基、硫氰基、 其中 R7 为氢或 C1-C4 烷基、 R8 和 R9 各自独立地为氢、C1-C3 烷基，或与氮原子一起形成吗啉环或 N-甲基哌嗪环、 R 是氢、C1-C4 烷基或-CH2COOR7，p 是 0、1 或 2； R5 和 R6 各自独立地为氢或 C1-C3 烷基；n 为 0-10 的白三烯拮抗剂。
• MARSHALL, WINSTON S.;VERGE, JOHN P.
  作者：MARSHALL, WINSTON S.、VERGE, JOHN P.

  DOI：——

  日期：——
• MARSHALL W. S.; GOODSON T.; CULLINAN G. J.; SWANSON-BEAN D.; HAISCH K. D.+, J. MED. CHEM., 30,(1987) N 4, 682-689
  作者：MARSHALL W. S.、 GOODSON T.、 CULLINAN G. J.、 SWANSON-BEAN D.、 HAISCH K. D.+

  DOI：——

  日期：——
• US4661505A
  申请人：——

  公开号：US4661505A

  公开（公告）日：1987-04-28
• US4769482A
  申请人：——

  公开号：US4769482A

  公开（公告）日：1988-09-06