AGN 191347 | 119435-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: AGN 191347
• 英文别名: 4-[(E)-(5,5,8,8-tetramethyl-1,2,6,7-tetrahydrocyclopenta[b]naphthalen-3-ylidene)methyl]benzoic acid
• CAS: 119435-88-0
• 化学式: C₂₅H₂₈O₂
• 分子量: 360.496
• InChiKey: GSEDYDKZYWSPMV-QGOAFFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,5,8,8-四甲基-5,6,7,8-四氢-2-萘甲醛 在 palladium on activated charcoal 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 三氯化铝 、 氯化亚砜 、 氢气 、 三溴化磷 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 正己烷 、 苯 为溶剂， 反应 15.5h， 生成 AGN 191347
  参考文献：
  名称：

  Retinobenzoic acids. 3. Structure-activity relationships of retinoidal azobenzene-4-carboxylic acids and stilbene-4-carboxylic acids

  摘要：

  Alkyl-substituted azobenzene-4-carboxylic acids are potent differentiation inducers of human promyelocytic leukemia cell line HL-60 to mature granulocytes. Their structure-activity relationships are very similar to those of other retinoidal benzoic acids which are generally represented by 4 and named retinobenzoic acids. The structure-activity relationships of azobenzenecarboxylic acids can also be applied to the known retinoid TTNPB (3). Thus, (E)-4-[2-(3,4-diisopropylphenyl)-1-propenyl]benzoic acid (St30 (28] and (E)-4-[2-(3-tert-butylphenyl)ethenyl]benzoic acid (St40 (29], the acyclic alkyl analogues of TTNPB, are nearly as active as retinoic acid. Among the oxidatively derived compounds (Az90, Ep series and Ox series) of azobenzene- or stilbenecarboxylic acids, Az90 (71) and Ep80 (61) have strong activities. However, all the bishydroxylated derivatives of TTNPB are inactive, while a diketo analogue Ox580 (69) has only weak potency. The activities of conformationally restricted compounds of TTNPB offer some information on the stereochemistry of the active form of these retinoidal compounds.

  DOI：

  10.1021/jm00125a027