Methyl 4-(3-carbamoyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphtho<2,3-b>furan-2-yl)benzoate | 119436-00-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: Methyl 4-(3-carbamoyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphtho<2,3-b>furan-2-yl)benzoate
• 英文别名: Methyl 4-(3-carbamoyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphtho[2,3-b]furan-2-yl)benzoate
• CAS: 119436-00-9
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: QGGISUREHQLAPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl 4-(3-carbamoyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphtho<2,3-b>furan-2-yl)benzoate 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 41.0h， 生成 2-(4-Carboxy-phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphtho[2,3-b]furan-3-carboxylic acid
  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
• 作为产物：
  描述：

  Methyl 4-malonamoyl>benzoate 在 三氟乙酸 作用下， 反应 16.0h， 以12%的产率得到Methyl 4-(3-carbamoyl-6,7,8,9-tetrahydro-6,6,9,9-tetramethylnaphtho<2,1-b>furan-2-yl)benzoate
  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