4-[3-Methyl-3-(5,5,8,8-tetra-methyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-oxiranyl]-benzoic acid | 102121-03-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 4-[3-Methyl-3-(5,5,8,8-tetra-methyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-oxiranyl]-benzoic acid
• 英文别名: 4-[3-Methyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-oxiranyl]benzoic acid；4-[3-methyl-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)oxiran-2-yl]benzoic acid
• CAS: 102121-03-9
• 化学式: C₂₄H₂₈O₃
• 分子量: 364.485
• InChiKey: MJVVETLXZJGUTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzoic acid methyl ester 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.0h， 生成 4-[3-Methyl-3-(5,5,8,8-tetra-methyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-oxiranyl]-benzoic 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

文献信息

• USE OR RETINOIDS TO LOWER PLASMA LEVELS OF LIPOPROTEIN (a)
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0808159A1

  公开（公告）日：1997-11-26
• US5489611A
  申请人：——

  公开号：US5489611A

  公开（公告）日：1996-02-06
• [EN] USE OR RETINOIDS TO LOWER PLASMA LEVELS OF LIPOPROTEIN (a)<br/>[FR] UTILISATION DES RETINOIDES POUR ABAISSER LES NIVEAUX DU PLASMA DANS LA LIPOPROTEINE (a)
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1996024344A1

  公开（公告）日：1996-08-15

  (EN) Retinoids are effective to lower plasma levels of Lp(a) in mammals.(FR) L'invention concerne des rétinoïdes dont l'action est efficace pour abaisser les niveaux du plasma dans la lipoprotéine (a) chez les mammifères.
• [EN] RETINOID-GLITAZONE COMBINATIONS<br/>[FR] COMBINAISONS RETINOIDES-GLITAZONE
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1999048529A1

  公开（公告）日：1999-09-30

  (EN) Cell proliferation is inhibited by administering a combination of a retinoid and a glitazone, thereby treating disease states caused by uncontrolled cell proliferation, including cancer, restenosis, and atherosclerosis.(FR) L'invention porte sur l'inhibition de la prolifération cellulaire par l'administration d'une combinaison comprenant un rétinoïde et un glitazone, afin de traiter les états pathologiques dus à une prolifération cellulaire incontrôlée, notamment le cancer, la resténose et l'athérosclérose.
• Retinobenzoic acids. 3. Structure-activity relationships of retinoidal azobenzene-4-carboxylic acids and stilbene-4-carboxylic acids
  作者：Hiroyuki Kagechika、Toshiyuki Himi、Koushi Namikawa、Emiko Kawachi、Yuichi Hashimoto、Koichi Shudo

  DOI：10.1021/jm00125a027

  日期：1989.5

  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.