methyl 4-((Z)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)benzoate | 119436-53-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 4-((Z)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)benzoate
• 英文别名: methyl 4-[(Z)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoate
• CAS: 119436-53-2
• 化学式: C₂₄H₂₈O₂
• 分子量: 348.485
• InChiKey: SEVVMRGYRRMLPU-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-((Z)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)benzoate 在 吡啶 、 sodium hydroxide 、 四氧化锇 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-[(4R,5S)-2,2-Dimethyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-[1,3]dioxolan-4-yl]-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
• 作为产物：
  描述：

  6-(溴甲基)-1,2,3,4-四氢-1,1,4,4,-四甲基萘 在 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 5.0h， 生成 methyl 4-((Z)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)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

文献信息

• Tricyclic hydroxamate and benzaminde derivatives, compositions and methods
  申请人：Exonhit Therapeutics S.A.

  公开号：EP1541549A1

  公开（公告）日：2005-06-15

  The present invention relates to compounds and methods for inhibiting histone deacetylase enzymatic activity. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit histone deacetylases (HDACs), and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, and also central nervous system diseases. It further deals with processes for preparing said compounds.

  本发明涉及抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还涉及包含这些化合物的药物组合物，以及在体外和体内使用这些化合物和组合物来抑制组蛋白去乙酰化酶（HDACs）并治疗由HDAC介导的疾病，如癌症、增生性疾病、牛皮癣以及中枢神经系统疾病。此外，本发明还涉及制备上述化合物的方法。
• Tricyclic hydroxamate and benzamide derivatives, compositions and methods
  申请人：Leblond Bertrand

  公开号：US20070129368A1

  公开（公告）日：2007-06-07

  The present invention relates to compounds and methods for inhibiting histone deacetylase enzymatic activity. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit histone deacetylases (IIDACs), and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, and also central nervous system diseases. It further deals with processes for preparing said compounds.

  本发明涉及化合物和方法，用于抑制组蛋白去乙酰化酶的酶活性。本发明还涉及包含这种化合物的制药组合物，以及在体外和体内使用这种化合物和组合物来抑制组蛋白去乙酰化酶（IIDACs）并用于治疗由HDAC介导的疾病，如癌症，增殖性疾病，牛皮癣以及中枢神经系统疾病。此外，本发明还涉及制备所述化合物的过程。
• Strong Bicyclic Guanidine Base-Promoted Wittig and Horner−Wadsworth−Emmons Reactions
  作者：Daniele Simoni、Marcello Rossi、Riccardo Rondanin、Angelica Mazzali、Riccardo Baruchello、Cinzia Malagutti、Marinella Roberti、Francesco Paolo Invidiata

  DOI：10.1021/ol0001665

  日期：2000.11.1

  [GRAPHICS]A convenient procedure to effect the Wittig and Horner-Wadsworth-Emmons reactions employs guanidine TBD and MTBD as base-promoters; mild reaction conditions, high efficiency, and facile isolation of the final products make the present methodology, at least in some cases, a practical alternative to known procedures.
• TRICYCLIC HYDROXAMATE AND BENZAMIDE DERIVATIVES, COMPOSITIONS AND METHODS
  申请人：Exonhit Therapeutics SA

  公开号：EP1692097A1

  公开（公告）日：2006-08-23
• US7923579B2
  申请人：——

  公开号：US7923579B2

  公开（公告）日：2011-04-12