methyl 7-methoxy-3,4-dihydro-2-hydroxy-1-naphthoate | 63491-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 7-methoxy-3,4-dihydro-2-hydroxy-1-naphthoate
• 英文别名: 2-hydroxy-7-methoxy-3,4-dihydronaphthalene-1-carboxylic acid methyl ester；methyl 2-hydroxy-7-methoxy-3,4-dihydronaphthalene-1-carboxylate；Methyl 2-hydroxy-7-methoxy-3,4-dihydro-1-naphthoate
• CAS: 63491-51-0
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: VQSYULOVJSHIQC-UHFFFAOYSA-N

物化性质

• 沸点：
  393.7±42.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 7-methoxy-3,4-dihydro-2-hydroxy-1-naphthoate 在 sodium ethanolate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 苯 为溶剂， 反应 25.5h， 生成 N-(1,2-dihydro-9-methoxy-1-oxobenzo[f]quinazolin-3-yl)pivalamide
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004
• 作为产物：
  描述：

  Methyl 2,7-dimethoxy-1,4-dihydro-1-naphthoate 在 草酸 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到methyl 7-methoxy-3,4-dihydro-2-hydroxy-1-naphthoate
  参考文献：
  名称：

  N-Substituted-6,8-dioxamorphinans

  摘要：

  N-取代-6,8-二氧吗啡酮类化合物已被发现具有强效的麻醉激动剂和/或拮抗剂活性。例如，化合物17-环丙基甲基-7,7-二甲基-3-羟基-6,8-二氧吗啡酮已被发现具有强效的激动剂-拮抗剂活性。这些化合物通过全合成制备，而非来源于鸦片生物碱。

  公开号：

  US04016167A1

文献信息

• Structurally Constrained Hybrid Derivatives Containing Octahydrobenzo[<i>g</i> or <i>f</i>]quinoline Moieties for Dopamine D2 and D3 Receptors: Binding Characterization at D2/D3 Receptors and Elucidation of a Pharmacophore Model
  作者：Dennis A. Brown、Prashant S. Kharkar、Ingrid Parrington、Maarten E. A. Reith、Aloke K. Dutta

  DOI：10.1021/jm8008629

  日期：2008.12.25

  series of structurally constrained analogues based on hybrid compounds containing octahydrobenzo[g or f]quinoline moieties were designed, synthesized, and characterized for their binding to dopamine D2 and D3 receptors expressed in HEK-293 cells. Among the newly developed constrained molecules, trans-octahydrobenzo[f]quinolin-7-ol (8) exhibited the highest affinity for D2 and D3 receptors, the (-)-isomer

  设计、合成了一系列基于含有八氢苯并[g 或 f] 喹啉部分的杂化化合物的结构受限类似物，并表征了它们与 HEK-293 细胞中表达的多巴胺 D2 和 D3 受体的结合。在新开发的受限分子中，trans-octahydrobenzo[f]quinolin-7-ol (8) 对 D2 和 D3 受体表现出最高的亲和力，(-)-异构体是 eutomer。有趣的是，当在相同条件下（K(i) 为 49.1 和 14.9 nM，8 对比 380 和 96.0 nM，K(i) 为1 分别在 D2 和 D3）。其他先导杂化化合物也发现了类似的结果，表明哌嗪部分对观察到的增强亲和力的贡献。基于我们开发的新型铅约束衍生物和其他铅杂化衍生物的数据，提出了一个独特的药效团模型，由三个药效团中心组成，两个具有芳香/疏水性，一个具有阳离子特征。
• Target-oriented multifunctional organocatalysis for enantioselective synthesis of bicyclo[3.3.1]nona-2,6-dien-9-ones. A formal asymmetric synthesis of huperzine A
  作者：Xiao-Hua Ding、Xiang Li、Dan Liu、Wei-Chen Cui、Xuan Ju、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1016/j.tet.2012.05.061

  日期：2012.8

  A target-oriented highly enantioselective multifunctional organocatalytic approach has been developed to construct the bicycle-[3.3.1]nona-2,6-dien-9-one core of (-)-huperzine A for the first time, with up to 95% ee in the gram-scale procedure. The newly established methodology is also eligible to synthesize a variety of bicyclo[3.3.1]nona-2,6-dien-9-ones in high enantiopurities, and thus is useful for the future development of novel huperzine A analogs with medicinal interests. (C) 2012 Elsevier Ltd. All rights reserved.