5-(2-Hydroxy-3-methoxy-phenyl)-valeriansaeure | 54131-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(2-Hydroxy-3-methoxy-phenyl)-valeriansaeure
• 英文别名: 5-(2-Hydroxy-3-methoxyphenyl)pentanoic acid
• CAS: 54131-06-5
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: LPZLMONXQLCMOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-Hydroxy-3-methoxy-phenyl)-valeriansaeure 在 咪唑 、 三氟甲磺酸 作用下， 生成 1-[(tert-butyldimethylsilyl)oxy]-2-methoxybenzocycloheptan-5-one
  参考文献：
  名称：

  New cytotoxic benzosuberene analogs. Synthesis, molecular modeling and biological evaluation

  摘要：

  In this Letter we describe the synthesis and biological evaluation of new benzosuberene analogs with structural modifications on the B-ring. The focus was initially to probe the chemical space around the B-ring C-8 position. This position was readily available for derivatization chemistry using our recently developed new synthesis for this compound class. Furthermore, we describe two new B-ring analogs, one containing a diene and the other a cyclic ether group. Both new analogs show excellent potencies in tumor cell proliferation assays. In addition, we describe molecular modeling studies that provide a binding rationale for reference compound 8 in the colchicine binding site using the known colchicine crystal structure. We also examine whether the cell based potency data obtained with selected new analogs are supported by modeling results. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.039
• 作为产物：
  描述：

  2-甲氧基苯基二乙基氨基甲酸酯 在 barium dihydroxide 、 sodium hydroxide 、 四甲基乙二胺 、 水 、 溴 、 仲丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 5-(2-Hydroxy-3-methoxy-phenyl)-valeriansaeure
  参考文献：
  名称：

  New Syntheses of the Benzoquinone Primin and its Water-Soluble Analog Primin Acid via Heck Reactions

  摘要：

  DOI：

  10.1055/s-1999-3515

文献信息

• Synthesis of the Antibacterial Benzoquinone Primin and its Water-Soluble Analogue, Primin Acid
  作者：Asish Bhattacharya、Tanpreet Kaur、Krishna Ganesh

  DOI：10.1055/s-0029-1218666

  日期：2010.4

  The biologically active natural product, primin and its water-soluble acid analogue, primin acid are prepared in 34% and 25% overall yields, respectively, from a common intermediate using a Grignard reaction and a Johnson-Claisen rearrangement as the key steps.

  利用格氏反应和约翰逊-克莱森重排作为关键步骤，从一种普通中间体制备出了具有生物活性的天然产物--骁悉及其水溶性酸类似物--骁悉酸，总产率分别为 34% 和 25%。
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18
• [EN] SALTS OF PAROXETINE<br/>[FR] SELS DE PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2000001692A1

  公开（公告）日：2000-01-13

  Piperidine compounds, processes for preparing them, pharmaceutical compositions comprising them and their use in therapy are disclosed.
• New Syntheses of the Benzoquinone Primin and its Water-Soluble Analog Primin Acid via Heck Reactions
  作者：Stéphane Mabic

  DOI：10.1055/s-1999-3515

  日期：1999.7
• New cytotoxic benzosuberene analogs. Synthesis, molecular modeling and biological evaluation
  作者：Zecheng Chen、Andreas Maderna、Sai Chetan K. Sukuru、Melissa Wagenaar、Christopher J. O’Donnell、My-Hanh Lam、Sylvia Musto、Frank Loganzo

  DOI：10.1016/j.bmcl.2013.10.039

  日期：2013.12

  In this Letter we describe the synthesis and biological evaluation of new benzosuberene analogs with structural modifications on the B-ring. The focus was initially to probe the chemical space around the B-ring C-8 position. This position was readily available for derivatization chemistry using our recently developed new synthesis for this compound class. Furthermore, we describe two new B-ring analogs, one containing a diene and the other a cyclic ether group. Both new analogs show excellent potencies in tumor cell proliferation assays. In addition, we describe molecular modeling studies that provide a binding rationale for reference compound 8 in the colchicine binding site using the known colchicine crystal structure. We also examine whether the cell based potency data obtained with selected new analogs are supported by modeling results. (C) 2013 Elsevier Ltd. All rights reserved.