(E)-6-Naphthalen-2-yl-hex-5-enoic acid | 128133-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-6-Naphthalen-2-yl-hex-5-enoic acid
• 英文别名: 6-Naphthalen-2-ylhex-5-enoic acid
• CAS: 128133-71-1
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: PHHNNTANZBVDCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-Naphthalen-2-yl-hex-5-enoic acid 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.73 kPa 条件下， 反应 2.92h， 生成 S-(6-naphthalen-2-ylhexyl) ethanethioate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 、 2-萘甲醛 在 dimsyl sodium 作用下， 生成 (E)-6-Naphthalen-2-yl-hex-5-enoic acid
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w

文献信息

• Lipoxygenase inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0199153A2

  公开（公告）日：1986-10-29

  Compounds of the formula where X is selected from hydrogen, C1 to C22 alkyl or alkenyl, or an electron withdrawing group; n =0 or 1 and m=0, 1, 2 or 3; but n and m are not 0 simultaneously; R1 and R2 independently are hydrogen, C1 to C6 alkyl, an electron withdrawing group, or R4; R3 is H, C1 to C6 alkyl or cycloalkyl, or R4; and R4 independently at each occurrence, has the formula where Y is hydrogen or an electron withdrawing group; and wherein M is a pharmaceutically acceptable cation, are potent inhibitors of lipoxygenase enzymes.

  式中X选自氢、C1至C22烷基或烯基或电子僻取基团；n＝0或1和m＝0、1、2或3；但n和m不同时为0；R1和R2独立地为氢、C1至C6烷基、电子僻取基团或R4； R3 是 H、C1 至 C6 烷基或环烷基，或 R4；以及 R4 在每次出现时独立地具有如下式 Y 是氢或取电子基团；其中 M 是药学上可接受的阳离子，它们是脂氧合酶的强效抑制剂。
• Controlling the regioselectivity of the bromolactonization reaction in HFIP
  作者：Tuong Anh To、Nhu T. A. Phan、Binh Khanh Mai、Thanh Vinh Nguyen

  DOI：10.1039/d4sc01503g

  日期：——

  bromolactonization reactions mediated by HFIP solvent. Two sets of reaction conditions were developed, each forming endo-products or exo-products in excellent regioselectivity. A combination of computational and experimental mechanistic studies not only confirmed the crucial role of HFIP, but also revealed the formation of endo-products under kinetic control and exo-products under thermodynamic control. This study

  卤内酯化反应提供了从不饱和羧酸中获得密集官能化内酯的快速途径。该环化反应的 endo/exo 区域选择性主要由烯烃取代基的电子稳定决定，因此它本质上依赖于底物结构。因此，这种方法通常只提供一种类型的卤内酯区域异构体。在此，我们介绍了一种简单有效的 HFIP 溶剂介导的区域选择性可切换溴酰化反应的方法。开发了两组反应条件，每组反应条件都形成具有优异区域选择性的内产物或外产物。计算和实验机理研究的结合不仅证实了 HFIP 的关键作用，而且还揭示了在动力学控制下形成内产物，在热力学控制下形成外产物。这项研究为未来使用全氟溶剂决定有机合成反应结果的工作铺平了道路。
• Sulphur-containing 5-hydroxy-alkanoic acid derivatives, their use as pharmaceutical preparations and process for their production
  申请人：Lilly Industries Limited

  公开号：EP0068739B1

  公开（公告）日：1984-11-14
• US4513005A
  申请人：——

  公开号：US4513005A

  公开（公告）日：1985-04-23
• US4608390A
  申请人：——

  公开号：US4608390A

  公开（公告）日：1986-08-26