3-biphenyl-4-ylmethylenedihydrofuran-2-one | 102271-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-biphenyl-4-ylmethylenedihydrofuran-2-one
• 英文别名: 3-[([1,1'-Biphenyl]-4-yl)methylidene]oxolan-2-one；3-[(4-phenylphenyl)methylidene]oxolan-2-one
• CAS: 102271-77-2
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: UHNHBUJCSZXEJS-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  476.9±44.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-biphenyl-4-ylmethylenedihydrofuran-2-one 在 盐酸羟胺 、 sodium ethanolate 、 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 以20%的产率得到3-biphenyl-4-ylmethylene-1-hydroxypyrrolidin-2-one
  参考文献：
  名称：

  Investigation on the ZBG-functionality of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase inhibitors

  摘要：

  A series of alternative Zn-binding groups were explored in the design of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds were less effective than the parent hydroxamic acid. However, the profile of activity shown by the analog bearing a hydroxyurea head group, makes this derivative promising for further investigation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.006
• 作为产物：
  描述：

  γ-丁内酯 、 对苯基苯甲醛 在 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 1.67h， 以89%的产率得到3-biphenyl-4-ylmethylenedihydrofuran-2-one
  参考文献：
  名称：

  Investigation on the ZBG-functionality of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase inhibitors

  摘要：

  A series of alternative Zn-binding groups were explored in the design of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds were less effective than the parent hydroxamic acid. However, the profile of activity shown by the analog bearing a hydroxyurea head group, makes this derivative promising for further investigation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.006

文献信息

• Studies on styrene derivatives. I. Synthesis and antiinflammatory activities of .ALPHA.-benzylidene-.GAMMA.-butyrolactone derivatives.
  作者：IKUO KATSUMI、HIDEO KONDO、KATSUJI YAMASHITA、TAKAYOSHI HIDAKA、KAZUNORI HOSOE、TOSHIAKI YAMASHITA、KIYOSHI WATANABE

  DOI：10.1248/cpb.34.121

  日期：——

  Two α-benzylidene-γ-butyrolactones, α-(3, 5-dimethyl-4-hydroxybenzylidene)-γ-butyrolactone and α-(3, 5-di-tert-butyl-4-hydroxybenzylidene)-γ-butyrolactone (KME-4), were found to have platelet aggregation inhibitory activity; the latter also had potent antiinflammatory activity and inhibited not only prostaglandin synthetase (PGS) but also 5-lipoxygenase. Further α-benzylidene-γ-butyrolactones were synthesized, and tested for antiinflammatory activity in carrageenin-induced rat paw edema assay (CPE) and for PGS inhibitory activity. It was found that the structural combination of a tert-butyl group at the 3 position, an alkyl group at the 5 position and an oxygen atom at the Δ position in α-benzylidene-γ-butyrolactone is necessary for antiinflammatory activity, and that rather broad structural variation is possible for inhibitors of PGS. The structural requirements for antiinflammatory activity in the CPE assay also seem to be partial requirements for inhibitory activity against PGS.

  两种α-苄叉基-γ-丁内酯，即α-(3, 5-二甲基-4-羟基苄叉基)-γ-丁内酯和α-(3, 5-二叔丁基-4-羟基苄叉基)-γ-丁内酯（KME-4），被发现具有血小板聚集抑制活性；后者还具有强效的抗炎活性，不仅抑制前列腺素合成酶（PGS），还抑制5-脂氧合酶。进一步合成了α-苄叉基-γ-丁内酯，并测试了它们在卡拉胶诱导的大鼠足跖水肿试验（CPE）中的抗炎活性和PGS抑制活性。研究发现，在α-苄叉基-γ-丁内酯中，3位叔丁基、5位烷基和Δ位氧原子的结构组合对发挥抗炎活性是必要的，而且对PGS抑制剂来说，其结构变化非常广泛。在CPE试验中对发挥抗炎活性的结构要求似乎也是对PGS抑制活性的部分要求。
• Investigation on the ZBG-functionality of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase inhibitors
  作者：Loana Musso、Raffaella Cincinelli、Valentina Zuco、Franco Zunino、Alessandra Nurisso、Muriel Cuendet、Giuseppe Giannini、Loredana Vesci、Claudio Pisano、Sabrina Dallavalle

  DOI：10.1016/j.bmcl.2015.09.006

  日期：2015.10

  A series of alternative Zn-binding groups were explored in the design of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds were less effective than the parent hydroxamic acid. However, the profile of activity shown by the analog bearing a hydroxyurea head group, makes this derivative promising for further investigation. (C) 2015 Elsevier Ltd. All rights reserved.