2-(3-trifluoromethoxy-benzylidene)-malononitrile | 149550-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-trifluoromethoxy-benzylidene)-malononitrile
• 英文别名: 2-(3-trifluoromethoxybenzylidene)malononitrile；3-Trifluoromethoxybenzylidenemalononitrile；Propanedinitrile, 2-[[3-(trifluoromethoxy)phenyl]methylene]-；2-[[3-(trifluoromethoxy)phenyl]methylidene]propanedinitrile
• CAS: 149550-24-3
• 化学式: C₁₁H₅F₃N₂O
• 分子量: 238.169
• InChiKey: ILHFXEHGTMBGEU-UHFFFAOYSA-N

物化性质

• 沸点：
  298.3±35.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-trifluoromethoxy-benzylidene)-malononitrile 在 sodium sulfide 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-amino-4-(3-trifluoromethoxyphenyl)-6-mercaptopyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  A Series of Ligands Displaying a Remarkable Agonistic−Antagonistic Profile at the Adenosine A₁ Receptor

  摘要：

  Adenosine receptor agonists are usually variations of the natural ligand, adenosine. The ribose moiety in the ligand has previously been shown to be of great importance for the agonistic effects of the compound. In this paper, we present a series of nonadenosine ligands selective for the adenosine A(1) receptor with an extraordinary pharmacological profile. 2-Amino-4-benzo[1,3]dioxol-5-yl-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile (70, LUF 5853) shows full agonistic behavior comparable with the reference compound CPA, while also displaying comparable receptor binding affinity (K-i = 11 nM). In contrast, compound 58 (2-amino-4-(3-trifluoromethylphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5948) has a binding affinity of 14 nM and acts as an inverse agonist. Also present within this same series are compounds that show neutral antagonism of the adenosine A(1) receptor, for example compound 65 (2-amino-4-(4-difluoromethoxyphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5826).

  DOI：

  10.1021/jm049597+
• 作为产物：
  描述：

  3-(三氟甲氧基)苯甲醛 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以87%的产率得到2-(3-trifluoromethoxy-benzylidene)-malononitrile
  参考文献：
  名称：

  2-Amino-6-furan-2-yl-4-substituted Nicotinonitriles as A_2A Adenosine Receptor Antagonists

  摘要：

  A2A adenosine receptor antagonists usually have bi- or tricyclic N aromatic systems with varying substitution patterns to achieve desired receptor affinity and selectivity. Using a pharmacophore model designed by overlap of nonxanthine type of previously known A2A antagonists, we synthesized a new class of compounds having a 2-amino nicotinonitrile core moiety. From our data, we conclude that the presence of at least one furan group rather than phenyl is beneficial for high affinity on the A2A adenosine receptor. Compounds 39 (LUF6050) and 44 (LUF6080) of the series had Ki values of 1.4 and 1.0 nM, respectively, with reasonable selectivity toward the other adenosine receptor subtypes, A,, A2B, and A3. The high affinity of 44 was corroborated in a cAMP second messenger assay, yielding subnanomolar potency for this compound.

  DOI：

  10.1021/jm701594y

文献信息

• Antiproliferative derivatives of 4H-naphtho 1,2-b pyran
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0537949A1

  公开（公告）日：1993-04-21

  A pharmaceutical compound of the formula in which n is 0, 1 or 2 and R¹ is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R¹ is halo, trifluoromethyl, C₁₋₄ alkoxy, hydroxy, nitro, C₁₋₄ alkyl, C₁₋₄ alkylthio, hydroxy-C₁₋₄ alkyl, hydroxy-C₁₋₄ alkoxy, trifluoromethoxy, carboxy, -COOR⁵ where R⁵ is an ester group, -CONR⁶R⁷ or -NR⁶R⁷ where R⁶ and R⁷ are each hydrogen or C₁₋₄alkyl;    R² is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofurangyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R² is furanyl optionally substituted with C₁₋₄ alkyl;    R³ is nitrile, carboxy, -COOR⁸ where R⁸ is an ester group, -CONR⁹R¹⁰ where R⁹ and R¹⁰ are each hydrogen or C₁₋₄ alkyl, or R¹¹SO₂- where R¹¹ is C₁₋₄ alkyl or optionally substituted phenyl; and    R⁴ is -NR¹²R¹³, -NHCOR¹², -N(COR¹²)₂ or -N=CHOCH₂R¹² where R¹² and R¹³ are each hydrogen or C₁₋₄ alkyl optionally substituted with carboxy, where X is C₂₋₄ alkylene, or -NHSO₂R¹⁴ where R¹⁴ is C₁₋₄ alkyl or optionally substituted phenyl;    provided that when n is 0, R³ is nitrile and R⁴ is -NH₂, R² is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent;    and salts thereof.

  一种药物化合物，其化学式为 其中 n 为 0、1 或 2，R¹ 连接在位置 5、6、7、8、9 或 10 中的任一位置，且每个 R¹ 为卤代、三氟甲基、C₁₋₄烷氧基、羟基、硝基、C₁₋₄烷基、C₁₋₄烷硫基、羟基-C₁₋₄ 烷基、羟基-C₁₋₄ 烷氧基、三氟甲氧基、羧基、-COOR⁵（其中 R⁵ 是酯基）、-CONR⁶R⁷ 或-NR⁶R⁷（其中 R⁶ 和 R⁷ 各为氢或 C₁₋₄烷基）； R²是苯基、萘基或选自噻吩基、吡啶基、苯并噻吩基、喹啉基、苯并呋喃基或苯并咪唑基的杂芳基，所述苯基、萘基和杂芳基被任选取代，或 R² 是被 C₁₋₄ 烷基任选取代的呋喃基； R³ 是腈、羧基、-COOR⁸（其中 R⁸ 是酯基）、-CONR⁹R¹⁰（其中 R⁹ 和 R¹⁰ 分别是氢或 C₁₋₄ 烷基）或 R¹SO₂-（其中 R¹ 是 C₁₋₄ 烷基或任选取代的苯基）；以及 R⁴是-NR¹²R¹³、-NHCOR¹²、-N(COR¹²)₂或-N=CHOCH₂R¹²，其中 R¹² 和 R¹³ 分别是氢或任选被羧基取代的 C₁₋₄ 烷基、 其中 X 是 C₂₋₄亚烷基，或 -NHSO₂R¹⁴ 其中 R¹⁴ 是 C₁₋₄ 烷基或任选被取代的苯基； 但当 n 为 0，R³ 为腈且 R⁴ 为 -NH₂ 时，R² 不是苯基或在对位被单个氯、羟基或甲氧基取代的苯基； 及其盐类。
• US5281619A
  申请人：——

  公开号：US5281619A

  公开（公告）日：1994-01-25
• US5284868A
  申请人：——

  公开号：US5284868A

  公开（公告）日：1994-02-08