2-氨基-5-(4-溴苯基)-3-呋喃甲腈 | 26454-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-5-(4-溴苯基)-3-呋喃甲腈
• 中文别名: 2-氨基-5-(4-溴苯基)呋喃-3-甲腈
• 英文名称: 2-amino-5-(4-bromophenyl)furan-3-carbonitrile
• CAS: 26454-86-4
• 化学式: C₁₁H₇BrN₂O
• mdl: MFCD06016434
• 分子量: 263.093
• InChiKey: OPAVHIMDYMQERE-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230 °C(Solv: ethanol (64-17-5))
• 沸点：
  425.1±45.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  2-氨基-5-(4-溴苯基)-3-呋喃甲腈 在 甲酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 6-(4-溴-苯基)-4-氯-呋喃并[2,3-d]嘧啶
  参考文献：
  名称：

  Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors

  摘要：

  Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo [2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-pi interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N-1, N-1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFR(L858R) reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.054
• 作为产物：
  描述：

  2-(2-(4-bromophenyl)-2-oxoethyl)malononitrile 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以67%的产率得到2-氨基-5-(4-溴苯基)-3-呋喃甲腈
  参考文献：
  名称：

  微波辐射下新他克林类似物的合成及生物学评价。

  摘要：

  已经合成了合成并入对卤代苯基部分的各种杂环的有效途径。通过Thorpe-Ziegler环化，也已经合成了不同的吡咯衍生物。因此，我们通过邻氨基腈（吡唑并，呋喃和吡咯并）与不同环烷酮的弗里德兰德反应合成了他克林的不同类似物。微波辐射的使用缩短了生产时间，提高了产品转化率。这些合成的化合物通过对乙酰胆碱酯酶抑制作用的埃尔曼试验进行了生物学评估。

  DOI：

  10.1248/cpb.c17-00113

文献信息

• One-Pot Synthesis of Substituted 2-Amino-3-Furonitriles
  作者：Mehdi Bakavoli、Mohammad Rahimizadeh、Zinat Gordi

  DOI：10.3184/030823408x356314

  日期：2008.10

  Solvent-free reaction of substituted α-haloketones with malononitrile in the presence of diethylamine provides an efficient one-pot synthesis of 2-amino-5-aryl (alkyl)-3-furonitriles in high yield.

  在二乙胺存在下，取代的 α-卤酮与丙二腈进行无溶剂反应，可高效地一次合成 2-氨基-5-芳基（烷基）-3-呋喃腈，产量高。
• [EN] INHIBITORS OF EPIDERMAL GROWTH FACTOR RECEPTOR<br/>[FR] INHIBITEURS DU RÉCEPTEUR DU FACTEUR DE CROISSANCE ÉPIDERMIQUE
  申请人：ORIC PHARMACEUTICALS INC

  公开号：WO2023076849A1

  公开（公告）日：2023-05-04

  Disclosed herein are compounds of Formula (I), or a pharmaceutically acceptable salt thereof, that are inhibitors of inhibitors of epidermal growth factor receptor (EGFR), including EGFR C797S mutants. Also disclosed herein are pharmaceutical compositions comprising the compounds of Formula (I), or pharmaceutically acceptable salts thereof, and one or more pharmaceutically acceptable excipients. Further disclosed herein are methods of treating cancer in a subject in need thereof, comprising administering to the subject an amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof. Formula (I)

  本文披露了公式（I）的化合物，或其药学上可接受的盐，它们是表皮生长因子受体（EGFR）的抑制剂，包括EGFR C797S突变体的抑制剂。本文还披露了包含公式（I）的化合物或其药学上可接受的盐和一种或多种药学上可接受的赋形剂的制药组合物。本文还披露了治疗需要的患者的癌症的方法，包括向患者投予公式（I）的化合物或其药学上可接受的盐的剂量。公式（I）如下：
• Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors
  作者：Jin Han、Svein Jacob Kaspersen、Sondre Nervik、Kristin G. Nørsett、Eirik Sundby、Bård Helge Hoff

  DOI：10.1016/j.ejmech.2016.04.054

  日期：2016.8

  Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo [2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-pi interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N-1, N-1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFR(L858R) reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Synthesis and Biological Evaluation of New Tacrine Analogues under Microwave Irradiation
  作者：Hossa Fahad Alshareef、Heba Abd El Hady Mohamed、Abdellatif Mohamed Salaheldin

  DOI：10.1248/cpb.c17-00113

  日期：——

  Efficient routes to various kinds of heterocycles incorporating the p-halophenyl moiety have been synthesized. Different pyrrole derivatives have been synthesized, as well, by Thorpe-Ziegler cyclization. Therefore, we synthesized different analogues of tacrine by Friedländer reaction of o-amino nitriles (pyrazolo, furano and pyrrolo) with different cycloalkanones. The use of microwave irradiation leads

  已经合成了合成并入对卤代苯基部分的各种杂环的有效途径。通过Thorpe-Ziegler环化，也已经合成了不同的吡咯衍生物。因此，我们通过邻氨基腈（吡唑并，呋喃和吡咯并）与不同环烷酮的弗里德兰德反应合成了他克林的不同类似物。微波辐射的使用缩短了生产时间，提高了产品转化率。这些合成的化合物通过对乙酰胆碱酯酶抑制作用的埃尔曼试验进行了生物学评估。