2-amino-4-(4-bromophenyl)-6-(4-hydroxyphenyl)nicotinonitrile | 1380592-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-(4-bromophenyl)-6-(4-hydroxyphenyl)nicotinonitrile
• 英文别名: 2-Amino-4-(4-bromophenyl)-6-(4-hydroxyphenyl)pyridine-3-carbonitrile
• CAS: 1380592-79-9
• 化学式: C₁₈H₁₂BrN₃O
• 分子量: 366.217
• InChiKey: MNHWEZLWCQWHLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 丙二腈 、 对羟基苯乙酮 在 ammonium acetate 作用下， 以 水 为溶剂， 反应 2.0h， 以95%的产率得到2-amino-4-(4-bromophenyl)-6-(4-hydroxyphenyl)nicotinonitrile
  参考文献：
  名称：

  以纤维素硫酸为有效催化剂制备2-氨基-4,6-二苯基烟腈的水性介质

  摘要：

  描述了一种通过芳族醛，苯乙酮衍生物，丙二腈和乙酸铵的四组分反应合成2-氨基-4,6-二苯基烟腈的简便方法。反应以纤维素硫酸为催化剂，在水为溶剂中进行。这种简单的方案具有诸如缩短反应时间，简化后处理程序，优异的收率和催化剂回收率等优点。

  DOI：

  10.1007/s11164-012-1008-9

文献信息

• Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation
  作者：Mohammad Rahmati、Davood Habibi

  DOI：10.1007/s11164-020-04361-y

  日期：2021.4

  Abstract In the current study, a novel acidic ionic liquid catalyst based on 8-hydroxyquinoline, namely 8,8′,8″-([1,3,5-triazine-2,4,6-triyl]tris[oxy])tris(1-sulfoquinolin-1-ium)chloride (TTS), was designed and synthesized. The structure of the prepared acidic ionic liquid (AIL) was fully investigated by using Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis,

  摘要 在当前的研究中，一种基于8-羟基喹啉的新型酸性离子液体催化剂，即8,8'，8”-（[[1,3,5-triazine-2,4,6-triyl] tris [oxy]）tris设计并合成了（1-磺基喹啉-1-鎓）氯化物（TTS）。使用傅立叶变换红外（FT-IR）光谱，能量色散X射线（EDX）分析，热重分析/差热分析（​​TGA / DTA），1 HNMR对制备的酸性离子液体（AIL）的结构进行了全面研究，13 CNMR和质谱。然后，通过基于乙烯基乙烯基端基的协同氧化，成功地检测了所述AIL的催化性能对吡啶衍生物的四组分合成。 图形摘要 新型AIL（TTS）在吡啶的合成中显示出很高的效率。
• Ultrasound-promoted an efficient method for one-pot synthesis of 2-amino-4,6-diphenylnicotinonitriles in water: A rapid procedure without catalyst
  作者：Javad Safari、Sayed Hossein Banitaba、Shiva Dehghan Khalili

  DOI：10.1016/j.ultsonch.2012.01.005

  日期：2012.9

  A green and convenient approach to the synthesis of 2-amino-4,6-diphenylnicotinonitriles via four-component reaction of malononitrile, aromatic aldehydes, acetophenone derivatives and ammonium acetate in water under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison

  描述了一种绿色便捷的方法，可在超声波辐射下通过丙二腈，芳族醛，苯乙酮衍生物和乙酸铵的四组分反应在水中合成2-氨基-4,6-二苯基烟腈。使用水作为绿色溶剂，同时应用超声波照射，可以实现此方法的组合合成。与常规方法相比，该超声催化方法的突出特点是实验简便，官能团耐受性好，产率高，常规时间短，选择性好，而无需过渡金属或碱催化剂。
• 一种3-氰基-2-氨基吡啶类衍生物及其制备方 法与应用
  申请人：广西民族大学

  公开号：CN109020883B

  公开（公告）日：2022-02-08

  本申请公开了一种3‑氰基‑2‑氨基吡啶类衍生物及其制备方法与应用，该吡啶类衍生物如1)‑5)中的任一所示：1)名称为2‑氨基‑4‑(4‑溴苯基)‑6‑(4‑羟苯基)氰吡啶；2)2‑氨基‑4‑(4‑溴苯基)‑6‑(4‑溴苯基)氰吡啶；3)2‑氨基‑4‑(4‑溴苯基)‑6‑(5‑氟‑2苄氧苯基)氰吡啶；4)2‑氨基‑4‑(4‑溴苯基)‑6‑(2，4‑二苄氧苯基)氰吡啶；5)2‑氨基‑4‑(4‑溴苯基)‑6‑(2，4二氟苯基)氰吡啶；本发明的化合物以取代苯乙酮、取代苯甲醛为原料，采用一步合成法，合成3‑氰基‑2‑氨基吡啶衍生物。经MTT法测试该药物具有良好的抗肿瘤活性，在筛选抗肿瘤药物上具有良好的前景。
• <p>Design, Synthesis, And Evaluation Of Cyanopyridines As Anti-Colorectal Cancer Agents Via Inhibiting STAT3 Pathway</p>
  作者：Lingyuan Xu、Lingxi Shi、Sensen Qiu、Siyu Chen、Mengsha Lin、Youqun Xiang、Chengguang Zhao、Jiandong Zhu、Liqun Shen、Zhigui Zuo

  DOI：10.2147/dddt.s217800

  日期：——

  Background: Colorectal cancer is one of the common malignant tumors. Cyanopyridine and aminocyanopyridine having a carbon-nitrogen bond have been shown to have significant anticancer effects. STAT3 is a promising therapeutic target in multiple cancers. However, there are currently no effective STAT3 inhibitors in clinical practice for the treatment of colorectal cancer.Materials and methods: We screened 27 cyanopyridines for their anticancer activity by cell viability. The HCT-116, RKO, and DLD-1 cell lines were used to evaluate the anti-colorectal cancer effect of 3n. Scratch experiments and colony formation assays were used for the assessment of cell migration and proliferation capacity. Phosphorylated STAT3, STAT3, MCL-1, and Survivin levels were assessed by Western blot analysis.Results: In this study, we synthesized 27 cyanopyridines and screened their anticancer activities in three human tumor cells, HCT-116, Hela229, and A375. We found that 2-amino-3-cyanopyridine 3n has better anticancer activity with IC50 values in the low micromolar range. Furthermore, 3n significantly inhibited the migration and colony formation of colorectal cancer cells. Mechanistically, 3n inhibited the expression of STAT3 phosphorylation in a dose- and time-dependent manner.Conclusion: 3n is worth of further investigations toward the discovery of STAT3 inhibitor as a drug candidate for cancer therapy.