2-氨基-4-(4-氟苯基)噻吩-3-甲腈 | 519016-84-3

• 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-4-(4-氟苯基)噻吩-3-甲腈
• 英文名称: 2-amino-4-(4-fluorophenyl)thiophene-3-carbonitrile
• CAS: 519016-84-3
• 化学式: C₁₁H₇FN₂S
• 分子量: 218.254
• InChiKey: LBDBBGMNVRDQID-UHFFFAOYSA-N

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：
  78
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-4-(4-氟苯基)噻吩-3-甲腈 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 4-(4-Fluoro-phenyl)-2-methylamino-thiophene-3-carbonitrile
  参考文献：
  名称：

  Novel thiophenes and analogues with anthelmintic activity against Haemonchus contortus

  摘要：

  A new series of analogues of 4-(4-fluorophenyl)-2-methylthio-thiophene-3-carbonitrile (1) were synthesized and evaluated for their in vitro and in vivo anthelmintic activity against Haemonchus contortus. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.044
• 作为产物：
  描述：

  2-氯代-4'-氟苯乙酮 在 sodium hydrogensulfide 、 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 生成 2-氨基-4-(4-氟苯基)噻吩-3-甲腈
  参考文献：
  名称：

  Novel thiophenes and analogues with anthelmintic activity against Haemonchus contortus

  摘要：

  A new series of analogues of 4-(4-fluorophenyl)-2-methylthio-thiophene-3-carbonitrile (1) were synthesized and evaluated for their in vitro and in vivo anthelmintic activity against Haemonchus contortus. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.044

文献信息

• Synthesis, in vivo anti-inflammatory, COX-1/COX-2 and 5-LOX inhibitory activities of new 2,3,4-trisubstituted thiophene derivatives
  作者：Nermeen A. Qandeel、Ashraf K. El-Damasy、Maha H. Sharawy、Said M. Bayomi、Nadia S. El-Gohary

  DOI：10.1016/j.bioorg.2020.103890

  日期：2020.9

  highest selectivity towards COX-2 (IC50 = 5.45 μM) with selectivity index value of 8.37 being comparable to celecoxib. In addition, 5b showed reasonable in vivo anti-inflammatory activity compared to celecoxib. Moreover, it showed acceptable 5-LOX inhibitory activity (IC50 = 4.33 μM) compared to NDGA (IC50 = 2.46 μM). Molecular modeling study was conducted to study the postulated binding of compound 5b

  合成了一系列新的噻吩衍生物（36种化合物），并使用角叉菜胶诱导的爪水肿模型评估了它们的体内抗炎活性。进一步评估了活性最高的化合物5b，11b，14c，18c，19c和20d的双重COX-2和5-LOX抑制活性。在体外和体内测定的结果表明，ñ - （4-（4-氯苯基）-3-氰基噻吩-2-基）-2- morpholinoacetamide（5B）具有朝向COX-2（IC选择性最高50= 5.45μM），选择性指数值为8.37，与塞来昔布相当。另外，与塞来昔布相比，5b显示出合理的体内抗炎活性。此外，与NDGA（IC 50 = 2.46μM）相比，它显示出可接受的5-LOX抑制活性（IC 50 = 4.33μM ）。进行了分子建模研究，以研究假定的化合物5b结合至COX-2和5-LOX的活性位点，表明其分别与celecoxib和NDGA相似地结合。总体而言，吗啉代乙酰胺噻吩5b可以用作进一步开发新型有效的双重COX-2
• Ethylene diamine grafted nanoporous UiO-66 as an efficient basic catalyst in the multi-component synthesis of 2-aminithiophenes
  作者：N. Erfaninia、R. Tayebee、M. Dusek、M.M. Amini

  DOI：10.1002/aoc.4307

  日期：2018.5

  effective solid nanoporous basic catalyst prepared through the amine grafting onto the pores of UiO‐66. The manufactured nanoparticles were identified by FT‐IR, XRD, TGA, FESEM, TEM, CHN and BET and the characterization results certified formation of a single phase nanoporous substance with the medium grain size less than 90 nm. The synthesized material was employed as an efficient catalyst for the preparation

  这项研究表明ED‐UiO‐66是一种通过胺接枝到UiO‐66的孔中而制备的新型有效的固体纳米多孔碱性催化剂。通过FT-IR，XRD，TGA，FESEM，TEM，CHN和BET对制成的纳米颗粒进行鉴定，并且鉴定结果证明形成了中等粒径小于90 nm的单相纳米多孔物质。合成的材料被用作通过Gewald方法制备2-氨基噻吩的有效催化剂。这种热化学稳定的纳米催化剂对环境安全，可重复使用且经济。因此，可以将该方法简单地扩展到工业目标。
• <scp>2‐Amino</scp>‐4‐arylthiophene‐3‐carbonitrile and formamidine acetate as key building units for the synthesis of <scp>5‐arylthieno</scp>[2,3‐<i>d</i>]pyrimidin‐4‐amines
  作者：Farzaneh Alizadeh‐Bami、Hossein Mehrabi、Maryam Hosseini‐pour

  DOI：10.1002/jhet.4727

  日期：2023.11

  method for the synthesis of 5-arylthieno[2,3-d]pyrimidin-4-amine analogues via three-step reactions and examined the changes in the solvent, time, and temperature. A novel condition has been developed for the preparation of substituted 2-aminothiophenes employing the Knoevenagel condensation followed by the Gewald method and in the last step to form thieno[2,3-d]pyrimidines by using formamidine acetate

  我们试图建立一种通过三步反应合成5-芳基噻吩并[2,3- d ]嘧啶-4-胺类似物的方法，并考察了溶剂、时间和温度的变化。开发了一种新的条件，用于制备取代的 2-氨基噻吩，采用 Knoevenagel 缩合，然后采用 Gewald 方法，最后一步使用乙酸甲脒形成噻吩并[2,3- d ]嘧啶。所有合成的5-芳基噻吩并[2,3- d ]嘧啶-4-胺都是未知的，并通过IR、1 H-NMR、13 C-NMR和CHN分析进行了表征。
• Discovery of novel thiophene-3-carboxamide derivatives as potential VEGFR-2 inhibitors with anti-angiogenic properties
  作者：Tai Li、Jiawei Wang、Limiao Feng、Qi Zhou、Qian Xie、Yanni Shen、Rongxin Ji、Xiaoping Liu、Yan Wang、Chun Hu

  DOI：10.1016/j.bioorg.2024.107358

  日期：2024.6

  VEGFR-2 is an attractive target for the development of anti-tumor drugs and plays a crucial role in tumor angiogenesis. This study reports a series of novel thiophene-3-carboxamide derivatives based on PAN-90806 as VEGFR-2 inhibitors, among which compound exhibits excellent anti-proliferative activity against HCT116, MCF7, PC3, and A549 cell lines, and has effective VEGFR-2 inhibitory activity with

  VEGFR-2是抗肿瘤药物开发的一个有吸引力的靶点，在肿瘤血管生成中发挥着至关重要的作用。本研究报告了一系列基于PAN-90806的新型噻吩-3-甲酰胺衍生物作为VEGFR-2抑制剂，其中化合物对HCT116、MCF7、PC3和A549细胞系表现出优异的抗增殖活性，并且具有有效的VEGFR-2抑制剂。 2 抑制活性，IC 值为 191.1 nM。此外，CETSA结果表明，VEGFR-2是细胞系中化合物的相关靶点，并且化合物还可以抑制A549细胞系中的VEGFR-2蛋白磷酸化。此外，化合物以剂量依赖性方式抑制集落形成、细胞迁移和HUVEC管形成。诱导癌细胞死亡的机制包括阻断细胞周期、增加ROS产生、诱导细胞凋亡以及剂量依赖性地降低磷酸化ERK和MEK的水平。分子对接和分子动力学模拟表明该化合物能够稳定地结合VEGFR-2的活性位点。这些结果证实该化合物可能是一种有前途的抗血管生成先导化合物。
• Discovery of novel c-Met kinase inhibitors bearing a thieno[2,3-d]pyrimidine or furo[2,3-d]pyrimidine scaffold
  作者：Ailing Zhao、Xin Gao、Yuanxiang Wang、Jing Ai、Ying Wang、Yi Chen、Meiyu Geng、Ao Zhang

  DOI：10.1016/j.bmc.2011.05.038

  日期：2011.7

  A series of thieno[2,3-d]pyrimidines and furo[2,3-d] pyrimidines were synthesized and evaluated for the c-Met inhibition. Thieno[2,3-d]pyrimidine 6b stood out as the most potent showing an IC(50) of 35.7 nM. This compound displayed high inhibitory effect on cell proliferation in BaF3-TPR-Met cells and showed high selectivity for c-Met family against other 14 tested kinases. However, compound 6b was found ineffective in the c-Met-dependent U-87MG human gliobastoma xenograft model that may be relevant to its poor PK profile. (C) 2011 Elsevier Ltd. All rights