4-methyl-2-(thiophen-3-yl)aniline

• 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: 4-methyl-2-(thiophen-3-yl)aniline
• 英文别名: 4-Methyl-2-thiophen-3-ylaniline
• 化学式: C₁₁H₁₁NS
• 分子量: 189.281
• InChiKey: BJAXFQWEWCGOAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(thiophen-3-yl)aniline 、 5,10-dioxo-N¹,N⁶-diphenyl-5,10-dihydrodiimidazo[1,5-a:1',5'-d]pyrazine-1,6-dicarboxamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到N⁴-(4-methyl-2-(thiophen-3-yl)phenyl)-N⁵-phenyl-1H-imidazole-4,5-dicarboxamide
  参考文献：
  名称：

  Synthesis and evaluation of imidazole-4,5- and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus

  摘要：

  The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DC5) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 = 1.85 mu M. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 = 0.93 mu M) in Vero cells. (c) 2014 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.09.062
• 作为产物：
  描述：

  3-噻吩硼酸 、 2-溴-4-甲基苯胺 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以87 %的产率得到4-methyl-2-(thiophen-3-yl)aniline
  参考文献：
  名称：

  使用胺氧化酶启发的催化剂合成呋喃和噻吩并喹啉

  摘要：

  我们报道了通过使用胺氧化酶启发的催化剂（1,10-菲咯啉-5,6-二酮）和丰富的路易斯酸（FeCl 3 ）作为助催化剂，区域选择性合成呋喃喹啉和噻吩并喹啉。需氧胺脱氢在温和条件下进行并以高产率产生喹啉。机理研究有助于确定可能的反应中间体以及催化剂在多步级联中的具体作用。

  DOI：

  10.1055/a-2103-9629

文献信息

• Saudi, Milind; Zmurko, Joanna; Kaptein, Suzanne, European Journal of Medicinal Chemistry, 2016, vol. 121, p. 158 - 168
  作者：Saudi, Milind、Zmurko, Joanna、Kaptein, Suzanne、Rozenski, Jef、Gadakh, Bharat、Chaltin, Patrick、Marchand, Arnaud、Neyts, Johan、Van Aerschot, Arthur

  DOI：——

  日期：——
• Synthesis and evaluation of imidazole-4,5- and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus
  作者：Milind Saudi、Joanna Zmurko、Suzanne Kaptein、Jef Rozenski、Johan Neyts、Arthur Van Aerschot

  DOI：10.1016/j.ejmech.2014.09.062

  日期：2014.11

  The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DC5) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 = 1.85 mu M. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 = 0.93 mu M) in Vero cells. (c) 2014 The Authors. Published by Elsevier Masson SAS.
• Synthesis of Furo- and Thienoquinolines by Using an Amine Oxidase-Inspired Catalyst
  作者：Biplab Maji、Pradip Ramdas Thorve

  DOI：10.1055/a-2103-9629

  日期：2023.12

  We report the regioselective synthesis of furo- and thienoquinolines by using an amine oxidase-inspired catalyst (1,10-phenanthroline-5,6-dione) and an abundant Lewis acid (FeCl3) as a co-catalyst. The aerobic amine dehydrogenation proceeds under mild conditions and produces the quinolines in high yields. Mechanistic studies helped to identify the possible reaction intermediates and the specific role

  我们报道了通过使用胺氧化酶启发的催化剂（1,10-菲咯啉-5,6-二酮）和丰富的路易斯酸（FeCl 3 ）作为助催化剂，区域选择性合成呋喃喹啉和噻吩并喹啉。需氧胺脱氢在温和条件下进行并以高产率产生喹啉。机理研究有助于确定可能的反应中间体以及催化剂在多步级联中的具体作用。