5-(4-methoxyphenyl)thiophen-3-amine | 1253594-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxyphenyl)thiophen-3-amine
• 英文别名: 5-(4-Methoxyphenyl)thiophen-3-amine
• CAS: 1253594-43-2
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: SGJJJRLOJMPSCV-UHFFFAOYSA-N

物化性质

• 熔点：
  216 °C
• 沸点：
  408.5±40.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenyl)thiophen-3-amine 在 sodium acetate 、 碳酸氢钠 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 3-(4-methoxyphenyl)-2-{[5-(4-methoxyphenyl)-3-thienyl]imino}-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-heteroarylimino-1,3-thiazolidin-4-ones as potential anti-tumor agents

  摘要：

  A series of 35 heteroarylimino-1,3-thiazolidinones with three sites of functionalization were synthesized and their antiproliferative properties were studied. The in vitro screening by MTT assay was performed against five cancer cell lines (human colon cancer cell lines HT29, HCT116 and SW620 and breast cancer cell lines MCF7 and MDA-MB-231). It was observed that N3-substituted thiazolidinones had moderate activities whereas 5-benzylidene thiazolidinones showed promising activities. To investigate the mechanism of action, detailed biological studies of six selected compounds (those presenting the lower mitotic index) were carried out on the human colon cancer HT29 cell line. Cell cycle assay revealed that those compounds induced cell accumulation in G2/M and in subG0/G1 phases of cell cycle. Moreover, dissipation of mitochondria membrane potential was observed as well as redox changes in treated cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.053
• 作为产物：
  描述：

  3-氨基-5-(4-甲氧基苯基)噻吩-2-羧酸 在 草酸 作用下， 以 异丙醇 为溶剂， 以98%的产率得到5-(4-methoxyphenyl)thiophen-3-amine
  参考文献：
  名称：

  Synthesis of Novel 2-Thienylimino-1,3-thiazolidin-4-ones

  摘要：

  本文介绍了用 3-氨基噻吩-2-羧酸酯通过简单的四步程序制备新的 2-噻吩亚氨基-1,3-噻唑烷-4-酮的方法。

  DOI：

  10.1055/s-0029-1218780

文献信息

• Synthesis of Novel N-Substituted 2-(Hetero)arylimino-1,3-thiazolidin-4-ones
  作者：Stéphanie Hesse、Germain Revelant、Gilbert Kirsch

  DOI：10.1055/s-0030-1257867

  日期：2010.10

  The preparation of new N-substituted 2-arylimino-1,3-thiazolidin-4-ones from 5-substituted-3-aminothiophenes using an easy three-step procedure is described. 5-substituted 3-aminothiophenes - isothiocyanates - thioureas - N-substituted 1,3-thiazolidin-4-ones

  描述了使用简单的三步程序从5个取代的3-氨基噻吩制备新的N-取代的2-limlinino-1,3-thiazolidin-4-ones。 5-取代的3-氨基噻吩-异硫氰酸酯-硫脲-N-取代的1,3-噻唑烷-4-酮
• NOVEL THIENO[3,2-B]PYRIDINE-5(4H)-ONE DERIVATIVE COMPOUND, PREPARATION METHOD THEREOF AND USE THEREOF
  申请人：Korea Institute of Ocean Science & Technology

  公开号：US20210171539A1

  公开（公告）日：2021-06-10

  The present invention relates to a novel thieno[3,2-b]pyridine-5(4H)-one derivative compound, a preparation method thereof, and a use thereof. The novel thieno[3,2-b]pyridine-5(4H)-one derivative compound according to the present invention is synthesized via an aza-[3+3] cyclization addition reaction using BOP, wherein the compound is obtained by synthesizing a 4-arylthiophen-3-amine in which aryl groups such as 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, and 4-F3COC6H4 are introduced via a synthesis process by a bromination reaction, a hydrolysis reaction, a decarboxylation reaction, and a Suzuki coupling reaction of methyl 3-aminothiophene carboxylate, and by synthesizing 4-arylthiophen-3-amine and mono-methyl fumarate via a formal aza-[3+3] cyclization addition reaction using BOP and conjugation. Accordingly, novel thieno[3,2-b]pyridine-5(4H)-one derivative compounds according to the present invention have fluorescence properties with a wide range of emission wavelengths and thus may be utilized in various industrial fields such as physics, chemistry, and biomedical research.

  本发明涉及一种新型噻吩[3,2-b]吡啶-5(4H)-酮衍生物化合物，其制备方法及用途。根据本发明，所述新型噻吩[3,2-b]吡啶-5(4H)-酮衍生物化合物是通过使用BOP进行一种aza-[3+3]环化加成反应合成的，其中该化合物是通过合成一种4-芳基噻吩-3-胺获得的，其中芳基基团如4-哌啶基-C6H4、4-吡咯基- 、4-MeO 、3,4,5-(MeO)3 、C6H5、4- 和4-F3CO 等通过溴化反应、水解反应、脱羧反应和甲基3-氨基噻吩羧酸酯的铂催化偶联反应的合成过程引入，通过使用BOP和共轭进行形式aza-[3+3]环化加成反应合成4-芳基噻吩-3-胺和单甲基富马酸。因此，根据本发明，所述新型噻吩[3,2-b]吡啶-5(4H)-酮衍生物化合物具有广泛的发射波长范围的荧光性能，因此可以应用于物理学、化学和生物医学研究等各种工业领域。
• Thieno[3,2-b]pyridine-5(4H)-one derivative compound, preparation method thereof and use thereof
  申请人：Korea Institute of Ocean Science & Technology

  公开号：US11306103B2

  公开（公告）日：2022-04-19

  The present invention relates to a novel thieno[3,2-b]pyridine-5(4H)-one derivative compound, a preparation method thereof, and a use thereof. The novel thieno[3,2-b]pyridine-5(4H)-one derivative compound according to the present invention is synthesized via an aza-[3+3] cyclization addition reaction using BOP, wherein the compound is obtained by synthesizing a 4-arylthiophen-3-amine in which aryl groups such as 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, and 4-F3COC6H4 are introduced via a synthesis process by a bromination reaction, a hydrolysis reaction, a decarboxylation reaction, and a Suzuki coupling reaction of methyl 3-aminothiophene carboxylate, and by synthesizing 4-arylthiophen-3-amine and mono-methyl fumarate via a formal aza-[3+3] cyclization addition reaction using BOP and conjugation. Accordingly, novel thieno[3,2-b]pyridine-5(4H)-one derivative compounds according to the present invention have fluorescence properties with a wide range of emission wavelengths and thus may be utilized in various industrial fields such as physics, chemistry, and biomedical research.

  本发明涉及一种新型噻吩并[3,2-b]吡啶-5(4H)-酮衍生物化合物、其制备方法及其用途。根据本发明的新型噻吩并[3,2-b]吡啶-5(4H)-酮衍生物化合物是利用 BOP 通过氮杂-[3+3]环化加成反应合成的、其中，该化合物是通过合成 4-芳基噻吩-3-胺得到的，其中芳基如 4-哌啶基-C6H4、4-吡咯烷基- 、4-MeO 、3,4,5-(MeO)3 、C6H5、4- 、和 4-F3CO 是通过 3-氨基噻吩羧酸甲酯的溴化反应、水解反应、脱羧反应和铃木偶联反应的合成过程，以及通过使用 BOP 和共轭的形式偶氮-[3+3] 环化加成反应合成 4-芳基噻吩-3-胺和富马酸单甲酯的过程引入的。因此，根据本发明的新型噻吩并[3,2-b]吡啶-5(4H)-酮衍生物化合物具有发射波长范围广的荧光特性，因此可用于各种工业领域，如物理学、化学和生物医学研究。
• Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa
  作者：J. Henning Sahner、Martin Empting、Ahmed Kamal、Elisabeth Weidel、Matthias Groh、Carsten Börger、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2015.04.007

  日期：2015.5

  Pseudomonas aeruginosa employs a quorum sensing (QS) communication system that makes use of small diffusible molecules. Among other effects, the QS system coordinates the formation of biofilm which decisively contributes to difficulties in the therapy of Pseudomonas infections. The present work deals with the structure-activity exploration of ureidothiophene-2-carboxylic acids as inhibitors of PqsD, a key enzyme in the biosynthetic pathway of signal molecules in the Pseudomonas QS system. We describe an improvement of the inhibitory activity by successfully combining features from two different PqsD inhibitor classes. Furthermore the functional groups, which are responsible for the inhibitory potency, were identified. Moreover, the inability of the new inhibitors, to prevent signal molecule formation in whole cell assays, is discussed. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Gold(I)-Catalyzed Intramolecular Hydrothiophenylation of <i>N</i>-Thiophen-3-yl Alkynylamides for Accessing Thieno[3,2-<i>b</i>]pyridine-5(4<i>H</i>)-ones: Development of F-Actin Specific Fluorescent Probes
  作者：Dan-Bi Sung、Jang Hee Han、Yong-Keon Kim、Bo Hyun Mun、Sol Park、Hyun Seok Kim、Jong Seok Lee

  DOI：10.1021/acs.joc.1c02923

  日期：2022.4.1