23917-22-8Relevant articles and documents
Calcined Mg-Al hydrotalcite as a heterogeneous base catalyst for gewald aminothiophene synthesis
Rajagopal,Jyothi,Daniel,Srinivasan,Rao
, p. 3113 - 3117 (2001)
Calcined Mg-Al hydrotalcite (Mg/Al=4) has been conveniently employed as a heterogeneous base catalyst in the synthesis of 2-amino-3-cyanothiophenes adopting a one pot Gewald aminothiophene methodology.
An innovative synthesis of tertiary hydroxyl thieno[2,3-d]pyrimidinone skeleton: Natural-like product from the tandem reaction of o-aminothienonitrile and carbonyl compound
Yang, Junjuan,Shi, Daxin,Hao, Pengfei,Yang, Deli,Zhang, Qi,Li, Jiarong
, p. 2455 - 2461 (2016)
A straightforward base accelerant tandem protocol for the synthesis of the tertiary hydroxyl natural-like thieno[2,3-d]pyrimidinone skeleton was developed from the cyclocondensation of o-aminothienonitrile and carbonyl compound. The reaction process includes PDF conversion and photo-catalytic oxygenation. This synthetic strategy offers an alternative method for regioselective construction of tertiary hydroxylated thieno[2,3-d]pyrimidinone architectures with kinetic, thermodynamic control, and six-member ring effect.
Novel thienopyrimidine derivatives as dual EGFR and VEGFR-2 inhibitors: design, synthesis, anticancer activity and effect on cell cycle profile
Mghwary, Aml E.-S.,Gedawy, Ehab M.,Kamal, Aliaa M.,Abuel-Maaty, Suzan M.
, p. 838 - 852 (2019)
Aim: Design and synthesis of thienopyrimidine derivatives as dual EGFR and VEGFR-2 inhibitors.Material and methods: A series of novel 6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidine derivatives with different substituents on C-4 position was synthesized and evaluated for their anticancer activity against MCF-7 cell line. EGFR, VEGFR-2 inhibitory assay, the cell cycle analysis and apoptosis induction ability of the most potent compound 5f were evaluated.Results: Most of the compounds showed moderate to significant anticancer activity. Compound 5f exhibited the most potent anticancer activity being 1.73- and 4.64-folds more potent than erlotinib and doxorubicin, respectively. Compound 5f showed potent EGFR inhibitory activity being 1.18-folds more potent than reference standard erlotinib and it also showed good VEGFR-2 inhibitory activity at the micromolar level with IC50 value 1.23?μM. Compound 5f caused induction of cell cycle arrest at G2/M phase and accumulation of cells in pre-G1 phase. Compound 5f induced cellular apoptosis.
KG-60-piperazine as a new heterogeneous catalyst for gewald three-component reaction
Rezaei-Seresht, Esmail,Tayebee, Reza,Yasemi, Mohammad
, p. 1859 - 1864 (2013)
Piperazine supported on amorphous silica (KG-60-piperazine) as a basic catalyst acts in the Gewald three-component reaction of some aldehydes and ketones with malononitrile as well as ethyl cyanoacetate. The catalyst shows general utility with a variety of starting carbonyl compounds. Moreover, the catalyst can be reused for four additional cycles without significant loss of the activity. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Convenient synthesis of 2-aminothiophene derivatives by acceleration of gewald reaction under ultrasonic aqueous conditions
Mojtahedi, Mohammad M.,Abaee, M. Saeed,Mahmoodi, Peyman,Adib, Mehdi
, p. 2067 - 2074 (2010)
Under ultrasound irradiation and in the presence of H2O/Et 2NH, ethyl cyanoacetate or malononitrile can combine with-methylene carbonyl compounds and elemental sulfur to efficiently yield 2-aminothiophene derivatives within a few minutes. Products are easily obtained by simple filtration because of their spontaneous precipitation in the reaction mixtures. Copyright Taylor & Francis Group, LLC.
Preparation of magnetically recyclable ZnFe2O4 nanoparticles by easy single-step co-precipitation method and their catalytic performance in the synthesis of 2-aminothiophenes
Erfaninia,Tayebee,Foletto,Amini,Dusek,Zonoz
, (2018)
In this work, a new synthetic route for the preparation of ZnFe2O4 nanoparticles through the chemical co-precipitation using Fe2+ and Fe3+ ions in an alkaline solution was developed. The synthesized nanoparticles were characterized by XRD, FTIR, SEM, ICP-MS, DRS, TGA, VSM and elemental analysis. Characterization results confirmed the formation of single ZnFe2O4 phase, with an average particle size of 40?nm and a high saturation magnetization of 34?emu g?1. The prepared material was employed as a catalyst for the synthesis of 2-aminotiophene derivatives through the Gewald reaction. This thermally and chemically stable nanocatalyst is environmentally benign, economical and reusable which can be easily recovered using an external magnet. Therefore, it appears that this methodology can be simply extended for industrial purposes.
New thiophene–acridine compounds: Synthesis, antileishmanial activity, DNA binding, chemometric, and molecular docking studies
de Lima Serafim, Vanessa,Félix, Mayara Barbalho,Frade Silva, Daiana Karla,Rodrigues, Klinger Ant?nio da Franca,Andrade, Patrícia Néris,de Almeida, Sinara M?nica Vitalino,de Albuquerque dos Santos, Sanderssonilo,de Oliveira, Jamerson Ferreira,de Lima, Maria do Carmo Alves,Mendon?a-Junior, Francisco Jaime Bezerra,Scotti, Marcus Tullius,de Oliveira, Márcia Rosa,de Moura, Ricardo Olímpio
, p. 1141 - 1155 (2018)
In this study, we synthesized eight new compounds containing the 2-amino-cycloalkyl[b]thiophene and acridine moieties (ACT01 and ACS01-ACS07). None tested compounds presented human erythrocyte cytotoxicity. The new compounds presented antipromastigote activity, where ACS01 and ACS02 derivatives presented significant antileishmanial activity, with better performance than the reference drugs (tri and pentavalent antimonials), with respective IC50 values of 9.60?±?3.19 and 10.95?±?3.96?μm. Additionally, these two derivatives were effective against antimony-resistant Leishmania (Leishmania) amazonensis strains. In addition, binding and fragmentation DNA assays were performed. It was observed that the antileishmanial activity of ACS01 is not associated with DNA fragmentation of the promastigote forms. However, it interacted with DNA with a binding constant of 104?m?1. In partial least-squares studies, it was observed that the most active compounds (ACS01 and ACS02) showed lower values of amphiphilic moment descriptor, but there was a correlation between the lipophilicity of the molecules and antileishmanial activity. Furthermore, the docking molecular studies showed interactions between thiophene–acridine derivatives and the active site of pyruvate kinase enzyme with the major contribution of asparagine 152 residue for the interaction with thiophene moiety. Thus, the results suggested that the new thiophene–acridine derivatives are promising molecules as potential drug candidates.
Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction
Zhao, Dan-Dan,Li, Li,Xu, Fan,Wu, Qi,Lin, Xian-Fu
, p. 29 - 35 (2013)
A novel bovine serum albumin (BSA)-catalyzed Gewald reaction in one-pot was developed in this work. The influence of reaction conditions including solvent, temperature and catalyst loading was investigated, and 12 multi-substituted 2-aminothiophene derivatives were prepared with moderate to excellent yields. Recycle experiments were designed to demonstrate the reusability of BSA. This novel activity of BSA to catalyze Gewald reaction is of practical significance in expanding the application of biocatalysts.
Solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives using high-speed vibration milling
Xu, Fang,Li, Yujin,Xu, Fengshuang,Ye, Qing,Han, Liang,Gao, Jianrong,Yu, Wubin
, p. 450 - 452 (2014)
The solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives by high-speed vibration milling using the inexpensive and environmentally friendly Et2NH as a catalyst was studied. The reaction conditions were optimised and the derivatives were obtained in good yield. This method has advantages in terms of short reaction time and facile conditions.
Synthesis and biological evaluation of novel hybrid compounds derived from gallic acid and the 2-aminothiophene derivatives
Falanji, Farahnaz,Hosseyni-Tabar, Seyed Mahmood,Mahdavi, Behnam,Rezaei-Seresht, Esmail,Rezaei-Seresht, Hasan
, p. 809 - 815 (2020)
Abstract: Gallic acid (GA) and its benzamide derivatives have a wide variety of biological activities, such as antimicrobial, antioxidant, anticancer. In this study, we have reported the synthesis of some new hybrid compounds comprised of the 2-aminothiophene and GA moieties and evaluation of their cytotoxic activities against HeLa (cervical cancer), HCT116 (human colon cancer), and FT (fibroblast) cell lines as well as antimicrobial activities against some Gram-positive and Gram-negative bacteria. The reaction of some 2-aminothiophene derivatives (previously prepared from the Gewald reaction) with galloyl chloride having the acetylated hydroxyl groups and the subsequent deprotection of the hydroxyl groups gave the desired hybrid compounds. Then, the antimicrobial activity of the compounds was evaluated using disc diffusion and minimum inhibitory concentration assays. Finally, the MTT assay was carried out to evaluate the cytotoxicity of the synthesized compounds on the mentioned cell lines. The structure of the synthesized compounds was elucidated by conventional spectroscopic methods such as NMR, FT-IR, and UV–Vis spectroscopy. All compounds prevented the growth of Staphylococcus coagulase more than the positive control of chloramphenicol, and one compound was more sensitive to the growth of Klebsiella pneumonia compared to the standard antibiotic. All compounds showed acceptable activity against cancer cells. The highest activity was observed against HeLa with an IC50 value of 3.2 μg/mL for compound 3d and against HCT116 with IC50 of 59.4 μg/mL for 3b. The high anticancer activity of compound 3d against HeLa allows us to consider it as a good lead compound for the development of new potent anticancer agents for the treatment of cervical cancer. Graphic abstract: [Figure not available: see fulltext.]
