4651-94-9

Usage

Chemical Properties

Yellow solid

InChI:InChI=1/C7H8N2S/c1-4-5(2)10-7(9)6(4)3-8/h9H2,1-2H3

Upstream product

• 78-93-3 butanone 
• 109-77-3 malononitrile 
• 13017-50-0 1,1-dicyano-2-methyl-1-butene 
• 565-80-0 2,4-dimethylpentan-3-one 

Downstream Products

• 4994-89-2 4-amino-5,6-dimethylthieno[2,3-d]pyrimidine 
• 137056-26-9 2,4-dithioxo-2,4-dihydro-1H,3H-5,6-dimethylthieno<2,3-d>pyrimidine 
• 28586-90-5 2,2'-Thioureylen-bis-(4,5-dimethyl-thiophen-3-carbonitril) 
• 102-08-9 N,N-diphenylthiourea 
• 128276-98-2 4-Chloro-2-dichloromethyl-5,6-dimethyl-thieno[2,3-d]pyrimidine 
• 143932-80-3 2-chloro-3-<4-chlorophenyl>-4-imino-5,6-dimethylthieno<2,3-d>pyrimidine hydrochloride 
• 143932-81-4 3-<4-bromophenyl>-2-chloro-4-imino-5,6-dimethylthieno<2,3-d>pyrimidine hydrochloride 
• 51486-04-5 2-amino-4,5-dimethylthiophene-3-carboxamide 
• 126105-79-1 4-Imino-5,6-dimethyl-3-phenyl-3,4-dihydro-1H-thieno[2,3-d]pyrimidine-2-thione 
• 132424-59-0 1-(3-Cyano-4,5-dimethyl-thiophen-2-yl)-3-phenyl-thiourea 
• 126105-81-5 3-(4-Chloro-phenyl)-4-imino-5,6-dimethyl-3,4-dihydro-1H-thieno[2,3-d]pyrimidine-2-thione 
• 88203-19-4 4-Chloro-2-chloromethyl-5,6-dimethyl-thieno[2,3-d]pyrimidine 
• 101130-15-8 5,6-Dimethyl-2-((E)-styryl)-thieno[2,3-d]pyrimidin-4-ylamine 
• 121746-07-4 2-(3-Benzoyl-thioureido)-4,5-dimethyl-thiophen-3-carbonitril 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel hybrid compounds derived from gallic acid and the 2-aminothiophene derivatives

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.]

Design, synthesis, and cytotoxicity screening of 5-aryl-3-(2-(pyrrolyl) thiophenyl)-1, 2, 4-oxadiazoles as potential antitumor molecules on breast cancer MCF-7 cells

The work representing the design and the cytotoxic screening of synthetic small molecules (SSMs) such as carbonitriles 3a-c, carboximidamides 4a-c, and oxadiazoles 5–19 as antitumor molecules. Molecules 4c, 9, 12, and 14 show promising cytotoxicity profiles against two cell lines higher than prodigiosin (PG). The results of topoisomerase enzyme inhibition assay show that compounds 4c and 14 display potent inhibitory activity in nano-molar concentration. In addition, DNA-flow cytometry and annexin V analysis also display that compounds 4c, 9, 12, and 14 exhibit antiproliferative activities over MCF-7 cells by cell cycle arrest at G1 phase and apoptosis-inducing activity by increasing cell percentages at pre G1 phase. Moreover, Elisa measurement of p53 and apoptosis mediators, show that carboximidamide 4c and oxadiazoles 9, 12, and 14 significantly up-regulate p53 and cell death mediators as puma and Bax/Bcl-2 ratio levels. Subsequently, pro-apoptotic activities are confirmed by active caspase 3/7 percentages green fluorescence assay.

Design, Synthesis, and Screening of 5-Aryl-3-(2-(pyrrolyl)thiophenyl)-1,2,4-oxadiazoles as Potential Antitumor Molecules on Breast Cancer MCF-7 Cell Line

The work reported the design and cytotoxic screening of synthetic small molecules: carbonitriles 3a–c, carboximidamides 4a–c, and oxadiazoles 5–19 as antitumor molecules. Molecules 4c, 9, 12, and 14 show promising cytotoxicity profiles against two cell lines higher than prodigiosin (PG). The results of topoisomerase enzyme inhibition assay show that carboximidamide 4c and oxadiazole 14 display potent inhibitory activity in nano-molar concentration higher than PG. In addition, carboximidamide 4c and oxadiazoles 9, 12, and 14 exhibit antiproliferative activities over MCF-7 cells by cell cycle arrest at G1 phase and apoptosis inducing activity by increasing cell population percentages at pre G1 and G2/M phases as shown by DNA-flow cytometry assay and annexin V analysis. Moreover, measurement of p53 and cell death mediators, show that carboximidamide 4c and oxadiazoles 9, 12, and 14 significantly up-regulate p53, Puma and Bax/Bcl-2 ratio levels. Subsequently, pro-apoptotic activities are confirmed by active caspase 3/7 percentages green fluorescence assay.

Basic Ionic Liquid [bmIm]OH-Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes

A simple, efficient, and environmental friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields.

A convenient synthesis of new 2-cyanomethylthieno[3,2-e]1[1,2,4]- triazolo[1,5-c]pyrimidine derivatives

A new series of 2-cyanomethylthienotriazolopyrimidines has been synthesized in good yield through a facile method using substituted aminothiophene-3- carbonitrile as building block and cyanoacetic acid hydrazide as reagent in one framework. The structure of the synthesized compounds was established on the basis of their mass and spectral data.

Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction

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.

KG-60-piperazine as a new heterogeneous catalyst for gewald three-component reaction

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.

New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides

A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A2A adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist.

Mg/La mixed oxide as an efficient heterogeneous basic catalyst for synthesis of 2-aminothiophenes under microwave irradiation

Microwave-assisted synthesis of 2-aminothiophenes via a Gewald reaction using a heterogeneous strong basic Mg/La mixed oxide catalyst is described.

A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction

A simple and efficient procedure was developed for the synthesis of multisubstituted 2-aminothiophene derivatives. In the presence of catalytic amount of imidazole, ketones or aldehydes, dicyanomethane and elemental sulfur were converted into the corresponding 2-aminothiophene derivatives in moderate to high yields in DMF at 60 °C.