5039-16-7

Upstream product

• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 2010-06-2 2-Amino-4-phenylthiazole 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 66179-98-4 4-phenyl-2-(N-piperidinoacetamido)thiazole 
• 66180-00-5 4-phenyl-2-(N-morpholinoacetamido)thiazole 
• 6122-22-1 2-(2-methyl-benzoimidazol-1-yl)-N-(4-phenyl-thiazol-2-yl)-acetamide 
• 104295-43-4 2,6-bis-(4-methoxy-phenyl)-4-oxo-1-[(4-phenyl-thiazol-2-ylcarbamoyl)-methyl]-piperidine-3-carboxylic acid ethyl ester 
• 5039-17-8 N,N-diethyl-glycine 4-phenyl-thiazol-2-ylamide 
• 6674-33-5 N-benzyl-N-phenyl-glycine 4-phenyl-thiazol-2-ylamide 
• 6664-49-9 N-methyl-N-phenyl-glycine 4-phenyl-thiazol-2-ylamide 
• 79420-10-3 2-(Benzothiazol-2-ylsulfanyl)-N-(4-phenyl-thiazol-2-yl)-acetamide 
• 178617-81-7 3-Amino-4-methyl-thieno[2,3-b]quinoline-2-carboxylic acid (4-phenyl-thiazol-2-yl)-amide 
• 131213-50-8 2-imino-3-(4-phenylthiazol-2-yl)-thiazolidin-4-one 
• 928341-43-9 2-(2'-hydrazinoacetyl)-amino-4-phenyl-1,3-thiazole 
• 135747-47-6 3-Amino-4-(4-chloro-phenyl)-5,6,7,8-tetrahydro-thieno[2,3-b]quinoline-2-carboxylic acid (4-phenyl-thiazol-2-yl)-amide 
• 135747-53-4 5-(4-Chloro-phenyl)-2-(4-phenyl-thiazol-2-yl)-6,7,8,9-tetrahydro-2H-11-thia-2,3,4,10-tetraaza-benzo[b]fluoren-1-one 
• 725225-01-4 2-(4-phenyl-piperazin-1-yl)-N-(4-phenyl-thiazole-2-yl)acetamide 

Relevant academic research and scientific papers

Novel thienopyrimidine-aminothiazole hybrids: Design, synthesis, antimicrobial screening, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and VEGFR-2 inhibition

A series of novel hybrid compounds of hexahydrobenzo[4,5]thieno[2,3-d]pyrimidine with aminothiazole scaffolds were synthesized. The synthesized compounds were evaluated for their cytotoxic activity against the NCI-60 human tumor cell line panel. Compounds 7c, 7d and 7e exhibited significant antiproliferative activities at 10?5 M dose. Compound 7c exhibited excellent cytotoxic activity against CNS cancer cell lines including SNB-75 and SF-295 as well as renal cancer cell line CAKI-1 when compared with sorafenib as standard anticancer drug. In addition, compound 7d showed almost comparable anticancer activity to sorafenib against SNB-75 cell line and displayed moderate activity against SF-295 and CAKI-1 cell lines in comparison to sorafenib. Compound 7c inhibited the vascular endothelial growth factor receptor 2 (VEGFR-2) with IC50 of 62.48 ± 3.7 nM and decreased both total VEGFR-2 and phosphorylated VEGFR-2 in treated SNB-75 cells suggesting its ability to down regulate cell proliferation, growth, and survival. The flow cytometric analysis showed that 7c displayed its cytotoxic activity through the reduction of the cellular proliferation and induction of cell cycle arrest at the G2/M phase. Compound 7c clearly boosted the level of the apoptotic caspase-3. All the synthesized compounds were also screened for their antibacterial and antifungal activity against four pathogenic strains of both Gram-positive and Gram-negative as well as Candida albicans. Only compound 7d exhibited antifungal activity against Candida albicans compared to nystatin as the standard antifungal compound.

Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors

A novel series of phenoxymethybenzoimidazole derivatives (9a-n) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC50 values in the range of 6.31 to 49.89?μM compared to standard drug acarbose (IC50 = 750.0 ± 10.0?μM). Enzyme kinetic studies on 9c, 9g, and 9m as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor.

Synthesis of New Binary Thiazole-Based Heterocycles and Their Molecular Docking Study as COVID-19 Main Protease (Mpro) Inhibitors

Abstract: Isolated polynuclear binary heterocyclic compounds containing thiazole building block combined with benzofuran, pyrrole, thiazole, or thiophene via carboxamide and/or secondary amine as a junction are presented. The synthetic strategy of those is based on utilization of 2-chloroacetamido-4-phenylthiazole in the synthesis of binary heterocyclic compounds by cyclocondensation with salicylic aldehyde, acetonitrile derivatives, ammonium thiocyanate, 3-mercaptoacrylonitrile derivatives, and/or 3-mercaptoacrylate derivatives. The prepared binary thiazole-based heterocycles have been studied as protease (Mpro) inhibitors by molecular docking for visualization of their orientation and interactions with COVID-19 units using hydroxychloroquine as a reference molecule.

Synthesis, biological evaluation, and docking studies of novel 5,6-diaryl-1,2,4-triazine thiazole derivatives as a new class of α-glucosidase inhibitors

A novel 5,6-diaryl-1,2,4-triazine thiazole derivatives (7a-7q) were synthesized and characterized by 1H NMR and 13C NMR and evaluated for their α-glucosidase inhibitory activity. All tested compounds displayed good α-glucosidase inhibitory activity with IC50 values ranging between 2.85 ± 0.13 and 14.19 ± 0.23 μM when compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 7i (IC50 = 2.85 ± 0.13 μM) exhibited the highest activity among this series of compounds. Molecular docking studies were carried out in order to investigate the binding mode of this class of compounds to α-glucosidase. This study showed that these 5,6-diaryl-1,2,4-triazine thiazole derivatives are a new class of α-glucosidase inhibitors.

Β - secretase enzyme has the function of inhibiting compound, the preparation of the compounds and use thereof

The invention discloses a compound capable of inhibiting beta-secretase, and a preparation method and application thereof. The structure of the compound is shown in a formula I, formula II or formula III as described in the specification. In the formula I, X is S or NH; R1 is selected from hydrogen and nitro group; R2 and R4 are same or different and independently selected from the group consisting of hydrogen, halogen, nitro group and substituted aryl group; R3 is selected from the group consisting of hydrogen, nitro group, straight-chain and branched-chain alkyl and substituted alkyl groups with a carbon number of 1 to 4, alkylamino or alkyloxy group with a carbon number of 1 to 4 and alkylamido group with a carbon number of 1 to 4; R is located at position 2, 3 or 4 of a benzene ring and selected from the group consisting of hydrogen, straight-chain and branched-chain alkyl and substituted alkyl groups with a carbon number of 1 to 4, alkylamino or alkyloxy group with a carbon number of 1 to 4 and alkylamido group with a carbon number of 1 to 4. In the formula II, R is selected from different substituted aryl groups. In the formula III, R is selected from hydrogen or cyano group. Experiments prove that the compound provided by the invention has good beta-secretase inhibitory activity and has wide application values as a beta-secretase inhibitor.

Synthesis and biological screening of diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates

A three-step synthesis, involving condensation of bromomethyl aryl ketones with urea to afford 2- aminothiazoles, their chloroacetylation and subsequent solvent-free Arbuzov phosphonation has afforded a series of novel diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates 3a-3f in good overall yields; the 4- carboxythiazole analogue 3g was obtained by selective hydrolysis of the corresponding ethyl ester 3f. The phosphonate esters exhibited significant anti-cancer activity (nM - low μM IC50 values) against SH-SY5Y cells and, in one case, 7.6 μM MIC90 anti-TB activity against the virulent M. tuberculosis H37Rv strain; the chloroacetamido precursors all exhibited some antimalarial (PfLDH) activity, three with IC50 values in the range 1.0 - 8.9 μM.

Synthesis, characterization and drug-likeness predictions of 1,3-thiazole and benzothiazole derivatives

Heterocyclic compounds bearing nitrogen and sulphur in the main skeleton are reported to be a bioactive group. Thiazole and benzothiazole moieties are biologically significant class of this group. This research focus on the synthesis and characterization of 1,3-thiazole and benzothiazole derivatives. Drug likeness predictions were also undertaken for these newly synthesized compounds.

2-Substituted-thio-N-(4-substituted-thiazol/1H-imidazol-2-yl)acetamides as BACE1 inhibitors: Synthesis, biological evaluation and?docking studies

In this work, a series of 2-substituted-thio-N-(4-substituted-thiazol/1H-imidazol-2-yl)acetamide derivatives were developed as β-secretase (BACE-1) inhibitors. Supported by docking study, a small library of derivatives were designed, synthesized and biologically evaluated in vitro. In addition, the selected compounds were tested with affinity (KD) towards BACE-1, blood brain barrier (BBB) permeability and cytotoxicity. The studies revealed that the most potent analog 41 (IC50 = 4.6 μM) with high predicted BBB permeability and low cellular cytotoxicity, could serve as a good lead structure for further optimization.

Design and discovery of novel thiazole derivatives as potential MMP inhibitors to protect against acute lung injury in sepsis rats: Via attenuation of inflammation and apoptotic oxidative stress

Acute lung injury (ALI) is considered to be an inflammatory syndrome of the airway system that is initiated by failure of the respiratory system. In this study, we evaluated the possible benefits of some novel thiazole derivatives against ALI. These derivatives were synthesised and evaluated for the inhibition of MMP-8 and MMP-2. Most of the tested compounds had better inhibitory activity for MMP-8 than for MMP-2, with compound 26 being the most potent analogue among the tested series. Thus, compound 26 was further investigated to determine its beneficial effects in an ALI model of rats with sepsis. In vivo results suggested that compound 26 significantly reduced the protein concentration together with a decline in enhanced leukocytes compared with those in ALI induced by cecal ligation and puncture. The effect of compound 26 on myeloperoxidase activity was also quantified, which was found to be significantly reduced at the maximum tested dose of 20 mg kg-1. The protective effect of compound 26 against ALI was also established to occur via the significant modulation of various biomarkers; for example, the malondialdehyde level was found to be reduced, while there were increased levels of superoxide dismutase and glutathione. Thus, it is proposed that compound 26 exerts a protective effect against ALI via modulation of the antioxidant status. Furthermore, the compounds tested caused significant attenuation of the levels of tumour necrosis factor-α, interleukin-1β, and interleukin-6, and protected the lung through the modulation of systemic inflammatory mediators in septic rats. In conclusion, we identified a novel series of thiazoles, which potentially exert protective effects against ALI via the inhibition of numerous pathways.

Synthesis, antibacterial, antifungal, and antioxidant evaluation of some new thiazole clubbed oxadiazole derivatives

A series of thiazole incorporated oxadiazole derivatives (6a-6f) was synthesized by reacting 2-chloro-N-(4-(4-substituted phenyl) thiazol-2-yl) acetamide with 5-pyridine-1,3,4-oxadiazole-2-thione using multistep solution phase chemistry. The synthesized compounds were structurally characterized on the basis of elemental analysis and using various spectral data. All the compounds were evaluated for their in vitro antibacterial, antifungal, and antioxidant activity. Some of the new compounds exhibited good antimicrobial and antioxidant activity and are suitable candidates for further scientific explorations.