6125-32-2

Usage

InChI:InChI=1/C14H24N2OS/c1-5-6-7-12-11(4)15-14(16-13(12)17)18-9-8-10(2)3/h10H,5-9H2,1-4H3,(H,15,16,17)

Upstream product

• 2103-94-8 4-(4-bromophenyl)-1,3-thiazol-2-amine 
• 79-04-9 chloroacetyl chloride 
• 99-90-1 para-bromoacetophenone 
• 99-73-0 para-bromophenacyl bromide 

Downstream Products

• 103041-76-5 N-[4-(4-bromo-phenyl)-thiazol-2-yl]-2-piperidin-1-yl-acetamide 
• 93946-34-0 N-[4-(4-bromo-phenyl)-thiazol-2-yl]-2-morpholin-4-yl-acetamide 
• 6122-42-5 N,N'-bis-[4-(4-bromo-phenyl)-thiazol-2-yl]-2,2'-piperazine-1,4-diyl-bis-acetamide 
• 6121-91-1 N-benzyl-N-phenyl-glycine 4-(4-bromo-phenyl)-thiazol-2-ylamide 
• 6122-07-2 2-benzoimidazol-1-yl-N-[4-(4-bromo-phenyl)-thiazol-2-yl]-acetamide 
• 6122-25-4 4-(4-Brom-phenyl-2-(α-<2-methyl-benzimidazolyl-(1)>-acetamino)-thiazol 
• 85842-81-5 2-(Acridin-9-ylsulfanyl)-N-[4-(4-bromo-phenyl)-thiazol-2-yl]-acetamide 
• 79420-02-3 2-(Benzooxazol-2-ylsulfanyl)-N-[4-(4-bromo-phenyl)-thiazol-2-yl]-acetamide 
• 6664-52-4 N-methyl-N-phenyl-glycine 4-(4-bromo-phenyl)-thiazol-2-ylamide 
• 100974-57-0 N,N-diethyl-glycine 4-(4-bromo-phenyl)-thiazol-2-ylamide 
• 6664-68-2 N-ethyl-N-phenyl-glycine 4-(4-bromo-phenyl)-thiazol-2-ylamide 
• 79420-20-5 2-((1H-benzo[d]imidazol-2-yl)thio)-N-(4-(4-bromophenyl)thiazol-2-yl)acetamide 

Relevant academic research and scientific papers

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.

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.

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.

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 and free radical scavenging activity of 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamide compounds

The synthesis of a new series of organochalcogen-derivatives, 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamides 5a-r, provided products in satisfactory yields, which varied from 42% to 95%. All these novel compounds were screened for their in vitro free radical scavenging activity against 2,2-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radicals. Compounds 5 (m, h, i, f, q, g, l, c, n) were effective scavengers against the ABTS radical species but less effective on scavenging the DPPH radical, indicating that the antioxidant effect of these compounds were related to protonated radical scavenger activity.

Design and Synthesis of 3-Substituted-thiazolyl-2-iminothiazolidin-4-ones as a New Class of Anticonvulsants

A new series of 3-substituted-thiazolyl-2-iminothiazolidin-4-ones were synthesized by nucleophilic substitution of p-substituted-thiazol-2-yl-chloroacetamides with potassium thiocyanide by cyclization. The starting material p-substituted-thiazol-2-yl-chloroacetamides were synthesized from p-substituted-thiazol-2-yl-amines with chloroacetyl chloride, which in turn was prepared from one pot reaction of substituted aryl acetophenone and amino group of thiourea. The title compounds were investigated for their anticonvulsant activity. Among the tested compounds, compound 3-(4-(4-fluorophenyl)thiazol-2-yl)-2-iminothiazolidin-4-one (16) emerged as the most active compound of the series, and it is moderately more potent than the reference standard diazepam.

SYNTHESIS AND TRANSFORMATIONS OF 4-SUBSTITUTED 2-AMINOTHIAZOLES

4-Substituted 2-aminothiazoles were synthesized and some of the transformations of these compounds at the amino group were studied.A number of new thiazole derivatives were obtained.