6125-37-7

Usage

Uses

Used in Pesticide Industry:
2-(2-CHLORO-ACETYLAMINO)-4-METHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER is used as an active ingredient in the pesticide industry for its ability to control and eliminate pests that can damage crops and affect agricultural productivity. Its chemical structure allows it to target specific pests, reducing the need for broad-spectrum chemicals that may have negative environmental impacts.
Used in Pharmaceutical Industry:
2-(2-CHLORO-ACETYLAMINO)-4-METHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER is used as a neoplasm inhibitor for its anti-tumoral activity. It has the potential to be developed into a pharmaceutical compound that targets cancer cells, inhibiting their growth and proliferation. This application is particularly relevant for the development of targeted therapies that can minimize side effects and improve patient outcomes.

Upstream product

• 141-97-9 ethyl acetoacetate 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 7210-76-6 ethyl-2-amino-4-methylthiazole-5-carboxylate 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 6697-53-6 2-[(N-ethyl-N-phenyl-glycyl)-amino]-4-methyl-thiazole-5-carboxylic acid ethyl ester 
• 6664-63-7 4-methyl-2-[(N-methyl-N-phenyl-glycyl)-amino]-thiazole-5-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Design and synthesis of novel 2,4,5-thiazole derivatives as 6-APA mimics and antimicrobial activity evaluation

Nine new thiazole derivatives were synthesized considering 6-acetyl penicillanic acid (6-APA) and investigated for their antimicrobial activity. Ethyl 2-(2-mercaptoacetamido)-4-methylthiazole-5-carboxylate derivatives (3a–3i) were gained with a two-step synthetic method using conventional Hantzsch thiazole synthesis. The structural elucidation of the compounds was performed by 1H-NMR, 13C-NMR spectral data and HRMS. All compounds were tested on eleven bacteria and sixteen fungi species and minimum inhibitory concentration (MIC) was determined for each. Compounds 3d (4-methyl-2-(2-((5-methyl-1,3,4-thiadiazol-2-yl), 3f (4-methyl-2-(2-((5-nitro-1H-benzimidazol-2-yl) and 3g (4-methyl-2-(2-((5-methyl-4H-1,2,4-triazol-3-yl) bearing thiazole, 5-nitrobenzimidazole and triazole rings respectively exhibited high antimicrobial activity against most of the strains. In silico physicochemical properties were calculated for the compounds and it was detected that they comply with the rules of drug availability.

Design, synthesis, and bioassay of 4-thiazolinone derivatives as influenza neuraminidase inhibitors

A series of 4-thiazolinone derivatives (D1-D58) were designed and synthesized. All of the derivatives were evaluated in vitro for neuraminidase (NA) inhibitory activities against influenza virus A (H1N1), and the inhibitory activities of the five most pot

Regioselectivity evaluation of the (Z)-5-(4-hydroxybenzylidene)-thiazolidine-2,4?dione alkylation in alkaline environment

Thiazolidine-2,4?dione represents a key heterocyclic core in medicinal chemistry because it has the ability to bind to a wide variety of protein targets and has been intensively studied for developing bioactive multitargeting agents. The N-alkylation of i

Novel indole-thiazolidinone conjugates: Design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents

In connection with our research program on the development of novel anti-tubercular candidates, herein we report the design and synthesis of two different sets of indole-thiazolidinone conjugates (8a,b; 11a-d) and (14a-k; 15a-h). The target compounds were evaluated for their in vitro antibacterial and antifungal activities against selected human pathogens viz. Staphylococcus aureus (Gram positiveve), Pseudomonas aeruginosa, Escherichia coli (Gram negative), Mycobacterium tuberculosis (Acid-fast bacteria), Aspergillus fumigates and Candida albicans (fungi). Moreover, eukaryotic cell-toxicity was tested via an integrated ex vivo drug screening model in order to evaluate the selective therapeutic index (SI) towards antimicrobial activity when microbes are growing inside primary immune cells. Also, the cytotoxicity towards a panel of cancer cell lines and human lung fibroblast normal cell line, WI-38 cells, was explored to assure their safety. Compound 15b emerged as a hit in this study with potent broad spectrum antibacterial (MIC: 0.39–0.98 μg/mL) and antifungal (MIC: 0.49–0.98 μg/mL) activities, in addition to its ability to kill mycobacteria M. aurum inside an infected macrophage model with good therapeutic window. Moreover, compound 15b displayed promising activity towards resistant bacteria strains MRSA and VRE with MIC values equal 3.90 and 7.81 μg/mL, respectively. These results suggest compound 15b as a new therapeutic lead with good selectivity for further optimization and development.

2-(4-thiazolinone-2-imino)thiazole-5-carboxylate and preparation method and application thereof

The invention relates to 2-(4-thiazolinone-2-imino)thiazole-5-carboxylate as shown in chemical structural formulas I and II. The structural formulas are shown in the specification, wherein R is selected from C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl; R1 is selected from C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl and trifluoromethyl; Y1 is selected from hydrogen, C1-C2 alkyl, C3-C4 linear alkyl, C3-C4 branched alkyl, carboxyl, C1-C2 alkoxycarbonyl, hydroxyl, and C1-C2 alkoxy; Y2 and Y4 are selected from hydrogen, C1-C2 alkyl, C3-C4 linear alkyl, C3-C4 branched alkyl, hydroxyl, C1-C2 alkoxy, fluorine, chlorine, bromine, iodine, amino and nitro; Y3 is selected from hydrogen, C1-C2 alkyl, C3-C4 linear alkyl, C3-C4 branched alkyl, carboxyl, C1-C2 alkoxycarbonyl, hydroxyl, C1-C2 alkoxy, amino, acetamido and nitro; R2 is selected from hydrogen, C1-C2 alkyl, C3-C4 linear alkyl, C3-C4 branched alkyl, phenyl and phenyl substituted by C1-C2 alkyl. The invention further relates to application of 2-(4-thiazolinone-2-imino)thiazole-5-carboxylate in preparation of influenza neuraminidase inhibitors.

1-Piperazinylphthalazines as potential VEGFR-2 inhibitors and anticancer agents: Synthesis and in vitro biological evaluation

In our endeavor towards the development of effective VEGFR-2 inhibitors, three novel series of phthalazine derivatives based on 1-piperazinyl-4-arylphthalazine scaffold were synthesized. All the newly prepared phthalazines 16a-k, 18a-e and 21a-g were evaluated in vitro for their inhibitory activity against VEGFR-2. In particular, compounds 16k and 21d potently inhibited VEGFR-2 at sub-micromolar IC50 values 0.35 ± 0.03 and 0.40 ± 0.04 μM, respectively. Moreover, seventeen selected compounds 16c-e, 16g, 16h, 16j, 16k, 18c-e and 21a-g were evaluated for their in vitro anticancer activity according to US-NCI protocol, where compounds 16k and 21d proved to be the most potent anticancer agents. While, compound 16k exhibited potent broad spectrum anticancer activity with full panel GI50 (MG-MID) value of 3.62 μM, compound 21d showed high selectivity toward leukemia and prostate cancer subpanels [subpanel GI50 (MG-MID) 3.51 and 5.15 μM, respectively]. Molecular docking of compounds16k and 21d into VEGFR-2 active site was performed to explore their potential binding mode.

Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings

The synthesis of 2-(substituted phenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A1-A24) derivatives and 2-(4-substituted thiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B1-B14) derivatives was undertaken starting from the potassium salt of 4-(2-pyrimidinyl)piperazine dithiocarbamate. The structures of the obtained compounds were elucidated by1H NMR,13C NMR, MS spectral data, and elemental analysis. The antimicrobial activity of the thirty eight newly synthesized compounds were tested against 12 microorganism strains using the microdilution technique. Compounds 2-(4-ethoxycarbonylthiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B12), 2-(3-fluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A18) and 2-(3,4-difluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A21) were determined to possess high antimicrobial activity.

Synthesis and antimicrobial evaluation of novel ethyl 2-(2-(4-substituted)acetamido)-4-subtituted-thiazole-5-carboxylate derivatives

A series of novel molecules containing thiazole ring structure were designed and synthesized. The structures of the synthesized compounds were elucidated and confirmed by1H NMR,13C NMR, Mass spectrum and the purity was checked through HPLC analysis. Among these synthesized compounds, 3a–3i and 6a–6c were tested for their antimicrobial activity (minimum inhibitory concentration) against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus niger for antifungal activity respectively. The results of the antimicrobial screening data revealed that most of the tested compounds showed moderate to good microbial inhibitions.

Bifunctional ethyl 2-amino-4-methylthiazole-5-carboxylate derivatives: Synthesis and in vitro biological evaluation as antimicrobial and anticancer agents

Thirty thiazole compounds bearing chemotherapeutically-active pharmacophores were synthesized and evaluated for their preliminary in vitro antimicrobial and anticancer activities. Nineteen compounds displayed obvious antibacterial potential, with special

Synthesis and biological activity of thiazole dithiocarbamate derivatives

In this study, we aimed at the synthesis of new 2-((5-substituted-4- methylthiazol-2-yl)amino)-2-oxoethyl 4- substitutedpiperazine-1-carbodithioate derivatives and their antibacterial, antifungal, antioxidant and AChE inhibitory evaluations. A set of fift