54032-88-1

Usage

Molecular structure

Consists of a thiazole ring with a methyl and methoxyphenyl group attached, as well as an ethyl ester functional group.

Type of compound

Organic compound.

Potential biological activity

May have antifungal or antibacterial properties due to the presence of the thiazole ring in its structure.

Use in research

Commonly used in pharmaceutical and medicinal research as a building block for the synthesis of other compounds.

Drug candidate potential

Its biological activity and structural features make it a promising candidate for further investigation as a potential drug.

Pharmacokinetic properties

The ethyl ester functional group suggests that the compound can be easily modified to improve its pharmacokinetic properties, making it more suitable for drug development.

Upstream product

• 2362-64-3 p-methoxythiobenzamide 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 84911-18-2 ethyl 2-bromoacetoacetate 
• 161797-99-5 (2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester) 
• 74-88-4 methyl iodide 
• 3424-93-9 4-methoxyphenylacetamide 

Downstream Products

• 54001-06-8 1-(4-methyl-2-(4'-methoxyphenyl)thiazole-5-yl)ethane-1-one 
• 54001-35-3 2-bromo-1-(4-methyl-2- (4'-methoxyphenylthiazole-5-yl))ethan-1-one 
• 82875-44-3 2-(4-methoxyphenyl)-4-methylthiazole-5carboxamide 
• 161797-99-5 (2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester) 
• 1384111-05-0 C₁₆H₁₈N₂O₄S 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel thiazole-derivatives as mitochondrial targeting inhibitors of cancer cells

Mitochondria are pivotal energy production sources for cells to maintain necessary metabolism activities. Targeting dysfunctional mitochondrial features has been a hotspot for mitochondrial-related disease researches. Investigation with cancerous mitochondrial metabolism is a continuing concern within tumor therapy. Herein, we set out to assess the anti-cancer activities of a novel family of TPP-thiazole derivatives based on our earlier research on mitochondrial targeting agents. Specifically, we designed and synthesized a series of TPP-thiazole derivatives and revealed by the MTT assay that most synthesized compounds effectively inhibited three cancer cell lines (HeLa, PC3 and MCF-7). After structure modifications, we explored the SAR relationships and identified the most promising compound R13 (IC50 of 5.52 μM) for further investigation. In the meantime, we performed ATP production assay to assess the selected compounds inhibitory effect on HeLa cells energy production. The results displayed the test compounds significantly restrained ATP production of cancer cells. Overall, we have designed and synthesized a series of compounds which exhibited significant cytotoxicity against cancer cells and effectively inhibited mitochondrial energy production.

Design, synthesis, biological evaluation, common feature pharmacophore model and molecular dynamics simulation studies of ethyl 4-(phenoxymethyl)-2-phenylthiazole-5-carboxylate as Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2) inhi

SHP2 is a non-receptor protein tyrosine phosphatase (PTP) encoded by the PTPN11 gene involved in cell death pathway (PD-1/PD-L1) and cell growth and differentiation pathway (MAPK). Moreover, mutations in SHP2 have been implicated in Leopard syndrome (LS),

miRNA biosynthesis inhibitor

The invention provides a compound shown as a formula I, or a conformational isomer thereof, or an optical isomer thereof, or a pharmaceutically acceptable salt thereof. The compound can be tightly combined with related binding proteins in an miRNA biosynthesis process and can effectively inhibit the synthesis of miRNA-21. The prepared active compound provided by the invention can be used as an miRNA-21 inhibitor, and further as a potential drug for treating malignant tumors. The formula I is shown in the description.

Discovery of first-in-class thiazole-based dual FFA1/PPARδ agonists as potential anti-diabetic agents

The free fatty acid receptor 1 (FFA1 or GPR40) and peroxisome proliferator-activated receptor δ (PPARδ) have attracted a lot of attention due to their role in promoting insulin secretion and sensibility, respectively, which are two major features of diabetes. Therefore, the dual FFA1/PPARδ agonists would increase insulin secretion and sensibility by FFA1 and PPARδ activation. In this study, we hybrid FFA1 agonist AM-4668 with PPARδ agonist GW501516, leading to the identification of orally bioavailable dual agonist 32, which revealed high selectivity over other PPARs. Moreover, compound 32 exhibited good pharmacokinetic profiles with high plasma concentration, sustained half-life and low clearance in vivo. During the hypoglycemic test, a dual agonist 32 enhanced the tolerance of ob/ob mice for glucose loading in a dose-dependent manner. Our results suggest that dual FFA1/PPARδ agonist could be a valuable therapy for type 2 diabetes.

Biphenyl heterocyclic derivatives, their preparation and their use as medicaments (by machine translation)

The present invention relates to a novel biphenyl heterocyclic derivative represented by a general formula (I) and a preparation method thereof and use of a pharmaceutical composition containing the derivative for preparation of a drug for treating diabetes. The biphenyl heterocyclic derivative has extremely excellent hypoglycemic activity in vivo, and excellent in vivo safety and low liver toxicity risk of the compound having such a structure are unexpectedly found, and the novel biphenyl heterocyclic derivative may be used for preventing or treating diabetes.

2-substitution-4-methyl-5-(4, 5-thiazoline-2-base)-1, 3-thiazole compound, method for preparing same and evaluation of biological activity

The invention belongs to the field of technologies for chemically synthesizing thiazole derivatives and evaluating the biological activity, and relates to a 2-substitution-4-methyl-5-(4, 5-thiazoline-2-base)-1, 3-thiazole compound shown as a formula I, and further provides a method for preparing 2-substitution-4-methyl-5-(4, 5-thiazoline-2-base)-1, 3-thiazole and evaluation of the biological activity for inhibiting the activity of urease and inhibiting the activity of Escherichia coli, Bacillus subtilis and Staphylococcus aureas. The 2-substitution-4-methyl-5-(4, 5-thiazoline-2-base)-1, 3-thiazole compound, the method and the evaluation have the advantages that the 2-substitution-4-methyl-5-(4, 5-thiazoline-2-base)-1, 3-thiazole compound has certain biological activity, and accordingly the 2-substitution-4-methyl-5-(4, 5-thiazoline-2-base)-1, 3-thiazole compound, the method and the evaluation have excellent application prospects in the industries of medicines, pesticides and the like.

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.

Identification, synthesis and photo-protection evaluation of arylthiazole derivatives as a novel series of sunscreens

A novel series of arylthiazole derivatives have been designed, synthesized and evaluated in preventing keratinocytes cell (HaCaT) from UVB exposure induced cellar damage. The structure-activity relationship (SAR) was discussed. More importantly, compound 5a significantly protected the dorsal skin of BALB/c-nu mice against UVB-induced decrustation in vivo. The in vitro and in vivo data for these arylthiazole derivatives suggest further studies for their potential use as photo-protection agents as well as sunscreen candidates.

COMPOUNDS AND METHODS FOR MODULATING FXR

Compounds of formula. wherein variables are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating dyslipidemia and related diseases.

Substituted 2-[(4-aminomethyl)phenoxy]-2-methylpropionic acid PPARα agonists. 1. Discovery of a novel series of potent HDLc raising agents

The peroxisome proliferator activated receptors PPARα, PPARγ, and PPARδ are ligand-activated transcription factors that play a key role in lipid homeostasis. The fibrates raise circulating levels of high-density lipoprotein cholesterol and lower levels of triglycerides in part through their activity as PPARα agonists; however, the low potency and restricted selectivity of the fibrates may limit their efficacy, and it would be desirable to develop more potent and selective PPARα agonists. Modification of the selective PPARδ agonist 1 (GW501516) so as to incorporate the 2-aryl-2-methylpropionic acid group of the fibrates led to a marked shift in potency and selectivity toward PPARα agonism. Optimization of the series gave 25a, which shows EC50 = 4 nM on PPARα and at least 500-fold selectivity versus PPARγ and PPARγ. Compound 25a (GW590735) has been progressed to clinical trials for the treatment of diseases of lipid imbalance.