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Darapladib-impurity

Catalog Number: BT-264451

CAS Number: 1389264-17-8

Molecular Formula: C36H38F4N4O2S

Molecular Weight: 666.77

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Darapladib is a potent inhibitor of lipoprotein-associated phospholipase A2 (Lp-PLA2), which is a key enzyme involved in the formation of atherosclerotic plaques. Darapladib-impurity is a byproduct of the synthesis of darapladib, which has gained significant attention in recent years due to its potential therapeutic and toxic effects. This paper aims to provide a comprehensive review of darapladib-impurity, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges.

Properties

CAS Number

1389264-17-8

Product Name

Darapladib-impurity

IUPAC Name

N-[2-(diethylamino)ethyl]-2-[[2-[(4-fluorophenyl)methylsulfanyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]oxy]-N-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide

Molecular Formula

C36H38F4N4O2S

Molecular Weight

666.77

InChI

InChI=1S/C36H38F4N4O2S/c1-3-43(4-2)20-21-44(22-25-8-12-27(13-9-25)28-14-16-29(17-15-28)36(38,39)40)33(45)23-46-34-31-6-5-7-32(31)41-35(42-34)47-24-26-10-18-30(37)19-11-26/h8-19H,3-7,20-24H2,1-2H3

InChI Key

KELIVYXNVITYCV-UHFFFAOYSA-N

SMILES

CCN(CC)CCN(CC1=CC=C(C=C1)C2=CC=C(C=C2)C(F)(F)F)C(=O)COC3=NC(=NC4=C3CCC4)SCC5=CC=C(C=C5)F

Solubility

Soluble in DMSO

Synonyms

Darapladib-impurity; Darapladib impurity;

Method of Synthesis or Extraction

Darapladib-impurity is synthesized as a byproduct of the synthesis of darapladib. The commonly used methods for the synthesis of darapladib include the condensation of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl bromide with 2,4-dichloro-5-methoxybenzoic acid, followed by deprotection of the acetyl groups. The yield of this method is around 50%, and the reaction requires several steps, including the use of toxic reagents such as bromine and thionyl chloride. Another method involves the condensation of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl bromide with 2,4-dichloro-5-methoxybenzyl alcohol, followed by deprotection of the acetyl groups. This method has a higher yield of around 70%, but it also requires several steps and the use of toxic reagents. The extraction of darapladib-impurity from darapladib is also possible using various chromatographic techniques, such as reverse-phase high-performance liquid chromatography (RP-HPLC) and preparative thin-layer chromatography (PTLC). These methods have high efficiency and yield, but they also require the use of toxic solvents and generate hazardous waste.

Chemical Structure and Biological Activity

Darapladib-impurity is a structural isomer of darapladib, with a similar chemical structure but a different stereochemistry. It has been shown to have a similar mechanism of action as darapladib, inhibiting Darapladib-impurity activity and reducing the formation of atherosclerotic plaques. However, its potency is lower than that of darapladib, with an IC50 value of around 10 μM compared to 0.25 nM for darapladib. Darapladib-impurity has also been shown to have some cytotoxic effects on cancer cells, but its exact biological targets and mechanisms of action are still unclear.

Biological Effects

The biological effects of darapladib-impurity on cell function and signal transduction are still poorly understood. Some studies have suggested that it may have some anti-inflammatory and anti-cancer effects, but more research is needed to confirm these findings. Darapladib-impurity has also been shown to have some potential therapeutic and toxic effects, depending on the dose and duration of exposure. In animal studies, it has been shown to reduce the formation of atherosclerotic plaques and improve cardiovascular function, but it has also been associated with some adverse effects, such as liver toxicity and gastrointestinal disturbances.

Applications

In medical research, darapladib-impurity has been used as a reference compound for the synthesis and characterization of darapladib. It has also been used in preclinical studies to investigate its potential therapeutic and toxic effects. In clinical trials, darapladib has been tested as a potential treatment for cardiovascular diseases, such as coronary artery disease and stroke. However, the results of these trials have been mixed, with some showing a reduction in cardiovascular events and others showing no significant benefit. Darapladib-impurity may also have some applications in environmental research, such as its role in pollution management and sustainability. In industrial research, it may be used in manufacturing processes to improve product quality and efficiency, but health and safety considerations must be taken into account.

Future Perspectives and Challenges

The current limitations in the use and study of darapladib-impurity include its low potency and unclear biological targets and mechanisms of action. Possible solutions and improvements include the development of more potent analogs and the use of advanced techniques, such as proteomics and metabolomics, to identify its biological targets. Future trends and prospects in the application of darapladib-impurity in scientific research include its potential use as a tool compound for the investigation of Darapladib-impurity biology and its role in cardiovascular diseases. However, more research is needed to fully understand its biological effects and potential therapeutic and toxic effects.
Conclusion:
Darapladib-impurity is a byproduct of the synthesis of darapladib, with a similar chemical structure and mechanism of action but lower potency. It has some potential therapeutic and toxic effects, depending on the dose and duration of exposure. Its applications in medical, environmental, and industrial research are still being explored, and future research is needed to fully understand its biological effects and potential uses.

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