Stereochemistry of phenylpiracetam and its methyl derivative: improvement of the pharmacological profile

Вейнберг, Г.; Vāvers, Edijs; Орлова, Н. А.; Kuznecovs, Jevgenijs; Домрачева, Илона; Vorona, M.; Zvejniece, Liga; Dambrova, Maija

doi:10.1007/s10593-015-1747-9

Cited by 9 publications

(3 citation statements)

References 16 publications

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“…Methylphenylpiracetam is a complex molecule in terms of its stereochemistry. There are two chiral centers in the molecular structure of methylphenylpiracetam; therefore, it is possible to isolate four individual stereoisomers, which are denoted E1R, T1R, E1S, and T1S (reviewed in Veinberg et al, 2015 ; Figure 3 ).…”

Section: Comparison Of the Effects Of Allosteric Sig1r Modulatorsmentioning

confidence: 99%

Allosteric Modulators of Sigma-1 Receptor: A Review

et al. 2019

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Allosteric modulators of sigma-1 receptor (Sig1R) are described as compounds that can increase the activity of some Sig1R ligands that compete with (+)-pentazocine, one of the classic prototypical ligands that binds to the orthosteric Sig1R binding site. Sig1R is an endoplasmic reticulum membrane protein that, in addition to its promiscuous high-affinity ligand binding, has been shown to have chaperone activity. Different experimental approaches have been used to describe and validate the activity of allosteric modulators of Sig1R. Sig1R-modulatory activity was first found for phenytoin, an anticonvulsant drug that primarily acts by blocking the voltage-gated sodium channels. Accumulating evidence suggests that allosteric Sig1R modulators affect processes involved in the pathophysiology of depression, memory and cognition disorders as well as convulsions. This review will focus on the description of selective and non-selective allosteric modulators of Sig1R, including molecular structure properties and pharmacological activity both in vitro and in vivo, with the aim of providing the latest overview from compound discovery approaches to eventual clinical applications. In this review, the possible mechanisms of action will be discussed, and future challenges in the development of novel compounds will be addressed.

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Section: Comparison Of the Effects Of Allosteric Sig1r Modulatorsmentioning

confidence: 99%

Allosteric Modulators of Sigma-1 Receptor: A Review

et al. 2019

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“…Carboxamides are a desirable functional group among all, thanks to having both carbonyl and amino functional groups beside each other, which leads to unique features . Based on biomedical studies, carboxamides are so promising because they can connect to overexpressed on-the-cell receptors and disrupt their uncontrolled functionality and also have DNA intercalation ability, which is a trigger of apoptosis. , Cancer treatments have shifted from one drug for all types (for instance, DOX has been widely used for the treatment of breast, stomach, lung, testicle, and ovary cancers) to a more specific treatment for each patient in the past few years. Biochemical and biomedical scientists’ findings give physicians more options to remedy each type of cancer by taking a more relatable and effective drug .…”

Section: Introductionmentioning

confidence: 99%

Bioengineered Smart Nanocarriers for Breast Cancer Treatment: Adorned Carbon-Based Nanocomposites with Silver and Palladium Complexes for Efficient Drug Delivery

Safarkhani,

Moghaddam,

Taghavimandi

et al. 2023

ACS Omega

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Biocompatible and bioactive carbon-based nanocomposites are ingeniously designed and fabricated with the aim of enhancing drug delivery applicability in breast cancer treatment. Reduced graphene oxide (rGO) and multiwalled carbon nanotubes (MWCNTs) are utilized as nanocarriers for increasing penetrability into cells and the loading capacity. What sets our study apart is the strategic incorporation of the two different complexes of silver (AgL2) and palladium (PdL2) with the carboxamide-based ligand C9H7N3OS (L), which have been synthesized and decorated on nanocarriers alongside doxorubicin (DOX) for stabilizing DOX by π–π interactions and hydrogen bonding. Although DOX is a well-known cancer therapy agent, the efficacy of DOX is hindered owing to drug resistance, poor internalization, and limited site specificity. Aside from stabilizing DOX on nanocarriers, our carbon-based nanocarriers are tailored to act as a precision-guided missile, strategically by adorning with target-sensitive complexes. Based on the literature, carboxamide ligands can connect to overexpressed receptors on cancerous cells and inhibit them from proliferation signaling. Also, the complexes have an antibacterial activity that can control the infection caused by decreasing white blood cells and necrosis of cancerous cells. A high-concentration cytotoxicity assay revealed that decorating PdL2 on a DOX-containing nanocarrier not only increased cytotoxicity to breast cancerous cell lines (MDA-MB-231 and MCF-7) but also revealed higher cell viability on a normal cell line (MCF-10A). The drug release screening results showed that the presence of PdL2 led to 72 h correlate release behavior in acidic and physiological pH profiles, while the AgL2‑containing nanocomposite showed an analogue behavior for just 6 h and the release of DOX continued and after about 100 h hit the top.

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“…Five-membered N -containing heterocycles are important chemical frameworks that represent the core structures of many natural products, pharmaceutically active compounds, or agrochemicals. − Some examples of biologically active compounds that contain differently substituted N -heterocycles with different degrees of unsaturation and levels of oxidation are shown in Figure . The fully saturated pyrrolidine, for instance, is the common structure of a number of hNK1 antagonists represented with structure 1 , and the aromatic pyrrole is contained in the naturally occurring pyrrolnitrin ( 2 ), which shows antimycobacterial and antifungal activities. − Pyrrolidin-2-ones and pyrrolin-2-ones are found in compounds such as (−)-Clausenamide ( 3 ), isolated from Clausena lansium , , and related derivatives, , which are multitarget nootropics, or in structures of type 4 , acting as mineralocorticoid receptor antagonists, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted α-Amino Acids

Barceló

Bienz

2018

J. Org. Chem.

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Highly functionalized 5-membered N-heterocyclic compounds, 4-aryl-3-chloro-5-methoxy-1-methyl-3-pyrrolin-2-ones, have been synthesized in moderate to high yields by the reaction of N,N-dimethylated aromatic α-amino acids with oxalyl chloride, followed by solvolysis with MeOH. The products possess a number of functional groups such as an amide, a mixed amido/alkoxy acetal, a vinyl halide, and an alkene and thus are promising candidates to be used as starting materials for the synthesis of diverse five-membered N-heterocyclic compounds.

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Stereochemistry of phenylpiracetam and its methyl derivative: improvement of the pharmacological profile

Cited by 9 publications

References 16 publications

Allosteric Modulators of Sigma-1 Receptor: A Review

Allosteric Modulators of Sigma-1 Receptor: A Review

Bioengineered Smart Nanocarriers for Breast Cancer Treatment: Adorned Carbon-Based Nanocomposites with Silver and Palladium Complexes for Efficient Drug Delivery

Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted α-Amino Acids

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