Category: piperazines

Malinka, W. published the artcileSynthesis of some N-substituted 3,4-pyrroledicarboximides as potential CNS depressive agents, Related Products of piperazines, the publication is Pharmazie (2000), 55(1), 9-16, database is CAplus and MEDLINE.

Several novel N-substituted 3,4-pyrroledicarboximides were prepared and eleven representatives were examined in a series of in vivo CNS tests. A few of these compounds displayed a similar profile of biol. selectivity to that of 3,4-pyrroledicarboximides described previously; their structure-activity relationships are discussed.

Pharmazie published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C13H18N2, Related Products of piperazines.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Yadav, Mangal S. published the artcileSilicon Industry Waste Polymethylhydrosiloxane-Mediated Benzotriazole Ring Cleavage: A Practical and Green Synthesis of Diverse Benzothiazoles, Application of (E)-1-Cinnamylpiperazine, the publication is ACS Omega (2019), 4(4), 6681-6689, database is CAplus and MEDLINE.

A green modification has been introduced to the synthesis of benzothiazoles by using polymethylhydrosiloxane (PMHS) for successive steps of benzotriazole ring cleavage (BtRC) and cyclization; an approach which was previously developed in our lab by use of n-Bu₃SnH. The use of silicone industry byproduct PMHS makes this protocol cost-effective and non-toxic one and thus may be considered for the industrial importance.

ACS Omega published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C26H41N5O7S, Application of (E)-1-Cinnamylpiperazine.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Chen, Yan published the artcileDiscovery of 5-Aryl-2,4-diaminopyrimidine Compounds as Potent and Selective IRAK4 Inhibitors, Category: piperazines, the publication is ACS Medicinal Chemistry Letters (2022), 13(4), 714-719, database is CAplus and MEDLINE.

IRAK4 kinase plays a key role in TLR/IL-1R signaling pathways that regulate innate immune responses, and if uncontrolled, it is responsible for various inflammatory disorders. By high-throughput screening (HTS) and hit-to-lead optimization, compounds with a 5-aryl-2,4-diaminopyrimidine core structure have been identified as potent IRAK4 inhibitors. A cocrystal structure of IRAK4 protein with an early lead mol. helped with understanding the structure-activity relationship and the design of the new compounds Initial HTS hits from this series of compounds were also found to inhibit TAK1 kinase, which would cause liver toxicity and potentially bone marrow failure. Optimization of this series resulted in improved selectivity over TAK1 kinase. The TAK1 selectivity was found to be closely associated with different sizes and types of substituents at the 5-position of the pyrimidine. The impact of other pyrimidine substituents on the potency and selectivity was also explored. A few representative compounds were evaluated in IL-1β-induced IL-6 inhibition animal model studies and showed modest efficacy.

ACS Medicinal Chemistry Letters published new progress about 55403-35-5. 55403-35-5 belongs to piperazines, auxiliary class Pyridine,Piperazine,Amine, name is 6-(4-Methylpiperazin-1-yl)pyridin-3-amine, and the molecular formula is C10H16N4, Category: piperazines.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Niewiadomy, Andrzej published the artcileSynthesis and biological activity of novel N,n-cyclic-2,4-dihydroxythiobenzamide derivatives, Name: (E)-1-Cinnamylpiperazine, the publication is Acta Poloniae Pharmaceutica (2015), 72(5), 943-950, database is CAplus.

A series of novel N,N-cyclic-2,4-dihydroxythiobenzamide derivatives is described. Test compounds were formed by the reaction of the com. available reagents with sulfinylbis[(2,4- dihydroxyphenyl)methanethione] (STB). The chem. structures were confirmed by IR, 1H NMR, 13CNMR, EI-MS, and elemental anal. For the estimation of potential activity in vitro, the MIC values against strains of Candida were determined Antifungal properties of selected compounds under in vitro conditions against five phytopathogenic fungi were estimated Furthermore, the antiproliferative activity against the HCV29T cancer cell lines has been studied. These compounds exhibited antiproliferative activity in the range of 33.98 n 10.51 μg/mL.

Acta Poloniae Pharmaceutica published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C13H18N2, Name: (E)-1-Cinnamylpiperazine.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Roy, Saikat published the artcileStructural and Physicochemical Aspects of Dasatinib Hydrate and Anhydrate Phases, Safety of N-(2-Chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide hydrate, the publication is Crystal Growth & Design (2012), 12(4), 2122-2126, database is CAplus and MEDLINE.

Crystal structures for the com. monohydrate form and an anhydrate form of dasatinib, an oral anticancer agent, are presented along with characterization by Raman spectroscopy, powder X-ray diffraction, differential scanning calorimetry, and thermogravimetric anal. Solubility measurements conducted in water reveal that the anhydrate has dramatically improved solubility compared to the com. hydrate form. Finally, dasatinib is a rare example of a promiscuous solvate former, and the basis for this behavior can now be understood by examining the poor packing efficiency in the unsolvated form.

Crystal Growth & Design published new progress about 863127-77-9. 863127-77-9 belongs to piperazines, auxiliary class TGF-beta/Smad,Bcr-Abl,Natural product, name is N-(2-Chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide hydrate, and the molecular formula is C22H28ClN7O3S, Safety of N-(2-Chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide hydrate.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Beiginejad, Hadi published the artcileDependence of mechanisms to thermodynamics in the electrochemical study of different electrophiles in the presence of some sulfur nucleophiles, COA of Formula: C12H16N2O2, the publication is Monatshefte fuer Chemie, database is CAplus.

Abstract: Electrochem. study of different electrophiles in the presence of p-toluenesulfinic acid and 2-mercaptobenzothiazole as sulfur nucleophiles was investigated. Mechanistic study of the electrochem. reactions indicates that the electrochem. oxidation of some species in the presence of the sulfur groups has different mechanisms, but some other species in the presence of both sulfur nucleophiles have the same mechanism. To explain the reason for this difference, the computational study was used. Thermodn. investigation shows that when ΔG_tot of the electrochem. oxidation of products are less than that of initial species, the electrochem. produced species can be oxidized during controlled-potential coulometry. The results of this work indicate that the computational study can be used to justify the reaction mechanisms. Cyclic voltammetry, linear sweep voltammetry, and controlled-potential coulometry were used to obtain the exptl. results. Also, by the use of BP86 level of theory and 6-31 + G(d,p) basis set, the theor. data were obtained.

Monatshefte fuer Chemie published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, COA of Formula: C12H16N2O2.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Foley, Timothy L. published the artcile4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a Potent Inhibitor of Bacterial Phosphopantetheinyl Transferase That Attenuates Secondary Metabolism and Thwarts Bacterial Growth, Formula: C11H13N3, the publication is Journal of Medicinal Chemistry (2014), 57(3), 1063-1078, database is CAplus and MEDLINE.

4′-Phosphopantetheinyl transferases (PPTases) catalyze a post-translational modification essential to bacterial cell viability and virulence. We present the discovery and medicinal chem. optimization of 2-pyridinyl-N-(4-aryl)-piperazine-1-carbothioamides, which exhibit submicromolar inhibition of bacterial Sfp-PPTase with no activity toward the human orthologue. Moreover, compounds within this class possess antibacterial activity in the absence of a rapid cytotoxic response in human cells. An advanced analog of this series, ML267 (55), was found to attenuate production of an Sfp-PPTase-dependent metabolite when applied to Bacillus subtilis at sublethal doses. Addnl. testing revealed antibacterial activity against methicillin-resistant Staphylococcus aureus, and chem. genetic studies implicated efflux as a mechanism for resistance in Escherichia coli. Addnl., we highlight the in vitro absorption, distribution, metabolism, and excretion and in vivo pharmacokinetic profiles of compound 55 to further demonstrate the potential utility of this small-mol. inhibitor.

Journal of Medicinal Chemistry published new progress about 178928-58-0. 178928-58-0 belongs to piperazines, auxiliary class Piperazine,Nitrile,Benzene, name is 1-(3-Cyanophenyl)piperazine, and the molecular formula is C11H13N3, Formula: C11H13N3.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Povedano, Juan Manuel published the artcileA Multipronged Approach Establishes Covalent Modification of β-Tubulin as the Mode of Action of Benzamide Anti-cancer Toxins, Application of 1-(3-Cyanophenyl)piperazine, the publication is Journal of Medicinal Chemistry (2020), 63(22), 14054-14066, database is CAplus and MEDLINE.

A phenotypic high-throughput screen identified a benzamide small mol. with activity against small cell lung cancer cells. A “clickable” benzamide probe was designed that irreversibly bound a single 50 kDa cellular protein, identified by mass spectrometry as β-tubulin. Moreover, the anti-cancer potency of a series of benzamide analogs strongly correlated with probe competition, indicating that β-tubulin was the functional target. Addnl. evidence suggested that benzamides covalently modified Cys239 within the colchicine binding site. Consistent with this mechanism, benzamides impaired growth of microtubules formed with β-tubulin harboring Cys239, but not β₃ tubulin encoding Ser239. We therefore designed an aldehyde-containing analog capable of trapping Ser239 in β₃ tubulin, presumably as a hemiacetal. Using a forward genetics strategy, we identified benzamide-resistant cell lines harboring a Thr238Ala mutation in β-tubulin sufficient to induce compound resistance. The disclosed chem. probes are useful to identify other colchicine site binders, a frequent target of structurally diverse small mols.

Journal of Medicinal Chemistry published new progress about 178928-58-0. 178928-58-0 belongs to piperazines, auxiliary class Piperazine,Nitrile,Benzene, name is 1-(3-Cyanophenyl)piperazine, and the molecular formula is C11H13N3, Application of 1-(3-Cyanophenyl)piperazine.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Zhang, Lei published the artcileA multiplexed cell assay in HepG2 cells for the identification of Δ5, Δ6, and Δ9 desaturase and elongase inhibitors, Related Products of piperazines, the publication is Journal of Biomolecular Screening (2010), 15(2), 169-176, database is CAplus and MEDLINE.

A multiplexed cell assay has been optimized to measure the activities of fatty acyl-CoA elongase, Δ5 desaturase (Δ5D), Δ6 desaturase (Δ6D), and Δ9 desaturase (Δ9D) together using ¹⁴C-labeled tracers in HepG2 cells, which express the human stearoyl-CoA desaturase-1 isoform (SCD1) exclusively. The Δ5 and Δ9 desaturase activities are indexed by the efficient conversion of [1-¹⁴C]-eicosatrienoic acid (C20:3, cis-8,11,14) to ¹⁴C-arachidonic acid (C20:4, cis-5,8,11,14) and the conversion of [1-¹⁴C]-stearic acid to ¹⁴C-oleic acid (C18:1, cis-9), resp. CP-74006 potently blocks the Δ5D activity with an IC₅₀ value of 20 nM and simplifies the metabolism of [1-¹⁴C]-α-linolenate (C18:3, cis-9,12,15) by accumulating ¹⁴C-eicosatetraenoic acid (C20:4, cis-8,11,14,17) as the major ¹⁴C-eicosatrienoic acid (C20:3, cis-11,14,17) and ¹⁴C-docosatetraenoic acid (C22:4, cis-10,13,16,19) as the minor metabolites through Δ6 desaturation and elongation. This simplified metabolite spectrum enables the delineation of the Δ6D activity by comparing the combined Δ6D/elongase activity index of the ¹⁴C-(C20:4/C18:3) ratio with the corresponding elongation index of the ¹⁴C-(C20:3/C18:3) ratio following compound treatment. SC-26196 and sterculic acid specifically inhibit the Δ6D and Δ9D activities with an IC₅₀ value of 0.1 μM and 0.9 μM, resp. This medium-throughput cell assay provides an efficient tool in the identification of specific desaturase and elongase inhibitors.

Journal of Biomolecular Screening published new progress about 218136-59-5. 218136-59-5 belongs to piperazines, auxiliary class Metabolic Enzyme,D6D, name is 2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile, and the molecular formula is C8H8O2, Related Products of piperazines.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Szkaradek, Natalia published the artcileSynthesis and preliminary evaluation of pharmacological properties of some piperazine derivatives of xanthone, Category: piperazines, the publication is Bioorganic & Medicinal Chemistry (2013), 21(2), 514-522, database is CAplus and MEDLINE.

A series of 9 piperazine derivatives of xanthone were synthesized and evaluated for cardiovascular activity. The following pharmacol. experiments were conducted: the binding affinity for adrenoceptors, the influence on the normal ECG, the effect on the arterial blood pressure and prophylactic antiarrhythmic activity in adrenaline induced model of arrhythmia (rats, iv). Three compounds revealed nanomolar affinity for α₁-adrenoceptor which was correlated with the strongest cardiovascular (antiarrhythmic and hypotensive) activity in animals’ models. The most promising compound was 4-(3-(4-(2-methoxyphenyl)piperazine-1-yl)propoxy)-9H-xanthen-9-one hydrochloride (12) which revealed antiarrhythmic activity with ED₅₀ value of 0.69 mg/kg in adrenaline induced arrhythmia (rats, iv). Other synthesized xanthone derivatives, i.e., (R,S)-4-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazine-1-yl)propoxy)-9H-xanthen-9-one hydrochloride (10) and (R,S)-4-(2-acetoxy-3-(4-(2-methoxyphenyl)piperazine-1-yl)propoxy)-9H-xanthen-9-one hydrochloride (11) also acted as potential antiarrhythmics in adrenaline induced model of arrhythmia in rats after i.v. injection (ED₅₀ = 0.88 mg/kg and 0.89 mg/kg, resp.). These values were lower than values obtained for reference drugs such as propranolol and urapidil, but not carvedilol. Results were quite promising and suggested that in the group of xanthone derivatives new potential antiarrhythmics and hypotensives might be found.

Bioorganic & Medicinal Chemistry published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C17H16O2, Category: piperazines.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics