Category: piperazines

Ben Salah, Assila Maatar’s team published research in Monatshefte fuer Chemie in 2014 | CAS: 34352-59-5

1-Methylpiperazine dihydrochloride(cas: 34352-59-5) is used in the preparation of 2-(4-Methyl-1-piperazinylmethyl)acrylophenone(MPMAP), 1-methylpiperazine-1,4-diium tetrachloridozincate hemihydrate, 2-(4-Methyl-1-piperazinylmethyl)acrylophenone(MPMAP), an antimicrotubular drug..Category: piperazines

Category: piperazinesOn October 31, 2014 ,《Crystal growth, thermal and magnetic characterizations of a new ferromagnetic Ni(II) dimer》 appeared in Monatshefte fuer Chemie. The author of the article were Ben Salah, Assila Maatar; Walha, Sondra; Yahyaoui, Samia; Abdalrahman, Mahmoud; Turnbull, Mark M.; Mhiri, Tahar; Naili, Houcine. The article conveys some information:

Abstract: Single crystals of 1-methylpiperazine-1,4-diium hexaaquatetrachlorodinickel(II) dichloride, (C5H14N2)[Ni2Cl4(H2O)6]Cl2, were grown by hydrothermal techniques in aqueous solution The compound was characterized by DTA (TG-TDXD), single crystal x-ray diffraction, and variable temperature magnetic susceptibility. The compound crystallizes in the triclinic system (space group P1̅, Z = 2) with the following unit cell dimensions: a 6.611(3), b 8.776(4), c 17.457(8) Å, α 101.34(2), β 96.31(2), and γ 105.38(2)°. The structure was solved using 4,243 independent reflections and refined to R = 0.024. The structure of (C5H14N2)[Ni2Cl4(H2O)6]Cl2 can be described as mixed organic-inorganic layers along the [-101] direction. The Ni dimers show ferromagnetic exchange (J ∼ 15 K), while the interactions between the dimers are antiferromagnetic (J approx. -3 K). The 3-dimensional network is further linked by three types of H bonds (N-H···Cl, OW-H···Cl, and N-H···O), to build cation-anion cohesion. Dehydration of the precursor proceeds through three stages, leading to crystalline intermediary hydrate phases and an anhydrous compound Crystallog. data are given. In the part of experimental materials, we found many familiar compounds, such as 1-Methylpiperazine dihydrochloride(cas: 34352-59-5Category: piperazines)

1-Methylpiperazine dihydrochloride(cas: 34352-59-5) is used in the preparation of 2-(4-Methyl-1-piperazinylmethyl)acrylophenone(MPMAP), 1-methylpiperazine-1,4-diium tetrachloridozincate hemihydrate, 2-(4-Methyl-1-piperazinylmethyl)acrylophenone(MPMAP), an antimicrotubular drug..Category: piperazines

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Jaen-Oltra, Jose’s team published research in Journal of Medicinal Chemistry in 2000 | CAS: 182868-72-0

1-Cyclopropyl-8-ethoxy-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(cas: 182868-72-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Product Details of 182868-72-0

Product Details of 182868-72-0On March 23, 2000, Jaen-Oltra, Jose; Salabert-Salvador, Ma. Teresa; Garcia-March, Francisco J.; Perez-Gimenez, Facundo; Tomas-Vert, Francisco published an article in Journal of Medicinal Chemistry. The article was 《Artificial neural network applied to prediction of fluorquinolone antibacterial activity by topological methods》. The article mentions the following:

A new topol. method that makes it possible to predict the properties of mols. on the basis of their chem. structures is applied in the present study to quinolone antimicrobial agents. This method uses neural networks in which training algorithms are used as well as different concepts and methods of artificial intelligence with a suitable set of topol. descriptors. This makes it possible to determine the minimal inhibitory concentration (MIC) of quinolones. Anal. of the results shows that the exptl. and calculated values are highly similar. It is possible to obtain a QSAR interpretation of the information contained in the network after the training has been carried out.1-Cyclopropyl-8-ethoxy-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(cas: 182868-72-0Product Details of 182868-72-0) was used in this study.

1-Cyclopropyl-8-ethoxy-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(cas: 182868-72-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Product Details of 182868-72-0

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Basu, Debjit’s team published research in Bioorganic & Medicinal Chemistry in 2015 | CAS: 1213269-26-1

4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine(cas: 1213269-26-1) is a member of pyrimidine. Pyrimidine derivatives are an important class of N-heterocycles. They are well-known for their wide spectrum of promising biological activities such as antitumors, bactericidals, and fungicidal.Recommanded Product: 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine

Basu, Debjit; Richters, Andre; Rauh, Daniel published their research in Bioorganic & Medicinal Chemistry on August 1 ,2015. The article was titled 《Structure-based design and synthesis of covalent-reversible inhibitors to overcome drug resistance in EGFR [Erratum to document cited in CA163:000258]》.Recommanded Product: 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine The article contains the following contents:

On page 2768, Figure 1B contained an error in structure CO-1686; the corrected figure is given. After reading the article, we found that the author used 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine(cas: 1213269-26-1Recommanded Product: 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine)

4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine(cas: 1213269-26-1) is a member of pyrimidine. Pyrimidine derivatives are an important class of N-heterocycles. They are well-known for their wide spectrum of promising biological activities such as antitumors, bactericidals, and fungicidal.Recommanded Product: 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Donald, Craig S’s team published research in Tetrahedron Letters in 2014-05-28 | 374930-88-8

Tetrahedron Letters published new progress about Dehalogenation. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application In Synthesis of 374930-88-8.

Donald, Craig S.; Moss, Thomas A.; Noonan, Gary M.; Roberts, Bryan; Durham, Emma C. published the artcile< Deuterodehalogenation, a mild method for synthesising deuterated heterocycles>, Application In Synthesis of 374930-88-8, the main research area is heterocyclic halide ethyldeuterosilane deuteroisopropanol deuterodehalogenation palladium catalyst; deuterated heterocycle preparation.

This article reported a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogs in a deuterodehalogenation reaction using D8-isopropanol or Et3SiD under palladium-catalyzed condition.

Tetrahedron Letters published new progress about Dehalogenation. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application In Synthesis of 374930-88-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Bavetsias, Vassilios’s team published research in Journal of Medicinal Chemistry in 2010-07-22 | 197638-83-8

Journal of Medicinal Chemistry published new progress about Antitumor agents. 197638-83-8 belongs to class piperazines, and the molecular formula is C16H22N2O3, HPLC of Formula: 197638-83-8.

Bavetsias, Vassilios; Large, Jonathan M.; Sun, Chongbo; Bouloc, Nathalie; Kosmopoulou, Magda; Matteucci, Mizio; Wilsher, Nicola E.; Martins, Vanessa; Reynisson, Johannes; Atrash, Butrus; Faisal, Amir; Urban, Frederique; Valenti, Melanie; Brandon, Alexis de Haven; Box, Gary; Raynaud, Florence I.; Workman, Paul; Eccles, Suzanne A.; Bayliss, Richard; Blagg, Julian; Linardopoulos, Spiros; McDonald, Edward published the artcile< Imidazo[4,5-b]pyridine Derivatives As Inhibitors of Aurora Kinases: Lead Optimization Studies toward the Identification of an Orally Bioavailable Preclinical Development Candidate>, HPLC of Formula: 197638-83-8, the main research area is imidazopyridine derivative arsenic inhibitor Aurora kinase orally bioavailable development.

Lead optimization studies using an imidazo[4,5-b]pyridinylpiperazine as the starting point led to a new class of imidazo[4,5-b]pyridine-based inhibitors of Aurora kinases that possessed the 1-benzylpiperazinyl motif at the 7-position, and displayed favorable in vitro properties. Cocrystn. of Aurora-A with a morpholinylmethylphenylimidazopyridinyl chlorobenzyl piperazine (CCT137444) provided a clear understanding into the interactions of this novel class of inhibitors with the Aurora kinases. Subsequent physicochem. property refinement by the incorporation of solubilizing groups led to the identification of 3-((4-(6-bromo-2-(4-(4-methylpiperazin-1-yl)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)methyl)-5-methylisoxazole (CCT137690)(I) which is a potent inhibitor of Aurora kinases (Aurora-A IC50 = 0.015±0.003 μM, Aurora-B IC50 = 0.025 μM, Aurora-C IC50 = 0.019 μM). I is highly orally bioavailable, and in in vivo efficacy studies it inhibited the growth of SW620 colon carcinoma xenografts following oral administration with no observed toxicities as defined by body weight loss.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 197638-83-8 belongs to class piperazines, and the molecular formula is C16H22N2O3, HPLC of Formula: 197638-83-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Ensan, Deeba’s team published research in Journal of Medicinal Chemistry in 2020-05-14 | 229009-40-9

Journal of Medicinal Chemistry published new progress about Activin receptor ACVRLK2 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (inhibitor). 229009-40-9 belongs to class piperazines, and the molecular formula is C11H17BN2O2, Product Details of C11H17BN2O2.

Ensan, Deeba; Smil, David; Zepeda-Velazquez, Carlos A.; Panagopoulos, Dimitrios; Wong, Jong Fu; Williams, Eleanor P.; Adamson, Roslin; Bullock, Alex N.; Kiyota, Taira; Aman, Ahmed; Roberts, Owen G.; Edwards, Aled M.; O’Meara, Jeff A.; Isaac, Methvin B.; Al-Awar, Rima published the artcile< Targeting ALK2: An Open Science Approach to Developing Therapeutics for the Treatment of Diffuse Intrinsic Pontine Glioma>, Product Details of C11H17BN2O2, the main research area is diffuse intrinsic pontine glioma ALK2 inhibitor brain potassium channel.

Diffuse intrinsic pontine glioma is an aggressive pediatric cancer for which no effective chemotherapeutic drugs exist. Anal. of the genomic landscape of this disease has led to the identification of the serine/threonine kinase ALK2 as a potential target for therapeutic intervention. In this work, we adopted an open science approach to develop a series of potent type I inhibitors of ALK2 which are orally bio-available and brain-penetrant. Initial efforts resulted in the discovery of M4K2009 (I), an analog of the previously reported ALK2 inhibitor LDN-214117. Although highly selective for ALK2 over the TGF-βR1 receptor ALK5, M4K2009 is also moderately active against the hERG potassium channel. Varying the substituents of the trimethoxyphenyl moiety gave rise to an equipotent benzamide analog M4K2149 (II) with reduced off-target affinity for the ion channel. Addnl. modifications yielded 2-fluoro-6-methoxybenzamide derivatives (26a(III)-c), which possess high inhibitory activity against ALK2, excellent selectivity, and superior pharmacokinetic profiles.

Journal of Medicinal Chemistry published new progress about Activin receptor ACVRLK2 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (inhibitor). 229009-40-9 belongs to class piperazines, and the molecular formula is C11H17BN2O2, Product Details of C11H17BN2O2.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Wiles,RebeccaJ.’s team published research in Chemical Science in 2018 | 374930-88-8

Chemical Science published new progress about Addition reaction. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Formula: C13H19BrN4O2.

Phelan, James P.; Wiles, Rebecca J.; Lang, Simon B.; Kelly, Christopher B.; Molander, Gary A. published the artcile< Correction: Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies [Erratum to document cited in CA169:178001]>, Formula: C13H19BrN4O2, the main research area is trifluoromethyl alkene preparation erratum; silyl alc trifluoromethyl cross coupling palladium erratum; Peterson elimination erratum; organotrifluoroborate cross coupling palladium erratum.

in the original article the Electronic Supplementary Information footnote included addnl. incorrect CCDC numbers for the crystal data reported; the correction is provided here.

Chemical Science published new progress about Addition reaction. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Formula: C13H19BrN4O2.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Wang, Lun’s team published research in European Journal of Medicinal Chemistry in 2020-08-01 | 197638-83-8

European Journal of Medicinal Chemistry published new progress about Antiparkinsonian agents. 197638-83-8 belongs to class piperazines, and the molecular formula is C16H22N2O3, Formula: C16H22N2O3.

Wang, Lun; Cai, Xiaoying; Shi, Mingsong; Xue, Linlin; Kuang, Shuang; Xu, Ruiling; Qi, Wenyan; Li, Yan; Ma, Xu; Zhang, Ruijia; Hong, Feng; Ye, Haoyu; Chen, Lijuan published the artcile< Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson's disease via the activation of Nrf2/keap1 pathway>, Formula: C16H22N2O3, the main research area is piperine analog preparation neuroprotective Parkinsons disease treatment; MPTP; Nrf2 activation; Parkinson’s disease; Piperine analogues.

Parkinson’s disease (PD) is a slowly progressive and complex neurodegenerative disorder. Up to date, there are no approved drugs that could slow or reverse the neurodegenerative process of PD. Here, we reported the synthesis of series of piperine analogs and the evaluation of their neuroprotective effects against hydrogen peroxide (H2O2) induced damage in the neuron-like PC12 cells. Among these analogs, I exhibited the most potent protection effect and its underlying mechanism was further investigated. Further results indicated that the ROS scavenging and cytoprotection effect of I might be related to the Nrf2 activation and upregulation of related phase II antioxidant enzymes, such as HO-1 and NQO1. In in vivo study, oral administration (100 mg/kg) of I significantly attenuated PD-associated behavioral deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD and protected tyrosine hydroxylase-immunopos. dopaminergic neurons. Our results provided evidence that I might be a promising candidate for Parkinson’s disease treatment.

European Journal of Medicinal Chemistry published new progress about Antiparkinsonian agents. 197638-83-8 belongs to class piperazines, and the molecular formula is C16H22N2O3, Formula: C16H22N2O3.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Aspinall, Samuel R’s team published research in Journal of the American Chemical Society in 1940 | 22476-74-0

Journal of the American Chemical Society published new progress about 22476-74-0. 22476-74-0 belongs to class piperazines, and the molecular formula is C6H12N2O, Safety of 3,3-Dimethylpiperazin-2-one.

Aspinall, Samuel R. published the artcile< Synthesis of monoketopiperazines>, Safety of 3,3-Dimethylpiperazin-2-one, the main research area is .

ClCH2CO2Et (20.4 g.) in 100 cc. absolute EtOH, added slowly at room temperature to 60 g. (CH2NH2)2 in 300 cc. absolute EtOH (3 hrs.) and the mixture allowed to stand an addnl. 2 hrs., after which 11.3 g. EtONa in EtOH is added, the NaCl filtered, the solvent and excess (CH2NH2)2 removed by distillation and the residue heated at 200°/5 mm., give 45% of 2-ketopiperazine (I), b5 165°, m. 136° (m. ps. corrected); benzenesulfonamide, m. 188°. Similar yields were obtained at -15°, 0° and 80°. No I was formed when the reactants were used in the ratio of 1:1; with 1 mole (CH2NH2)2 and 1/8 mole of ClCH2CO2Et the yield is 25%; thus the reaction must be carried out under conditions which favor the formation of a monoalkyl derivative of the (CH2NH2)2. BrCH2CO2Et may be used but the yield is the same and the reaction has the disadvantage that the NaBr is soluble in the reaction mixture; if the EtOH is removed and EtONa in C6H6 is used, the NaBr may be separated, being insoluble in C6H6. Addnl. derivatives of I: picrate, m. 180°; HCl salt, m. 208°; phenylurea, m. 171°; phenylthiourea, m. 199°. Et α-bromobutyrate gives 60% of 3-ethyl-2-ketopiperazine, m. 60°; benzenesulfonamide, m. 148°; Et α-bromoisobutyrate gives 40% of 3,3-dimethyl-2-ketopiperazine, m. 134°; benzenesulfonamide, m. 206°.

Journal of the American Chemical Society published new progress about 22476-74-0. 22476-74-0 belongs to class piperazines, and the molecular formula is C6H12N2O, Safety of 3,3-Dimethylpiperazin-2-one.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Rabal, Obdulia’s team published research in ACS Chemical Neuroscience in 2019-03-20 | 374930-88-8

ACS Chemical Neuroscience published new progress about Alzheimer disease. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Formula: C13H19BrN4O2.

Rabal, Obdulia; Sanchez-Arias, Juan A.; Cuadrado-Tejedor, Mar; de Miguel, Irene; Perez-Gonzalez, Marta; Garcia-Barroso, Carolina; Ugarte, Ana; Estella-Hermoso de Mendoza, Ander; Saez, Elena; Espelosin, Maria; Ursua, Susana; Haizhong, Tan; Wei, Wu; Musheng, Xu; Garcia-Osta, Ana; Oyarzabal, Julen published the artcile< Discovery of in Vivo Chemical Probes for Treating Alzheimer's Disease: Dual Phosphodiesterase 5 (PDE5) and Class I Histone Deacetylase Selective Inhibitors>, Formula: C13H19BrN4O2, the main research area is sildenafil vardenafil orthoaminoanilide synthesis antiAlzheimer SAR PDE5 histone deacetylase; Alzheimer’s disease; PDE5 inhibition; chemical probes; class I HDAC selective inhibition; dual inhibitors; in vivo test.

In order to determine the contributions of histone deacetylase (HDAC) isoforms to the beneficial effects of dual phosphodiesterase 5 (PDE5) and pan-HDAC inhibitors on in vivo models of Alzheimer’s disease (AD), we have designed, synthesized, and tested novel chem. probes with the desired target compound profile of PDE5 and class I HDAC selective inhibitors. Compared to previous hydroxamate-based series, these mols. exhibit longer residence times on HDACs. In this scenario, shorter or longer preincubation times may have a significant impact on the IC50 values of these compounds and therefore on their corresponding selectivity profiles on the different HDAC isoforms. On the other hand, different chem. series have been explored and, as expected, some pairwise comparisons show a clear impact of the scaffold on biol. responses. The lead identification process led to compound I, which shows an adequate ADME-Tox profile and in vivo target engagement (histone acetylation and cAMP/cGMP response element-binding (CREB) phosphorylation) in the central nervous system (CNS), suggesting that this compound represents an optimized chem. probe; thus, I has been assayed in a mouse model of AD (Tg2576).

ACS Chemical Neuroscience published new progress about Alzheimer disease. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Formula: C13H19BrN4O2.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics