Heterocyclic Building Blocks-piperazine

Muraglia, Ester; Kinzel, Olaf; Gardelli, Cristina; Crescenzi, Benedetta; Donghi, Monica; Ferrara, Marco; Nizi, Emanuela; Orvieto, Federica; Pescatore, Giovanna; Laufer, Ralph; Gonzalez-Paz, Odalys; Di Marco, Annalise; Fiore, Fabrizio; Monteagudo, Edith; Fonsi, Massimiliano; Felock, Peter J.; Rowley, Michael; Summa, Vincenzo published an article on February 28 ,2008. The article was titled 《Design and Synthesis of Bicyclic Pyrimidinones as Potent and Orally Bioavailable HIV-1 Integrase Inhibitors》, and you may find the article in Journal of Medicinal Chemistry.SDS of cas: 1688-95-5 The information in the text is summarized as follows:

HIV integrase is one of the three enzymes encoded by HIV genome and is essential for viral replication, but integrase inhibitors as marketed drugs have just very recently started to emerge. In this study, the evolution from the N-methylpyrimidinone structure to bicyclic pyrimidinones, e.g., I and II, is shown. Introduction of a suitably substituted amino moiety modulated the phys.-chem. properties of the mols. and conferred nanomolar activity in the inhibition of spread of HIV-1 infection in cell culture. An extensive SAR study led to sulfamide I, which inhibited the strand transfer with an IC50 of 7 nM and HIV infection in MT4 cells with a CIC95 of 44 nM, and ketoamide II that inhibited strand transfer with an IC50 of 12 nM and the HIV infection in MT4 cells with a CIC95 of 13 nM and exhibited a good pharmacokinetic profile when dosed orally to preclin. species. The experimental process involved the reaction of 4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5SDS of cas: 1688-95-5)

4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5) is a member of sulfamide. Sulfamide was used in the synthesis of: Schiff bases of the type ArCH=NSO2NH2; 1H,3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BTDD); sulfamide analogs of oleoylethanolamide analogs in a study of PPARα activation.SDS of cas: 1688-95-5

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

The author of 《Synthesis of dithioacetylenic piperazine derivatives》 were Mukanova, M. S.; Sycheva, Ye. S.; Seilkhanov, T. M.; Yu, V. K.. And the article was published in Khimicheskii Zhurnal Kazakhstana in 2019. COA of Formula: C5H12N2 The author mentioned the following in the article:

The conditions for the three-component one-pot synthesis of dithioacetylenic piperazine derivatives was developed. As a result prop-2-yn-1-yl-4-methylpiperazine-1-carbodithioate (73.4%) and prop-2-yn-1-yl-4-diphenylmethylpiperazine-1-carbodithioate (93.6%) were synthesized. Structure of dithioacetylenic piperazine derivatives were established based on IR and NMR(1H and 13C) spectroscopic data. In addition to this study using 1-Methylpiperazine, there are many other studies that have used 1-Methylpiperazine(cas: 109-01-3COA of Formula: C5H12N2) was used in this study.

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..COA of Formula: C5H12N2

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

《Effects of selective dopaminergic compounds on a delay-discounting task》 was written by Koffarnus, Mikhail N.; Newman, Amy H.; Grundt, Peter; Rice, Kenner C.; Woods, James H.. Electric Literature of C17H19N5 And the article was included in Behavioural Pharmacology on August 31 ,2011. The article conveys some information:

Impulsivity is widely regarded as a multidimensional trait that encompasses two or more distinct patterns of behavior, and dopaminergic systems are implicated in the expression of impulsive behavior in both humans and animal subjects. Impulsive choice, or the tendency to choose rewards associated with relatively little or no delay, has been extensively studied in humans and animal subjects using delay-discounting tasks. Here, delay-discounting procedures were used to assess the effects of receptor-selective dopaminergic agonists, antagonists, and dopamine transporter ligands on choices of immediate vs. delayed sucrose pellets. The effects of d-amphetamine, GBR 12909, apomorphine, SKF 81297, sumanirole, pramipexole, ABT-724, SCH 23390, L-741,626, PG01037, and L-745,870 were assessed in 24 Sprague-Dawley rats. The only drugs to affect impulsive choice selectively without altering undelayed choice were the D1-like antagonist, SCH 23390 (0.01 mg/kg), and the D4 partial agonist, ABT-724 (3.2 mg/kg), which both increased impulsive choice. The shared effects of these compounds may be explained by their localization within the prefrontal cortex on different groups of neurons. None of the selective agonists and antagonists tested reduced impulsive choice, so further research is needed to determine if direct dopaminergic agonists or antagonists may be therapeutically useful in the treatment of impulse-control disorders. In the experiment, the researchers used many compounds, for example, Abt-724(cas: 70006-24-5Electric Literature of C17H19N5)

Abt-724(cas: 70006-24-5) belongs to piperazines. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines.Electric Literature of C17H19N5

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

COA of Formula: C22H25ClN6O2On October 1, 2020 ,《Design, synthesis and SAR study of 2-aminopyrimidines with diverse Michael addition acceptors for chemically tuning the potency against EGFRL858R/T790M》 was published in Bioorganic & Medicinal Chemistry. The article was written by Shao, Jiaan; Liu, Shuangrong; Liu, Xingyu; Pan, Youlu; Chen, Wenteng. The article contains the following contents:

Design, synthesis and SAR study of 2-aminopyrimidines I [R1 = H, 3-Me, 2-OMe, etc.; R2 = Me, COMe; R3 = CF3, Cl; X = Me, F, Cl, Ph; Y = CH, N; Z = NH, O] and II with diverse Michael addition acceptors for chem. tuning the potency against EGFRL858R/T790M were described. By perturbing the electronic nature of acrylamide moiety, with a chloro-group at the α-position of the Michael addition acceptor was identified. It was found that I [R1 = H; R2 = COMe; R3 = Cl; X = Cl; Y = CH; Z = NH] retained the excellent EGFRL858R/T790M potency (IC50 = 3.9 nM) and exhibited good anti-proliferative activities against the gefitinib-resistant NCI-H1975 cells (IC50 = 0.75μM). Moreover, I [R1 = H; R2 = COMe; R3 = Cl; X = Cl; Y = CH; Z = NH] displayed a significant EGFRWT selectivity and much weaker inhibitory activity against non-EGFR dependent SW620 cell and COS7. Preliminary study showed that I [R1 = H; R2 = COMe; R3 = Cl; X = Cl; Y = CH; Z = NH] could arrest NCI-H1975 cells in G0/G1 phase. This work provided a promising chem. tuned strategy for balancing the mutant-EGFR potency and selectivity as well as ‘off-target’ toxicity. In the experimental materials used by the author, we found 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine(cas: 1213269-26-1COA of Formula: C22H25ClN6O2)

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.COA of Formula: C22H25ClN6O2

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

Zhou, Wenjun; Ercan, Dalia; Chen, Liang; Yun, Cai-Hong; Li, Danan; Capelletti, Marzia; Cortot, Alexis B.; Chirieac, Lucian; Iacob, Roxana E.; Padera, Robert; Engen, John R.; Wong, Kwok-Kin; Eck, Michael J.; Gray, Nathanael S.; Janne, Pasi A. published their research in Nature (London, United Kingdom) on December 31 ,2009. The article was titled 《Novel mutant-selective EGFR kinase inhibitors against EGFR T790M》.HPLC of Formula: 1213269-26-1 The article contains the following contents:

The clin. efficacy of epidermal growth factor receptor (EGFR) kinase inhibitors in EGFR-mutant non-small-cell lung cancer (NSCLC) is limited by the development of drug-resistance mutations, including the gatekeeper T790M mutation. Strategies targeting EGFR T790M with irreversible inhibitors have had limited success and are associated with toxicity due to concurrent inhibition of wild-type EGFR. All current EGFR inhibitors possess a structurally related quinazoline-based core scaffold and were identified as ATP-competitive inhibitors of wild-type EGFR. Here we identify a covalent pyrimidine EGFR inhibitor by screening an irreversible kinase inhibitor library specifically against EGFR T790M. These agents are 30- to 100-fold more potent against EGFR T790M, and up to 100-fold less potent against wild-type EGFR, than quinazoline-based EGFR inhibitors in vitro. They are also effective in murine models of lung cancer driven by EGFR T790M. Co-crystallization studies reveal a structural basis for the increased potency and mutant selectivity of these agents. These mutant-selective irreversible EGFR kinase inhibitors may be clin. more effective and better tolerated than quinazoline-based inhibitors. Our findings demonstrate that functional pharmacol. screens against clin. important mutant kinases represent a powerful strategy to identify new classes of mutant-selective kinase inhibitors. In addition to this study using 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine, there are many other studies that have used 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine(cas: 1213269-26-1HPLC of Formula: 1213269-26-1) was used in this study.

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.HPLC of Formula: 1213269-26-1

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

Bouassiria, M.; Laabaissi, T.; Benhiba, F.; El Faydy, M.; Fakhry, H.; Oudda, H.; Assouag, M.; Touir, R.; Guenbour, A.; Lakhrissi, B.; Warad, I.; Zarrouk, A. published an article in 2021. The article was titled 《Corrosion inhibition effect of 5-(4-methylpiperazine)-methylquinoline-8-ol on carbon steel in molar acid medium》, and you may find the article in Inorganic Chemistry Communications.Application In Synthesis of 1-Methylpiperazine The information in the text is summarized as follows:

The present study provides a new application of the 5-(4-methylpiperazinyl)-methylquinolin-8-ol (MPMQ) as an inhibitor for corrosion of carbon steel (CS) in acidic media (1 M HCl). The inhibition performance of MPMQ was evaluated using various methods including electrochem. impedance spectroscopy (EIS), potentiodynamic polarization (PDP), surface morphol. anal. (SEM), quantum chem. computations (DFT), and Monte Carlo simulations (MC). The obtained results, indicating that the compound as a mixed-type inhibitor significantly reduced the corrosion rate of CS due to the formation of a stable protective film on the metal surface. As confirmed by EIS, SEM and theor. studies, chem. adsorbed MPMQ mol. is a better corrosion inhibitor with higher corrosion performance of about 95% at room temperature Langmuir isotherm model is the most acceptable one to describe the MPMQ mols. adsorption on the CS-surface. Finally, the exptl. data correlated well with the theor. study. In the experiment, the researchers used many compounds, for example, 1-Methylpiperazine(cas: 109-01-3Application In Synthesis of 1-Methylpiperazine)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Application In Synthesis of 1-Methylpiperazine

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

《1-Aryl-3-(4-pyridine-2-ylpiperazin-1-yl)propan-1-one Oximes as Potent Dopamine D4 Receptor Agonists for the Treatment of Erectile Dysfunction》 was written by Kolasa, Teodozyj; Matulenko, Mark A.; Hakeem, Ahmed A.; Patel, Meena V.; Mortell, Kathleen; Bhatia, Pramila; Henry, Rodger; Nakane, Masaki; Hsieh, Gin C.; Terranova, Marc A.; Uchic, Marie E.; Miller, Loan N.; Chang, Renje; Donnelly-Roberts, Diana L.; Namovic, Marian T.; Hollingsworth, Peter R.; Martino, Brenda; El Kouhen, Odile; Marsh, Kennan C.; Wetter, Jill M.; Moreland, Robert B.; Brioni, Jorge D.; Stewart, Andrew O.. Computed Properties of C17H19N5 And the article was included in Journal of Medicinal Chemistry on August 24 ,2006. The article conveys some information:

A new series of dopamine D4 receptor agonists, 1-aryl-3-(4-pyridinepiperazin-1-yl)propanone oximes, was designed through the modification of known dopamine D4 receptor agonist PD 168077. Replacement of the amide group with a methylene-oxime moiety produced compounds with improved stability and efficacy. Structure-activity relationships (SAR) of the aromatic ring linked to the N-4-piperazine ring confirmed the superiority of 2-pyridine as a core for D4 agonist activity. A two-methylene linker between the oxime group and the N-1-piperazine ring displayed the best profile. New dopamine D4 receptor agonists, exemplified by (E)-1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime(I) (59a) and (E)-1-(3-chloro-4-fluorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (II) (64a), exhibited favorable pharmacokinetic profiles and showed oral bioavailability in rat and dog. Subsequent evaluation of 59a in the rat penile erection model revealed in vivo activity, comparable in efficacy to apomorphine. Our results suggest that the oximes provide a novel structural linker for 4-arylpiperazine-based D4 agonists, possessing leadlike quality and with potential to develop a new class of potent and selective dopamine D4 receptor agonists. In the experiment, the researchers used many compounds, for example, Abt-724(cas: 70006-24-5Computed Properties of C17H19N5)

Abt-724(cas: 70006-24-5) belongs to piperazines. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines.Computed Properties of C17H19N5

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

Recommanded Product: 1-(Isopropylsulfonyl)piperazineOn September 28, 2017 ,《Structure-Activity Relationships of Potent, Targeted Covalent Inhibitors That Abolish Both the Transamidation and GTP Binding Activities of Human Tissue Transglutaminase》 was published in Journal of Medicinal Chemistry. The article was written by Akbar, Abdullah; McNeil, Nicole M. R.; Albert, Marie R.; Ta, Viviane; Adhikary, Gautam; Bourgeois, Karine; Eckert, Richard L.; Keillor, Jeffrey W.. The article contains the following contents:

Human tissue transglutaminase (hTG2) is a multifunctional enzyme. It is primarily known for its calcium-dependent transamidation activity that leads to formation of an isopeptide bond between glutamine and lysine residues found on the surface of proteins, but it is also a GTP binding protein. Overexpression and unregulated hTG2 activity have been associated with numerous human diseases, including cancer stem cell survival and metastatic phenotype. Herein, the authors present a series of targeted covalent inhibitors (TCIs) based on the previously reported Cbz-Lys scaffold. From this structure-activity relationship (SAR) study, novel irreversible inhibitors were identified that block the transamidation activity of hTG2 and allosterically abolish its GTP binding ability with a high degree of selectivity and efficiency (kinact/KI > 105 M-1 min-1). One optimized inhibitor (VA4) was also shown to inhibit epidermal cancer stem cell invasion with an EC50 of 3.9 μM, representing a significant improvement over the previously reported “”hit”” NC9. After reading the article, we found that the author used 1-(Isopropylsulfonyl)piperazine(cas: 534615-34-4Recommanded Product: 1-(Isopropylsulfonyl)piperazine)

1-(Isopropylsulfonyl)piperazine(cas: 534615-34-4) is a member of sulfamide. Sulfamide was used in the synthesis of: Schiff bases of the type ArCH=NSO2NH2; 1H,3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BTDD); sulfamide analogs of oleoylethanolamide analogs in a study of PPARα activation.Recommanded Product: 1-(Isopropylsulfonyl)piperazine

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

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

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