Category: piperazines

Sweeney, Joseph B. published the artcileA Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols, SDS of cas: 87179-40-6, the publication is Angewandte Chemie, International Edition (2018), 57(32), 10202-10206, database is CAplus and MEDLINE.

The first broad-scope nickel-catalyzed direct amination of allyl alcs., using an inexpensive Ni^II/Zn couple enabling the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques, was reported. Under mild conditions, primary and secondary aliphatic amines reacted smoothly with a range of allyl alcs., giving secondary and tertiary amines efficiently. This “totally catalytic” method was also applied to electron-deficient nitrogen nucleophiles and the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).

Angewandte Chemie, International Edition 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 C6H13BO3, SDS of cas: 87179-40-6.

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

Spencer, John published the artcileMicrowave-mediated synthesis of an arylboronate library, Product Details of C22H35BN2O4, the publication is ACS Combinatorial Science (2011), 13(1), 24-31, database is CAplus and MEDLINE.

A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane resp. with a range of N-, S-, and O-nucleophiles, using microwave-mediated chem. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The x-ray structures of five boronates were determined

ACS Combinatorial Science published new progress about 1012785-48-6. 1012785-48-6 belongs to piperazines, auxiliary class Boronic acid and ester, name is tert-Butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine-1-carboxylate, and the molecular formula is C3H5F3O, Product Details of C22H35BN2O4.

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

Liang, Honggang published the artcileSynthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines, Formula: C10H17N3O2, the publication is Synlett (2017), 28(19), 2675-2679, database is CAplus.

Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the com. availability of the starting materials, this new method represented a valuable tool for the synthesis of cyanamides through an N-deallylation reaction and an N-cyanation reaction in one pot.

Synlett published new progress about 113534-02-4. 113534-02-4 belongs to piperazines, auxiliary class Piperazine,Nitrile,Amide, name is tert-Butyl 4-cyanopiperazine-1-carboxylate, and the molecular formula is C10H17N3O2, Formula: C10H17N3O2.

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

Chapman, David R. published the artcileSynthesis of diastereomeric ketoconazole analogs, SDS of cas: 67914-60-7, the publication is Journal of Heterocyclic Chemistry (1990), 27(7), 2063-8, database is CAplus.

Syntheses of trans-isomers of ketoconazole (I) and the corresponding des-acetyl, 1-Me, 1-formyl and 1-methanesulfonyl analogs were investigated. These isomers, along with the corresponding cis-diastereomers were characterized by their carbon-13 NMR spectra.

Journal of Heterocyclic Chemistry 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, SDS of cas: 67914-60-7.

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

Spadoni, Gilberto published the artcileTowards the development of 5-HT₇ ligands combining serotonin-like and arylpiperazine moieties, Safety of 1-Biphenyl-4-yl-piperazine, the publication is European Journal of Medicinal Chemistry (2014), 8-35, database is CAplus and MEDLINE.

Many known 5-HT₇ ligands contain either a serotonin-like or an arylpiperazine structure that, in published SAR studies, are generally supposed to bind the same receptor pocket. Conversely, the authors explored the hypothesis that two such moieties can coexist in the same ligand, binding to different pockets. The authors thus designed and synthesized a set of compounds including both a 5-hydroxyindol-3-ylethyl and a 1-arylpiperazine moieties connected by a short linker, e.g. I [R¹ = HO, NH₂, Cl, etc.; R² = Ph, α-naphthyl, β-naphthyl, etc.; X = CH₂, O, NH, etc.; Y = (CH₂)_n; n = 2, 3, 4, 5, 6]. The compounds were tested for their affinity for human 5-HT₇ serotonin receptor. The authors further prepared a novel series of 5-HT₇ ligands, where the 5-hydroxyindol-3-ylethyl moiety was bioisosterically replaced by a 3-hydroxyanilinoalkyl one. Among the newly synthesized compounds, potent ligands at the 5-HT₇ receptor, behaving as antagonists in functional tests, were identified, even if they showed limited subtype selectivity. Docking studies within a model of the 5-HT₇ receptor showed that the binding site can actually accommodate both moieties, with the serotonin-like one in the putative orthosteric site and the arylpiperazine one occupying an accessory pocket. The present results demonstrate that it is possible to devise and develop new 5-HT₇ ligands merging two privileged structures in the same mol.

European Journal of Medicinal Chemistry published new progress about 180698-19-5. 180698-19-5 belongs to piperazines, auxiliary class Piperazine,Benzene, name is 1-Biphenyl-4-yl-piperazine, and the molecular formula is C6H12N2O, Safety of 1-Biphenyl-4-yl-piperazine.

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

Kaoukabi, Asma published the artcileEfficient Synthesis of New 2H-Chromene Retinoid Hybrid Derivatives by Suzuki Cross-Coupling Reactions, Recommanded Product: 1-Methyl-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfonyl)piperazine, the publication is Journal of Heterocyclic Chemistry (2019), 56(4), 1260-1274, database is CAplus.

In an attempt to improve anticancer activity, a series of retinoid-chromene hybrids were prepared The novel heterocyclic chromene-retinoid hybrids that include oxygen as a heteroatom in a six-membered cyclic ring (2H-chromene or 2H-1-benzopyran) were designed and synthesized by introducing different groups such as an aromatic or styrylphenyl group in the 6-position of 2H-chromene. These novel compounds were synthesized by using the efficient cascade one-pot process involving Wittig-Horner-Emmons reaction and Suzuki-Miyaura cross-coupling palladium-catalyzed reactions with 60% to 90% overall yields. These new compounds were tested against glioblastoma multiforme brain cancer, medulloblastoma, neuroblastoma cell lines and breast cancer MCF-7 cell lines. Two of them exhibited an appreciable antitumor activity in the low micromolar range, which opens new perspectives for therapeutic application on humans.

Journal of Heterocyclic Chemistry published new progress about 914610-39-2. 914610-39-2 belongs to piperazines, auxiliary class Piperazine,Boronic acid and ester,Sulfamide,Benzene,Piperazine,Boronate Esters,Boronic acid and ester,, name is 1-Methyl-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfonyl)piperazine, and the molecular formula is C17H27BN2O4S, Recommanded Product: 1-Methyl-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfonyl)piperazine.

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

Leopoldo, Marcello published the artcileStructure-Affinity Relationship Study on N-(1,2,3,4-Tetrahydronaphthalen-1-yl)-4-Aryl-1-Piperazinealkylamides, a New Class of 5-Hydroxytryptamine₇ Receptor Agents, Application of 1-(3-Cyanophenyl)piperazine, the publication is Journal of Medicinal Chemistry (2004), 47(26), 6616-6624, database is CAplus and MEDLINE.

A series of N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4-aryl-1-piperazinealkylamides I (n = 3-5, R¹ = OMe, H, R² = OMe, CN, Ac, SMe, OH, etc.) was prepared and their affinity for serotonin (5-hydroxytryptamine, 5-HT) 5-HT₇, 5-HT_1A, and 5-HT_2A receptors was measured by in vitro binding assays. In relation to 5-HT₇ receptor affinity, receptor binding studies indicated that (i) the optimal alkyl chain length was five methylenes, (ii) an unsubstituted 1,2,3,4-tetrahydronaphthalenyl nucleus was preferred, and (iii) the substitution pattern of the aryl ring linked to the piperazine ring played a crucial role. Several compound with high affinity for 5-HT₇ receptors were identified. Among them, piperazinehexanamides I [n = 5, R¹ = H, R² = 2-OMe (II), 2-Ac (III), 2-SMe (IV), 2-OH (V), and 2-Me (VI)] were assayed for the 5-HT₇ receptor-mediated relaxation of substance P-induced guinea pig ileum contraction. Compounds II, IV, and VI behaved as full agonists and compound III as a partial agonist, whereas derivative V acted as an antagonist. Among the compounds presented here, it emerged that IV was identified as a potent 5-HT₇ receptor agonist (K_i = 0.22 nM, EC₅₀ = 2.56 μM), endowed with selectivity over 5-HT_1A and 5-HT_2A receptors (200-fold and >1000-fold, resp.).

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

Sardana, Malvika published the artcileVisible-Light-Enabled Aminocarbonylation of Unactivated Alkyl Iodides with Stoichiometric Carbon Monoxide for Application on Late-Stage Carbon Isotope Labeling, Application In Synthesis of 87179-40-6, the publication is Journal of Organic Chemistry (2019), 84(24), 16076-16085, database is CAplus and MEDLINE.

A visible-light-mediated late-stage aminocarbonylation of unactivated alkyl iodides with stoichiometric amounts of carbon monoxide is presented. The method provides a mild, one-step route to [carbonyl-^13/14C] alkyl amides, thereby reducing radioactive waste, and handling of radioactive materials. Easily accessible and low-cost equipment and a palladium catalyst were successfully used for the synthesis of a wide range of alkyl amides.

Journal of Organic 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 C13H18N2, Application In Synthesis of 87179-40-6.

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

Couchman, L. published the artcileAn automated method for the measurement of a range of tyrosine kinase inhibitors in human plasma or serum using turbulent flow liquid chromatography-tandem mass spectrometry, Synthetic Route of 863127-77-9, the publication is Analytical and Bioanalytical Chemistry (2012), 403(6), 1685-1695, database is CAplus and MEDLINE.

Tyrosine kinase inhibitors (TKIs) are used to treat a number of cancers, including chronic myeloid leukemia and hepatocellular carcinoma. Therapeutic drug monitoring (TDM) may be indicated to (1) monitor adherence, (2) guide dosage, and (3) minimise the risk of drug-drug interactions and dose-related toxicity. Online, automated sample preparation provided by TurboFlow technol. (ThermoFisher Scientific) in conjunction with the sensitivity and selectivity of tandem mass spectrometry (MS/MS) detection may be applied to the anal. of single drugs and metabolites. We report the use of TurboFlow LC-MS/MS for the anal. of nine TKIs and metabolites (imatinib, N-desmethylimatinib, dasatinib, nilotinib, erlotinib, gefitinib, lapatinib, sorafenib, sunitinib) in human plasma or serum for TDM purposes. An Aria Transcend TLX-II system coupled with a TSQ Vantage was used. Samples (50 μL) were vortex mixed with internal standard solution (150 μL imatinib-D₈, gefitinib-D₈, sunitinib-D₁₀, and nilotinib-¹³C₂¹⁵N₂ in acetonitrile) and, after centrifugation 100 μL supernatant were injected directly onto a 50 × 0.5-mm Cyclone TurboFlow column. Analytes were focussed onto a 50 × 2.1-mm (3 μm) Hypersil GOLD anal. column and eluted with an acetonitrile/water gradient. Analytes were monitored in selected reaction monitoring mode (pos. APCI). Total anal. time was 7 min without multiplexing. Calibration was linear (R² > 0.99) for all analytes. Inter- and intra-assay precision (in percent relative standard deviation, RSD) was <11 % and accuracy 89-117 % for all analytes. No matrix effects were observed This method is suitable for high-throughput TDM in patients undergoing chronic therapy with TKIs and has been utilized in the anal. of clin. samples.

Analytical and Bioanalytical Chemistry 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, Synthetic Route of 863127-77-9.

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

Faudone, Giuseppe published the artcilePropranolol Activates the Orphan Nuclear Receptor TLX to Counteract Proliferation and Migration of Glioblastoma Cells, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, the publication is Journal of Medicinal Chemistry (2021), 64(12), 8727-8738, database is CAplus and MEDLINE.

The ligand-sensing transcription factor tailless homolog (TLX, NR2E1) is an essential regulator of neuronal stem cell homeostasis with appealing therapeutic potential in neurodegenerative diseases and central nervous system tumors. However, knowledge on TLX ligands is scarce, providing an obstacle to target validation and medicinal chem. To discover TLX ligands, we have profiled a drug fragment collection for TLX modulation and identified several structurally diverse agonists and inverse agonists of the nuclear receptor. Propranolol evolved as the strongest TLX agonist and promoted TLX-regulated gene expression in human glioblastoma cells. Structure-activity relationship elucidation of propranolol as a TLX ligand yielded a structurally related neg. control compound In functional cellular experiments, we observed an ability of propranolol to counteract glioblastoma cell proliferation and migration, while the neg. control had no effect. Our results provide a collection of TLX modulators as initial chem. tools and set of lead compounds and support therapeutic potential of TLX modulation in glioblastoma.

Journal of Medicinal Chemistry 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, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone.

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