Heterocyclic Building Blocks-piperazine

Hattori, Kazuyuki published the artcilePd/C(en)-catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations, Application In Synthesis of 87179-40-6, the publication is Tetrahedron (2000), 56(43), 8433-8441, database is CAplus.

A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodol. were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chem., especially in peptide synthesis.

Tetrahedron 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

Boeckler, Frank published the artcileFAUC 213, a highly selective dopamine D₄ receptor full antagonist, exhibits atypical antipsychotic properties in behavioural and neurochemical models of schizophrenia, SDS of cas: 337972-47-1, the publication is Psychopharmacology (Berlin, Germany) (2004), 175(1), 7-17, database is CAplus and MEDLINE.

2-[4-(4-Chlorophenyl)piperazin-1-ylmethyl]pyrazolo[1,5-a]pyridine (FAUC 213) is a highly selective antagonist at the dopamine D₄ receptor subtype. It was designed as a derivative of two partial antagonists and has been proven to be a complete antagonist in mitogenesis assay. In the present study, FAUC 213 was examined for antipsychotic properties in animal models of behavioral neurobiol. and neurochem. Different concentrations of FAUC 213 were screened for effects on spontaneous, as well as amphetamine-induced, locomotor activity and apomorphine-induced prepulse disruption. The liability of causing extrapyramidal side effects was investigated in models of catalepsy and by high-performance liquid chromatog. (HPLC) detection of dopamine turnover in several brain regions. The application schedule was validated, and the bioavailability of the compound determined, by a HPLC-pharmacokinetic study. A significant effect in both the reduction of amphetamine-induced locomotor hyperactivity and the restoration of apomorphine-disrupted prepulse inhibition was found at 30 mg/kg. This dose proved not to be high enough to induce catalepsy or to increase dopamine turnover in the dorsal striatum, nucleus accumbens and medial prefrontal cortex. The selective D₄ antagonist FAUC 213, therefore, is not believed to mediate the above-mentioned effects via D₂ receptor antagonism, but a partial involvement of 5-HT₂– and α₁-receptors cannot be ruled out at present. We have gathered evidence that FAUC 213 exhibits atypical antipsychotic characteristics.

Psychopharmacology (Berlin, Germany) published new progress about 337972-47-1. 337972-47-1 belongs to piperazines, auxiliary class Inhibitor, name is 2-((4-(4-Chlorophenyl)piperazin-1-yl)methyl)pyrazolo[1,5-a]pyridine, and the molecular formula is C18H19ClN4, SDS of cas: 337972-47-1.

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

Duncton, Matthew A. J. published the artcileParallel synthesis of N-arylpiperazines using polymer-assisted reactions, Synthetic Route of 178928-58-0, the publication is Tetrahedron Letters (2006), 47(15), 2549-2552, database is CAplus.

A series of N-arylpiperazines were prepared in a parallel fashion using palladium-catalyzed cross-coupling, or nucleophilic aromatic displacement chemistries, and polymer-assisted sequestration and purification techniques as key steps.

Tetrahedron Letters 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, Synthetic Route of 178928-58-0.

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

Dyatkin, Alexey B. published the artcileThe solid phase synthesis of complex propargylamines using the combination of Sonogashira and Mannich reactions, Quality Control of 87179-40-6, the publication is Tetrahedron Letters (1998), 39(22), 3647-3650, database is CAplus.

The Sonogashira alkynylation reaction of resin-bound iodobenzoic acids, e.g. 4-IC₆H₄CO₂H, with Me₃SiCCH followed by TBAF desilylation provided polymer-supported aryl acetylenes, e.g. 4-(HCC)C₆H₄CO₂H. Treatment of the latter with aldehydes, e.g. R¹CHO [R¹ = 4-MeC₆H₄, 3-FC₆H₄, 3-(PhO)C₆H₄, 1-naphthyl, 4-PhC₆H₄] and secondary amines, e.g. piperazines I (R² = trans-PhCH:CHCH₂, 2,3-Me₂C₆H₃, 2-FC₆H₄, cyclohexyl, Ph) in dioxane in the presence of CuCl catalyst results in the generation of resin-bound propargylamines . The final products, e.g. II, were cleaved from the resin and obtained in excellent yields and purity. This method provides a straightforward synthesis of diverse libraries of complex propargylamines.

Tetrahedron Letters 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, Quality Control of 87179-40-6.

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

Fujimoto, Teppei published the artcilePhenoFluorMix: Practical Chemoselective Deoxyfluorination of Phenols, Synthetic Route of 67914-60-7, the publication is Organic Letters (2015), 17(3), 544-547, database is CAplus and MEDLINE.

A practical deoxyfluorination with novel deoxyfluorinating reagent PhenoFluorMix, a mixture of N,N’-1,3-bis(2,6-diisopropylphenyl)chloroimidazolium chloride and CsF, is presented. PhenoFluorMix overcomes the challenges associated with hydrolysis of PhenoFluor. PhenoFluorMix does not hydrolyze, is readily available on decagram scale, and is storable in air. In this paper, we demonstrate the practicality of the reagent and exhibit the deoxyfluorination of a variety of phenols and heterocycles.

Organic Letters 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, Synthetic Route of 67914-60-7.

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

Zhang, Jun published the artcileCytotoxicity of 34 FDA approved small-molecule kinase inhibitors in primary rat and human hepatocytes, 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 Toxicology Letters (2018), 138-148, database is CAplus and MEDLINE.

Of the 34 FDA approved oral small-mol. kinase inhibitors (KI), 23 (68%) have warnings for hepatotoxicity in product labeling. To better understand the mechanisms of KI hepatotoxicity and whether such effects can be predicted, the authors examined 34 KIs for cytotoxicity in primary rat and human hepatocytes. The hepatocytes were treated with KIs at ten concentrations normalized to maximal therapeutic blood levels (Cmax). At 5 and 24 h post treatment, lactate dehydrogenase or alanine amtransferase leakage, caspase 3/7 activities and cellular ATP levels were measured. At 1 to 100-fold Cmax, while 5 KIs were neither toxic to human nor rat hepatocytes, 3 KIs showed similar cytotoxicity in both species and 26 KIs showed species-biased cytotoxicity, with 16 KIs being more toxic to human hepatocytes and 10 KIs being more toxic to rat hepatocytes. At concentrations of 1-, 2.5-, 5-, 10-, 100-fold Cmax, the number of cytotoxic KIs in human hepatocytes was 4, 8, 11, 14 and 27, resp., and the corresponding number in rat hepatocytes was 1, 4, 9, 12 and 27, resp. When hepatocyte cytotoxicity at 100-fold Cmax was used to predict KI clin. hepatotoxicity reflected in product labeling, the accuracy was 0.65 with human hepatocytes and 0.59 with rat cells. When the criterion of daily dose ≥100 mg or Cmax ≥1.1 μM was used to predict KI hepatotoxicity, the accuracy was 0.56 or 0.47, resp. These results suggest both indirect and direct drug-induced hepatocyte toxicity may contribute to the mechanisms of KI-induced hepatotoxicity seen clin. and use of primary hepatocytes is a useful in vitro model to help predict such toxicity.

Toxicology Letters 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 C7H5BClNO2, 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

Malinka, Wieslaw published the artcileDerivatives of pyrrolo[3,4-d]pyridazinone, a new class of analgesic agents, Recommanded Product: (E)-1-Cinnamylpiperazine, the publication is European Journal of Medicinal Chemistry (2011), 46(10), 4992-4999, database is CAplus and MEDLINE.

A series of N2-{2-[4-aryl(benzyl)-1-piperazinyl(piperidinyl)]ethyl}pyrrolo[3,4-d]pyridazinones, e.g. I (R = Ph, 2-FC₆H₄, 3-F₃CC₆H₄, 2-Me-5-ClC₆H₄, PhCH₂), and related derivatives, II (R¹ = H, R² = H, MeO; R¹ = CH₂OH, R² = MeO), were synthesized as potential analgesic agents. The structures of the new compounds were elucidated by micro, spectral and X-ray anal. Analgesic activity of the compounds was investigated in the phenylbenzoquinone induced writhing’ and hot plate’ test in mice and at radioligand binding assay. At writhing’ test all compounds, without exception, were more active than acetylsalicylic acid (ASA) with ED₅₀ values ranging from 0.04 to 11 mg/kg (i.p.) (ED₅₀ for ASA – 39.15 mg/kg). Analgesic effect at the hot plate’ test was observed for three compounds I (R = 2-FC₆H₄, 3-F₃CC₆H₄, 2-Me-5-ClC₆H₄) at the dose 3-5 times higher then that of morphine (ED₅₀-3.39 mg/kg). At radioligand binding assay of I (R = 2-FC₆H₄, 3-F₃CC₆H₄, 2-Me-5-ClC₆H₄) only compound I (R = 2-Me-5-ClC₆H₄) exhibited affinity for the μ-opioid receptors similar to that of Tramadol. The acute toxicity of the pyrrolopyridazinones were also studied and non toxic effect was observed at the 2000 mg/kg ( 1420 mg/kg) i.p. dose level for compound II (R¹ = H, R² = H). On the basis of the available pharmacol. data S-A relationship is discussed. The preferred conformational characteristic of the pyrrolopyridazinones was also described.

European Journal of 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 C13H18N2, Recommanded Product: (E)-1-Cinnamylpiperazine.

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

Kamal, Ahmed published the artcileBase-free monosulfonylation of amines using tosyl or mesyl chloride in water, HPLC of Formula: 87179-40-6, the publication is Tetrahedron Letters (2008), 49(2), 348-353, database is CAplus.

A mild and efficient procedure was developed for the monosulfonylation of various amines using mesyl or tosyl chlorides in water at room temperature to afford the corresponding sulfonamides in high yields.

Tetrahedron Letters 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, HPLC of Formula: 87179-40-6.

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

Reddy, B. Rasmitha published the artcileFormulation and evaluation of dasatinib immediate release tablets, Related Products of piperazines, the publication is World Journal of Pharmacy and Pharmaceutical Sciences (2014), 3(3), 1113-1123, database is CAplus.

Dasatinib is a selective Tyrosine Kinase Inhibitor (TKI) used in treatment of chronic myeloid leukemia (CML) and acute myeloid leukemia (AML). Dasatinib have become first line drug in the pharmacotherapy of patients with CML. This is because the drug possesses tolerability and safety advantages over the other Tyrosine Kinase Inhibitors. Tablets of Dasatinib were prepared using different superdisintegrants (Sodium Starch Glycolate, Croscarmellose, and Crospovidone) by wet granulation method. Nine formulations (F1-F9) of immediate release oral tablets were prepared by using different disintegrants to get desired release profile. The drug-excipients interaction was investigated by FTIR. The granules and tablets of Dasatinib evaluated for various pre and post compression parameters like Angle of repose Compressibility index, Hausner’s ratio, Tablet hardness, Friability, Weight variation, Drug content and in vitro dissolution Their results were found satisfactory. DSC studies have shown that drug is stable in the formulation. It is concluded that in vitro dissolution studies show the release is in the following order of superdisintegrants: Croscarmellose > Sodium Starch Glycolate > Crospovidone. Maximum in vitro dissolution was found to be with Formulation F-2 and it clearly shows due to Croscarmellose (7.9%).

World Journal of Pharmacy and Pharmaceutical Sciences 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, 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