Category: piperazines

Schiaffella, Fausto published the artcileNovel ketoconazole analogues based on the replacement of 2,4-dichlorophenyl group with 1,4-benzothiazine moiety: Design, synthesis, and microbiological evaluation, Category: piperazines, the publication is Bioorganic & Medicinal Chemistry (2006), 14(15), 5196-5203, database is CAplus and MEDLINE.

As a part of a program to develop novel antifungal agents, new compounds which incorporate the 1,4-benzothiazine moiety into the structure of ketoconazole (KTZ) were prepared These compounds were computationally investigated to assess whether the 1,4-benzothiazine moiety was a suitable bioisosteric replacement for the 2,4-dichlorophenyl group of KTZ in order to obtain a more potent inhibition of CYP51 enzyme of Candida albicans. Results of preliminary microbiol. studies show that the racemic cis-7 analog has a good in vivo activity, comparable to that of KTZ, but the best activity was observed in the racemic trans-7 analog.

Bioorganic & 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, Category: piperazines.

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

Wang, Chenxuan published the artcileInhibition of Δ-6 desaturase reduces fatty acid re-esterification in 3T3-L1 adipocytes independent of changes in n3-PUFA cellular content, Category: piperazines, the publication is Biochimica et Biophysica Acta, Molecular and Cell Biology of Lipids (2022), 1867(7), 159160, database is CAplus and MEDLINE.

Δ-6 Desaturase (D6D) is a key enzyme in the synthesis of long-chain polyunsaturated fatty acids (LC-PUFA). Evidence suggests that reduced D6D activity not only disrupts LC-PUFA production, but also impacts whole body lipid handling and body weight; however, the mechanisms remain largely unexplored. Therefore, we investigated the effect of D6D inhibition on the regulation of lipid accumulation in 3T3-L1 adipocytes with and without changes in n-3 PUFA content. 3T3-L1 cells were treated with a D6D inhibitor (SC-26196) in the presence or absence of α-linolenic acid (ALA) throughout differentiation. We found that D6D inhibition blocked the conversion of ALA to eicosapentaenoic acid (EPA) and docosapentaenoic acid (DPAn-3) when ALA was supplemented, while no changes in n-3 PUFA content were observed in cells treated with the D6D inhibitor alone. D6D inhibited cells had reduced triacylglycerol (TAG) accumulation despite an EPA/DPA deficiency. In addition, analyses of cellular protein markers, as well as non-esterified fatty acids and glycerol release in medium, suggested an increase in lipolysis and a decrease in fatty acid re-esterification in D6D-inhibited cells, independent of n-3 PUFA changes. To provide further evidence, we treated cells with the D6D inhibitor in the presence or absence of EPA and compared them with ALA-treated cells. Although EPA further reduced TAG content, the reduced markers of fatty acid re-esterification were not affected by ALA or EPA. Collectively, this study provides new insight showing that D6D inhibition reduces TAG accumulation and fatty acid re-esterification in adipocytes independent of changes in n-3 PUFA cellular content.

Biochimica et Biophysica Acta, Molecular and Cell Biology of Lipids 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 C13H16O2, Category: piperazines.

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

Prabhakaran, Jaya published the artcileSynthesis and in vivo evaluation of [¹¹C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors, Name: (E)-1-Cinnamylpiperazine, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(12), 3654-3657, database is CAplus and MEDLINE.

Radiosynthesis and in vivo evaluation of [N-methyl-¹¹C] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c]quinoline, I (R = ¹¹CH₃)(II), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard and corresponding desmethyl precursor I (R = Me, H) were achieved from 2-aminobenzaldehyde in 40% and 65% yields, resp. Methylation using [¹¹C]CH₃I in the presence of aqueous potassium hydroxide in DMSO afforded II in 25% yield (EOS, end of synthesis) with >99% chem. and radiochem. purities with a specific activity range from 3-4 Ci/μmol (n = 6). The total synthesis time was 30 min from EOB (end of bombardment). PET (Positron-emission tomog.) studies in anesthetized baboon show that II penetrates the BBB (blood brain barrier) and accumulates in alpha2A-AR enriched brain areas.

Bioorganic & Medicinal Chemistry 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, Name: (E)-1-Cinnamylpiperazine.

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

Beyzavi, Hudson published the artcile¹⁸F-Deoxyfluorination of Phenols via Ru π-Complexes, COA of Formula: C12H16N2O2, the publication is ACS Central Science (2017), 3(9), 944-948, database is CAplus and MEDLINE.

The deficiency of robust and practical methods for ¹⁸F-radiofluorination is a bottleneck for positron emission tomog. (PET) tracer development. Here, we report the first transition-metal-assisted ¹⁸F-deoxyfluorination of phenols. The transformation benefits from readily available phenols as starting materials, tolerance of moisture and ambient atm., large substrate scope, and translatability to generate doses appropriate for PET imaging.

ACS Central Science 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

Kulkarni, B. published the artcileDesign, synthesis and molecular docking studies of some 1-(5-(2-fluoro-5-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-3-yl)piperazine derivatives as potential anti-inflammatory agents, Category: piperazines, the publication is Molecular Diversity, database is CAplus and MEDLINE.

The facile synthesis of a series of piperazinyl-substituted 1,2,4-oxadiazoles I (R = 4-ClC₆H₄CH₂, PhSO₂, 2-pyrazinylcarbonyl, etc.) in good to excellent yields is reported. The anti-inflammatory potential of the newly synthesized compounds was evaluated by anti-denaturation assay using diclofenac sodium as the reference standard Some of the compounds exhibited profound activity profile when compared to the standard drug. The mol. docking and SAR studies were carried out at the later stage to gain more insights about the promising activity profile of the synthesized mols.

Molecular Diversity 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, Category: piperazines.

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

Sreenivasa, S. published the artcile(E)-tert-Butyl 4-(N’-hydroxycarbamimidoyl)piperazine-1-carboxylate, Name: tert-Butyl 4-cyanopiperazine-1-carboxylate, the publication is Acta Crystallographica, Section E: Structure Reports Online (2012), 68(12), o3347, database is CAplus and MEDLINE.

In the title compound, C₁₀H₂₀N₄O₃, the piperazine ring adopts a chair conformation. The mol. adopts an E conformation across the C=N double bond, with the -OH group and the piperazine ring trans to one another. Further, the H atom of the hydroxy group is directed away from the NH₂ group. An intramol. N-H···O contact occurs involving the NH₂ group and the oxime O atom. In the crystal, mols. are linked via strong N-H···O and O-H···N H bonds with alternating R₂²(6) and C(9) motifs into tetrameric units forming R₄⁴(28) motifs. Crystallog. data and at. coordinates are given.

Acta Crystallographica, Section E: Structure Reports Online 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 C12H14O2, Name: tert-Butyl 4-cyanopiperazine-1-carboxylate.

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

Tang, Yan-feng published the artcileSynthesis of preladenant, COA of Formula: C12H16N2O2, the publication is Jingxi Huagong (2014), 31(10), 1250-1254, database is CAplus.

An intermediate, 1-(4′-methoxyethoxyl phenyl) piperazine (III), was synthesized from 1-(4′-hydroxylphenyl)-piperazinyl ethanone (I) via etherification and hydrolysis. Another intermediate (VII) with a nitrogen condensed ring was prepared from Me furan-2-carboxylate (IV) by acylation, ring-closure and halogenation. Finally, Preladenant was prepared from the two intermediates by condensation reaction. FTIR, ¹HNMR and ESI-MS were employed to characterize these intermediates and the target compound Through common synthetic method, the yields of these 6 steps are 99.0%, 95.4%, 98.0%, 78.9%, 86.9% (calculated by Cl) and 52.5%, resp. To obtain a higher total yield, ultrasonic was used in the last condensation reaction. The results show that the condensation yield reached 85.4% when the reaction conditions were as follows: the ultrasonic power (150 W), the molar ratio of intermediate III to VII (1.2: 1), solvent (DMSO), acid-bonding agent (Na₂CO₃), reaction temperature (90°C) and reaction time (1.5 h). The yield of the condensation is greatly increased by ultrasonic method.

Jingxi Huagong 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 C11H12O4, COA of Formula: C12H16N2O2.

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

Yang, Shyh-Ming published the artcileDiscovery of Orally Bioavailable, Quinoline-Based Aldehyde Dehydrogenase 1A1 (ALDH1A1) Inhibitors with Potent Cellular Activity, COA of Formula: C8H16N2O, the publication is Journal of Medicinal Chemistry (2018), 61(11), 4883-4903, database is CAplus and MEDLINE.

Aldehyde dehydrogenases (ALDHs) are responsible for the metabolism of aldehydes (exogenous and endogenous) and possess vital physiol. and toxicol. functions in areas such as CNS, inflammation, metabolic disorders, and cancers. Overexpression of certain ALDHs (e.g., ALDH1A1) is an important biomarker in cancers and cancer stem cells (CSCs) indicating the potential need for the identification and development of small mol. ALDH inhibitors. Herein, a newly designed series of quinoline-based analogs of ALDH1A1 inhibitors is described. Extensive medicinal chem. optimization and biol. characterization led to the identification of analogs with significantly improved enzymic and cellular ALDH inhibition. Selected analogs, e.g., 86 (NCT-505) and 91 (NCT-506), demonstrated target engagement in a cellular thermal shift assay (CETSA), inhibited the formation of 3D spheroid cultures of OV-90 cancer cells, and potentiated the cytotoxicity of paclitaxel in SKOV-3-TR, a paclitaxel resistant ovarian cancer cell line. Lead compounds also exhibit high specificity over other ALDH isoenzymes and unrelated dehydrogenases. The in vitro ADME profiles and pharmacokinetic evaluation of selected analogs are also highlighted.

Journal of Medicinal Chemistry published new progress about 71260-16-7. 71260-16-7 belongs to piperazines, auxiliary class Piperazine, name is 2-Methyl-1-(piperazin-1-yl)propan-1-one, and the molecular formula is C5H10O2S, COA of Formula: C8H16N2O.

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

Kapanda, Coco N. published the artcileSynthesis and Pharmacological Evaluation of 2,4-Dinitroaryldithiocarbamate Derivatives as Novel Monoacylglycerol Lipase Inhibitors, Application of (E)-1-Cinnamylpiperazine, the publication is Journal of Medicinal Chemistry (2012), 55(12), 5774-5783, database is CAplus and MEDLINE.

Monoacylglycerol lipase (MAGL) is responsible for signal termination of 2-arachidonoylglycerol (2-AG), an endocannabinoid neurotransmitter endowed with several physiol. effects. Previously, we showed that the arylthioamide scaffold represents a privileged template for designing MAGL inhibitors. A series of 37 compounds resulting from pharmacomodulations around the arylthioamide template were synthesized and tested to evaluate their inhibitory potential on MAGL activity as well as their selectivity over fatty acid amide hydrolase (FAAH), another endocannabinoid-hydrolyzing enzyme. We have identified 2,4-dinitroaryldithiocarbamate derivatives as a novel class of MAGL inhibitors. Among the synthesized compounds, we identified [2,4-dinitrophenyl-4-(4-tert-butylbenzyl)piperazine-1-carbodithioate] (CK37, I), as the most potent MAGL inhibitor within this series (IC₅₀ = 154 nM). We have also identified [2,4-dinitrophenyl-4-benzhydrylpiperazine-1-carbodithioate] (CK16 ,II) as a selective MAGL inhibitor. These compounds are irreversible MAGL inhibitors that probably act by interacting with Cys208 or Cys242 and Ser122 residues of the enzyme. Moreover, CK37 is able to raise 2-arachidonoylglycerol (2-AG) levels in intact cells.

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, Application of (E)-1-Cinnamylpiperazine.

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