Category: piperazines

Computed Properties of C5H12N2In 2020 ,《Design, synthesis, antimicrobial activity and molecular docking studies of some novel di-substituted sulfonylquinoxaline derivatives》 was published in Bioorganic Chemistry. The article was written by Ammar, Yousry A.; Farag, Awatef A.; Ali, Abeer M.; Ragab, Ahmed; Askar, Ahmed A.; Elsisi, Doaa M.; Belal, Amany. The article contains the following contents:

Compound I [R = Cl] was prepared via reaction of o-phenylene diamine with oxalic acid followed by chlorosulfonation with excess chlorosulfonic acid. A series of new sulfonylquinoxaline derivatives I [R = 3-MeOC6H4, 1-piperidyl, 2-(cyanomethyl)benzimidazol-1-yl, etc.] were obtained upon reacting compound I [R = Cl] with different types of amines. Compound II [R1 = R2 = Cl] was reacted with different secondary amines yielded mono and di secondary aminoquinoxaline derivatives II [R1 = 1-piperidyl, 4-methylpiperazin-1-yl, morpholino; R2 = Cl, morpholino, NHNH2, etc.] depending on the reactivity difference of the two chlorine atoms. Hydrazinolysis of compound II [R1 = 1-piperidyl, 4-methylpiperazin-1-yl, morpholino; R2 = Cl] furnished hydrazino quinoxaline derivatives II [R1 = 1-piperidyl, 4-methylpiperazin-1-yl, morpholino; R2 = NHNH2]. Addnl. triazolo and pyrazolyl quinoxaline derivatives III and IV [R3 = 5-OH-3-Me-pyrazol-1-yl, 2-[(2,5-diphenylpyrazol-3-yl)methylene]hydrazino] were obtained through the reaction of compound II [R1 = 1-piperidyl; R2 = NHNH2] with Ph isothiocyanate, formylpyrazole and Et acetoacetate. All the synthesized compounds were screened for their antibacterial and antifungal activities. Compounds II [R1 = 1-piperidyl, R2 = Cl; R1 = R2 = 4-methylpiperazin-1-yl; R1 = 1-piperidyl, R2 = 4-methylpiperazin-1-yl; R1 = 4-methylpiperazin-1-yl, R2 = 1-piperidyl; R1 = morpholino, R2 = 4-methylpiperazin-1-yl; R1 = morpholino, R2 = NHNH2] showed good to moderate antimicrobial activity against the tested Gram-pos., Gram-neg. bacteria and fungi with MIC values ranging from 2.44 to 180.14μM. Their MBC values were also evaluated using the same tested microorganisms. Moreover, screening against multi-drug resistant strains revealed the promiscuity of these new derivatives, especially compound II [R1 = 1-piperidyl, R2 = Cl] that showed comparable antibacterial activity (MIC 4.91-9.82μM) with Norfloxacin (MIC 2.44-9.80μM). Furthermore, these compounds were evaluated as DNA Gyrase inhibitors and the obtained results were in the range of 15.69-23.72μM. Mol. docking studies of the promising derivatives into DNA Gyrase binding site proved the usefulness of hybridizing quinoxaline scaffold with SO2 and morpholine moieties as a hopeful strategy in designing new DNA Gyrase binding mols. In the experiment, the researchers used many compounds, for example, 1-Methylpiperazine(cas: 109-01-3Computed Properties of C5H12N2)

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..Computed Properties of C5H12N2

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

《Multi-cationic aminopyrene-based labeling tags for oligosaccharide analysis by capillary electrophoresis-mass spectrometry》 was published in Analytica Chimica Acta in 2020. These research results belong to Krenkova, Jana; Liskova, Marcela; Cmelik, Richard; Vigh, Gyula; Foret, Frantisek. Name: 1-Methylpiperazine The article mentions the following:

In this work, new multicationic aminopyrene-based labeling tags were designed and synthesized for oligosaccharide anal. by capillary electrophoresis-mass spectrometry (CE-MS). The starting compound, 8-aminopyrene-1,3,6-trisulfonic acid trisodium salt, was modified in order to form a sulfonamide derivative having three tertiary amines in the label structure. The sulfonamide derivative was further methylated to generate three permanently charged quaternary ammonium moieties on the label. The synthesized labels were characterized by NMR, IR, UV/Vis, fluorescence spectroscopy and mass spectrometry. Furthermore, the labels were applied for maltooligosaccharide standards as well as N-linked glycans labeling via reductive amination and followed by CE-MS anal. The CE-MS anal. of maltooligosaccharides labeled by these newly synthesized labels provided the sub-micromolar limit of detection based on the extracted ion electropherogram signals. After reading the article, we found that the author used 1-Methylpiperazine(cas: 109-01-3Name: 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..Name: 1-Methylpiperazine

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

The author of 《New phenolic Mannich bases with piperazines and their bioactivities》 were Gul, Halise Inci; Tugrak, Mehtap; Gul, Mustafa; Mazlumoglu, Sertac; Sakagami, Hiroshi; Gulcin, Ilhami; Supuran, Claudiu T.. And the article was published in Bioorganic Chemistry in 2019. Safety of 1-Methylpiperazine The author mentioned the following in the article:

New Mannich bases, 2-(4-hydroxy-3-methoxy-5-((substituted piperazin-1-yl)methyl)benzylidene)-2,3-dihydro-1H-inden-1-ones I [R = Me, Ph, benzyl, etc.] were synthesized with the reaction of vanillin derived chalcone compound (2-(4-hydroxy-3-methoxybenzylidene)indan-1-one), paraformaldehyde and suitable amine in 1:1.2:1 mol ratios. Compounds I were evaluated in terms of cytotoxic/anticancer and CA inhibitory effects. According to the results obtained, the compounds I [R = Ph, 3-trifluoromethylphenyl] had the highest potency selectivity expression (PSE) values (60.6 and 19.2, resp.). On the other hand, the compounds I [R = benzyl] (Ki = 209.6 ± 70.2 pM) and [R = 3-methoxyphenyl] (Ki = 342.66 ± 63.72 pM) had the lowest Ki values in CA inhibition experiments towards hCA I and hCA II, resp. In conclusion, the compounds I [R = phenyl] (with cytotoxic/anticancer activity), I [R = benzyl] (with hCA I inhibiting activity) and I [R = 3-methoxyphenyl] (with hCA II inhibiting activity) can be leading compounds of the study for further designs and evaluations. In the experiment, the researchers used many compounds, for example, 1-Methylpiperazine(cas: 109-01-3Safety 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..Safety of 1-Methylpiperazine

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

In 2022,Wangngae, Sirilak; Chansaenpak, Kantapat; Weeranantanapan, Oratai; Piyanuch, Pornthip; Sumphanapai, Thitima; Yamabhai, Montarop; Noisa, Parinya; Lai, Rung-Yi; Kamkaew, Anyanee published an article in Scientific Reports. The title of the article was 《Effect of morpholine and charge distribution of cyanine dyes on cell internalization and cytotoxicity》.Application In Synthesis of 1-Methylpiperazine The author mentioned the following in the article:

To improve the potency of Heptamethine cyanines (Hcyanines) in cancer research, we designed and synthesized two novel Hcyanines based theranostic probes, IR794-Morph and IR794-Morph-Mpip, to enhance cancer cell internalization and targeting. In acidic conditions that resemble to tumor environment, both IR794 derivatives exhibited broad NIR absorption band (704-794 nm) and fluorescence emission (798-828 nm) that is suitable for deep seated tumor imaging. Moreover, in vitro study revealed that IR794-Morph-Mpip exhibited better cancer targetability towards various cancer cell lines under physiol. and slightly acidic conditions compared to normal cells. IR794-Morph-Mpip was fast internalized into the cancer cells within the first 5 min and mostly localized in lysosomes and mitochondria. In addition, the internalized signal was brighter when the cells were in the hypoxic environment. Furthermore, cellular uptake mechanism of both IR794 dyes, investigated via flow cytometry, revealed that endocytosis through OATPs receptors and clathrin-mediated endocytosis were the main routes. Moreover, IR794-Morph-Mpip, displayed anti-cancer activity towards all tested cancer cell types with IC50 below 7 μM (at 6 h incubation), which is approx. three times lower than that of the normal cells. Therefore, increasing protonated cites in tumor environment of Hcyanines together with incorporating morpholine in the mol. can enhance structure-inherent targeting of these dyes. The results came from multiple reactions, including the reaction of 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

Application In Synthesis of 1-MethylpiperazineIn 2020 ,《Design, synthesis, molecular docking and antiproliferative activity of some novel benzothiazole derivatives targeting EGFR/HER2 and TS》 was published in Bioorganic Chemistry. The article was written by Abdellatif, Khaled R. A.; Belal, Amany; El-Saadi, Mohamed T.; Amin, Noha H.; Said, Eman G.; Hemeda, Loah R.. The article contains the following contents:

A new series of benzothiazoles hybridized with a pyrimidine moiety, e.g., I (R = Cl), was designed and synthesized using the lead compound II (R1 = Ph). Various chem. modifications on the pyrimidine ring of II (R1 = Ph) at four different positions were done in a trial to get new multi-targeted anticancer agents. The structures of the newly synthesized compounds were established by their elemental analyses and spectral data. All final synthesized derivatives were submitted to the National Cancer Institute (NCI), USA, to be screened for their in vitro anticancer activity. Further evaluation for the cytotoxic activity of the most active compounds was performed using the MTT assay method. Compounds I [R = (4-acetylphenyl)amino, morpholin-4-yl, 4-methylpiperazin-1-yl], II (R1 = 4-oxo-4H-chromen-3-yl), and III were then selected for examination of their in vitro inhibitory activities against EGFR, HER2 and TS enzymes using lapatinib and 5FU as standards Furthermore, cell cycle anal. and apoptosis induction detection were also evaluated. Finally, mol. docking studies were carried out for compounds I [R = (4-acetylphenyl)amino, morpholin-4-yl, 4-methylpiperazin-1-yl], II (R1 = 4-oxo-4H-chromen-3-yl), and III to interpret their observed enzymic activities based on the ligand-protein interactions. The results came from multiple reactions, including the reaction of 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

In 2022,Ashworth, Ian W.; Frodsham, Lianne; Moore, Peter; Ronson, Thomas O. published an article in Journal of Organic Chemistry. The title of the article was 《Evidence of Rate Limiting Proton Transfer in an SNAr Aminolysis in Acetonitrile under Synthetically Relevant Conditions》.Application In Synthesis of 1-Methylpiperazine The author mentioned the following in the article:

An early synthetic step in the synthesis of adavosertib, AZD1775, is the SNAr reaction between 4-fluoronitrobenzene and 1-methylpiperazine in acetonitrile. A simple kinetics-based design of four reaction profiling experiments was used to investigate the kinetics of the reaction for the purpose of building a kinetic model. Fitting of the reaction profile data from two experiments conducted at 70°C with a different excess of 1-methylpiperazine showed the reaction to follow a third-order rate law with a second-order dependence upon 1-methylpiperazine. This was rationalized in terms of the reaction following a rate-limiting proton transfer mechanism (base catalyzed) in which the progress to product is driven by a proton transfer involving a second mol. of 1-methylpiperazine. The exptl. determined entropy of activation of -180 J K-1 is consistent with this mechanism. The formation of a low level impurity was found to be due to the presence of traces of piperazine in the 1-methylpiperazine, which was shown to react approx. 15 times faster than 1-methylpiperazine at 70°C. The rate constants for the 1-methylpiperazine catalyzed reaction of piperazine, 1-methylpiperazine, and the piperazine derived impurity were found to correlate in a Bronsted type anal. with the pKa’s (acetonitrile) of the amine nucleophile. In the experiment, the researchers used 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