200-300 | Page 9 of 39 | Heterocyclic Building Blocks-piperazine

El-Gamal, Mohammed I. et al. published their research in Bulletin of the Korean Chemical Society in 2012 | CAS: 630125-91-6

4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline (cas: 630125-91-6) belongs to piperazine derivatives. The piperazine scaffold is often found in biologically active compounds in different therapeutic areas. These therapeutic areas include antifungals, antidepressants, antivirals, and serotonin receptor (5-HT) antagonists/agonists. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines. The connecting property of all these chemicals is the presence of a piperazine functional group.Name: 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline

Design and synthesis of an anticancer diarylurea derivative with multiple-kinase inhibitory effect was written by El-Gamal, Mohammed I.;Oh, Chang-Hyun. And the article was included in Bulletin of the Korean Chemical Society in 2012.Name: 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline This article mentions the following:

A pyrrolo[3,2-c]pyridine derivative [N-[1-[4-[[[[4-[(4-ethyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenyl]-1H-pyrrolo[3,2-c]pyridin-4-yl]benzamide (I)] was designed and the synthesis of the target compound was achieved using N-[1-(4-aminophenyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]benzamide and 4-[(4-ethyl-1-piperazinyl)methyl]-3-(trifluoromethyl)benzenamine as key reactants. I was evaluated in a five-dose mode to determine its IC₅₀, TGI, and LC₅₀ values over the 60 cell lines. I displayed high potency and good efficacy and was accordingly tested at a single dose concentration of 10 μM over a panel of 40 kinases. At this concentration, it completely inhibited the enzymic activities of a number of oncogenic kinases, including ABL [kinase (phosphorylating) gene abl protein], ALK [kinase (phosphorylating) gene ALK protein], c-RAF [kinase (phosphorylating) gene raf-1 protein], FLT3 [kinase (phosphorylating) gene FLT3 receptor], KDR [kinase (phosphorylating) gene flk-1 protein] and TrkB [kinase (phosphorylating) gene trkB neurotropic factor receptor]. I was subsequently tested over these 6 kinases in 10-dose testing mode in order to determine its IC₅₀ values. In the experiment, the researchers used many compounds, for example, 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline (cas: 630125-91-6Name: 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline).

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

Ikai, Tomoyuki et al. published their research in ACS Macro Letters in 2022 | CAS: 623586-00-5

(R)-1-Cbz-3-methylpiperazine (cas: 623586-00-5) belongs to piperazine derivatives. Piperazine causes primary dermal irritation and skin burns at high concentrations. Piperazine also causes eye irritation in humans. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ammonia with 1,2-dichloroethane, by the action of sodium and ethylene glycol on ethylene diamine hydrochloride, or by reduction of pyrazine with sodium in ethanol.Application In Synthesis of (R)-1-Cbz-3-methylpiperazine

Catalytic One-Handed Helix Induction and Subsequent Static Memory of Poly(biphenylylacetylene)s Assisted by a Small Amount of Carboxy Groups Introduced at the Pendants was written by Ikai, Tomoyuki;Takeda, Shoki;Yashima, Eiji. And the article was included in ACS Macro Letters in 2022.Application In Synthesis of (R)-1-Cbz-3-methylpiperazine This article mentions the following:

A dynamically racemic helical copolymer composed of an achiral biphenylylacetylene (BPA) bearing methoxymethoxy groups at the 2,2′-positions and 1 mol % of an achiral BPA carrying 2-carboxy-2′-methoxymethoxy groups at the biphenyl pendants was found to fold into an excess one-handed helix with significant amplification of the helicity in the presence of a small amount of optically active amines. The induced macromol. helicity was retained (“memorized”) after removal of the chiral amines. The copolymer had a significant sensitivity for detecting the chirality of chiral amines with a sensitivity more than 10000-fold higher than that of the corresponding homopolymers with no carboxy group, thus showing Cotton effects even in the presence of a 0.01 equiv of an optically active amine. The effects of the substituents at the 4′-position of the biphenyl pendants of the copolymers and the structures of the chiral amines on the macromol. helicity induction were also investigated. In the experiment, the researchers used many compounds, for example, (R)-1-Cbz-3-methylpiperazine (cas: 623586-00-5Application In Synthesis of (R)-1-Cbz-3-methylpiperazine).

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

Hubschwerlen, Christian et al. published their research in Bioorganic & Medicinal Chemistry in 2003 | CAS: 119285-07-3

tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate (cas: 119285-07-3) belongs to piperazine derivatives. A form in which piperazine is commonly available industrially is as the hexahydrate, C4H10N2. 6H2O, which melts at 44 °C and boils at 125–130 °C. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines. The connecting property of all these chemicals is the presence of a piperazine functional group.Reference of 119285-07-3

Design, synthesis and biological evaluation of oxazolidinone-quinolone hybrids was written by Hubschwerlen, Christian;Specklin, Jean-Luc;Sigwalt, Christine;Schroeder, Susanne;Locher, Hans H.. And the article was included in Bioorganic & Medicinal Chemistry in 2003.Reference of 119285-07-3 This article mentions the following:

Oxazolidinone-quinolone hybrids that combine the pharmacophores of a quinolone and an oxazolidinone were synthesized and shown to be active against a variety of resistant and susceptible Gram-pos. and fastidious Gram-neg. organisms. The best compounds in this series overcome all types of resistance in relevant clin. Gram-pos. pathogens. The nature of the spacer greatly influences the antibacterial activity. The dual mode of action could be demonstrated for compounds having a piperazinyl spacer. Antibacterial activity was higher at acidic pH. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate (cas: 119285-07-3Reference of 119285-07-3).

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

Schroth, W. et al. published their research in Journal fuer Praktische Chemie (Leipzig) in 1983 | CAS: 89026-59-5

4-(4-Methoxyphenyl)piperazine-1-carboxamide (cas: 89026-59-5) belongs to piperazine derivatives. Piperazine belongs to the family of medicines called anthelmintics. Piperazine is an anthelminthic especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine hydrate and piperazine citrate are the main anthelminthic piperazines.SDS of cas: 89026-59-5

The dehydration of ureas by two-phase dichlorocarbene reaction, a synthetic access to substituted cyanamides was written by Schroth, W.;Kluge, H.;Frach, R.;Hodek, W.;Schaedler, H. D.. And the article was included in Journal fuer Praktische Chemie (Leipzig) in 1983.SDS of cas: 89026-59-5 The following contents are mentioned in the article:

A wide variety of N,N-disubstituted ureas were dehydrated in the CHCl₃/NaOH catalytic 2-phase system under mild conditions. The sequence of urea transamidation and dehydration offers a profitable approach to aprotic cyanamides. Among various phase-transfer catalysts tertiary amines prove to be the most efficient. Tertiary amines may also be used in the transformation of carboxamides and thioamides to the corresponding nitriles. The application of the same technique is less suitable in the case of N-monosubstituted ureas, N,N‘-disubstituted ureas, and N-(dialkylaminomethylene)ureas, since subsequent reactions of the cyanamides predominate. The dehydration mechanism is elucidated in terms of HOMO-perturbation theory. This study involved multiple reactions and reactants, such as 4-(4-Methoxyphenyl)piperazine-1-carboxamide (cas: 89026-59-5SDS of cas: 89026-59-5).

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

Usui, Yoshihiro et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2017 | CAS: 911705-40-3

tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3) belongs to piperazine derivatives. Industrial applications of piperazine include the manufacture of plastics, resins, pesticides and brake fluids. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines. The connecting property of all these chemicals is the presence of a piperazine functional group.Electric Literature of C15H20N2O3

Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors was written by Usui, Yoshihiro;Uehara, Fumiaki;Hiki, Shinsuke;Watanabe, Kazutoshi;Tanaka, Hiroshi;Shouda, Aya;Yokoshima, Satoshi;Aritomo, Keiichi;Adachi, Takashi;Fukunaga, Kenji;Sunada, Shinji;Nabeno, Mika;Saito, Ken-ichi;Eguchi, Jun-ichi;Yamagami, Keiji;Asano, Shouichi;Tanaka, Shinji;Yuki, Satoshi;Yoshii, Narihiko;Fujimura, Masatake;Horikawa, Takashi. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Electric Literature of C15H20N2O3 The following contents are mentioned in the article:

The results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from authors’ promising compounds containing a 2-phenylmorpholine moiety are described. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the Ph moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies of (S)-isomer of I, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogs. Effect of the stereochem. of the phenylpiperazine moiety is also discussed. This study involved multiple reactions and reactants, such as tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3Electric Literature of C15H20N2O3).

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

Chrovian, Christa C. et al. published their research in ACS Chemical Neuroscience in 2016 | CAS: 911705-40-3

tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3) belongs to piperazine derivatives. Piperazine belongs to the family of medicines called anthelmintics. Piperazine is an anthelminthic especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine hydrate and piperazine citrate are the main anthelminthic piperazines.Category: piperazines

Novel Phenyl-Substituted 5,6-Dihydro-[1,2,4]triazolo[4,3-a]pyrazine P2X7 Antagonists with Robust Target Engagement in Rat Brain was written by Chrovian, Christa C.;Soyode-Johnson, Akinola;Ao, Hong;Bacani, Genesis M.;Carruthers, Nicholas I.;Lord, Brian;Nguyen, Leslie;Rech, Jason C.;Wang, Qi;Bhattacharya, Anindya;Letavic, Michael A.. And the article was included in ACS Chemical Neuroscience in 2016.Category: piperazines The following contents are mentioned in the article:

Novel 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine P2X7 antagonists were optimized to allow for good blood-brain barrier permeability and high P2X7 target engagement in the brain of rats. Compound I (huP2X7 IC₅₀ = 9 nM; rat P2X7 IC₅₀ = 42 nM) achieved 80% receptor occupancy for 6 h when dosed orally at 10 mg/kg in rats as measured by ex vivo radioligand binding autoradiog. Structure-activity relationships within this series are described, as well as in vitro ADME results. In vivo pharmacokinetic data for key compounds is also included. This study involved multiple reactions and reactants, such as tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3Category: piperazines).

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

Rao, Divvela V. N. Srinivasa et al. published their research in ARKIVOC (Gainesville, FL, United States) in 2006 | CAS: 911705-40-3

tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3) belongs to piperazine derivatives. Piperazine causes primary dermal irritation and skin burns at high concentrations. Piperazine also causes eye irritation in humans. Piperazine is formed as a co-product in the ammoniation of 1,2-dichloroethane or ethanolamine. These are the only routes to the chemical used commercially.Electric Literature of C15H20N2O3

New intermediates for the selective synthesis of 1-methyl-3-phenylpiperazine and some phenylpiperazine derivatives was written by Rao, Divvela V. N. Srinivasa;Dandala, Ramesh;Handa, Vijay Kumar;Sivakumaran, Meenakshisunderam;Naidu, Andra. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2006.Electric Literature of C15H20N2O3 The following contents are mentioned in the article:

New intermediates 4-protected-1-alkyl-2-oxo-3-phenylpiperazines and 1-alkyl-2-oxo-3-phenylpiperazines for the selective synthesis of 1-alkyl-3-phenylpiperazines, e.g., I, are described. First method involves the reduction of the 4-protected-1-alkyl-2-oxo-3-phenylpiperazines followed by deprotection giving the 1-alkyl-3-phenylpiperazines. Second method involves the deprotection of 4-protected-1-alkyl-2-oxo-3-phenylpiperazines followed by reduction giving the 1-alkyl-3-phenylpiperazines. This study involved multiple reactions and reactants, such as tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3Electric Literature of C15H20N2O3).

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

Begunov, R. S. et al. published their research in Bashkirskii Khimicheskii Zhurnal in 2008 | CAS: 188604-99-1

2-(4-Methylpiperidin-1-yl)-5-nitroaniline (cas: 188604-99-1) belongs to piperazine derivatives. Simple N-substituted piperazines have been found in many drug molecules. Piperazine is formed as a co-product in the ammoniation of 1,2-dichloroethane or ethanolamine. These are the only routes to the chemical used commercially.Category: piperazines

Identification of 1-X-2,4-dinitro arenes with a sterically demanding substituent and their mono-reduction products using IR-spectroscopy was written by Begunov, R. S.;Shvyrkova, N. S.;Yakovleva, Yu. S.;Kosareva, T. N.. And the article was included in Bashkirskii Khimicheskii Zhurnal in 2008.Category: piperazines The following contents are mentioned in the article:

IR-spectral characteristic of title compounds were investigated. The more high-frequency component of antisym. valence vibrations in IR-spectrum of 1-substituted 2,4-dinitrobenzenes was proved by the exptl. method to cover a nitro group located in ortho position to the substituent. The isomeric nitroanilines forming in the process of their mono-reduction can be identified with absorption bonds of nitro group. This study involved multiple reactions and reactants, such as 2-(4-Methylpiperidin-1-yl)-5-nitroaniline (cas: 188604-99-1Category: piperazines).

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

Begunov, R. S. et al. published their research in Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya in 2004 | CAS: 188604-99-1

2-(4-Methylpiperidin-1-yl)-5-nitroaniline (cas: 188604-99-1) belongs to piperazine derivatives. The piperazine scaffold is often found in biologically active compounds in different therapeutic areas. These therapeutic areas include antifungals, antidepressants, antivirals, and serotonin receptor (5-HT) antagonists/agonists. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines. The connecting property of all these chemicals is the presence of a piperazine functional group.SDS of cas: 188604-99-1

Mechanism of monoreduction by variable valency metal salts in unsymmetrical heterocycle-containing dinitrobenzenes was written by Begunov, R. S.;Demidova, N. Yu.;Brodskii, I. I.;Orlov, V. Yu.. And the article was included in Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya in 2004.SDS of cas: 188604-99-1 The following contents are mentioned in the article:

The behavior of nitrogroups in 1-substituted saturated heterocycle-containing 2,4-dinitrobenzenes under Sn(II) and Ti(III) monoredn. has been investigated. A model of the process explaining the mechanism of conversion has been suggested. This study involved multiple reactions and reactants, such as 2-(4-Methylpiperidin-1-yl)-5-nitroaniline (cas: 188604-99-1SDS of cas: 188604-99-1).

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

Guan, Cheng-bo et al. published their research in Nanchang Daxue Xuebao, Likeban in 2012 | CAS: 911705-40-3

tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3) belongs to piperazine derivatives. A form in which piperazine is commonly available industrially is as the hexahydrate, C4H10N2. 6H2O, which melts at 44 °C and boils at 125–130 °C. Piperazine and its salts did not induce point mutations in a bacterial test. A series of mutagenicity studies in cells, both in vitro and in vivo, has been completed and showed no evidence of mutagenic effect.Quality Control of tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate

The preparation of 1-Methyl-3-phenylpiperazine was written by Guan, Cheng-bo;Zhang, Xue-mei;Wei, Meng;Lai, Kun-min;Yu, Zhang-xin;Yan, Zhao-hua. And the article was included in Nanchang Daxue Xuebao, Likeban in 2012.Quality Control of tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate The following contents are mentioned in the article:

1-Methyl-3-phenylpiperazine was prepared by using Et α-Bromophenylacetate and ethylenediamine as the starting materials in the cyclization. Then with N₄ protection of the Boc group, N1 methylation, N₄ deprotection and reduction of amide group, 1-Methyl-3-phenylpiperazine was synthesized. The total yield is 29%. On the basis of previously reported procedure, we further modified the work-up procedure in the first step of cyclization to increase the production quality and efficiency. The modification included dissolution of the crude product obtained in CH₂Cl₂, and subsequent reactions with a limited amount of di-tert-butyldicarbonate followed by precipitation in THF at low temperature Our modification improved the quality of the intermediate 3-phenyl-2-piperazinone and is easily repeatable. Moreover, in the steps of N₄ protection with Boc group and reduction of amide group, some changes were also made for easy application to industrial manufacturing This study involved multiple reactions and reactants, such as tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate (cas: 911705-40-3Quality Control of tert-Butyl 3-oxo-2-phenylpiperazine-1-carboxylate).

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