Category: piperazines

A Highly Regioselective Amination of 6-Aryl-2,4-dichloropyrimidine was written by Peng, Zhi-Hui;Journet, Michel;Humphrey, Guy. And the article was included in Organic Letters in 2006.Category: piperazines This article mentions the following:

A highly regioselective amination of 6-aryl-2,4-dichloropyrimidines with aliphatic secondary amines and aromatic amines which strongly favors the formation of the C4-substituted product has been developed. The reactions with aliphatic amines are carried out using LiHMDS as the base and are catalyzed by Pd, while the aromatic amines require no catalyst. In the experiment, the researchers used many compounds, for example, (R)-1-Cbz-3-methylpiperazine (cas: 623586-00-5Category: piperazines).

(R)-1-Cbz-3-methylpiperazine (cas: 623586-00-5) 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. Two common salts in the form of which piperazine is usually prepared for pharmaceutical or veterinary purposes are the citrate, 3C4H10N2.2C6H8O7 (i.e. containing 3 molecules of piperazine to 2 molecules of citric acid), and the adipate, C4H10N2.C6H10O4 (containing 1 molecule each of piperazine and adipic acid).Category: piperazines

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

Synthesis, biological evaluation, X-ray molecular structure and molecular docking studies of RGD mimetics containing 6-amino-2,3-dihydroisoindolin-1-one fragment as ligands of integrin 濞?sub>IIb閻?sub>3 was written by Krysko, Andrei A.;Samoylenko, Georgiy V.;Polishchuk, Pavel G.;Fonari, Marina S.;Kravtsov, Victor Ch.;Andronati, Sergei A.;Kabanova, Tatyana A.;Lipkowski, Janusz;Khristova, Tetiana M.;Kuz’min, Victor E.;Kabanov, Vladimir M.;Krysko, Olga L.;Varnek, Alexandre A.. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Synthetic Route of C16H22N2O4 This article mentions the following:

Acylaminooxoisoindolealkanoic acid RGD mimetics such as tetrahydroisoquinolinecarbonylamino oxoisoindolylpropanoic acid I闂佺偨鍎洪弫鐟縧 were prepared as integrin 濞?sub>IIb閻?sub>3 ligands for inhibiting platelet aggregation for potential use as antithrombotic agents. The inhibition of platelet aggregation by the oxoisoindolealkanoic acids was determined, and for some compounds, the inhibition of fluorescein-labeled fibrinogen binding to human platelets (and thus to integrin 濞?sub>IIb閻?sub>3) was also determined; for example, I闂佺偨鍎洪弫鐟縧 inhibited platelet aggregation with an IC₅₀ value of 1.1 婵炴挾鎷?and inhibited the binding of fluorescein-labeled fibrinogen to platelets with an IC₅₀ value of 6.5 nM. Mol. docking calculations of eight of the prepared compounds bound to integrin 濞?sub>IIb閻?sub>3 were performed, indicating the key interactions present; correlations between docking scores and binding affinities were also found. Of the motifs tried, the use of an N-terminal tetrahydroisoquinolinecarbonyl group and a C-terminal 閻?alanine moiety provided the most effective platelet aggregation inhibitors. The structures for a Me aminooxoisoindolebutanoate, a tetrahydroisoquinolinedicarboxylic acid mono-tert-Bu ester, and solvates, salts, or free bases of five of the oxoisoindolealkanoic acids prepared including I闂佺偨鍎洪弫?sub>2O were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid (cas: 162046-66-4Synthetic Route of C16H22N2O4).

4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid (cas: 162046-66-4) belongs to piperazine derivatives. Piperazine was first introduced as an anthelmintic in 1953. Piperazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism. 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.Synthetic Route of C16H22N2O4

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

Multistep Continuous-Flow Synthesis in Medicinal Chemistry: Discovery and Preliminary Structure-Activity Relationships of CCR8 Ligands was written by Petersen, Trine P.;Mirsharghi, Sahar;Rummel, Pia C.;Thiele, Stefanie;Rosenkilde, Mette M.;Ritzen, Andreas;Ulven, Trond. And the article was included in Chemistry – A European Journal in 2013.Recommanded Product: 623586-00-5 This article mentions the following:

A three-step continuous-flow synthesis system and its application to the assembly of a new series of chemokine receptor ligands directly from com. building blocks is reported. No scavenger columns or solvent switches are necessary to recover the desired test compounds, which were obtained in overall yields of 49-94%. The system is modular and flexible, and the individual steps of the sequence can be interchanged with similar outcome, extending the scope of the chem. Biol. evaluation confirmed activity on the chemokine CCR8 receptor and provided initial structure-activity-relationship (SAR) information for this new ligand series, with the most potent member displaying full agonist activity with single-digit nanomolar potency. To the best of the knowledge, this represents the first published example of efficient use of multistep flow synthesis combined with biol. testing and SAR studies in medicinal chem. In the experiment, the researchers used many compounds, for example, (R)-1-Cbz-3-methylpiperazine (cas: 623586-00-5Recommanded Product: 623586-00-5).

(R)-1-Cbz-3-methylpiperazine (cas: 623586-00-5) 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. 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.Recommanded Product: 623586-00-5

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

Tetrahydroquinoline sulfonamides as 缂?secretase inhibitors was written by Asberom, Theodros;Bara, Thomas A.;Clader, John W.;Greenlee, William J.;Guzik, Henry S.;Josien, Hubert B.;Li, Wei;Parker, Eric M.;Pissarnitski, Dmitri A.;Song, Lixin;Zhang, Lili;Zhao, Zhiqiang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Synthetic Route of C7H16N2 This article mentions the following:

The development of a novel series of tetrahydroquinoline-derived 缂?secretase inhibitors for the potential treatment of Alzheimer’s disease is described. Incorporation of a fluorine substituent at position 7 resulted in the most potent compound I. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Synthetic Route of C7H16N2).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine is a fairly basic compound and is an amine solvent. Intermediate for a wide range of pharmaceuticals, polymers, dyes, corrosion inhibitors, rubber accelerators and surfactants.Synthetic Route of C7H16N2

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

Chemotherapeutically active anthraquinones. II. Aminomethylanthraquinones was written by Winkelmann, E.;Raether, W.. And the article was included in Arzneimittel-Forschung in 1986.SDS of cas: 21867-64-1 This article mentions the following:

Anthraquinones [I, R = OAc, S₂CNEt₂, Sc(:NH)NH₂, NH₂, dialkylamino, heterocyclic, S(CH₂)₂NEt₂, OC₆H₄NH₂, R¹ = H, XR, R² = H, XR, Me, R³ = R⁵ = H, OH, heterocyclic, R⁴ = H, OH] were prepared and tested in vitro and in vivo (in hamster) against Entamoeba闁?em>histolytica and interferon-inducing property in mice. Activity against Trichomonas闁?em>foetus (in mice) was also tested. Most of the compounds showed chemotherapeutic activities in these tests. Structure-activity relations are discussed. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1SDS of cas: 21867-64-1).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Industrial applications of piperazine include the manufacture of plastics, resins, pesticides and brake fluids. 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.SDS of cas: 21867-64-1

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

Molecular iodine-catalyzed facile procedure for N-Boc protection of amines was written by Varala, Ravi;Nuvula, Sreelatha;Adapa, Srinivas R.. And the article was included in Journal of Organic Chemistry in 2006.Application of 780705-64-8 This article mentions the following:

An efficient and practical protocol for the protection of various structurally and electronically divergent aryl and aliphatic amines using (Boc)₂O in the presence of a catalytic amount of mol. iodine under solvent-free conditions at ambient temperature is presented. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-(pyrimidin-2-yl)piperazine-1-carboxylate (cas: 780705-64-8Application of 780705-64-8).

tert-Butyl 4-(pyrimidin-2-yl)piperazine-1-carboxylate (cas: 780705-64-8) belongs to piperazine derivatives. Piperazine was first introduced as an anthelmintic in 1953. Piperazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism. Intermediate for a wide range of pharmaceuticals, polymers, dyes, corrosion inhibitors, rubber accelerators and surfactants.Application of 780705-64-8

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

An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base was written by Peng, Wei;Chen, Jian;Liu, Hui;Li, Xiufang;Deng, Zhiwei;Yuan, Jing;Peng, Yizhou;Yang, Yanjing;Zhong, Shian. And the article was included in Chemical Papers in 2019.HPLC of Formula: 780705-64-8 This article mentions the following:

A method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the com. available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50 闁硅櫣鐓?for 16 h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50 闁硅櫣鐓?for 12 h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the com. availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible com. applications. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-(pyrimidin-2-yl)piperazine-1-carboxylate (cas: 780705-64-8HPLC of Formula: 780705-64-8).

tert-Butyl 4-(pyrimidin-2-yl)piperazine-1-carboxylate (cas: 780705-64-8) belongs to piperazine derivatives. Industrial applications of piperazine include the manufacture of plastics, resins, pesticides and brake fluids. 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.HPLC of Formula: 780705-64-8

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

Synthesis and evaluation of thiopyrano[3,4-c]quinoline-9-carboxamide derivatives as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1) was written by Park, Chun-Ho;Chun, Kwangwoo;Joe, Bo-Young;Choi, Jong-Hee;Lee, Han-Chang;Ku, Il-Whea;Kim, Hyun Young;Koh, Seong-Ho;Cho, Goang Won;Kim, Seung Hyun;Kim, Myung-Hwa. And the article was included in Medicinal Chemistry Research in 2012.Product Details of 21867-64-1 This article mentions the following:

A series of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors, 5-oxo-2,4,5,6-tetrahydro-1H-thiopyrano[3,4-c]quinoline-9-carboxamides, were successfully synthesized, and their PARP-1 inhibitory activity was evaluated. These compounds were prepared from the corresponding carboxylate and appropriate amines, and a number of the synthesized compounds were found to have significant PARP-1 activity. Among them, one compound showed potent activity in a PARP-1 enzymic and cell-based assay (IC₅₀ = 0.045 婵炴挾鎷? ED₅₀ = 0.54 婵炴挾鎷?. Mol. modeling confirmed the obtained biol. results. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Product Details of 21867-64-1).

1-Propylpiperazine (cas: 21867-64-1) 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.Product Details of 21867-64-1

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

Development of Gleevec Analogues for Reducing Production of 閻?Amyloid Peptides through Shifting 閻?Cleavage of Amyloid Precursor Proteins was written by Sun, Weilin;Netzer, William J.;Sinha, Anjana;Gindinova, Katherina;Chang, Emily;Sinha, Subhash C.. And the article was included in Journal of Medicinal Chemistry in 2019.SDS of cas: 162046-66-4 This article mentions the following:

Imatinib mesylate, I, inhibits production of 閻?amyloid (A閻? peptides both in cells and in animal models. It reduces both the 閻?secretase and 缂?secretase cleavages of the amyloid precursor protein (APP) and mediates a synergistic effect, when combined with a 閻?secretase inhibitor, BACE IV. Toward developing more potent brain-permeable leads, we have synthesized and evaluated over 75 I-analogs. Several compounds inhibited production of A閻?peptides with improved activity in cells. These compounds affected 閻?secretase cleavage of APP similarly to I. Compound II significantly reduced production of the A閻?2 peptide, when administered (100 mg/kg, twice daily by oral gavage) to 5 mo old female mice for 5 days. A combination of compound II with BACE IV also reduced A閻?levels in cells, more than the additive effect of the two compounds These results open a new avenue for developing treatments for Alzheimer’s disease using I-analogs. In the experiment, the researchers used many compounds, for example, 4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid (cas: 162046-66-4SDS of cas: 162046-66-4).

4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid (cas: 162046-66-4) belongs to piperazine derivatives. A form in which piperazine is commonly available industrially is as the hexahydrate, C4H10N2. 6H2O, which melts at 44 闁硅櫣鐓?and boils at 125闂?30 闁硅櫣鐓? 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.SDS of cas: 162046-66-4

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

Discovery of the selective and efficacious inhibitors of FLT3 mutations was written by Zhi, Yanle;Li, Baoquan;Yao, Chao;Li, Hongmei;Chen, Puzhou;Bao, Jiyin;Qin, Tianren;Wang, Yue;Lu, Tao;Lu, Shuai. And the article was included in European Journal of Medicinal Chemistry in 2018.Reference of 182618-86-6 This article mentions the following:

Fms-like tyrosine kinase 3 (FLT3) is among the most frequently mutated protein in acute myeloid leukemia (AML), which has been confirmed as an important drug target for AML chemotherapy. Starting from the lead compound LT-106-175, a series of 1-H-pyrazole-3-carboxamide derivatives were synthesized to improve the FLT3 inhibitory potency and selectivity. Among them, compound 50 (4-((2-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazole-3-carboxamide) was identified as a highly potent and selective FLT3 inhibitor (IC₅₀ = 0.213 nM), which showed equal activities against various mutants of FLT3 including FLT3 (ITD)-D835V and FLT3 (ITD)-F691L that is resistant to quizartinib. Compound 50 also exhibited efficacy against the human AML cell line MV4-11 (IC₅₀ = 16.1 nM) harboring FLT3-ITD mutants. Inversely, compound 50 displayed no cytotoxicity to FLT3-independent cells, and the biochem. analyses showed that its effects were related to the inhibition of FLT3 signal pathways. Addnl., compound 50 induced apoptosis in MV4-11 cell as demonstrated by flow cytometry. Moreover, compound 50 showed enhanced metabolic stability. Altogether, it was concluded that compound 50 could be a promising FLT3 inhibitor for further developing therapeutic remedy of AML. In the experiment, the researchers used many compounds, for example, 1-Boc-4-(4-Nitrophenyl)piperazine (cas: 182618-86-6Reference of 182618-86-6).

1-Boc-4-(4-Nitrophenyl)piperazine (cas: 182618-86-6) belongs to piperazine derivatives. Simple N-substituted piperazines have been found in many drug molecules. 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.Reference of 182618-86-6

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