22746-09-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(4,6-DIMETHYL-2-PYRIMIDYL)PIPERAZINE is used as a building block for the synthesis of various drugs due to its chemical structure and pharmacological properties.
Used in Allergy Treatment:
1-(4,6-DIMETHYL-2-PYRIMIDYL)PIPERAZINE is used as a therapeutic agent for treating allergies, leveraging its potential as a serotonin receptor antagonist to alleviate allergic symptoms.
Used in Anxiety and Depression Treatment:
1-(4,6-DIMETHYL-2-PYRIMIDYL)PIPERAZINE is used as a treatment for anxiety and depression, potentially modulating serotonin receptor activity to improve mood and reduce anxiety levels.
Used in Antitumor Research:
1-(4,6-DIMETHYL-2-PYRIMIDYL)PIPERAZINE is used in research for its potential antitumor activity, with investigations ongoing to understand its effects on cancer cells and its potential role in cancer treatment.

Upstream product

• 110-85-0 piperazine 
• 35144-22-0 4,6-dimethyl-2-methylsulfonylpyrimidine 
• 4472-44-0 2-chloro-4,6-dimethylpyrimidine 
• 14001-64-0 4,6-dimethyl-2-methylsulfanyl-pyrimidine 
• 22325-27-5 4,6-dimethyl-2-meraptopyrimidine 
• 123-54-6 acetylacetone 
• 767-15-7 2-Amino-4,6-dimethylpyrimidine 
• 34289-60-6 4,6-dimethyl-2-hydroxy-pyrimidine hydrochloride 

Downstream Products

• 1224727-24-5 C₂₁H₂₂ClF₃N₈S 
• 1224727-21-2 C₂₁H₂₂F₄N₈S 
• 1224727-22-3 C₂₂H₂₅F₃N₈OS 
• 1224727-23-4 C₂₃H₂₇F₃N₈S 
• 1224727-25-6 C₂₁H₂₂F₃N₉O₂S 
• 1224727-20-1 C₂₁H₂₃F₃N₈S 

Relevant academic research and scientific papers

Design, synthesis and evaluation of new indolylpyrimidylpiperazines for gastrointestinal cancer therapy

Human A3 adenosine receptor hA3AR has been implicated in gastrointestinal cancer, where its cellular expression has been found increased, thus suggesting its potential as a molecular target for novel anticancer compounds. Observation

Discovery of indolylpiperazinylpyrimidines with dual-target profiles at adenosine A2A and dopamine D2 receptors for Parkinson’s disease treatment

Parkinson’s disease (PD) is a neurodegenerative disorder characterized by progressive loss of dopaminergic neurons in the substantia nigra of the human brain, leading to depletion of dopamine production. Dopamine replacement therapy remains the mainstay for attenuation of PD symptoms. Nonetheless, the potential benefit of current pharmacotherapies is mostly limited by adverse side effects, such as drug-induced dyskinesia, motor fluctuations and psychosis. Non-dopaminergic receptors, such as human A2A adenosine receptors, have emerged as important therapeutic targets in potentiating therapeutic effects and reducing the unwanted side effects. In this study, new chemical entities targeting both human A2A adenosine receptor and dopamine D2 receptor were designed and evaluated. Two computational methods, namely support vector machine (SVM) models and Tanimoto similarity-based clustering analysis, were integrated for the identification of compounds containing indole-piperazine-pyrimidine (IPP) scaffold. Subsequent synthesis and testing resulted in compounds 5 and 6, which acted as human A2A adenosine receptor binders in the radioligand competition assay (Ki = 8.7–11.2 μM) as well as human dopamine D2 receptor binders in the artificial cell membrane assay (EC50 = 22.5–40.2 μM). Moreover, compound 5 showed improvement in movement and mitigation of the loss of dopaminergic neurons in Drosophila models of PD. Furthermore, in vitro toxicity studies on compounds 5 and 6 did not reveal any mutagenicity (up to 100 μM), hepatotoxicity (up to 30 μM) or cardiotoxicity (up to 30 μM).

Synthesis and biological activity of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives

A series of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives have been conveniently synthesized via Mannich reaction in good yields. Their structures were identified by IR,1H NMR,13C NMR, and elemental analysis. The preliminary bioassays showed that among 14 new compounds, the trifluoromethyl-containing compounds exhibited superior activity than the methyl-containing ones; some of the compounds displayed significant in vitro and in vivo fungicidal activity against several plant fungi and were comparable with the control Triadimefon; several compounds exhibited certain herbicidal activity against Brassica campestris; several compounds possessed favorable KARI inhibitory activity, especially 8D could be a promising KARI inhibitor for further study. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic Mannich base structures containing piperazine moiety.

Synthesis and Fungicidal Activities of Novel 1,2,4-Triazole Thione Derivatives Containing 1,2,3-Triazole and Substituted Piperazine Moieties

A series of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties were synthesized via the Mannich reaction of 1,2,3-triazole-containing 1,2,4-triazole thiol intermediates with various substituted piperazines and formaldehyde in high yields. The structures of 14 title compounds were confirmed by melting points, IR, 1H NMR, 13C NMR, and elemental analysis. The bioassay results showed that some of the title compounds exhibit significant fungicidal activities against several plant fungi at 50 μg/mL, especially trifluoromethyl-containing triazole thione derivative 9g showed broad activities and could be made further structural optimization for novel fungicides innovation research.

Synthesis and biological activity of novel N-glucosides containing substituted piperazine moiety

A series of novel acetylated piperazine-containing N-glucosides and bis(N-glucoside) 8a-i were synthesized by the nucleophilic addition of acetylated glucopyranosyl isothiocyanate with various substituted piperazines in THF with high yields. Their novel deacetylated products 9a-i were also synthesized after Me-ONa/MeOH treatment. The preliminary bioassays for 18 novel title compounds showed that several compounds have significant fungicidal activity against Fusarium omysporum, Cercospora arachidicola and Phytophthora capsici at 50 μg/mL.

Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties

A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.

Synthesis and biological activities of novel 1,2,4-triazole thiones and bis(1,2,4-triazole thiones) containing phenylpyrazole and piperazine moieties

A series of novel 1,2,4-triazole thione and bis(1,2,4-triazole thione) derivatives containing phenylpyrazole and substituted piperazine moieties have been conveniently synthesized via Mannich reaction using various 1,2,4-triazole thiols, substituted piperazines, and formaldehyde at room temperature in short time. Their structures were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. The preliminary bioassays for 27 new title compounds have shown that some of them possess certain herbicidal activities against Echinochloa crusgalli at 100 μg/mL concentration. Some of the compounds exhibited significant in vitro fungicidal activities, especially against Cercospora arachidicola and Rhizoctonia cerealis at the concentration of 50 μg/mL, and were comparable with that of control Triadimefon. Meanwhile, IXp held the control efficacy of 60% against Puccinia sorghi Schw. at 200 μg/mL concentration in the in vivo test. The SAR analysis has indicated that compounds with two CF3 groups both on triazole and pyrazole rings are more effective than compounds with one CF3 group or two CH3 groups according to their fungicidal activity data. On the whole, compounds VIIIg, IXi, IXo and IXp could be used as novel lead structures for the design and discovery of new fungicides.

Synthesis and Biological Activity of Novel Furan/Thiophene and Piperazine-Containing (Bis)1,2,4-triazole Mannich Bases

Series of novel furan/thiophene and piperazine-containing 1,2,4-triazole Mannich bases and bis(1,2,4-triazole) Mannich bases have been conveniently synthesized via Mannich reaction with triazole Schiff bases, various piperazine derivatives, and formaldehyde as intermediates in good yields. Their structures were characterized by melting points, 1H NMR, 13C NMR, IR and elemental analysis. The preliminary bioassay showed that most compounds exhibited significant in vitro and in vivo fungicidal activity against several test plant fungi. Among 32 new compounds, the trifluoromethyl-containing compounds showed superior activity than the methyl-containing ones. Several compounds, such as F8, F9, F10, G5, H7, H8, I3 and I4, were comparable with some commercial fungicides against different fungi during the present study and could be further structurally optimized. Meanwhile, several compounds showed good herbicidal activity against Brassica campestris at 100 μg/mL and KARI inhibitory activity at 200 μg/mL. However, compounds exhibited poor insecticidal activity against oriental armyworm at 200 μg/mL in the preliminary studies. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic structures.

SUBSTITUTED HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are novel heteroaryl compounds, pharmaceutically acceptable salts and pharmaceutical formulations thereof for selectively inhibiting serotonin reuptake and/or acting as 5-HT1A receptor agonists. Also provided herein are pharmaceutical compositions comprising the heteroaryl compounds and methods of using the pharmaceutical compositions in treating central nervous system (CNS) dysfunction in a mammal, especially a human being.

Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-Triazole) mannich bases containing piperazine rings

A series of trifluoromethyl-substituted 1,2,4-triazole Mannich base 6 and bis(1,2,4-triazole) Mannich base 7 containing pyrimidinylpiperazine rings via the Mannich reaction were synthesized and characterized by infrared (IR), 1H nuclear magnetic resonance (NMR), and elemental analysis. The fungicidal tests indicated that most of compounds 6 and 7 possessed excellent fungicidal activity. Among 19 novel compounds, some showed superiority over commercial fungicides Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin. Some compounds also exhibited favorable herbicidal activity in the preliminary studies. On the basis of the comparative molecular field analysis (CoMFA), five novel compounds were subsequently synthesized, their activities were estimated fairly accurately, and compounds 6-A1 and 7-A2 displayed good fungicidal activity against Pseudoperonospora cubensis (96.9 and 84.9%) as 6h and 7c, respectively.