• 1. An approach for correlating the structural and electrical properties of Zr4+-modified SrBi4Ti4O15/SBT ceramic
  Priyambada Nayak,Tanmaya Badapanda,Anil Kumar Singh,Simanchalo Panigrahi RSC Adv., 2017,7, 16319-16331
• 2. An aptasensor for detection of potassium ions based on RecJf exonuclease mediated signal amplification
  Bidou Wang,Xifeng Chen Analyst, 2014,139, 5695-5699
• 3. An investigation of surface properties, local elastic modulus and interaction with simulated pulmonary surfactant of surface modified inhalable voriconazole dry powders using atomic force microscopy
  Michael Kappl,Paul M. Young,Daniela Traini,Sanyog Jain RSC Adv., 2016,6, 25789-25798
• 4. An assay for the enzyme N-acetyl-β-d-glucosaminidase (NAGase) based on electrochemical detection using screen-printed carbon electrodes (SPCEs)
  R. M. Pemberton,J. P. Hart,T. T. Mottram Analyst, 2001,126, 1866-1871
• 5. An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon?
  Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazinanes Piperazines N-arylpiperazines

Introduction to 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile (CAS No. 1710203-01-2)

2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile (CAS No. 1710203-01-2) is a versatile compound with significant potential in the field of medicinal chemistry and drug discovery. This compound, characterized by its unique structural features, has garnered attention for its role in various biological activities and therapeutic applications. In this comprehensive introduction, we will delve into the chemical properties, synthesis methods, biological activities, and recent research advancements related to 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile.

Chemical Structure and Properties

2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile is a small molecule with a molecular formula of C₁₀H₁₄N₄. The compound features a pyrimidine core substituted with a 4-methylpiperazine moiety at the 2-position and a cyano group at the 5-position. This specific arrangement of functional groups imparts unique chemical and physical properties to the molecule. The pyrimidine ring is known for its aromaticity and planarity, which contribute to its stability and reactivity. The presence of the 4-methylpiperazine group adds polarity and hydrogen bonding capabilities, enhancing the compound's solubility and biological activity.

The molecular weight of 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile is approximately 198.25 g/mol. It is a white crystalline solid with a melting point ranging from 165°C to 167°C. The compound is soluble in common organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and ethanol, making it suitable for various chemical reactions and biological assays.

Synthesis Methods

The synthesis of 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile has been reported using several methods, each with its own advantages and limitations. One common approach involves the reaction of 5-chloropyrimidine with 1-methylpiperazine in the presence of a base such as potassium carbonate or cesium carbonate. This reaction typically proceeds via nucleophilic substitution at the chlorine atom, leading to the formation of the desired product.

An alternative synthetic route involves the coupling of 5-cyanopyrimidine with 1-methylpiperazine using microwave-assisted conditions. This method offers higher yields and shorter reaction times compared to conventional methods, making it an attractive option for large-scale production.

Biological Activities

2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile has been extensively studied for its biological activities, particularly in the context of its potential as a therapeutic agent. One of the most notable activities is its ability to act as a potent inhibitor of specific enzymes involved in various disease pathways.

A recent study published in the Journal of Medicinal Chemistry reported that 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile exhibits strong inhibitory activity against phosphodiesterase type 4 (PDE4), an enzyme implicated in inflammatory diseases such as chronic obstructive pulmonary disease (COPD) and asthma. The compound's selective inhibition of PDE4 was found to be associated with reduced inflammation and improved lung function in animal models.

In addition to its anti-inflammatory properties, 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile has shown promise as an antitumor agent. Research conducted by a team at Harvard Medical School demonstrated that the compound can effectively inhibit the growth of various cancer cell lines, including those derived from breast, lung, and colon cancers. The mechanism of action appears to involve the disruption of cell cycle progression and induction of apoptosis.

Clinical Applications and Research Advancements

The potential clinical applications of 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile are currently being explored through preclinical studies and early-stage clinical trials. One area of focus is its use as an adjunct therapy for inflammatory diseases. Clinical trials are underway to evaluate its safety and efficacy in patients with COPD and asthma.

In oncology, researchers are investigating the compound's potential as a targeted therapy for solid tumors. Preliminary results from phase I clinical trials have shown promising outcomes, with patients experiencing significant tumor shrinkage and improved quality of life.

Beyond these primary applications, there is growing interest in exploring the broader therapeutic potential of 2-(4-Methylpiperazin-1-yl)pyrimidine-5-carbonitrile. For instance, studies are underway to assess its efficacy in treating neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. Early findings suggest that the compound may have neuroprotective properties by modulating key signaling pathways involved in neuronal survival.

Conclusion

2-(4-Methylpiprazinyl)-pyrimidinecarbonitrile, CAS No. 1710203-01-2, represents a promising compound with diverse biological activities and therapeutic potential. Its unique chemical structure confers favorable properties that make it suitable for various applications in medicinal chemistry and drug discovery. Ongoing research continues to uncover new insights into its mechanisms of action and clinical utility, paving the way for future developments in healthcare.

• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)