Cas no 82183-24-2 (4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile)

4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile structure
82183-24-2 structure
Product Name:4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile
CAS No:82183-24-2
MF:C7H7ClN4
MW:182.610279321671
CID:1090751
PubChem ID:12936202
Update Time:2025-11-01

4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile
    • SB56529
    • 82183-24-2
    • DTXSID40513402
    • MDL: MFCD27923176
    • Inchi: 1S/C7H7ClN4/c1-12(2)7-10-4-5(3-9)6(8)11-7/h4H,1-2H3
    • InChI Key: WKWJLPHVJAUOLS-UHFFFAOYSA-N
    • SMILES: ClC1=C(C#N)C=NC(=N1)N(C)C

Computed Properties

  • Exact Mass: 182.0359239g/mol
  • Monoisotopic Mass: 182.0359239g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 197
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.3
  • Topological Polar Surface Area: 52.8?2

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Additional information on 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile

4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile (CAS No. 82183-24-2): An Overview of a Versatile Compound in Pharmaceutical Research

4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile (CAS No. 82183-24-2) is a versatile compound that has garnered significant attention in the field of pharmaceutical research due to its unique chemical structure and potential biological activities. This compound belongs to the class of pyrimidines, which are essential building blocks in nucleic acids and have been extensively studied for their roles in various biological processes.

The chemical structure of 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile features a pyrimidine ring with a chlorine atom at the 4-position, a dimethylamino group at the 2-position, and a cyano group at the 5-position. This specific arrangement of functional groups imparts unique properties to the molecule, making it an attractive candidate for drug discovery and development.

Recent studies have highlighted the potential of 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile in various therapeutic areas. One notable application is its use as a lead compound in the development of antiviral agents. Research has shown that this compound exhibits potent antiviral activity against several RNA viruses, including influenza and respiratory syncytial virus (RSV). The mechanism of action is believed to involve inhibition of viral replication through interference with key viral enzymes.

In addition to its antiviral properties, 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile has also been investigated for its anticancer potential. Studies have demonstrated that this compound can selectively inhibit the growth of certain cancer cell lines, particularly those derived from solid tumors such as lung and breast cancer. The anticancer activity is thought to be mediated by its ability to disrupt DNA synthesis and induce apoptosis in cancer cells.

The pharmacokinetic properties of 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile have also been evaluated in preclinical studies. These studies have shown that the compound exhibits favorable absorption, distribution, metabolism, and excretion (ADME) profiles, making it suitable for further development as a therapeutic agent. Its oral bioavailability and stability in physiological conditions are particularly noteworthy.

Furthermore, 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile has been explored for its potential as a modulator of G protein-coupled receptors (GPCRs). GPCRs are a large family of membrane receptors involved in numerous physiological processes and are important targets for drug discovery. Research has indicated that this compound can modulate the activity of specific GPCRs, which could have implications for treating conditions such as hypertension and neurological disorders.

The synthesis of 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile involves several well-established chemical reactions. One common synthetic route starts with the reaction of 2-chloroacetonitrile with guanidine hydrochloride to form 4-chloropyrimidine-5-carbonitrile, which is then treated with dimethylamine to introduce the dimethylamino group at the 2-position. This synthetic pathway is efficient and scalable, making it suitable for large-scale production.

In conclusion, 4-Chloro-2-(dimethylamino)pyrimidine-5-carbonitrile (CAS No. 82183-24-2) is a promising compound with diverse applications in pharmaceutical research. Its unique chemical structure and favorable biological properties make it an attractive candidate for further investigation and development as a therapeutic agent. Ongoing research continues to uncover new potential uses for this compound, highlighting its versatility and importance in the field of medicinal chemistry.

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