Cas no 677762-57-1 (1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid)

1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid is a pyridine derivative with a cyclopropyl substituent at the 1-position and a carboxylic acid functional group at the 3-position. This compound serves as a key intermediate in the synthesis of pharmaceuticals, particularly quinolone antibiotics, due to its structural resemblance to bioactive scaffolds. The cyclopropyl group enhances metabolic stability, while the carboxylic acid moiety allows for further derivatization. Its rigid heterocyclic core contributes to improved binding affinity in target interactions. The compound is typically employed in research and development settings for constructing complex molecules with potential antibacterial or therapeutic applications. High purity and well-defined synthetic routes ensure reproducibility in industrial and academic use.
1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid structure
677762-57-1 structure
Product Name:1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid
CAS No:677762-57-1
MF:C9H9NO3
MW:179.172662496567
MDL:MFCD16041994
CID:1089691
PubChem ID:21885909
Update Time:2025-05-21

1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid
    • 1-CYCLOPROPYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID
    • 1-cyclopropyl-6-oxopyridine-3-carboxylic acid
    • AT13796
    • Z854062396
    • 1-cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylicacid
    • SB54667
    • CCB76257
    • EN300-268291
    • 677762-57-1
    • AKOS009159262
    • DTXSID30619447
    • CS-0243779
    • SCHEMBL3160335
    • DB-363545
    • MDL: MFCD16041994
    • Inchi: 1S/C9H9NO3/c11-8-4-1-6(9(12)13)5-10(8)7-2-3-7/h1,4-5,7H,2-3H2,(H,12,13)
    • InChI Key: WTEIFYMIOHDHRC-UHFFFAOYSA-N
    • SMILES: O=C1C=CC(C(=O)O)=CN1C1CC1

Computed Properties

  • Exact Mass: 179.058243149g/mol
  • Monoisotopic Mass: 179.058243149g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 326
  • 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: 0.2
  • Topological Polar Surface Area: 57.6?2

1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid Security Information

1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid Pricemore >>

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Additional information on 1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic Acid: A Comprehensive Overview

1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (CAS No. 677762-57-1) is a compound of significant interest in the field of organic chemistry and pharmacology. This compound belongs to the class of dihydropyridines, which are well-known for their structural versatility and potential applications in drug discovery. The molecule features a cyclopropyl group attached to the dihydropyridine ring, along with a carboxylic acid moiety at the 3-position and a ketone group at the 6-position. These structural elements contribute to its unique chemical properties and biological activity.

Recent studies have highlighted the importance of dihydropyridine derivatives in various therapeutic areas, including cardiovascular diseases, neurodegenerative disorders, and cancer. The cyclopropyl substitution in this compound introduces steric hindrance and enhances the stability of the molecule, making it a promising candidate for further exploration. Researchers have also investigated the synthesis pathways of this compound, focusing on optimizing reaction conditions to achieve higher yields and purities.

The carboxylic acid group in 1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid plays a crucial role in its chemical reactivity. This functional group can undergo various transformations, such as esterification or amidation, to generate derivatives with enhanced bioavailability or target specificity. For instance, recent advancements in click chemistry have enabled the creation of bioconjugates that retain the core structure of this compound while improving its pharmacokinetic properties.

In terms of biological activity, this compound has shown potential as a modulator of ion channels, particularly voltage-gated calcium channels. Experimental data suggest that it may exert its effects through interactions with specific residues within the channel's transmembrane domains. Furthermore, computational modeling studies have provided insights into the molecular docking patterns of this compound, revealing key interactions that could be exploited for drug design.

The cyclopropyl group also imparts unique electronic properties to the molecule, influencing its ability to penetrate cellular membranes and interact with target proteins. Preclinical studies have demonstrated that this compound exhibits moderate cytotoxicity against certain cancer cell lines, suggesting its potential as an anticancer agent. However, further research is required to elucidate its mechanism of action and identify optimal dosing regimens.

From a synthetic perspective, the preparation of 1-Cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid involves multi-step reactions that require precise control over reaction conditions. The use of transition metal catalysts has been explored to facilitate key transformations, such as cyclopropanation or oxidation steps. These advancements have not only improved synthetic efficiency but also opened avenues for scaling up production for preclinical testing.

Looking ahead, the development of this compound into a clinically relevant drug will depend on several factors, including its pharmacokinetic profile, safety profile, and efficacy in animal models. Collaborative efforts between academic researchers and pharmaceutical companies are essential to overcoming these challenges and translating laboratory findings into real-world applications.

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