Cas no 1368466-66-3 (1-Cyclopropyl-1H-imidazole-4-carboxylic acid)

1-Cyclopropyl-1H-imidazole-4-carboxylic acid is a heterocyclic carboxylic acid derivative featuring a cyclopropyl-substituted imidazole core. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. Its rigid cyclopropyl group enhances steric and electronic properties, making it valuable for modulating biological activity and improving metabolic stability in drug candidates. The carboxylic acid functionality allows for further derivatization, enabling the formation of amides, esters, and other key pharmacophores. With high purity and well-defined reactivity, this compound is suitable for research and industrial applications requiring precise structural modifications. Its stability under standard conditions ensures reliable handling and storage.
1-Cyclopropyl-1H-imidazole-4-carboxylic acid structure
1368466-66-3 structure
Product Name:1-Cyclopropyl-1H-imidazole-4-carboxylic acid
CAS No:1368466-66-3
MF:C7H8N2O2
MW:152.150621414185
MDL:MFCD07376045
CID:4727155
PubChem ID:82467807
Update Time:2025-06-09

1-Cyclopropyl-1H-imidazole-4-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 1-cyclopropyl-1H-imidazole-4-carboxylic acid
    • 1-cyclopropylimidazole-4-carboxylic acid
    • 1-cyclopropyl-1H-imidazole-4-carboxylicacid
    • G74060
    • SCHEMBL16268981
    • DS-021694
    • 1368466-66-3
    • CS-0527854
    • EN300-317750
    • 1-Cyclopropyl-1H-imidazole-4-carboxylic acid
    • MDL: MFCD07376045
    • Inchi: 1S/C7H8N2O2/c10-7(11)6-3-9(4-8-6)5-1-2-5/h3-5H,1-2H2,(H,10,11)
    • InChI Key: QAIVKRZQVRDEPE-UHFFFAOYSA-N
    • SMILES: OC(C1=CN(C=N1)C1CC1)=O

Computed Properties

  • Exact Mass: 152.058577502g/mol
  • Monoisotopic Mass: 152.058577502g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 179
  • 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
  • Topological Polar Surface Area: 55.1
  • XLogP3: 0.3

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Additional information on 1-Cyclopropyl-1H-imidazole-4-carboxylic acid

Introduction to 1-Cyclopropyl-1H-imidazole-4-carboxylic acid (CAS No. 1368466-66-3)

1-Cyclopropyl-1H-imidazole-4-carboxylic acid, identified by its Chemical Abstracts Service (CAS) number 1368466-66-3, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology. This compound belongs to the imidazole class, a structural motif widely recognized for its biological activity and versatility in drug design. The presence of a cyclopropyl substituent at the 1-position of the imidazole ring introduces unique electronic and steric properties, making it a valuable scaffold for developing novel therapeutic agents.

The 1-cyclopropyl-1H-imidazole-4-carboxylic acid structure is characterized by a five-membered aromatic ring containing two nitrogen atoms, with a carboxylic acid functional group at the 4-position and a cyclopropyl group attached to the 1-position. This configuration imparts distinct physicochemical properties, including solubility, stability, and metabolic profiles, which are critical factors in drug development. The cyclopropyl group, in particular, is known to enhance binding affinity and selectivity by introducing steric hindrance and modulating electronic distributions.

In recent years, there has been a surge in research focused on imidazole derivatives due to their broad spectrum of biological activities. 1-Cyclopropyl-1H-imidazole-4-carboxylic acid has been investigated for its potential in various pharmacological applications, including antimicrobial, anti-inflammatory, and anticancer therapies. The carboxylic acid moiety at the 4-position provides a reactive site for further functionalization, enabling the synthesis of more complex derivatives with tailored biological properties.

One of the most compelling aspects of 1-cyclopropyl-1H-imidazole-4-carboxylic acid is its role as a key intermediate in the synthesis of biologically active molecules. Researchers have leveraged this scaffold to develop inhibitors targeting enzymes involved in critical metabolic pathways. For instance, studies have demonstrated its utility in generating compounds that modulate the activity of poly(ADP-ribose) polymerases (PARPs), which are implicated in DNA repair and inflammation. The cyclopropyl group has been shown to enhance binding interactions with target proteins, leading to improved efficacy and selectivity.

The pharmaceutical industry has shown particular interest in 1-cyclopropyl-1H-imidazole-4-carboxylic acid due to its potential as a lead compound for drug discovery. Its structural features make it an ideal candidate for further derivatization, allowing chemists to explore diverse chemical spaces while maintaining core pharmacophoric elements. This flexibility has enabled the development of novel analogs with enhanced pharmacokinetic profiles and reduced side effects.

Recent advancements in computational chemistry have further accelerated the exploration of 1-cyclopropyl-1H-imidazole-4-carboxylic acid derivatives. Molecular docking studies have identified promising scaffolds for drug development by predicting binding affinities and interactions with biological targets. These computational approaches have complemented experimental efforts, providing insights into structure-activity relationships that guide rational drug design.

In clinical settings, 1-cyclopropyl-1H-imidazole-4-carboxylic acid derivatives have been evaluated in preclinical models for their therapeutic potential. Preliminary results suggest that certain analogs exhibit significant efficacy against cancer cell lines by inhibiting key signaling pathways involved in tumor growth and progression. Additionally, their ability to modulate inflammatory responses has opened avenues for treating chronic inflammatory diseases.

The synthesis of 1-cyclopropyl-1H-imidazole-4-carboxylic acid involves multi-step organic transformations that highlight its synthetic accessibility. Modern synthetic methodologies have improved yields and purity levels, making it feasible to produce sufficient quantities for both research and commercial purposes. Advances in green chemistry principles have also been applied to optimize synthetic routes, reducing environmental impact while maintaining efficiency.

The future prospects of 1-cyclopropyl-1H-imidazole-4-carboxylic acid are promising, with ongoing research aimed at expanding its therapeutic applications. Collaborative efforts between academia and industry are expected to yield innovative drug candidates based on this scaffold. As computational tools continue to evolve, the discovery of new derivatives will likely accelerate, further solidifying its importance in medicinal chemistry.

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