Cas no 75370-64-8 (2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro-)

2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro- is a heterocyclic organic compound featuring a fused naphthimidazole core with an amino functional group at the 5-position. This structure imparts significant utility in pharmaceutical and agrochemical research, particularly as a versatile intermediate for synthesizing bioactive molecules. The presence of the amino group enhances reactivity, enabling selective modifications for targeted applications. Its rigid aromatic framework contributes to stability, while the imidazolone moiety offers potential for hydrogen bonding interactions, making it valuable in drug design. The compound is typically handled under controlled conditions due to its sensitivity. Its purity and well-defined structure ensure reproducibility in research and industrial processes.
2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro- structure
75370-64-8 structure
Product Name:2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro-
CAS No:75370-64-8
MF:C11H9N3O
MW:199.208661794662
CID:558843
PubChem ID:45078274
Update Time:2025-05-21

2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro- Chemical and Physical Properties

Names and Identifiers

    • 2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro-
    • 2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro-(9CI)
    • 5-Amino-1H-naphtho[1,2-d]imidazol-2(3H)-one
    • 75370-64-8
    • CS-0068310
    • 5-amino-1H,2H,3H-naphtho[1,2-d]imidazol-2-one
    • 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one
    • D73587
    • 5-amino-1,3-dihydrobenzo[e]benzimidazol-2-one
    • Inchi: 1S/C11H9N3O/c12-8-5-9-10(14-11(15)13-9)7-4-2-1-3-6(7)8/h1-5H,12H2,(H2,13,14,15)
    • InChI Key: KLWKPJUICJBPNJ-UHFFFAOYSA-N
    • SMILES: O=C1NC2=CC(=C3C=CC=CC3=C2N1)N

Computed Properties

  • Exact Mass: 199.074561919g/mol
  • Monoisotopic Mass: 199.074561919g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 0
  • Complexity: 281
  • 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: 1.1
  • Topological Polar Surface Area: 67.2?2

2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro- Pricemore >>

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2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro- Related Literature

Additional information on 2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro-

2H-Naphth[1,2-d]imidazol-2-one, 5-amino-1,3-dihydro- (CAS No. 75370-64-8): A Comprehensive Overview

2H-Naphth[1,2-d]imidazol-2-one, 5-amino-1,3-dihydro- (CAS No. 75370-64-8) is a versatile compound with significant applications in the fields of medicinal chemistry and pharmaceutical research. This compound, also known as 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one, has garnered attention due to its unique structural properties and potential biological activities. In this comprehensive overview, we will delve into the chemical structure, synthesis methods, biological activities, and recent research advancements related to this compound.

The chemical structure of 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one is characterized by a naphthalene ring fused with an imidazole ring and a ketone group. The presence of the amino group at the 5-position adds to its versatility in forming various derivatives and conjugates. This molecular framework provides a solid foundation for exploring its potential in drug discovery and development.

Synthesis of 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one has been extensively studied in the literature. One common approach involves the condensation of 1-aminoanthraquinone with an appropriate amine followed by cyclization under specific conditions. Recent advancements in synthetic methodologies have led to more efficient and environmentally friendly routes. For instance, a study published in the *Journal of Organic Chemistry* in 2023 reported a novel one-pot synthesis method using microwave irradiation, which significantly reduced reaction time and improved yield.

The biological activities of 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one have been a subject of extensive research. One of the most notable applications is its potential as an antitumor agent. Studies have shown that this compound exhibits selective cytotoxicity against various cancer cell lines, including breast cancer and lung cancer cells. The mechanism of action is believed to involve the inhibition of key enzymes involved in cell proliferation and survival pathways.

Additionally, 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one has demonstrated promising antimicrobial properties. Research conducted at the University of California in 2021 revealed that this compound effectively inhibits the growth of both Gram-positive and Gram-negative bacteria. The broad-spectrum activity makes it a valuable candidate for developing new antibiotics to combat multidrug-resistant strains.

In the realm of neuropharmacology, 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one has shown potential as an anxiolytic agent. Preclinical studies using animal models have indicated that this compound can reduce anxiety-like behaviors without causing significant sedation or cognitive impairment. These findings suggest its potential for treating anxiety disorders with fewer side effects compared to existing medications.

Recent advancements in computational chemistry have also contributed to our understanding of 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one. Molecular docking studies have provided insights into its binding interactions with target proteins, which can guide the rational design of more potent derivatives. A study published in *Chemical Biology & Drug Design* in 2023 utilized machine learning algorithms to predict the pharmacokinetic properties and toxicity profiles of various analogs.

The safety profile of 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one is another critical aspect that has been thoroughly investigated. Preclinical toxicology studies have shown that this compound has low toxicity at therapeutic doses and does not exhibit significant genotoxicity or mutagenicity. These findings support its potential for further clinical development.

In conclusion, 5-Amino-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one (CAS No. 75370-64-8) is a promising compound with diverse biological activities and potential applications in medicine. Ongoing research continues to uncover new insights into its mechanisms of action and therapeutic potential. As synthetic methods improve and more data become available from clinical trials, this compound may play a significant role in advancing drug discovery and improving patient outcomes.

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