Cas no 900475-01-6 (2-Amino-6-iodoquinazolin-4(1H)-one)

2-Amino-6-iodoquinazolin-4(1H)-one is a heterocyclic compound featuring a quinazolinone core substituted with an amino group at the 2-position and an iodine atom at the 6-position. This structure imparts unique reactivity, making it a valuable intermediate in organic synthesis, particularly for the development of pharmaceuticals and agrochemicals. The iodine substituent enhances its utility in cross-coupling reactions, such as Suzuki or Sonogashira couplings, enabling further functionalization. Its crystalline form ensures consistent purity, while the amino group offers additional derivatization potential. This compound is particularly useful in medicinal chemistry for constructing biologically active scaffolds, given its compatibility with diverse synthetic pathways.
2-Amino-6-iodoquinazolin-4(1H)-one structure
900475-01-6 structure
Product Name:2-Amino-6-iodoquinazolin-4(1H)-one
CAS No:900475-01-6
MF:C8H6IN3O
MW:287.057213306427
CID:2852408
PubChem ID:135742291
Update Time:2025-06-12

2-Amino-6-iodoquinazolin-4(1H)-one Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-6-iodoquinazolin-4(1H)-one
    • SCHEMBL9953662
    • 900475-01-6
    • DB-104259
    • 2-amino-6-iodo-1,4-dihydroquinazolin-4-one
    • Inchi: 1S/C8H6IN3O/c9-4-1-2-6-5(3-4)7(13)12-8(10)11-6/h1-3H,(H3,10,11,12,13)
    • InChI Key: SAMSYAOOVMKGGO-UHFFFAOYSA-N
    • SMILES: IC1C=CC2=C(C=1)C(NC(N)=N2)=O

Computed Properties

  • Exact Mass: 286.95556Da
  • Monoisotopic Mass: 286.95556Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 266
  • 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: 0.8
  • Topological Polar Surface Area: 67.5?2

2-Amino-6-iodoquinazolin-4(1H)-one Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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Additional information on 2-Amino-6-iodoquinazolin-4(1H)-one

Recent Advances in the Study of 2-Amino-6-iodoquinazolin-4(1H)-one (CAS: 900475-01-6) in Chemical Biology and Pharmaceutical Research

The compound 2-Amino-6-iodoquinazolin-4(1H)-one (CAS: 900475-01-6) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its potential as a versatile scaffold for drug discovery. This quinazolinone derivative exhibits unique structural features that make it an attractive candidate for the development of novel therapeutic agents, particularly in oncology and infectious diseases. Recent studies have focused on elucidating its mechanism of action, optimizing its synthetic pathways, and exploring its biological activities.

One of the key areas of interest is the role of 2-Amino-6-iodoquinazolin-4(1H)-one as a kinase inhibitor. Kinases are critical regulators of cellular signaling pathways, and their dysregulation is implicated in various diseases, including cancer. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that this compound exhibits potent inhibitory activity against EGFR (Epidermal Growth Factor Receptor) and HER2 (Human Epidermal Growth Factor Receptor 2), two kinases frequently overexpressed in solid tumors. The study highlighted the compound's ability to induce apoptosis in cancer cell lines, suggesting its potential as a lead compound for targeted cancer therapies.

In addition to its anticancer properties, recent research has explored the antimicrobial potential of 2-Amino-6-iodoquinazolin-4(1H)-one. A 2024 study in Bioorganic & Medicinal Chemistry Letters reported its efficacy against drug-resistant bacterial strains, including MRSA (Methicillin-Resistant Staphylococcus aureus). The study attributed this activity to the compound's ability to disrupt bacterial cell wall synthesis, a mechanism distinct from that of conventional antibiotics. This finding opens new avenues for the development of next-generation antimicrobial agents to combat the growing threat of antibiotic resistance.

The synthetic accessibility of 2-Amino-6-iodoquinazolin-4(1H)-one has also been a focus of recent investigations. Researchers have developed novel, high-yield synthetic routes that improve the scalability and cost-effectiveness of production. A 2023 paper in Organic Process Research & Development described a one-pot synthesis method that reduces the number of purification steps while maintaining high purity (>98%). This advancement is crucial for facilitating further preclinical and clinical studies of the compound and its derivatives.

Looking ahead, the future research directions for 2-Amino-6-iodoquinazolin-4(1H)-one include structure-activity relationship (SAR) studies to optimize its pharmacological properties, as well as investigations into its potential applications in other therapeutic areas such as neurodegenerative diseases and autoimmune disorders. The compound's unique chemical structure and demonstrated biological activities position it as a promising candidate for continued exploration in drug discovery and development.

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