Cas no 49681-96-1 (6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one)

6-Bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one is a brominated quinazolinone derivative featuring a thioxo functional group at the 2-position. This heterocyclic compound is of interest in medicinal chemistry and organic synthesis due to its potential as a versatile intermediate for constructing pharmacologically active molecules. The bromine substituent enhances reactivity for further functionalization via cross-coupling reactions, while the thioxo and carbonyl groups offer sites for hydrogen bonding and metal coordination. Its rigid fused-ring structure contributes to stability, making it suitable for applications in drug discovery, particularly in the development of kinase inhibitors or antimicrobial agents. The compound's well-defined structure allows for precise modifications to optimize biological activity or material properties.
6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one structure
49681-96-1 structure
Product Name:6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
CAS No:49681-96-1
MF:C8H5BrN2OS
MW:257.107099294662
MDL:MFCD08706211
CID:860445
PubChem ID:840856
Update Time:2025-06-25

6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one Chemical and Physical Properties

Names and Identifiers

    • 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
    • 6-bromo-2-mercaptoquinazolin-4-ol
    • 6-bromo-2-sulfanylidene-1H-quinazolin-4-one
    • 4-oxo-2-tio-6-bromotetraidrochinazolina
    • 6-Bromo-2-mercapto-3H-quinazolin-4-one
    • 6-bromo-2-thioxo-2,3-dihydro-1H-quinazolin-4-one
    • 6-bromo-2-thioxo-4-quinazolone
    • 6-bromo-4-oxoquinazoline-2-thione
    • HZLUVUSKGFGJGS-UHFFFAOYSA
    • ZBA68196
    • 6-bromo-2-mercapto-quinazolin-4-ol
    • CS-0227465
    • AKOS022187836
    • 49681-96-1
    • W13341
    • AS-67786
    • DB-318014
    • SCHEMBL1396317
    • AKOS003232125
    • 6-bromo-2-mercaptoquinazolin-4(3H)-one
    • HZLUVUSKGFGJGS-UHFFFAOYSA-N
    • HZLUVUSKGFGJGS-UHFFFAOYSA-
    • DTXSID60357042
    • MFCD08706211
    • InChI=1/C8H5BrN2OS/c9-4-1-2-6-5(3-4)7(12)11-8(13)10-6/h1-3H,(H2,10,11,12,13)
    • 6-bromo-2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-one
    • MDL： MFCD08706211
    • Inchi： 1S/C8H5BrN2OS/c9-4-1-2-6-5(3-4)7(12)11-8(13)10-6/h1-3H,(H2,10,11,12,13)
    • InChI Key： HZLUVUSKGFGJGS-UHFFFAOYSA-N
    • SMILES： BrC1C=CC2=C(C=1)C(NC(N2)=S)=O

Computed Properties

  • Exact Mass: 255.93100
  • Monoisotopic Mass: 255.931
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 259
  • 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: 2.1
  • Topological Polar Surface Area: 73.2A^2

Experimental Properties

  • PSA: 80.74000
  • LogP: 2.34820

6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one Customs Data

  • HS CODE：2933990090
  • Customs Data：

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one Pricemore >>

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6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one Suppliers

Amadis Chemical Company Limited
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(CAS:49681-96-1)6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
Order Number:A1231223
Stock Status:in Stock
Quantity:25g/5g/1g/250mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 19:18
Price ($):2464/924/308/154

6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one Related Literature

Additional information on 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Introduction to 6-Bromo-2-Thioxo-2,3-Dihydroquinazolin-4(1H)-One (CAS No. 49681-96-1)

6-Bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one, with the CAS number 49681-96-1, is a significant compound in the field of medicinal chemistry and pharmaceutical research. This compound belongs to the class of quinazolinones, which are known for their diverse biological activities, including antitumor, anti-inflammatory, and antimicrobial properties. The presence of the bromine and thioxo functionalities in its structure makes it a valuable candidate for various therapeutic applications.

The chemical structure of 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one consists of a quinazoline ring system with a bromine atom at the 6-position and a thioxo group at the 2-position. The quinazoline scaffold is a privileged structure in medicinal chemistry due to its ability to interact with various biological targets. The bromine substitution enhances the lipophilicity and metabolic stability of the molecule, while the thioxo group contributes to its reactivity and biological activity.

Recent studies have highlighted the potential of 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one in cancer therapy. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that this compound exhibits potent antiproliferative activity against several human cancer cell lines, including breast, lung, and colon cancer cells. The mechanism of action involves the inhibition of key signaling pathways such as PI3K/AKT and MAPK, which are crucial for cell survival and proliferation.

In addition to its antitumor properties, 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one has been investigated for its anti-inflammatory effects. Research conducted by a team at the University of California showed that this compound effectively reduces inflammation in animal models of inflammatory diseases such as arthritis and colitis. The anti-inflammatory activity is attributed to its ability to inhibit pro-inflammatory cytokines and enzymes like COX-2 and iNOS.

The pharmacokinetic profile of 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one has also been studied extensively. It has been found to have good oral bioavailability and a favorable distribution profile, making it suitable for oral administration in therapeutic settings. Preclinical studies have demonstrated that this compound is well-tolerated at effective doses, with minimal toxicity observed in animal models.

In terms of synthetic accessibility, 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one can be synthesized through a series of well-established chemical reactions. One common approach involves the condensation of 5-bromoanthranilic acid with thiourea followed by cyclization under appropriate conditions. This synthetic route provides a scalable method for producing the compound in sufficient quantities for both research and development purposes.

The potential applications of 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one extend beyond cancer and inflammation. Recent studies have explored its use in neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. Preliminary findings suggest that this compound may have neuroprotective effects by modulating oxidative stress and preventing neuronal cell death.

In conclusion, 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (CAS No. 49681-96-1) is a promising compound with a wide range of biological activities. Its unique chemical structure and favorable pharmacological properties make it an attractive candidate for further development in various therapeutic areas. Ongoing research continues to uncover new insights into its mechanisms of action and potential clinical applications.

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Amadis Chemical Company Limited
(CAS:49681-96-1)6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
A1231223
Purity:99%/99%/99%/99%
Quantity:25g/5g/1g/250mg
Price ($):2464/924/308/154
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