Cas no 33289-49-5 (6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid)

6-Bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid is a heterocyclic compound featuring a quinoline core substituted with a bromo group at the 6-position and a thiophene moiety at the 2-position, along with a carboxylic acid functionality at the 4-position. This structure imparts versatility in synthetic applications, particularly as a building block for pharmaceuticals, agrochemicals, and materials science. The bromo group enhances reactivity for further functionalization via cross-coupling reactions, while the thiophene and carboxylic acid groups offer additional sites for derivatization. Its well-defined molecular architecture makes it valuable for designing biologically active compounds or functional materials with tailored properties. Suitable for research and industrial applications requiring precise molecular modifications.
6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid structure
33289-49-5 structure
Product Name:6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid
CAS No:33289-49-5
MF:C14H8BrNO2S
MW:334.187821388245
MDL:MFCD00178255
CID:917796
PubChem ID:755656
Update Time:2025-06-12

6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 6-BROMO-2-THIOPHEN-2-YL-QUINOLINE-4-CARBOXYLIC ACID
    • 6-bromo-2-(2-thienyl)-4-Quinolinecarboxylic acid
    • 6-bromo-2-thiophen-2-ylquinoline-4-carboxylic acid
    • 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid
    • 6-Bromo-2-thiophen-2-yl-quinoline-4-carboxylicacid
    • SMR000567820
    • CS-0271004
    • STK409471
    • 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylicacid
    • TimTec1_006743
    • 6-bromo-2-(2-thienyl)quinoline-4-carboxylic acid
    • SB72922
    • SR-01000635839-4
    • SR-01000635839
    • MLS001182077
    • HMS1553C11
    • J-019132
    • DB-068800
    • cid_755656
    • SR-01000635839-1
    • DTXSID90353850
    • 6-bromo-2-(2-thienyl)cinchoninic acid
    • 6-bromanyl-2-thiophen-2-yl-quinoline-4-carboxylic acid
    • CCG-46122
    • 6-bromo-2-thien-2-ylquinoline-4-carboxylic acid
    • A821713
    • AKOS000600457
    • CHEMBL450135
    • 33289-49-5
    • EN300-86815
    • BDBM66192
    • 6-bromo-2-thiophen-2-yl-4-quinolinecarboxylic acid
    • ALBB-035142
    • AG-690/12868818
    • MDL： MFCD00178255
    • Inchi： 1S/C14H8BrNO2S/c15-8-3-4-11-9(6-8)10(14(17)18)7-12(16-11)13-2-1-5-19-13/h1-7H,(H,17,18)
    • InChI Key： KYHKYEUYJZTRCP-UHFFFAOYSA-N
    • SMILES： BrC1C=CC2C(C=1)=C(C(=O)O)C=C(C1=CC=CS1)N=2

Computed Properties

  • Exact Mass: 332.94591g/mol
  • Monoisotopic Mass: 332.94591g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 2
  • Complexity: 354
  • 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: 3.8
  • Topological Polar Surface Area: 78.4?2

6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid Pricemore >>

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6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid Related Literature

Additional information on 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid

Research Brief on 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid (CAS: 33289-49-5)

In recent years, the compound 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid (CAS: 33289-49-5) has garnered significant attention in the field of chemical biology and medicinal chemistry. This quinoline derivative has shown promising potential in various therapeutic applications, particularly in the development of novel kinase inhibitors and antimicrobial agents. The unique structural features of this compound, including the bromo-substituted quinoline core and the thiophene moiety, contribute to its diverse biological activities and make it a valuable scaffold for drug discovery.

Recent studies have focused on the synthesis and optimization of 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid derivatives to enhance their pharmacological properties. A study published in the Journal of Medicinal Chemistry (2023) demonstrated that this compound exhibits potent inhibitory activity against several protein kinases, including EGFR and VEGFR-2, which are critical targets in cancer therapy. The researchers utilized structure-activity relationship (SAR) analysis to identify key modifications that improve both potency and selectivity, paving the way for the development of next-generation kinase inhibitors.

Another significant area of research involves the antimicrobial properties of 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid. A recent publication in Bioorganic & Medicinal Chemistry Letters (2024) highlighted its efficacy against drug-resistant bacterial strains, such as methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum β-lactamase (ESBL)-producing Escherichia coli. The study revealed that the compound disrupts bacterial cell membrane integrity and inhibits essential enzymatic pathways, offering a dual mechanism of action that could mitigate resistance development.

In addition to its therapeutic potential, 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid has also been explored as a fluorescent probe for bioimaging applications. A 2023 study in Analytical Chemistry demonstrated its utility in visualizing cellular processes due to its high quantum yield and photostability. This application underscores the versatility of the compound beyond traditional drug development, opening new avenues for diagnostic and research tools.

Despite these advancements, challenges remain in the clinical translation of 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid-based therapeutics. Issues such as bioavailability, metabolic stability, and off-target effects need to be addressed through further preclinical studies. However, the growing body of research supports its potential as a multifunctional agent in chemical biology and medicine. Future directions may include the development of prodrug formulations and combination therapies to maximize its therapeutic efficacy.

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