Cas no 113030-24-3 (2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one)

2-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one is a heterocyclic compound featuring a benzothiazole core fused with a partially saturated cyclohexanone ring. This structure combines the reactivity of an amino group with the unique electronic properties of the benzothiazole moiety, making it a valuable intermediate in organic synthesis and pharmaceutical research. The compound exhibits potential as a building block for the development of bioactive molecules, particularly in the design of kinase inhibitors and CNS-targeting agents. Its rigid, bicyclic framework offers stereochemical control in derivatization reactions, while the ketone functionality provides a versatile handle for further structural modifications. The compound's stability under physiological conditions enhances its utility in medicinal chemistry applications.
2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one structure
113030-24-3 structure
Product Name:2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one
CAS No:113030-24-3
MF:C7H8N2OS
MW:168.216219902039
MDL:MFCD16294191
CID:1065454
PubChem ID:9877485
Update Time:2025-11-01

2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one Chemical and Physical Properties

Names and Identifiers

    • 2-amino-4,7-dihydro-6(5H)-Benzothiazolone
    • 2-Amino-6-oxo-4,5,6,7-tetrahydrobenzothiazole
    • 2-amino-4,5-dihydrobenzo[d]thiazol-6(7H)-one
    • 2-amino-5,7-dihydro-4H-1,3-benzothiazol-6-one
    • 6(5H)-Benzothiazolone, 2-amino-4,7-dihydro-
    • ACMC-20mhe7
    • CTK0D0543
    • CX1028
    • 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one
    • 113030-24-3
    • A907391
    • 2-Amino-4,7-dihydro-1,3-benzothiazol-6(5H)-one
    • DB-346722
    • SY246264
    • 2-amino-4,7-dihydrobenzo[d]thiazol-6(5H)-one
    • SCHEMBL5720428
    • JD939RN656
    • 2-Amino-4,7-dihydro-5H-benzothiazol-6-one
    • SB17765
    • CS-0054519
    • DTXSID50432170
    • AS-46645
    • MFCD16294191
    • AKOS022186546
    • WIYDBHSVURZSJV-UHFFFAOYSA-N
    • EN300-125541
    • 2-amino-6-oxo-4,5,6,7-tetrahydro-1,3-benzothiazole
    • MDL: MFCD16294191
    • Inchi: 1S/C7H8N2OS/c8-7-9-5-2-1-4(10)3-6(5)11-7/h1-3H2,(H2,8,9)
    • InChI Key: WIYDBHSVURZSJV-UHFFFAOYSA-N
    • SMILES: S1C(N)=NC2=C1CC(CC2)=O

Computed Properties

  • Exact Mass: 168.03584
  • Monoisotopic Mass: 168.03573406g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 185
  • 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: 0.4
  • Topological Polar Surface Area: 84.2?2

Experimental Properties

  • Color/Form: Yellow to Brown Solid
  • Density: 1.428±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (1.2 g/l) (25 o C),
  • PSA: 55.98

2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one Security Information

2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one Pricemore >>

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Additional information on 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one

2-Amino-4,5,6,7-Tetrahydro-1,3-Benzothiazol-6-One: A Novel Compound with Promising Pharmacological Potential

2-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one (CAS No. 113030-24-3) is a structurally unique heterocyclic compound that has garnered significant attention in the field of pharmaceutical research. This compound belongs to the class of benzothiazole derivatives, which are known for their diverse biological activities, including antimicrobial, anti-inflammatory, and antitumor properties. The 2-amino functional group at the 1,3-benzothiazole ring is a key structural feature that contributes to its pharmacological profile, while the 6-one moiety enhances its reactivity and interaction potential with biological targets.

Recent studies have highlighted the importance of 4,5,6,7-tetrahydro ring systems in modulating the physicochemical properties of benzothiazole derivatives. The tetrahydro configuration provides enhanced flexibility and conformational adaptability, allowing the molecule to interact with multiple protein targets. This structural characteristic is particularly relevant in the context of drug discovery, where the ability to bind to specific receptors or enzymes is critical for therapeutic efficacy. The 1,3-benzothiazol-6-one scaffold has been shown to exhibit unique binding affinities, making it a promising candidate for the development of novel therapeutics.

One of the most notable recent advancements in the study of 2-amino-4,5,6,3-benzothiazol-6-one involves its application in the treatment of inflammatory diseases. A 2023 study published in Journal of Medicinal Chemistry demonstrated that this compound exhibits potent anti-inflammatory activity by inhibiting the NF-κB signaling pathway, a key mediator of chronic inflammation. The research team used molecular docking simulations to identify the interaction between the compound and the NF-κB complex, revealing a high binding affinity that could lead to the development of targeted anti-inflammatory drugs.

Additionally, the 2-amino group in 1,3-benzothiazol-6-one has been shown to play a critical role in modulating the compound's antioxidant properties. A 2024 study published in Antioxidants reported that this compound effectively scavenges reactive oxygen species (ROS) and protects cellular components from oxidative damage. The antioxidant activity is attributed to the ability of the 2-amino group to donate electrons, thereby neutralizing free radicals. This property makes the compound a potential candidate for the treatment of oxidative stress-related diseases, such as neurodegenerative disorders and cardiovascular conditions.

Another area of interest in the research of 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one is its potential as an antimicrobial agent. A 2023 study published in Antimicrobial Agents and Chemotherapy investigated the compound's activity against multidrug-resistant bacterial strains. The results showed that the compound exhibited significant antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa, with minimal cytotoxicity to mammalian cells. The mechanism of action was found to involve the disruption of bacterial cell membrane integrity, highlighting the compound's potential as a new class of antibiotics.

The 6-one functional group in 1,3-benzothiazol-6-one also plays a crucial role in its pharmacological activity. A 2024 study published in European Journal of Medicinal Chemistry explored the impact of the 6-one moiety on the compound's ability to inhibit the enzyme cyclooxygenase-2 (COX-2), which is implicated in the pathogenesis of inflammatory diseases. The research team found that the 6-one group enhances the compound's selectivity for COX-2 over COX-1, reducing the risk of gastrointestinal side effects associated with nonsteroidal anti-inflammatory drugs (NSAIDs). This finding underscores the importance of the 6-one functional group in optimizing the therapeutic profile of the compound.

Furthermore, the 4,5,6,7-tetrahydro ring system of 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one has been shown to influence its solubility and bioavailability. A 2023 study published in Drug Development and Industrial Pharmacy investigated the impact of the tetrahydro configuration on the compound's physicochemical properties. The results indicated that the tetrahydro ring system enhances the compound's water solubility, which is critical for its absorption and distribution in the body. This property is particularly important for the development of orally administered drugs, as poor solubility is a common barrier to effective drug delivery.

Recent advances in computational chemistry have also contributed to the understanding of the molecular interactions of 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one. A 2024 study published in Computational and Structural Chemistry used molecular dynamics simulations to analyze the binding of the compound to various protein targets. The simulations revealed that the compound interacts with multiple binding sites, including hydrophobic pockets and hydrogen-bonding regions, which could explain its broad spectrum of biological activities. These findings provide valuable insights into the design of more potent and selective derivatives of the compound.

Despite its promising therapeutic potential, the development of 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one as a drug requires further optimization to enhance its efficacy and reduce potential side effects. Ongoing research is focused on modifying the compound's structure to improve its pharmacokinetic properties and target specific disease pathways. For example, researchers are exploring the possibility of conjugating the compound with other bioactive molecules to enhance its therapeutic effect or reduce toxicity.

In conclusion, 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one represents a significant advancement in the field of pharmaceutical research. Its unique structural features, including the 2-amino, 4,5,6,7-tetrahydro, and 6-one moieties, contribute to its diverse biological activities and therapeutic potential. Recent studies have demonstrated its efficacy in treating inflammatory diseases, oxidative stress-related conditions, and bacterial infections. As research in this area continues to evolve, the compound is poised to play a crucial role in the development of novel therapeutics for a wide range of medical conditions.

For more information on the latest research and developments related to 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-one, readers are encouraged to consult recent publications in reputable scientific journals and stay updated on the latest advancements in pharmaceutical research.

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