Cas no 28599-72-6 (4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine)

4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine structure
28599-72-6 structure
Product Name:4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine
CAS No:28599-72-6
MF:C14H20N2S
MW:248.387001991272
CID:290350
PubChem ID:2836061
Update Time:2025-11-02

4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine Chemical and Physical Properties

Names and Identifiers

    • 2-Thiazolamine,4-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-
    • 4-(1-adamantylmethyl)-1,3-thiazol-2-amine
    • 4-ADAMANTAN-1-YLMETHYL-THIAZOL-2-YLAMINE
    • 2-Thiazolamine, 4-(tricyclo[3.3.1.1~3,7~]dec-1-ylmethyl)-
    • 4-(Adamantan-1-ylmethyl)-1,3-thiazol-2-amine
    • 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine
    • VU0009333-2
    • 2-Thiazolamine, 4-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-
    • EN300-02564
    • 4-[(ADAMANTAN-1-YL)METHYL]-1,3-THIAZOL-2-AMINE
    • 4-(Adamantan-1-ylmethyl)thiazol-2-amine
    • AKOS000122077
    • SR-01000395774
    • Z57228830
    • SR-01000395774-1
    • F0451-0857
    • 28599-72-6
    • DTXSID40385469
    • Oprea1_014968
    • G47045
    • STK836430
    • 4-(tricyclo[3.3.1.1~3,7~]dec-1-ylmethyl)-1,3-thiazol-2-amine
    • Inchi: 1S/C14H20N2S/c15-13-16-12(8-17-13)7-14-4-9-1-10(5-14)3-11(2-9)6-14/h8-11H,1-7H2,(H2,15,16)
    • InChI Key: LANJJRUDAXCWPQ-UHFFFAOYSA-N
    • SMILES: S1C(N)=NC(=C1)CC12CC3CC(CC(C3)C1)C2

Computed Properties

  • Exact Mass: 248.1349
  • Monoisotopic Mass: 248.134719
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 276
  • 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: 4.4
  • Topological Polar Surface Area: 67.2

Experimental Properties

  • Density: 1.257
  • Boiling Point: 396.4°Cat760mmHg
  • Flash Point: 193.5°C
  • Refractive Index: 1.649
  • PSA: 38.91

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4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine Related Literature

Additional information on 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine

Introduction to 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine (CAS No. 28599-72-6)

4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine, identified by the Chemical Abstracts Service Number (CAS No.) 28599-72-6, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the thiazole derivatives, a class of heterocyclic compounds known for their diverse biological activities and potential therapeutic applications. The structural uniqueness of 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine arises from the combination of an adamantanyl moiety with a thiazole ring, which imparts distinct chemical and pharmacological properties that make it a valuable scaffold for drug discovery and development.

The adamantan-1-yl group, characterized by its rigid, spherical structure, contributes to the compound's stability and lipophilicity, enhancing its ability to cross biological membranes. This feature is particularly advantageous in drug design, as it can improve oral bioavailability and target specificity. The thiazole ring, on the other hand, is a well-known pharmacophore found in numerous bioactive molecules, including antibiotics, antifungals, and anti-inflammatory agents. The presence of the 1,3-thiazol-2-amine moiety introduces a basic nitrogen atom, which can participate in hydrogen bonding interactions with biological targets, further influencing the compound's binding affinity and selectivity.

In recent years, there has been growing interest in exploring the pharmacological potential of 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine and its derivatives. Researchers have been investigating its role in various therapeutic contexts, including anti-inflammatory, anticancer, and antimicrobial applications. Preliminary studies suggest that this compound may exhibit inhibitory effects on certain enzymes and receptors involved in disease pathways. For instance, its structural framework could mimic natural substrates or modulate the activity of key enzymes such as kinases or proteases.

The rigid structure provided by the adamantanyl group also makes 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine a promising candidate for designing molecules with enhanced binding stability to biological targets. This property is particularly relevant in the development of small-molecule inhibitors for therapeutic purposes. Additionally, the thiazole ring's ability to engage in redox reactions adds another layer of complexity to its potential biological functions. Thiazole derivatives are known to participate in various metabolic processes and can act as intermediates in enzymatic reactions.

Recent advancements in computational chemistry and molecular modeling have facilitated a deeper understanding of the interactions between 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine and biological targets. These studies have helped identify key binding pockets and residues that could be optimized to improve drug efficacy and reduce off-target effects. The integration of experimental data with computational predictions has allowed researchers to design more sophisticated derivatives with tailored pharmacological profiles.

The synthesis of 4-(adamantan-1-yl)methyl-1,3-thiazol-2-amine involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include nucleophilic substitution reactions followed by functional group transformations to introduce the desired substituents. The use of advanced catalytic systems has also been explored to enhance reaction efficiency and selectivity. Given its structural complexity, the synthesis may pose challenges but also offers opportunities for innovation in synthetic methodology.

From a medicinal chemistry perspective, 4-(adamantan-1-ylmethyl)-1H-thiazole[2′a:3′c]adamantane (CAS No. 28599–72–6) represents an intriguing example of how structural modifications can influence biological activity. The combination of the adamantine core with the thiazole scaffold creates a molecule with unique physicochemical properties that could be leveraged for developing novel therapeutics. Further exploration of its pharmacokinetic behavior and toxicological profile will be essential to assess its potential as a lead compound or intermediate in drug development pipelines.

The growing body of research on thiazole derivatives underscores their significance in modern drug discovery. Compounds like 4-(adamantan-methyl)-thiazolo[5′d][1]benzazepine (CAS No 28599–72–6) continue to inspire new synthetic strategies and pharmacological investigations. As our understanding of disease mechanisms evolves, so does the need for innovative molecular tools to address unmet medical needs. The versatility of 4-(adamantan-methyl)-thiazeno[5′d][1]benzazepine (CAS No 28599–72–6) makes it a valuable asset in this ongoing quest.

In conclusion,4-(adamantan-methyl)-thiazeno[5′d][1]benzazepine (CAS No 28599–72–6) is a structurally unique compound with promising applications in pharmaceutical research. Its combination of an adamantine moiety with a thiazole ring endows it with distinctive chemical properties that make it a compelling candidate for further exploration. As scientific methodologies advance,the potential uses for such specialized molecules will continue to expand,offering new hope for therapeutic breakthroughs across various medical disciplines。

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