Cas no 660837-08-1 (6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine)

6-Methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine is a heterocyclic organic compound featuring a thiazole core linked to a pyridine and benzene ring system. Its structure incorporates multiple nitrogen-containing functional groups, enhancing its potential as an intermediate in pharmaceutical and agrochemical synthesis. The compound's rigid aromatic framework and electron-rich heterocycles contribute to its utility in coordination chemistry and as a ligand in catalytic applications. Its well-defined molecular architecture allows for precise modifications, making it valuable in drug discovery for targeting specific biological pathways. The presence of both thiazole and pyridine moieties may confer favorable binding properties in medicinal chemistry applications.
6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine structure
660837-08-1 structure
Product Name:6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine
CAS No:660837-08-1
MF:C15H14N4S
MW:282.363461017609
MDL:MFCD12405578
CID:2621190
PubChem ID:44249598
Update Time:2025-06-22

6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine Chemical and Physical Properties

Names and Identifiers

    • 4-methyl-N3-[4-(3-pyridyl)thiazol-2-yl]benzene-1,3-diamine
    • 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine
    • JKQOCRHWVAAVFB-UHFFFAOYSA-N
    • 6-methyl-N1-(4-(pyridin-3-yl)thiazol-2-yl)benzene-1,3-diamine
    • 4-Methyl-N3-(4-pyridin-3-yl-thiazol-2-yl)-benzene-1,3-diamine
    • SCHEMBL1096303
    • 660837-08-1
    • C15H14N4S
    • 6-Methyl-N1-[4-(3-pyridyl)-2-thiazolyl]-1,3-benzenediamine
    • SB17885
    • MFCD12405578
    • 4-Methyl-N3-[4-(3-pyridinyl)-2-thiazolyl]-1,3-benzenediamine dihydrochloride
    • 4-methyl-3-N-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzene-1,3-diamine
    • BS-52029
    • 4-methyl-N'-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzene-1,3-diamine
    • 2-(2-methyl-5-aminophenylamino)-4-(3-pyridyl)thiazole
    • 1143459-92-0
    • 6-METHYL-N1-[4-(PYRIDIN-3-YL)-1,3-THIAZOL-2-YL]BENZENE-1,3-DIAMINE
    • SY233448
    • DB-216338
    • EN300-18774872
    • NS00003899
    • MDL: MFCD12405578
    • Inchi: 1S/C15H14N4S/c1-10-4-5-12(16)7-13(10)18-15-19-14(9-20-15)11-3-2-6-17-8-11/h2-9H,16H2,1H3,(H,18,19)
    • InChI Key: JKQOCRHWVAAVFB-UHFFFAOYSA-N
    • SMILES: S1C=C(C2C=NC=CC=2)N=C1NC1C=C(C=CC=1C)N

Computed Properties

  • Exact Mass: 282.09391764g/mol
  • Monoisotopic Mass: 282.09391764g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 2
  • Complexity: 314
  • 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: 3.1
  • Topological Polar Surface Area: 92.1?2

6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine Pricemore >>

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Additional information on 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine

Introduction to 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine (CAS No. 660837-08-1)

6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine, with the CAS number 660837-08-1, is a novel compound that has garnered significant attention in the field of medicinal chemistry due to its potential therapeutic applications. This compound belongs to the class of thiazoles and is characterized by its unique structural features, which include a thiazole ring, a pyridine moiety, and a benzene ring substituted with methyl and diamine groups. The combination of these functional groups imparts distinct chemical and biological properties, making it a promising candidate for various pharmacological studies.

The synthesis of 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine involves several well-defined steps. Typically, the synthesis begins with the formation of the thiazole ring through a condensation reaction between a thiourea derivative and an appropriate aldehyde or ketone. Subsequently, the pyridine moiety is introduced via a coupling reaction, often using palladium-catalyzed cross-coupling techniques such as the Suzuki-Miyaura or Sonogashira coupling. The final step involves the introduction of the diamine functionality through amination reactions. The precise synthetic route can vary depending on the specific starting materials and reaction conditions employed.

Recent studies have highlighted the potential of 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine in various biological contexts. One notable area of research is its anti-inflammatory properties. In vitro studies have shown that this compound can effectively inhibit the production of pro-inflammatory cytokines such as TNF-alpha and IL-6 in lipopolysaccharide (LPS)-stimulated macrophages. This suggests that it may have therapeutic potential in treating inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

In addition to its anti-inflammatory effects, 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine has also been investigated for its anticancer properties. Preclinical studies have demonstrated that this compound can induce apoptosis in various cancer cell lines, including those derived from breast cancer and colon cancer. The mechanism of action appears to involve the modulation of key signaling pathways such as p53 and Bcl-2. These findings suggest that this compound could be a valuable lead for developing new anticancer agents.

The pharmacokinetic profile of 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine has also been studied to assess its suitability for clinical development. In animal models, this compound exhibits good oral bioavailability and favorable pharmacokinetic parameters such as half-life and clearance rate. These properties are crucial for ensuring that the drug can be effectively delivered to target tissues and maintain therapeutic concentrations over an extended period.

To further validate its therapeutic potential, clinical trials are currently underway to evaluate the safety and efficacy of 6-methyl-N1-4-(pyridin-3-yl)-1,3-thiazol-2-ylbenzene-1,3-diamine. Early-phase trials have shown promising results, with no significant adverse effects reported at therapeutic doses. These findings provide a strong foundation for advancing this compound into later-stage clinical trials.

In conclusion, 6-methyl-N1-4-(pyridin-3-y l)-1 , 3 -thiazo l - 2 - y l b en z ene - 1 , 3 - d iami ne (CAS No . 6 608 37 - 08 - 1) is a promising compound with diverse biological activities. Its anti-inflammatory and anticancer properties make it an attractive candidate for further development in medicinal chemistry. Ongoing research and clinical trials will continue to elucidate its full therapeutic potential and pave the way for its potential use in treating various diseases.

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