Cas no 32294-42-1 (1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea)

1-(6-Methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea is a thiourea derivative featuring a methoxy-substituted benzothiazole core linked to a phenyl group via a thiourea bridge. This compound exhibits potential as a versatile intermediate in organic synthesis, particularly in the development of heterocyclic compounds with biological or pharmacological relevance. The benzothiazole moiety contributes to its stability and electronic properties, while the thiourea linkage offers reactivity for further functionalization. Its structural features make it suitable for applications in medicinal chemistry, such as enzyme inhibition or ligand design, due to its ability to engage in hydrogen bonding and π-stacking interactions. The methoxy group enhances solubility and modulates electronic effects, broadening its utility in synthetic pathways.
1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea structure
32294-42-1 structure
Product Name:1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea
CAS No:32294-42-1
MF:C15H13N3OS2
MW:315.41322016716
CID:1094214
PubChem ID:12511739
Update Time:2025-11-03

1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea Chemical and Physical Properties

Names and Identifiers

    • 1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea
    • 1-(6-methoxy-1,3-benzothiazol-2-yl)-3-phenylthiourea
    • CHEMBL213323
    • 32294-42-1
    • SCHEMBL10807219
    • 3-(6-METHOXY-1,3-BENZOTHIAZOL-2-YL)-1-PHENYLTHIOUREA
    • Oprea1_858509
    • Inchi： 1S/C15H13N3OS2/c1-19-11-7-8-12-13(9-11)21-15(17-12)18-14(20)16-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,20)
    • InChI Key： ISKMJDPVLAPPEY-UHFFFAOYSA-N
    • SMILES： S1C(NC(NC2C=CC=CC=2)=S)=NC2C=CC(=CC1=2)OC

Computed Properties

  • Exact Mass: 315.05019
  • Monoisotopic Mass: 315.05000439g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 5
  • Complexity: 363
  • 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: 107?2

Experimental Properties

  • PSA: 46.18

1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
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1-(6-Methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea
 32294-42-1 95%
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Chemenu
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SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
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1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea Related Literature

Additional information on 1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea

Research Briefing on 1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea (CAS: 32294-42-1)

The compound 1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea (CAS: 32294-42-1) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential therapeutic applications. This briefing synthesizes the latest research findings on this compound, focusing on its synthesis, biological activity, and mechanistic insights.

Recent studies have highlighted the role of 1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea as a promising scaffold for drug development, particularly in the context of kinase inhibition. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy as a selective inhibitor of cyclin-dependent kinases (CDKs), which are critical targets in cancer therapy. The compound exhibited nanomolar potency against CDK2 and CDK9, with favorable selectivity profiles over other kinases.

Structural analyses revealed that the methoxybenzo[d]thiazole moiety of the compound plays a crucial role in binding to the ATP-binding pocket of CDKs, while the phenylthiourea group enhances hydrophobic interactions with the kinase domain. Molecular dynamics simulations further supported these findings, showing stable binding conformations in silico.

In addition to its kinase inhibitory properties, recent preclinical studies have explored the compound's potential in neurodegenerative diseases. A 2024 study in ACS Chemical Neuroscience reported that 1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea could modulate tau protein aggregation, a hallmark of Alzheimer's disease, through a unique mechanism involving thiol-disulfide exchange.

The compound's pharmacokinetic properties have also been investigated. A recent ADMET study published in European Journal of Pharmaceutical Sciences (2024) showed acceptable oral bioavailability and blood-brain barrier penetration in rodent models, though with some limitations in metabolic stability that may require further structural optimization.

Ongoing research is exploring structure-activity relationships (SAR) around this scaffold, with particular focus on modifications to the phenyl and methoxy groups to enhance potency and selectivity. Several patent applications filed in 2023-2024 suggest growing commercial interest in derivatives of this compound for various therapeutic indications.

In conclusion, 1-(6-methoxybenzo[d]thiazol-2-yl)-3-phenylthiourea represents a versatile chemical scaffold with demonstrated activity against multiple disease-relevant targets. While challenges remain in optimizing its drug-like properties, the compound continues to serve as a valuable tool for understanding disease mechanisms and as a starting point for drug discovery programs.

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