Cas no 72401-54-8 (6-Methoxydihydrosanguinarine)

6-Methoxydihydrosanguinarine is a benzophenanthridine alkaloid derivative known for its potential biological activities, including antimicrobial and anti-inflammatory properties. This compound is structurally related to sanguinarine, with a methoxy substitution at the 6-position, which may influence its reactivity and pharmacological profile. It is of interest in biochemical and pharmaceutical research due to its potential interactions with cellular targets, such as enzyme inhibition or DNA binding. The compound's stability and solubility characteristics make it suitable for experimental studies in medicinal chemistry. Researchers value 6-Methoxydihydrosanguinarine for its role in exploring structure-activity relationships within the benzophenanthridine class.
6-Methoxydihydrosanguinarine structure
6-Methoxydihydrosanguinarine structure
Product Name:6-Methoxydihydrosanguinarine
CAS No:72401-54-8
MF:C21H17NO5
MW:363.363385915756
CID:2054806
PubChem ID:14847270
Update Time:2025-06-10

6-Methoxydihydrosanguinarine Chemical and Physical Properties

Names and Identifiers

    • 14-methoxy-13-methyl-13,14-dihydro-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
    • 14-Methoxydihydrosanguinarin
    • 6-methoxy-5,6-dihydrosanguinarine
    • 6-methoxydihydrosanguinarine
    • 8-Methoxydihydrosanguinarin
    • 8-methoxydihydrosanguinarine
    • O-methyl-sanguinarine
    • CS-0022888
    • (-)-14-Methoxy-13-methyl-13,14-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine
    • [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine, 13,14-dihydro-14-methoxy-13-methyl-
    • AKOS030524962
    • 6-Methoxydihydrosanguinarine72401-54-8
    • PD166537
    • CHEMBL4171637
    • 23-methoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene
    • 6-methoxydihydro-sanguinarine
    • MS-25777
    • 72401-54-8
    • BDBM50286635
    • HY-N3000
    • (-)-Sanguinarine pseudomethanolate
    • 23-methoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0(2),(1)?.0?,?.0(1)?,(2)(2).0(1)?,(2)(1)]tetracosa-1(13),2,4(8),9,11,14,16,21-octaene
    • G60998
    • DA-60526
    • XCA40154
    • 6-Methoxydihydrosanguinarine
    • Inchi: 1S/C21H17NO5/c1-22-19-13(4-3-11-7-16-17(8-14(11)19)26-9-25-16)12-5-6-15-20(27-10-24-15)18(12)21(22)23-2/h3-8,21H,9-10H2,1-2H3
    • InChI Key: MHPDDMNAUJQRSW-UHFFFAOYSA-N
    • SMILES: O(C)C1C2=C3C(=CC=C2C2C=CC4C=C5C(=CC=4C=2N1C)OCO5)OCO3

Computed Properties

  • Exact Mass: 363.11067264 g/mol
  • Monoisotopic Mass: 363.11067264 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 1
  • Complexity: 575
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 363.4
  • XLogP3: 4.1
  • Topological Polar Surface Area: 49.4?2

Experimental Properties

  • Color/Form: Powder

6-Methoxydihydrosanguinarine Security Information

6-Methoxydihydrosanguinarine Pricemore >>

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Additional information on 6-Methoxydihydrosanguinarine

Recent Advances in the Study of 6-Methoxydihydrosanguinarine (CAS: 72401-54-8)

6-Methoxydihydrosanguinarine (CAS: 72401-54-8), a derivative of the benzophenanthridine alkaloid family, has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, known for its unique structural and pharmacological properties, has been the subject of numerous studies aimed at exploring its potential therapeutic applications. The following research brief synthesizes the latest findings on 6-Methoxydihydrosanguinarine, focusing on its biological activities, mechanisms of action, and potential clinical implications.

Recent studies have highlighted the compound's promising anticancer properties. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that 6-Methoxydihydrosanguinarine exhibits potent cytotoxic effects against a range of cancer cell lines, including breast, lung, and colon cancers. The researchers employed a combination of in vitro assays and molecular docking simulations to elucidate the compound's interaction with key cellular targets, such as topoisomerase II and the PI3K/AKT signaling pathway. These findings suggest that 6-Methoxydihydrosanguinarine may serve as a lead compound for the development of novel anticancer agents.

In addition to its anticancer potential, 6-Methoxydihydrosanguinarine has also been investigated for its anti-inflammatory and antimicrobial activities. A recent study in the European Journal of Pharmacology (2024) reported that the compound significantly reduces the production of pro-inflammatory cytokines, such as TNF-α and IL-6, in macrophage cells. Furthermore, the study revealed that 6-Methoxydihydrosanguinarine exhibits broad-spectrum antimicrobial activity against both Gram-positive and Gram-negative bacteria, including drug-resistant strains. These findings underscore the compound's potential as a multi-target therapeutic agent.

The pharmacokinetic profile of 6-Methoxydihydrosanguinarine has also been a focus of recent research. A 2024 study published in Drug Metabolism and Disposition utilized advanced LC-MS/MS techniques to characterize the compound's absorption, distribution, metabolism, and excretion (ADME) properties in rodent models. The results indicated that 6-Methoxydihydrosanguinarine has favorable bioavailability and a relatively long half-life, making it a viable candidate for further drug development. However, the study also identified potential metabolic pathways that could lead to the formation of reactive metabolites, highlighting the need for further optimization to improve safety profiles.

Despite these promising findings, challenges remain in the clinical translation of 6-Methoxydihydrosanguinarine. Issues such as solubility, stability, and potential off-target effects need to be addressed through structural modifications and formulation strategies. Recent advances in nanotechnology-based drug delivery systems, as reported in a 2023 study in the International Journal of Pharmaceutics, offer potential solutions to these challenges. The study demonstrated that encapsulating 6-Methoxydihydrosanguinarine in polymeric nanoparticles significantly enhances its solubility and targeted delivery to tumor tissues.

In conclusion, 6-Methoxydihydrosanguinarine (CAS: 72401-54-8) represents a promising candidate for the development of novel therapeutic agents with diverse pharmacological activities. Ongoing research efforts are focused on optimizing its chemical structure, improving its pharmacokinetic properties, and exploring its potential in combination therapies. As the scientific community continues to unravel the molecular mechanisms underlying its biological effects, 6-Methoxydihydrosanguinarine is poised to play a significant role in the future of chemical biology and pharmaceutical innovation.

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