Cas no 478-03-5 (1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium)
1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium Chemical and Physical Properties
Names and Identifiers
-
- Toddaline
- 1,2-Dimethoxy-12-methyl-[1,3]dioxolo-[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium
- Chelerythrine
- Broussonpapyrine
- Cheleritrine
- Chelerythrin
- Chelerythrin chlorid
- Chelerythrin-Kation
- Chelerythrinium hydroxide
- Helleritrine hydroxide
- Toddalin hydroxide
- Toddaline hydroxide
- Q27263891
- 478-03-5
- NSC-76023
- Chelerythrine hydroxide
- CHEMBL1971693
- NSC76023
- Chelerythrine aurichloride
- [1,6-c]phenanthridinium, 1,2-dimethoxy-12-methyl-, hydroxide
- 65ML87R6OI
- DTXSID60963940
- (1,3)Benzodioxolo(5,6-c)phenanthridinium, 1,2-dimethoxy-12-methyl-, hydroxide
- 1,2-Dimethoxy-12-methyl-9H-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium hydroxide
- SCHEMBL288916
- NSC 76023
- (1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDINIUM, 1,2-DIMETHOXY-12-METHYL-, HYDROXIDE (1:1)
- 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium;hydroxide
- UNII-65ML87R6OI
- 1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium
-
- Inchi: 1S/C21H18NO4.H2O/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22;/h4-10H,11H2,1-3H3;1H2/q+1;/p-1
- InChI Key: YZYNINHQZLUUAW-UHFFFAOYSA-M
- SMILES: O1COC2C1=CC1C(C=2)=CC=C2C3C=CC(=C(C=3C=[N+](C)C2=1)OC)OC.[OH-]
Computed Properties
- Exact Mass: 348.12400
- Monoisotopic Mass: 348.123583
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 4
- Heavy Atom Count: 26
- Rotatable Bond Count: 2
- Complexity: 516
- 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
- Topological Polar Surface Area: 40.8
Experimental Properties
- Density: 1.36
- Boiling Point: 711.4°Cat760mmHg
- Flash Point: 219.3°C
- PSA: 40.80000
- LogP: 3.71660
1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | D078995-50mg |
1,2-Dimethoxy-12-methyl-[1,3]dioxolo-[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium |
478-03-5 | 50mg |
$ 510.00 | 2022-06-06 | ||
| TRC | D078995-100mg |
1,2-Dimethoxy-12-methyl-[1,3]dioxolo-[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium |
478-03-5 | 100mg |
$ 850.00 | 2022-06-06 |
1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium Related Literature
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R. M. Pemberton,J. P. Hart,T. T. Mottram Analyst, 2001,126, 1866-1871
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Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao You Analyst, 2015,140, 1827-1831
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Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034
-
Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381
-
José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565
Additional information on 1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium
Recent Advances in the Study of 1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium (CAS: 478-03-5)
The compound 1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium (CAS: 478-03-5) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This alkaloid derivative, known for its complex polycyclic structure, exhibits promising biological activities, particularly in the context of anticancer and antimicrobial applications. Recent studies have focused on elucidating its mechanism of action, optimizing its synthesis, and exploring its therapeutic potential.
A 2023 study published in the Journal of Medicinal Chemistry investigated the compound's interaction with DNA topoisomerase II, a critical enzyme in cancer cell proliferation. The research demonstrated that 1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium acts as a potent inhibitor, inducing DNA damage and apoptosis in various cancer cell lines. The study utilized molecular docking simulations and in vitro assays to validate its efficacy, with IC50 values ranging from 0.5 to 2.0 μM depending on the cell type.
Another significant advancement was reported in a 2024 Nature Communications article, which detailed a novel synthetic pathway for this compound. The researchers employed a cascade cyclization strategy, significantly improving yield (up to 78%) compared to traditional methods. This breakthrough not only facilitates large-scale production but also enables structural modifications to enhance bioavailability and reduce toxicity.
Pharmacokinetic studies have also progressed, with a recent Bioorganic & Medicinal Chemistry paper highlighting the compound's metabolic stability and tissue distribution profiles. Using LC-MS/MS techniques, researchers observed favorable plasma half-life (t1/2 = 6.8 hours in murine models) and blood-brain barrier penetration, suggesting potential applications in CNS malignancies.
Despite these advances, challenges remain in clinical translation. A 2023 review in Drug Discovery Today emphasized the need for comprehensive toxicity assessments, as preliminary data indicate dose-dependent hepatotoxicity at concentrations above 10 μM. Current research efforts are focused on developing prodrug formulations and targeted delivery systems to mitigate these effects while maintaining therapeutic efficacy.
The compound's antimicrobial properties have also been explored, with a 2024 Antimicrobial Agents and Chemotherapy study demonstrating broad-spectrum activity against drug-resistant Gram-positive bacteria (MIC = 1-4 μg/mL). Structural-activity relationship analyses suggest that the dimethoxy and dioxolo moieties are critical for this activity, providing a framework for further optimization.
In conclusion, 1,2-Dimethoxy-12-methyl-1,3dioxolo-4',5':4,5benzo1,2-cphenanthridin-12-ium represents a multifaceted lead compound with significant potential in oncology and infectious disease therapeutics. Ongoing research continues to unravel its molecular targets and refine its pharmaceutical properties, positioning it as a promising candidate for future drug development pipelines.
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