28233-43-4

Usage

Uses

Used in Pharmaceutical Industry:
4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one is used as a pharmaceutical compound for its potential therapeutic applications. The presence of the methylenedioxy group and phenolic hydroxyl groups may contribute to its biological activity, making it a candidate for further research and development in the field of medicine.
Used in Chemical Research:
This alkaloid is also used as a subject of study in chemical research, particularly in the investigation of its structural properties, spectroscopic characteristics, and potential synthetic applications. The complex ultraviolet spectrum and the ability to form derivatives such as diacetate and dimethyl ether make it an interesting compound for researchers to explore.
Used in Natural Product Chemistry:
4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one is used in the study of natural products, specifically in the context of alkaloids derived from the Narcissus plant species. Understanding the structure and properties of 4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one can provide insights into the chemical diversity and biological activities of natural products, which may lead to the discovery of new therapeutic agents or other applications.

References

Piozzi et al., Tetrahedron, 24, 1119 (1968)Revised structure: Mondon, Krohn., Tetrahedron Lett., 2123 (1970)Mondon, Krohn., Chem. Ber., 103,2729 (1970)Savona, Piozzi, Marino., Chem. Commun., 1006 (1970)

Upstream product

• 40041-97-2 (2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one 
• 40141-77-3 4-benzyloxy-6-bromo-benzo[1,3]dioxole-5-carboxylic acid 2-benzyloxy-anilide 
• 96203-70-2 pancratistatin 
• 29477-83-6 narciclasine 
• 28233-42-3 4-benzyloxy-7-hydroxy-5H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 

Relevant academic research and scientific papers

Antineoplastic Agents. 511. Direct Phosphorylation of Phenpanstatin and Pancratistatin

Selective phosphorylation of phenpanstatin (3a) with tetrabutylammonium dihydrogen phosphate and dicyclohexylcarbodiimide in pyridine followed by cation-exchange chromatographic procedures was found to provide an efficient route to a new series (3b-3d) of promising 3,4-O-cyclic phosphate prodrugs designated phenpanstatin phosphates. Application of analogous reaction conditions to pancratistatin (1a) led to a mixture of monophosphate derivatives where sodium pancratistatin 4-O-phosphate (4a) was isolated and the structure confirmed by X-ray crystallography. Modification of the reaction conditions allowed direct phosphorylation of pancratistatin followed by cation-exchange chromatography to afford sodium pancratistatin 3,4-O-cyclic phosphate (5a), which was selected for preclinical development.

Isolation, Synthesis, and Semisynthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De Novo Total Synthesis of 2-epi-Narciclasine

An efficient protocol for the isolation of narciclasine from common Amaryllidaceae bulbs, separation from haemanthamine, and the occurrence of a trace alkaloid, 2-epi-narciclasine, are reported. Attempts to convert natural narciclasine to its C-2 epimer by Mitsunobu inversion or oxidation/reduction sequences were compromised by rearrangement and aromatization processes, through which a synthesis of the alkaloid narciprimine was achieved. The methylation of the 7-hydroxy group of natural narciclasine followed by protection of the 3,4-diol function and oxidation/reduction sequence provided the target C-2 epimer. A de novo chemoenzymatic synthesis of 2-epi-narciclasine from m-dibromobenzene is also described. Haemanthamine and narciprimine were readily detected in the crude extracts of Narcissus and Galanthus bulbs containing narciclasine, and the occurrence of 2-epi-narciclasine as a trace natural product in Galanthus sp. is reported for the first time.