Synthesis of phenanthridines via palladium-catalyzed.
The synthesis of 6-amino-11,12-dihydrobenzo( c)phenanthridine 133 and 6-amino-benzo( c )phenanthridine derivatives 134 was accomplished in a very straightforward approach by the condensation of 2-methylbenzonitrile 135 with aromatic aldehydes 136 resulting in the 6-amino-11,12-dihydrobenzo( c )phenanthridine derivatives 133.
Figure 2: Substrate scope of this phenanthridine synthesis. All reactions were carried out in a 10 mL glass vial on a 0.2 mmol scale; yields are based on isolated product. All reactions were carried out in a 10 mL glass vial on a 0.2 mmol scale; yields are based on isolated product.
In this study, we report the synthesis, antibacterial and anticancer evaluation of 38 novel phenanthridines that were designed as analogs of the benzo(c)phenanthridine alkaloids. The prepared phenanthridines differ from the benzo(c)phenanthridines in the absence of a benzene A-ring. All novel compounds were prepared from 6-bromo-2-hydroxy-3-methoxybenzaldehyde in several synthetic steps.
Phenanthridine is an azaarene that is the 9-aza derivative of phenanthrene. The parent of the class of phenanthridines. The parent of the class of phenanthridines. It is a mancude organic heterotricyclic parent, a polycyclic heteroarene, a member of phenanthridines and an azaarene.
Our synthesis of desired phenanthridine compounds is based on our previous experience with the synthesis of isodecarine and metabolites of benzo(c)phenanthridines, where a radical cyclization leading to ring C closure was used to accomplish the construction of the benzo(c)phenanthridine heterocyclic system. By this method we prepared phenanthridine derivatives where the B ring is formed.
The Suzuki coupling reaction is able to be utilized in providing galanthindole-type 17 alkaloids with switching the structures of coupling partners. Thus, we prepared substrates 15 and 16 for the synthesis of other three Amaryllidaceae alkaloids galanthindole, lycosinine A and B 18 with similar structures.
The first section of this thesis examines the development and application of a novel intramolecular Heck cyclisation to the synthesis of core phenanthridine structure II, via precursor III (Chapter 2).The second section (Chapter 3) describes the extension of this methodology towards the development of a library of phenanthridines IV.
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Based on the structure of sanguinarine, fourteen phenanthridine derivatives were designed and synthesized in the current study. The cytotoxic activities of synthesized compounds were evaluated against five human cancer cell lines (MCF-7, PC3, Hela, A549, and HepG2 cell lines) via MTT assay.
Modular Synthesis of Phenanthridine Derivatives by Oxidative Cyclization of 2-Isocyanobiphenyls with Organoboron Reagents. Koh, K., Furukawa, T. and Chatani, N. (2012), Modular Synthesis of Phenanthridine Derivatives by Oxidative Cyclization of 2-Isocyanobiphenyls with Organoboron Reagents. Angew. Chem. Int.
Structure and synthesis ( edit ) Structurally, phenanthriplatin is similar to cisplatin, differing only in the presence of a phenanthridine ligand instead of a chloride in its structure. To synthesise phenanthriplatin, a one equivalent of silver nitrate is added to solution of cisplatin in dimethylformamide.
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