Synthesis of colchifulvin, a colchicine–griseofulvin hybrid

Marset, Azucena; Caprioglio, Diego; Torretta, Simone; Appendino, Giovanni; Minassi, Alberto

doi:10.1016/j.tetlet.2016.02.086

Cited by 3 publications

(4 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An example of a hybrid molecule with a bidirectional biological effect is colchifulvin 182 (202), a hybrid of colchicine (1), and the antifungal antibiotic griseofulvin (203) (Figure 20).…”

Section: ■ Hybrids Conjugates and Prodrugs Of Colchicinoids: Colchici...mentioning

confidence: 99%

Colchicine Alkaloids and Synthetic Analogues: Current Progress and Perspectives

et al. 2020

View full text Add to dashboard Cite

Colchicine, the main alkaloid of Colchicum autumnale, is one of the most famous natural molecules. Although colchicine belongs to the oldest drugs (in use since 1500 BC), its pharmacological potential as a lead structure is not yet fully exploited. This review is devoted to the synthesis and structure− activity relationships (SAR) of colchicine alkaloids and their analogues with modified A, B, and C rings, as well as hybrid compounds derived from colchicinoids including prodrugs, conjugates, and delivery systems. The systematization of a vast amount of information presented to date will create a paradigm for future studies of colchicinoids for neoplastic and various other diseases.

show abstract

“…An example of a hybrid molecule with a bidirectional biological effect is colchifulvin 182 (202), a hybrid of colchicine (1), and the antifungal antibiotic griseofulvin (203) (Figure 20).…”

Section: ■ Hybrids Conjugates and Prodrugs Of Colchicinoids: Colchici...mentioning

confidence: 99%

Colchicine Alkaloids and Synthetic Analogues: Current Progress and Perspectives

et al. 2020

View full text Add to dashboard Cite

show abstract

“…As a powerful reagent for oxidative dearomatization of electron‐rich arenes, [17,18] the commercially available hyperiodine reagent PhI(OAc) 2 (PIDA) [19] was chosen by us as the oxidant in this study. After a considerable number of condition screening and optimization, suberitine C ( 3 , 68 % yield, X‐ray crystallographic analysis) was finally obtained by complete oxidation and di‐ O,O ‐acetalization of 23 a with PIDA (3 equiv.)…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Suberitines A–D Featuring Tunable Biomimetic Late‐Stage Oxidative Dearomatization and Acetalization

Tang

Gao

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

Aaptaminoids are a unique family of marine alkaloids bearing a benzo[de][1,6]‐naphthyridine core. This work describes the first total synthesis of suberitines A–D (1–4), four typical dimeric natural aaptaminoids, employing a step‐saving bidirectional strategy. Key methods applied in the total synthesis include a cationic cascade to construct the bis‐isoquinoline(s) with Hendrickson reagent‐mediated Friedel‐Crafts‐type cyclization and eliminative aromatization, and a Bronsted acid‐promoted Vilsmeier cyclization to generate the naphthyridine(s). The conditionally tunable PIDA‐mediated oxidative dearomatization and subsequent methanolysis or hydrolysis successfully served as a powerful biomimetic tool to elaborate the essential oxygenated functionalities of suberitines A–D (1–4) in proper solvent‐combinations at the final stage of total synthesis. The biomimetic proposal employed in the late‐stage redox interchanges of related natural products was eventually supported by the isolation of synthetic intermediate 23 a as a natural product from the same natural source. Biological screening revealed that five of the synthetic samples including two natural suberitines and three full‐skeleton natural product‐like intermediates exhibited low micromolar inhibitory activities against the growth of cancer cell line K562.

show abstract

“…The synthesis of 22-25 involves the condensation and oxidative aromatization between an aryl substituted aldehyde and a substituted 2-aminophenylthiophenol (S6-1) to give intermediate S6-3, which was followed by debenzylation in the presence of concentrated hydrochloric acid (Scheme 6). The preparations of erianin, 24 21, 25 26, 27 and 30-44 were achieved through a Wittig reaction between triphenyl (substituted benzyl)-phosphonium bromide and the corresponding aldehydes to obtained alkenes, which was then followed by catalytic hydrogenation. Compounds 28 Organic & Biomolecular Chemistry Paper and 29 were obtained by direct alkylation of the hydroxyl group of erianin (Scheme 7).…”

Section: Papermentioning

confidence: 99%

“…The synthesis and characterization of compounds 1-7, 10, 14, 21, 39 and 40 had already been reported in previous studies. [21][22][23][24][25][26][27] The compounds 8, 9, 11-13, 15-20, 22-34, 36-38 and 41-47 were synthesized according to the route in Schemes 3-8. The structures of all compounds were confirmed from the analytical data obtained from 1 H NMR and 13 C NMR spectroscopies, and mass spectrometry.…”

Section: Chemistry and Synthesismentioning

confidence: 99%