Synonyms:pancratistatin
99% *data from raw suppliers
Pancratistatin *data from reagent suppliers
There total 185 articles about Pancratistatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 100.0%
Reference yield: 91.0%
Reference yield: 90.0%
The research focuses on the synthesis of the antitumor alkaloid (+)-pancratistatin, a compound isolated from the Hawaiian plant Pancratium littorale, which shows significant potential as a clinically useful antitumor agent. The study aims to develop a reliable and efficient synthetic route to (+)-pancratistatin due to the limited natural supply of the alkaloid. The synthesis process involves a series of chemical reactions, including dehydration, hydrogenation, hydrolysis, and the use of the [3-azidonation reaction on triisopropylsilyl (TIPS) enol ethers, leading to the formation of the key intermediates and ultimately (+)-pancratistatin. Key chemicals used in the synthesis include o-vanillin, n-BuLi/TI-IF, POCI3/pyridine/DBU, LiAlH4, MCPBA, KOBut/HMPA, and various other reagents and solvents. The successful synthesis was achieved in 22 steps from commercially available o-vanillin with an overall yield of 1.2%, marking a significant advancement in the field of alkaloid chemistry and potentially providing a more accessible source of this important antitumor agent.
The research focuses on the synthesis and biological evaluation of a b-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin. The purpose of the study was to develop a more soluble analogue of pancratistatin, which has shown activity against various cancer cell lines but has poor bioavailability. The researchers hypothesized that the potency of pancratistatin and related compounds might be due to the hydrogen-bonding donor-acceptor pairing of the b-ketoamide motifs present in these compounds. They synthesized compound 5, a b-carboline-1-one analogue of pancratistatin, to test this hypothesis and evaluated its activity against a series of cancer cell lines. The synthesis involved several interesting transformations and used chemicals such as vinylaziridine, methyl indole-2-carboxylate, tosylamide, and various reagents for hydrolysis, iodolactonization, and detosylation steps. The biological evaluation showed that compound 5 had borderline activity in a murine P388 lymphocytic leukemia assay, while some intermediates in the synthesis process showed promising activities against certain cancer cell lines. The study concluded that the presence of both oxygen atoms in the methylenedioxy bridge of pancratistatin is essential for high activity, and that future analogues could be structured around different scaffolds based on the activity of intermediates like iodolactone 11. The synthesis of compound 5, with nine steps, is the shortest existing preparation of pancratistatin analogues containing the aminoinositol motif, and the researchers plan to focus on heteroatom alterations in the aromatic portion of pancratistatin for future analogues.
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