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Synthesis of thioether phosphocholine analogues
E Bosies1, D B Herrmann, U Bicker
1Boehringer Mannheium GmbH, Department of Immunopharmacology and Cancer Research, Federal Republic of Germany.
Lipids
|November 1, 1987
Summary
This study details the synthesis of thioether phospholipids, a novel class of antitumor agents. Ilmofosine (BM 41.440), a potent derivative, was synthesized and tested in clinical trials.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Pharmacology
Background:
- Thioether phospholipids represent a new class of potential antitumor agents.
- Ilmofosine (BM 41.440) is a highly potent cytostatic and cytotoxic derivative within this class.
Purpose of the Study:
- To describe the detailed synthetic route for Ilmofosine (BM 41.440).
- To report on the synthesis of a novel class of antitumor agents: thioether phospholipids.
Main Methods:
- The synthesis involved multiple steps starting from diethyl bis-hydroxymethylmalonate.
- Key reactions included esterification, reduction, alkylation, ring-opening, thiol addition, phosphorylation, and amination.
Main Results:
- A detailed multi-step synthesis pathway for Ilmofosine (BM 41.440) was successfully established.
- The synthesis yielded the target thioether phospholipid, BM 41.440.
Conclusions:
- The synthesis of Ilmofosine (BM 41.440), a potent thioether phospholipid antitumor agent, has been achieved.
- Ilmofosine has progressed to clinical phase I/II trials, indicating its therapeutic potential.