Nafoxidine
 | |
| Systematic (IUPAC) name | |
|---|---|
| 1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine | |
| Clinical data | |
| Identifiers | |
| 1845-11-0 | |
| None | |
| PubChem | CID 4416 |
| ChemSpider | 4263 |
| UNII |
4RIY10WM82  |
| ChEMBL | CHEMBL28211 |
| Chemical data | |
| Formula | C29H31NO2 |
| 425.562 g/mol | |
|
SMILES
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Nafoxidine (U-11,000A) is a non-steroidal antiestrogenic drug that has been investigated to treat advanced breast cancer.[1] It is structurally related to tamoxifen.
The drug is one of a series of similar structures invented at Upjohn. An earlier compound known as U-11,555 is related to Nafoxidine was found to cause photosensitivity in human volunteers.[2][3]
U-11,555
Synthesis
The synthesis depicted is more modern, but also see Lasofoxifene for an earlier synthesis.
Cameron, C. O.; Dasilva Jardine, P. A.; Rosati, R. L.; 1996, U.S. Patent 5,552,412.
- 6-Methoxytetralone (Cas Number: 1078-19-9).
- Pyridinium tribromide (Pyridinium bromide perbromide)
- Suzuki–Miyaura reaction (Suzuki reaction)
References
- ↑ Steinbaum, F. L.; De Jager, R.; Krakoff, I. (1978). "Clinical trial of nafoxidine in advanced breast cancer". Medical and Pediatric Oncology 4 (2): 123–126. doi:10.1002/mpo.2950040207. PMID 661750.
- ↑ http://www.sciencebase.com/serendipity_and_science.html
- ↑ Lednicer,, D.; Babcock, J.C.; Marlatt, P.E.; Lyster, S.C.; Duncan, G.W. (1965). "Mammalian Antifertility Agents. I. Derivatives of 2,3-Diphenylindenes". J. Med. Chem. 8 (1): 52–57. doi:10.1021/jm00325a013.
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