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Phenylahistin

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Phenylahistin
Names
IUPAC name (3S,6Z)-3-Benzyl-6-{methylene}-2,5-piperazinedione
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H22N4O2/c1-4-20(2,3)17-14(21-12-22-17)11-16-19(26)23-15(18(25)24-16)10-13-8-6-5-7-9-13/h4-9,11-12,15H,1,10H2,2-3H3,(H,21,22)(H,23,26)(H,24,25)/b16-11-/t15-/m0/s1Key: GWMHBVLPNWHWGW-CNYBTUBUSA-N
SMILES
  • CC(C)(C=C)C1=C(N=CN1)/C=C\2/C(=O)N(C(=O)N2)CC3=CC=CC=C3
Properties
Chemical formula C20H22N4O2
Molar mass 350.422 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Phenylahistin is a metabolite produced by the fungus Aspergillus ustus that belongs to a class of naturally occurring 2,5-diketopiperazines featuring a dehydrohistidine residue that exhibit important biological activities, such as anti-cancer or neurotoxic effects.

Phenylahistin is a microtubule binding agent that exhibits cytotoxic activities against a wide variety of tumor cell lines. A series of synthetic analogs were prepared to remove the chirality and optimize biological activity. These studies led to the potent anti-tumor agent plinabulin, which is active in multidrug-resistant (MDR) tumor cell lines.

References

  1. Kanoh K, Kohno S, Asari T, Harada T, Katada J, Muramatsu M, Kawashima H, Sekiya H, Uno I (1997). "(−)-Phenylahistin: A new mammalian cell cycle inhibitor produced by aspergillus ustus". Bioorganic & Medicinal Chemistry Letters. 7 (22): 2847–2852. doi:10.1016/S0960-894X(97)10104-4.
  2. Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  3. Kanoh K, Kohno S, Katada J, Hayash Y, Muramatsu M, Uno I (1999). "Antitumor activity of phenylahistin in vitro and in vivo". Bioscience, Biotechnology, and Biochemistry. 63 (6): 1130–1133. doi:10.1271/bbb.63.1130. PMID 10427703.
  4. Nicholson B, Lloyd GK, Miller BR, Palladino MA, Kiso Y, Hayashi Y, Neuteboom ST (2006). "NPI-2358 is a tubulin-depolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent". Anticancer Drugs. 17 (1): 25–31. doi:10.1097/01.cad.0000182745.01612.8a. PMID 16317287. S2CID 33272285.
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