Chemistry:Dibenzoylmethane
Dibenzoylmethane (DBM) is an organic compound with the formula (C6H5C(O))2CH2. DBM is the name for a 1,3-diketone, but the compound exists primarily as one of two equivalent enol tautomers.[1] DBM is a white solid. Due UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.[2]
Synthesis and reactions
DBM is prepared by condensation of ethyl benzoate with acetophenone.[3]
Occurrence and medicinal properties
Dibenzoylmethane (DBM) is a minor constituent in the root extract of Licorice (Glycyrrhiza glabra in the family Leguminosae).[4] It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds.[5][6]
DBM (and trazodone) slow disease progression by preventing the cessation of protein synthesis in neurons.[7]
Related compounds
References
- ↑ Thomas, L. H.; Florence, A. J.; Wilson, C. C. (2009). "Hydrogen atom behaviour imaged in a short intramolecular hydrogen bond using the combined approach of X-ray and neutron diffraction". New Journal of Chemistry 33 (12): 2486–2490. doi:10.1039/B908915B.
- ↑ Freire, Thamires Batello (2022-01-17). Influência de antioxidantes na fotoestabilização da avobenzona (filtro UVA) e do >i/i (Doutorado em Produção e Controle Farmacêuticos thesis) (in português). São Paulo: Universidade de São Paulo. doi:10.11606/t.9.2022.tde-19052022-110821.
- ↑ Magnani, Arthur; McElvain, S. M. (1940). "Dibenzoylmethane". Org. Synth. 20: 32. doi:10.15227/orgsyn.020.0032.
- ↑ Jackson, Kimberly M.; Deleon, Marisela; Verret, C.Reynold; Harris, Wayne B. (2002). "Dibenzoylmethane Induces Cell Cycle Deregulation in Human Prostate Cancer Cells". Cancer Letters 178 (2): 161–165. doi:10.1016/S0304-3835(01)00844-8. PMID 11867200.
- ↑ Shishu; Singla, A.K.; Kaur, I.P. (2003). "Inhibitory Effect of Dibenzoylmethane on Mutagenicity of Food-Derived Heterocyclic Amine Mutagens". Phytomedicine 10 (6–7): 575–582. doi:10.1078/094471103322331575. PMID 13678246.
- ↑ Pan, Min-Hsiung; Huang, Mei-Chen; Wang, Ying-Jan; Lin, Jen-Kun; Lin, Chao-Hsien (2003). "Induction of Apoptosis by Hydroxydibenzoylmethane through Coordinative Modulation of Cyclin D3, BCL-XL, and Bax, Release of Cytochrome c, and Sequential Activation of Caspases in Human Colorectal Carcinoma Cells". Journal of Agricultural and Food Chemistry 51 (14): 3977–3984. doi:10.1021/jf034094i. PMID 12822933.
- ↑ Halliday, Mark; Radford, Helois; Zents, Karlijn A. M.; Molloy, Collin; Moreno, Julie A.; Verity, Nicholas C.; Smith, Ewan; Ortori, Catharine A. et al. (2017). "Repurposed Drugs Targeting eIF2α-P-Mediated Translational Repression Prevent Neurodegeneration in Mice". Brain 140 (6): 1768–1783. doi:10.1093/brain/awx074. PMID 28430857.
 |  |
