The influence of C=N-substitution on the sensitivity to aromatic substitution. Please enable it to take advantage of the complete set of features! Get the latest research from NIH: https://www.nih.gov/coronavirus. NLM 2010 Jan 28;15(2):660-71. doi: 10.3390/molecules15020660. 2012 Feb;94(2):533-40. doi: 10.1016/j.biochi.2011.09.002. Appl Biochem Biotechnol. | HHS eCollection 2019. 2013 Jul;111:62-7. doi: 10.1016/j.saa.2013.03.082. Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors. Ha YM, Uehara Y, Park D, Jeong HO, Park JY, Park YJ, Lee JY, Lee HJ, Song YM, Moon HR, Chung HY. HHS eCollection 2019 Mar 14. Biosci Biotechnol Biochem. An equal volume of aniline will have about 2% more mass than water. Drug Des Devel Ther. Epub 2013 Mar 28. The substituent dependence of delta(C)(C=N) was used as a tool to study electronic substituent effects on the azomethine unit. Synthesis, characterization and biological evaluation of paeonol thiosemicarbazone analogues as mushroom tyrosinase inhibitors. Neuvonen K, Fülöp F, Neuvonen H, Koch A, Kleinpeter E, Pihlaja K. J Org Chem. | Epub 2013 Oct 8. Comparison of the electronic structures of imine and hydrazone side-chain functionalities with the aid of 13C and 15N NMR chemical shifts and PM3 calculations. USA.gov. Epub 2012 Sep 12. Design, synthesis and biological evaluation of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors. Evaluation of novel pyrimidine derivatives as a new class of mushroom tyrosinase inhibitor. The electronic effects of the neighboring aromatic ring substituents systematically modify the sensitivity of the C=N group to the electronic effects of the benzylidene or aniline ring substituents. The present study was aimed at clarifying the conformation of benzylidene aniline with the aid of the CNDO/S method. J Org Chem. Get the latest public health information from CDC: https://www.coronavirus.gov. All rights reserved. Copyright © 2012 Elsevier Masson SAS. 2003 Mar 21;68(6):2151-60. doi: 10.1021/jo020608l. We attempted to design and synthesize (E)-N-substituted benzylidene-hydroxy or methoxy-aniline derivatives and to evaluate their inhibitory effect on tyrosinase activity and anti-melanogenesis activity in murine B16F10 melanoma cells. Whereas the isomerization in the organic solvents proceeds via an inversion mechanism this reaction is drastically hindered or even blocked in 98% H 2 SO 4. 2019 Mar 7;25(14):3440-3454. doi: 10.1002/chem.201803927. National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error. National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error. Author information: (1)Molecular Inflammation Research Center for Aging Intervention (MRCA), College of Pharmacy, Pusan National University, Kumjeong-Gu, Busan 609-735, Republic of Korea. In contrast, electron-withdrawing substituents on the benzylidene ring increase the sensitivity of delta(C)(C=N) to the substituent on the aniline ring, while electron-donating substituents act in the opposite way. 2019 Jul 8;13:2169-2178. doi: 10.2147/DDDT.S209324. 2013. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents. The non-planarity of benzylidene aniline is clearly established and the estimated deviation, 55°, is consistent with a recent experimental determination. Get the latest public health information from CDC: https://www.coronavirus.gov.