(Isocoumarin-3-yl)phenoxyacetic acids in the amino acid derivatives synthesis. Structure and activity

1Shilin, SV, 1Shablykina, OV, 1Ishchenko, VV, 1Khylia, VP
1Taras Shevchenko National University of Kyiv
Dopov. Nac. akad. nauk Ukr. 2017, 1:82-87
https://doi.org/10.15407/dopovidi2017.01.082
Section: Chemistry
Language: Ukrainian
Abstract: 

The relative reactivities of (isocoumarin-3-yl)- and (3,4-dihydroisocoumarin-3-yl)phenoxyacetic acids in the synthesis of amino acid derivatives, which includes the activated N-hydroxysuccinimide esters producing, are studied. It is found that, for the compounds with unsaturated isocoumarin cycle, the rate of activated ester formation is significantly reduced, when a substituent (regardless of size) in the ortho position to the oxyacetic acid fragment appears. While the slowing interaction of their saturated analogues with N-hydroxysuccinimide is not observed due to the presence of the ortho substituent.

Keywords: (3, (isocoumarin-3-yl)phenoxyacetic acids, 4-dihydroisocoumarin-3-yl)phenoxyacetic acids, activated ester method, amino acid derivatives, N-hydroxysuccinimide
References: 

1. Hill R.A. Naturally occurring isocoumarins, Progress in the Chemistry of Organic Natural Products, Vol. 49, Vienna: Springer, 1986, https://doi.org/10.1007/978-3-7091-8846-0.
2. Shilin S.V., Shablykina O.V., Ishchenko V.V., Khilya V.P. Chem. Nat. Compd., 2014, 50, Iss. 4: 638—643, https://doi.org/10.1007/s10600-014-1042-5.
3. Shilin S.V., Shablykina O.V., Zabolotnaya Yu.N., Ishchenko V.V., Khylia V.P. Khimiya prirodn. soyedin., 2016, No 4: 516—521 (in Russian).
4. Hershkovich A.A., Kibyrev V.K. Chemical synthesis of peptides, Kiev: Naukova Dumka, 1992 (in Russian).
5. Anderson G. W., Zimmerman J. E., Callahan F. M. J. Am. Chem. Soc., 1963, 85: 3039, https://doi.org/10.1021/ja00902a047
6. Ishchenko V.V., Voevoda N.M., Shablykina O.V., Turov A.V., Khilya V.P. Chem. Heterocycl. Comp., 2012, 47, No 10: 1212—1224, https://doi.org/10.1007/s10593-013-1183-7.