6-Oxyindan-1-ones with amino acid fragments

Abstract

New indan-1-one derivatives (8 examples) with amino acid fragments were synthesized through the N-acylation of the amino acids by 2-(3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetic acid using the method of activated N-hydroxysuccinimide esters. To obtain corresponding methyl esters (2 examples) two ways were possible: the N-acylation of the amino acid methyl esters by 2-(3-oxo-2,3-dihydro-1-inden-5-yloxy)acetic acid through the activated imidazole derivatives or methylation of the carboxylic function of preformed N-{[(1-oxoindan-6-yl)oxy]acetyl}amino acids.

6-Oxyindan-1-ones with dipeptide chains

“…products 7j-n were due the low yields of the corresponding initial transformation 58 (see in ref. [14]), and the yield of the conversion 57 after two steps was only 26 % for dipeptide 7j, 33 % -for 7k, 25 % -for 7l, and 42 % -for 7m, 34 % -for 7n respectively.…”

“…The reaction progress and identities of the products were controlled with TLC on Merck F254 plates using a chloroform:methanol The synthesis of 5 was performed using a previously described procedure [14,15]; for the synthesis of the amino acid derivatives 8, see ref. [14]. 1,42.0,67.6,106.7,123.8,128.3,138.2,148.8,157.7,168.2,169.4,171.5,206.2.…”

“…Along this line, we previously reported on the functionalization of 6-hydroxyindan-1-one with amino acid fragments through an oxyacetic linker, showing that the method of hydroxysuccinimide esters [12,13] is more efficient than the carbonylimidazole condensation method [14]. products 7j-n were due the low yields of the corresponding initial transformation 58 (see in ref.…”

“…Moderate to poor isolated yields were obtained in some cases (Scheme 1) because of the high solubility of the substance in the aqueous reaction medium (see Experimental part).The two-step method was tested on tryptophan and methionine derivatives, the expected low solubility these substances a priori can help to avoid the losses during workup and allowing a more accurate evaluation of the reaction efficiency. So, the carboxylic group of compounds 8a,b (Scheme 2, the synthesis was described in ref [14]…”