Premium
Lipophilicity Enhancing Substituents for ADDA Recognition Domains of DAAD·ADDA Heterodimers with Quadruple Hydrogen Bonds
Author(s) -
Otte Philipp,
Taubitz Jörg,
Lüning Ulrich
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201450
Subject(s) - chemistry , hydrogen bond , alkyl , amide , pyrimidinones , intramolecular force , lipophilicity , stereochemistry , molecular recognition , molecule , polyethylene glycol , crystallography , organic chemistry
Abstract Four new ADDA receptors for DAAD · ADDA heterodimer formation by quadruple hydrogen bonds have been prepared. Their solubility has been improved by substitution with polyethylene glycol or branched alkyl chains. Three ADDA urea structures 8 , 9 , and 10 possess stabilizing intramolecular hydrogen bonds, in contrast to a related amide 7 . The association constants K ass span several orders of magnitudes, with pyrimidinones 8 and 9 showing K ass values above 10 4 M –1 .