Amide isosteres in structure-activity studies of antibacterial minor groove binders was written by Khalaf, Abedawn I.;Anthony, Nahoum;Breen, David;Donoghue, Gavin;MacKay, Simon P.;Scott, Fraser J.;Suckling, Colin J.. And the article was included in European Journal of Medicinal Chemistry in 2011.Formula: C7H8N2O4 This article mentions the following:
Antibacterial minor groove binders related to the natural product, distamycin, are development candidates for novel antibiotics. Alkenes have been found to be effective substitutes for the isosteric amide links in some positions and alkyl groups larger than Me have been found to increase binding to DNA in both selectivity and affinity. However the impact of other isosteres such as diazenes and the position of an alkyl group with respect to DNA binding and antibacterial activity are not known. The effects of some systematic variations in the structure of polyamide minor groove binders are investigated. Isosteres of the amide link (alkenes and diazenes) are compared: it is shown that all three are competent for binding to DNA but that alkene links give the tightest binding and highest antibacterial activity; no significant antibacterial activity was found for compounds with a diazene link. Within a series of alkene linked compounds, the effect of branched N-alkyl substituents on binding to DNA and antibacterial activity is investigated: it was found that C3 and C4 branched chains are acceptable at the central pyrrole residue but that at the pyrrole ring adjacent to the basic tail group, a C4 branched chain was too large both for DNA binding and for antibacterial activity. The active branched alkyl chain compounds were found to be especially active against Mycobacterium aurum, a bacterium related to the causative agent of tuberculosis. In the experiment, the researchers used many compounds, for example, Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7Formula: C7H8N2O4).
Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters contain a carbonyl center, which gives rise to 120鎺?C閳ユ弲閳ユ彊 and O閳ユ弲閳ユ彊 angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C閳ユ彊閳ユ弲 bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Formula: C7H8N2O4
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics