Synthetic analogues of netropsin and distamycin--synthesis of a new pyridine and carbocyclic analogues of the pyrrolecarboxamide antitumour antibiotics.
A new series of pyridine-containing analogues III-XXII of distamycin A and netrop sin was investigated by the molecular mechanics technique and molecular modelling. A pyridine analogue of netropsin (VII) is described, the first compound based on molecular studies, and two carbocyclic analogues of distamycin A with an N-terminal chloro- or bromoacetyl group (VIa, VIIa) were synthesized, as well as carbocyclic analogues of netropsin (VIIIb, Xb), potential carriers of alkylating elements. The potential use of VIa, VII, VIIa, VIIIb and Xb as carriers to place into the minor groove of DNA chemical groups capable of modifying DNA, is discussed.
Department of Organic Chemistry, Medical Academy, Białystok, Poland.
D
D
Bartulewicz
K
K
Bielawski
A
A
Markowska
K
K
Zwierz
A
A
Pućkowska
A
A
Rózański
D000146:Acids, Carbocyclic; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D003198:Computer Simulation; D004214:Distamycins / Q000138:chemical synthesis; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009429:Netropsin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D011725:Pyridines / Q000138:chemical synthesis*
D000146:Acids, Carbocyclic; D000903:Antibiotics, Antineoplastic; D004214:Distamycins; D011725:Pyridines; D009429:Netropsin; C030000:stallimycin