TY - JOUR
T1 - Structural study of bioisosteric derivatives of 5-(1H-indol-3-yl)-benzotriazole and their ability to form chalcogen bonds
AU - MIRGAUX, Manon
AU - SCAILLET, Tanguy
AU - Kozlova, Arina
AU - Tumanov, Nikolay
AU - FREDERICK, Raphael
AU - Bodart, Laurie
AU - Wouters, Johan
N1 - Funding Information:
This research used resources of the ‘Plateforme Technolo-gique de Calcul Intensif (PTCI)’ (http://www.ptci.unamur.be), located at the University of Namur, Belgium, which is supported by the FNRS–FRFC, the Walloon Region, and the University of Namur (Conventions Nos. 2.5020.11, GEQU·G006.15, 1610468, and RW/GEQ2016). The PTCI is a member of the ‘Consortium des Equipements de Calcul Intensif (CÉCI)‘ (http://www.ceci-hpc.be). This work is supported by the Belgian Fonds National de la Recherche Scientifique (FRS–FNRS; grant Nos. 3.05557.43, 28252254 and 32704190), the French Community of Belgium (ARC 21/26– 115), the Fonds spéciaux de recherche (FSR) at UCLouvain, and a J. Maisin Foundation grant. AK and MM acknowledge the Fonds de la Recherche Scientifique (FRS–FNRS, Belgium) for their Research Fellow grants.
Publisher Copyright:
© 2022.
PY - 2022/4
Y1 - 2022/4
N2 - Recently, interest in the isosteric replacement of a nitrogen atom to selenium, sulfur or oxygen atoms has been highlighted in the design of potential inhibitors for cancer research. In this context, the structures of 5-(1H-indol-3-yl)-2,1,3-benzotriazole derivatives [5-(1H-indol-3-yl)-2,1,3-benzothiadiazole (bS, C14H9N3S) and 5-(1H-indol-3-yl)-2,1,3-benzoxadiazole (bO, C14H9N3O)], as well as a synthesis intermediate of the selenated bioisostere [5-[1-(benzensulfonyl)-1H-indol-3-yl]-2,1,3-benzoselenadiazole (p-bSe, C20H13N3O2SSe)] were determined using single-crystal X-ray diffraction (SCXRD) analyses. Despite being analogues, different crystal packing, torsion angles and supramolecular features were observed, depending on the substitution of the central atoms of the benzotriazole. In particular, chalcogen interactions were described in the case of p-bSe and not in the bS and bO derivatives. An investigation by ab initio computational methods was therefore conducted to understand the effect of the substitution on the ability to form chalcogen bonds and the flexibility of the compounds.
AB - Recently, interest in the isosteric replacement of a nitrogen atom to selenium, sulfur or oxygen atoms has been highlighted in the design of potential inhibitors for cancer research. In this context, the structures of 5-(1H-indol-3-yl)-2,1,3-benzotriazole derivatives [5-(1H-indol-3-yl)-2,1,3-benzothiadiazole (bS, C14H9N3S) and 5-(1H-indol-3-yl)-2,1,3-benzoxadiazole (bO, C14H9N3O)], as well as a synthesis intermediate of the selenated bioisostere [5-[1-(benzensulfonyl)-1H-indol-3-yl]-2,1,3-benzoselenadiazole (p-bSe, C20H13N3O2SSe)] were determined using single-crystal X-ray diffraction (SCXRD) analyses. Despite being analogues, different crystal packing, torsion angles and supramolecular features were observed, depending on the substitution of the central atoms of the benzotriazole. In particular, chalcogen interactions were described in the case of p-bSe and not in the bS and bO derivatives. An investigation by ab initio computational methods was therefore conducted to understand the effect of the substitution on the ability to form chalcogen bonds and the flexibility of the compounds.
KW - crystal structure
KW - bioisosterism
KW - chalcogen
KW - chalcogen interaction
KW - tryptophan-2,3-dioxygenase inhibitors
KW - X-ray crystallography
KW - bioisosterism
KW - chalcogen
KW - chalcogen interaction
KW - crystal structure
KW - tryptophan-2,3-dioxygenase inhibitors
KW - X-ray crystallography
UR - http://www.scopus.com/inward/record.url?scp=85128365801&partnerID=8YFLogxK
U2 - https://doi.org/10.1107/S2056989022002948
DO - https://doi.org/10.1107/S2056989022002948
M3 - Article
VL - 78
SP - 418
EP - 424
JO - Acta Crystallographica Section E
JF - Acta Crystallographica Section E
SN - 1600-5368
IS - 4
ER -