Antiprotozoal Activity of Azabicyclo-Nonanes Linked to Tetrazole or Sulfonamide Cores

Johanna Dolensky; Clemens Hinteregger; Andreas Leitner; Werner Seebacher; Robert Saf; Ferdinand Belaj; Pascal Maser; Marcel Kaiser; Robert Weis

doi:10.3390/molecules27196217

Antiprotozoal Activity of Azabicyclo-Nonanes Linked to Tetrazole or Sulfonamide Cores

Johanna Dolensky, Clemens Hinteregger, Andreas Leitner, Werner Seebacher, Robert Saf, Ferdinand Belaj, Pascal Maser, Marcel Kaiser, Robert Weis^*

^*Corresponding author for this work

Institute for Chemistry and Technology of Materials (6380)

Research output: Contribution to journal › Article › peer-review

Abstract

N-(Aminoalkyl)azabicyclo[3.2.2]nonanes possess antiplasmodial and antitrypanosomal activity. A series with terminal tetrazole or sulfonamido partial structure was prepared. The structures of all new compounds were confirmed by NMR and IR spectroscopy and by mass spectral data. A single crystal structure analysis enabled the distinction between isomers. The antiprotozoal activities were examined in vitro against strains of Plasmodium falciparum and Trypanosoma brucei rhodesiense (STIB 900). The most active sulfonamide and tetrazole derivates showed activities in the submicromolar range.

Original language	English
Article number	6217
Journal	Molecules
Volume	27
Issue number	19
DOIs	https://doi.org/10.3390/molecules27196217
Publication status	Published - Oct 2022

Keywords

antimalarial
antitrypanosomal
azabicyclo-nonanes
Plasmodium falciparum
tetrazoles
Trypanosoma brucei

ASJC Scopus subject areas

Drug Discovery
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Physical and Theoretical Chemistry
Pharmaceutical Science
Organic Chemistry

Access to Document

10.3390/molecules27196217Licence: CC BY 4.0

Cite this

@article{70fb68180ef04bf9a941f9293a4c3257,

title = "Antiprotozoal Activity of Azabicyclo-Nonanes Linked to Tetrazole or Sulfonamide Cores",

abstract = "N-(Aminoalkyl)azabicyclo[3.2.2]nonanes possess antiplasmodial and antitrypanosomal activity. A series with terminal tetrazole or sulfonamido partial structure was prepared. The structures of all new compounds were confirmed by NMR and IR spectroscopy and by mass spectral data. A single crystal structure analysis enabled the distinction between isomers. The antiprotozoal activities were examined in vitro against strains of Plasmodium falciparum and Trypanosoma brucei rhodesiense (STIB 900). The most active sulfonamide and tetrazole derivates showed activities in the submicromolar range.",

keywords = "antimalarial, antitrypanosomal, azabicyclo-nonanes, Plasmodium falciparum, tetrazoles, Trypanosoma brucei",

author = "Johanna Dolensky and Clemens Hinteregger and Andreas Leitner and Werner Seebacher and Robert Saf and Ferdinand Belaj and Pascal Maser and Marcel Kaiser and Robert Weis",

year = "2022",

month = oct,

doi = "10.3390/molecules27196217",

language = "English",

volume = "27",

journal = "Molecules ",

issn = "1420-3049",

publisher = "MDPI AG",

number = "19",

}

TY - JOUR

T1 - Antiprotozoal Activity of Azabicyclo-Nonanes Linked to Tetrazole or Sulfonamide Cores

AU - Dolensky, Johanna

AU - Hinteregger, Clemens

AU - Leitner, Andreas

AU - Seebacher, Werner

AU - Saf, Robert

AU - Belaj, Ferdinand

AU - Maser, Pascal

AU - Kaiser, Marcel

AU - Weis, Robert

PY - 2022/10

Y1 - 2022/10

N2 - N-(Aminoalkyl)azabicyclo[3.2.2]nonanes possess antiplasmodial and antitrypanosomal activity. A series with terminal tetrazole or sulfonamido partial structure was prepared. The structures of all new compounds were confirmed by NMR and IR spectroscopy and by mass spectral data. A single crystal structure analysis enabled the distinction between isomers. The antiprotozoal activities were examined in vitro against strains of Plasmodium falciparum and Trypanosoma brucei rhodesiense (STIB 900). The most active sulfonamide and tetrazole derivates showed activities in the submicromolar range.

AB - N-(Aminoalkyl)azabicyclo[3.2.2]nonanes possess antiplasmodial and antitrypanosomal activity. A series with terminal tetrazole or sulfonamido partial structure was prepared. The structures of all new compounds were confirmed by NMR and IR spectroscopy and by mass spectral data. A single crystal structure analysis enabled the distinction between isomers. The antiprotozoal activities were examined in vitro against strains of Plasmodium falciparum and Trypanosoma brucei rhodesiense (STIB 900). The most active sulfonamide and tetrazole derivates showed activities in the submicromolar range.

KW - antimalarial

KW - antitrypanosomal

KW - azabicyclo-nonanes

KW - Plasmodium falciparum

KW - tetrazoles

KW - Trypanosoma brucei

UR - http://www.scopus.com/inward/record.url?scp=85139812971&partnerID=8YFLogxK

U2 - 10.3390/molecules27196217

DO - 10.3390/molecules27196217

M3 - Article

SN - 1420-3049

VL - 27

JO - Molecules

JF - Molecules

IS - 19

M1 - 6217

ER -

Antiprotozoal Activity of Azabicyclo-Nonanes Linked to Tetrazole or Sulfonamide Cores

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this