English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Structural elucidation of the antitubercular benzothiazinone BTZ043: A combined X-ray, variable temperature NMR and DFT study

Richter, A., Patzer, M., Goddard, R., Lingnau, J. B., Imming, P., & Seidel, R. W. (2022). Structural elucidation of the antitubercular benzothiazinone BTZ043: A combined X-ray, variable temperature NMR and DFT study. Journal of Molecular Structure, 1248(1): 131419. doi:10.1016/j.molstruc.2021.131419.

Item is

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Richter, Adrian1, Author
Patzer, Michael2, Author           
Goddard, Richard2, Author           
Lingnau, Julia B.3, Author           
Imming, Peter1, Author
Seidel, Rüdiger W.1, Author
Affiliations:
1Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), Germany, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              
3Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

Content

show
hide
Free keywords: Benzothiazinone; Tuberculosis; Crystal structure; Pseudo symmetry; Variable temperature NMR; DFT calculations
 Abstract: A structural study of (S)-2-(2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one (BTZ043), a promising antitubercular drug candidate, is reported. The chiral compound crystallizes in the triclinic system (space group P1) with two molecules in the asymmetric unit (Z’ = 2), which are related by pseudo inversion symmetry. The two crystallographically distinct molecules represent diastereomeric conformers, which can be transformed to one another by an approximate 180° rotation about the C2BTZ−Npiperidine bond connecting the (S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]decane side chain to C2 of the benzothiazinone (BTZ) scaffold. Variable temperature 13C NMR measurements of BTZ043 in CDCl3 in the range 248-333 K indicate a rotational barrier of Ea = 17.1 ± 1 kcal mol−1 and ΔGǂ = 14.6 ± 1 kcal mol−1. DFT calculations reveal two barriers to rotation about the C2BTZ−Npiperidine bond, one larger than the other by 4.1 kcal mol−1.

Details

show
hide
Language(s): eng - English
 Dates: 2021-07-152021-09-042022-01-15
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/j.molstruc.2021.131419
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Journal of Molecular Structure
  Abbreviation : J. Mol. Struct.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Amsterdam : Elsevier
Pages: - Volume / Issue: 1248 (1) Sequence Number: 131419 Start / End Page: - Identifier: ISSN: 0022-2860
CoNE: https://pure.mpg.de/cone/journals/resource/954925415947