Cargando…

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

A new compound, C(23)H(20)BrN(3)OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P − 1 space group, with dimensions of a ...

Descripción completa

Detalles Bibliográficos
Autores principales: Mustafa, Muhammad Naeem, Channar, Pervaiz Ali, Ejaz, Syeda Abida, Afzal, Saira, Aziz, Mubashir, Shamim, Tahira, Saeed, Aamer, Alsfouk, Aisha A., Ujan, Rabail, Abbas, Qamar, Hökelek, Tuncer
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10408170/
https://www.ncbi.nlm.nih.gov/pubmed/37550776
http://dx.doi.org/10.1186/s13065-023-00985-4
_version_ 1785086129168449536
author Mustafa, Muhammad Naeem
Channar, Pervaiz Ali
Ejaz, Syeda Abida
Afzal, Saira
Aziz, Mubashir
Shamim, Tahira
Saeed, Aamer
Alsfouk, Aisha A.
Ujan, Rabail
Abbas, Qamar
Hökelek, Tuncer
author_facet Mustafa, Muhammad Naeem
Channar, Pervaiz Ali
Ejaz, Syeda Abida
Afzal, Saira
Aziz, Mubashir
Shamim, Tahira
Saeed, Aamer
Alsfouk, Aisha A.
Ujan, Rabail
Abbas, Qamar
Hökelek, Tuncer
author_sort Mustafa, Muhammad Naeem
collection PubMed
description A new compound, C(23)H(20)BrN(3)OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P − 1 space group, with dimensions of a = 9.2304 (6) Å, b = 11.1780 (8) Å, c = 11.3006 (6) Å, α = 107.146 (5)°, β = 93.701 (5)°, γ = 110.435 (6)°, Z = 2 and V = 1025.61 (12) Å(3). The crystal structure showed that C–H···N and C–H···O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R(2)(2)(14) and R(2)(2)(16) ring motifs. The Hirshfeld surface analysis revealed that H…H (44.1%) and H…C/C…H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 µM. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-023-00985-4.
format Online
Article
Text
id pubmed-10408170
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher Springer International Publishing
record_format MEDLINE/PubMed
spelling pubmed-104081702023-08-09 Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor Mustafa, Muhammad Naeem Channar, Pervaiz Ali Ejaz, Syeda Abida Afzal, Saira Aziz, Mubashir Shamim, Tahira Saeed, Aamer Alsfouk, Aisha A. Ujan, Rabail Abbas, Qamar Hökelek, Tuncer BMC Chem Research A new compound, C(23)H(20)BrN(3)OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P − 1 space group, with dimensions of a = 9.2304 (6) Å, b = 11.1780 (8) Å, c = 11.3006 (6) Å, α = 107.146 (5)°, β = 93.701 (5)°, γ = 110.435 (6)°, Z = 2 and V = 1025.61 (12) Å(3). The crystal structure showed that C–H···N and C–H···O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R(2)(2)(14) and R(2)(2)(16) ring motifs. The Hirshfeld surface analysis revealed that H…H (44.1%) and H…C/C…H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 µM. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-023-00985-4. Springer International Publishing 2023-08-07 /pmc/articles/PMC10408170/ /pubmed/37550776 http://dx.doi.org/10.1186/s13065-023-00985-4 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data.
spellingShingle Research
Mustafa, Muhammad Naeem
Channar, Pervaiz Ali
Ejaz, Syeda Abida
Afzal, Saira
Aziz, Mubashir
Shamim, Tahira
Saeed, Aamer
Alsfouk, Aisha A.
Ujan, Rabail
Abbas, Qamar
Hökelek, Tuncer
Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor
title Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor
title_full Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor
title_fullStr Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor
title_full_unstemmed Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor
title_short Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor
title_sort synthesis, dft and molecular docking of novel (z)-4-bromo-n-(4-butyl-3 (quinolin-3-yl)thiazol-2(3h)-ylidene)benzamide as elastase inhibitor
topic Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10408170/
https://www.ncbi.nlm.nih.gov/pubmed/37550776
http://dx.doi.org/10.1186/s13065-023-00985-4
work_keys_str_mv AT mustafamuhammadnaeem synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT channarpervaizali synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT ejazsyedaabida synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT afzalsaira synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT azizmubashir synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT shamimtahira synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT saeedaamer synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT alsfoukaishaa synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT ujanrabail synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT abbasqamar synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor
AT hokelektuncer synthesisdftandmoleculardockingofnovelz4bromon4butyl3quinolin3ylthiazol23hylidenebenzamideaselastaseinhibitor