Synthesis, anticancer evaluation in vitro, DFT, Hirshfeld surface analysis of some new 4-(1,3-benzothiazol-2-yl)-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one derivatives

A new method for synthesizing compounds having benzothiazole and pyrazole moieties in their backbone has been successfully performed, based on the rearrangement of pyrazolylylidene-pyranopyrazolone in the presence of o-aminothiophenol in hot n-butanol. The new compound has been alkylated with different alkylating agents under phase transfer catalysis conditions. A Hirshfeld surface analysis for visually analyzing intermolecular interactions in crystal structures employing molecular surface contours and 2D fingerprint plots has been used to examine molecular shapes. The gas-phase geometries of the new compound and one alkylated derivative were studied by the DFT-B3LYP method. The anticancer properties of the compounds obtained have been evaluated. © 2019 Elsevier B.V.

Authors
Chakib I.1 , El Bakri Y. , Lai C.-H.3, 4 , Benbacer L.5 , Zerzouf A.6 , Essassi E.M.1 , Mague J.T.7
Journal
Journal of Molecular Structure
Language
English
Status
Published
Link
External link
DOI
10.1016/j.molstruc.2019.126910
Number
126910
Volume
1198
Year
2019
Organizations
  • 1 Laboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des Médicaments, Pôle de Compétences Pharmacochimie, URAC 21, Faculté des Sciences, Université Mohammed V Rabat, Avenue Ibn Battouta, Rabat, BP 1014, Morocco
  • 2 Department of Organic Chemistry, Faculty of Science, RUDN University Miklukho-Maklaya St. 6Moscow 117198, Russian Federation
  • 3 Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung, 40241, Taiwan
  • 4 Department of Medical Education, Chung Shan Medical University Hospital, Taichung, 402, Taiwan
  • 5 Unité de Biologie et Recherche Médicale, Centre National de l'Energie, des, Sciences et des Techniques Nucléaires, (CNESTEN), BP 1382 RP, Rabat, 10001, Morocco
  • 6 Laboratoire de Chimie Organique et Etudes Physicochimique, ENS Takaddoum, Rabat, Morocco
  • 7 Department of Chemistry, Tulane University, New Orleans, LA 70118, United States
Keywords
1,3-Benzothiazole; Alkylation; Anticancer; Crystal structure; DFT; Pyrazole
Date of creation
24.12.2019
Date of change
24.12.2019
Short link
https://repository.rudn.ru/en/records/article/record/54805/
Share

Other records