Synthesis, molecular packing and anti-cholinesterase activity of some new C-2 N-substituted anthranilamide derivatives
-
Muhammad Sarfraz
,
Nargis Sultana
Abstract
Synthesis of C-2 N-substituted anthranilamide derivatives was carried out in a straight forward manner, utilizing 2-aminobenzamide and benzyl chloride as starting materials. Their crystal structures have been established by single crystal X-ray crystallographic method. In the molecules of 2-benzylamino-benzamide (3a), intramolecular hydrogen bonding b/w O atom and proton of –NH and classical intermolecular hydrogen bonding of the type N–H · · · O forming eight membered rings in R42(8) pattern. In both molecules of 2-(dibenzylamino)benzamide (3b), unlike the molecule in 3a, each H atoms is pointed towards N atom causing intramolecular hydrogen bonding interactions, resulting in S(6) motifs. However, it is interesting to note that both molecules in 3b are lying about inversion centres and form dimers in R42(8) motifs; the two dimers are linked via non-classical intermolecular hydrogen bonds C–H · · · O resulting in clusters of four molecules in the structure. In vitro assay results revealed that molecule 3b with IC50 values of 3.8 ± 0.08 μM (AChE) and 17.6 ± 1.10 μM (BChE) possessed better cholinesterase (AChE and BChE) inhibition potential as compared to standard drug galantamine. Preliminary in silico studies showed that more biological active derivatives were also having good pharmacokinetic profile with no AMES toxicity and carcinogenicity.
Acknowledgments
The authors (MS, NS and MIT) are grateful to the Higher Education Commission, Pakistan and University of Sargodha, Sargodha for financial assistance.
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©2019 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Graphical Synopsis
- Inorganic Crystal Structures
- Effect of shock waves on structural and dielectric properties of ammonium dihydrogen phosphate crystal
- Synthesis and crystal structure of a series of stoichiometric (n)-ITB molybdenum-bronze oxides containing trivalent arsenic
- La3Ni4Al2: a new layered aluminide
- Annealing of metamict gadolinite-(Y): X-ray diffraction, Raman, IR, and Mössbauer spectroscopy
- Explanation of structural differences and similarities between the AT2Al10 phases (where A=actinide, lanthanide or rare earth element and T=transition metal)
- Organic and Metalorganic Crystal Structures
- Synthesis, molecular packing and anti-cholinesterase activity of some new C-2 N-substituted anthranilamide derivatives
- O,O-diethyl O-[2-(dimethylamino)ethyl] phosphorothioate: structural evidence of the decomposition product and its oxalate salt
Articles in the same Issue
- Frontmatter
- Graphical Synopsis
- Inorganic Crystal Structures
- Effect of shock waves on structural and dielectric properties of ammonium dihydrogen phosphate crystal
- Synthesis and crystal structure of a series of stoichiometric (n)-ITB molybdenum-bronze oxides containing trivalent arsenic
- La3Ni4Al2: a new layered aluminide
- Annealing of metamict gadolinite-(Y): X-ray diffraction, Raman, IR, and Mössbauer spectroscopy
- Explanation of structural differences and similarities between the AT2Al10 phases (where A=actinide, lanthanide or rare earth element and T=transition metal)
- Organic and Metalorganic Crystal Structures
- Synthesis, molecular packing and anti-cholinesterase activity of some new C-2 N-substituted anthranilamide derivatives
- O,O-diethyl O-[2-(dimethylamino)ethyl] phosphorothioate: structural evidence of the decomposition product and its oxalate salt
