I found the field of Crystallography very interesting. Saw the article Synthesis, molecular packing and anti-cholinesterase activity of some new C-2 N-substituted anthranilamide derivatives published in 2019. Product Details of 88-68-6, Reprint Addresses Sarfraz, M; Tariq, MI (corresponding author), Univ Sargodha, Dept Chem, Sargodha 40100, Pakistan.. The CAS is 88-68-6. Through research, I have a further understanding and discovery of 2-Aminobenzamide
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 center dot center dot center dot O forming eight membered rings in R-4(2)(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 R-4(2)(8) motifs; the two dimers are linked via non-classical intermolecular hydrogen bonds C-H center dot center dot center dot 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 mu M (AChE) and 17.6 +/- 1.10 mu M (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.
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Reference:
Thiomorpholine – Wikipedia,
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