Metal-free synthesis and study of glycine betaine derivatives in water for antimicrobial and anticancer applications

Suchismita Rath; Debajit Maiti; Malvika Modi; Parul Pal; Subrata Munan; Biswajit Mohanty; Anjani Bhatia; Rohit Bhowal; Richa Priyadarshini; Animesh Samanta; Parthapratim Munshi; Subhabrata Sen

doi:10.1016/j.isci.2023.107285

Metal-free synthesis and study of glycine betaine derivatives in water for antimicrobial and anticancer applications

iScience. 2023 Jul 13;26(8):107285. doi: 10.1016/j.isci.2023.107285. eCollection 2023 Aug 18.

Affiliations

¹ Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India.
² Department of Life Sciences, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India.

Abstract

A sustainable synthesis of interesting glycine betaine derivatives from cyclic 3°-amines viz. N-methyl morpholine (NMM), N-methyl piperidine (NMP), and 1,4-diazabicyclo[2.2.2]octane (DABCO) with numerous aryl diazoacetates 1 in water and under blue LED is reported. Generally, 3°-amines and metal carbenoids (from diazoacetates with transition metal catalysts) provide C-H insertion at the α-position of the amines. Computational comparison of the metal carbenoid with the singlet carbene (metal free and generated under blue LED) realized the difference in reactivity. Next, experimental results corroborated the preliminary findings. The products were isolated either by precipitation of the solid or gel-like final products from the aqueous reaction mixture without any chromatographic purification. The reaction mechanism was realized by control experiments. These compounds exhibit selective bactericidal properties against Gram-positive S. aureus, induce lipid droplets (LDs) formation in HePG2 cells and single crystal X-ray diffraction study of their halogenated analogs reveal interesting Hal … Hal contacts.

Keywords: Chemical reaction; Chemistry; Organic chemistry.