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
Affiliations
Suchismita Rath
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India
Debajit Maiti
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India
Malvika Modi
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
Parul Pal
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
Subrata Munan
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India
Biswajit Mohanty
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India
Anjani Bhatia
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India
Rohit Bhowal
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India
Richa Priyadarshini
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
Animesh Samanta
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India
Parthapratim Munshi
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India; Corresponding author
Subhabrata Sen
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Gautam Buddha Nagar, Chithera, Dadri, UP 201310, India; Corresponding author
Summary: 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.
