Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity
Corina Cheptea,
Valeriu Sunel,
Ana Cezarina Morosanu,
Dan Gheorghe Dimitriu,
Mihaela Maria Dulcescu-Oprea,
Mihai-Daniel Angheluta,
Mihaela Miron,
Cristina Delia Nechifor,
Dana Ortansa Dorohoi,
Razvan Nicolae Malancus
Affiliations
Corina Cheptea
Department of Biomedical Sciences, Faculty of Biomedical Engineering, “Grigore T. Popa” University of Medicine and Pharmacy, 700115 Iasi, Romania
Valeriu Sunel
Faculty of Chemistry, Alexandru Ioan Cuza University, 700506 Iasi, Romania
Ana Cezarina Morosanu
Faculty of Physics, Alexandru Ioan Cuza University, 700506 Iasi, Romania
Dan Gheorghe Dimitriu
Faculty of Physics, Alexandru Ioan Cuza University, 700506 Iasi, Romania
Mihaela Maria Dulcescu-Oprea
Regional Institute of Oncology, 700483 Iasi, Romania
Mihai-Daniel Angheluta
Faculty of Medicine, “Iuliu Hateganu” University of Medicine and Pharmacy, 400012 Cluj-Napoca, Romania
Mihaela Miron
Faculty of Medicine, “Grigore T. Popa” University of Medicine and Pharmacy, 700115 Iasi, Romania
Cristina Delia Nechifor
Department of Physics, Faculty of Machine Manufacturing and Industrial Management, 700050 Iasi, Romania
Dana Ortansa Dorohoi
Faculty of Physics, Alexandru Ioan Cuza University, 700506 Iasi, Romania
Razvan Nicolae Malancus
Department of Physiology and Pathophysiology, Faculty of Veterinary Medicine, “Ion Ionescu de la Brad” University of Agricultural Sciences and Veterinary Medicine, 700490 Iasi, Romania
New di-(β-chloroethyl)-amides of some acids derived from 2-mercaptobenzoxazole were prepared by reaction of the corresponding pivalic mixed anhydrides with di-(β-chloroethyl)-amine. A study regarding the optimization of the chemical reactions was made for the case of di-(β-chloroethyl)-amines. The quantum chemical analysis by Spartan’14 was made in order to establish the most stable configuration of the ground electronic states for the obtained chemical structures and some physico-chemical parameters of N-mustards reported in this paper. Mercaptobenzoxazoles substituted in the side chain with the cytotoxic group show antitumor activity and they inhibit Ehrlich Ascites in an appreciable proportion compared to the drug I.O.B.-82, as our studies evidenced.
