Convenient synthesis, characterization and biological evaluation of novel 1-phenylcyclopropane carboxamide derivatives
Panasa Mahesh,
Parameswari Akshinthala,
Ashok Reddy Ankireddy,
Naresh Kumar Katari,
Lavleen Kumar Gupta,
Deepali Srivastava,
Sreekantha Babu Jonnalagadda,
Rambabu Gundla
Affiliations
Panasa Mahesh
Department of Chemistry, GITAM School of Science, GITAM Deemed to be University, Hyderabad, Telangana, 502329, India
Parameswari Akshinthala
Department of Science and Humanities, MLR Institute of Technology, Dundigal, Medchal, Hyderabad, 500 043, India
Ashok Reddy Ankireddy
Department of Chemistry, GITAM School of Science, GITAM Deemed to be University, Hyderabad, Telangana, 502329, India
Naresh Kumar Katari
Department of Chemistry, GITAM School of Science, GITAM Deemed to be University, Hyderabad, Telangana, 502329, India; School of Chemistry & Physics, College of Agriculture, Engineering & Science, University of KwaZulu-Natal, Westville Campus, P Bag X 54001, Durban, 4000, South Africa; Corresponding author. Department of Chemistry, GITAM School of Science, GITAM Deemed to be University, Hyderabad, Telangana, 502329, India
Lavleen Kumar Gupta
Drug Discovery Division, IgYImmunologix India Pvt Ltd, Hyderabad, Telangana, 500089 India
Deepali Srivastava
Drug Discovery Division, IgYImmunologix India Pvt Ltd, Hyderabad, Telangana, 500089 India
Sreekantha Babu Jonnalagadda
School of Chemistry & Physics, College of Agriculture, Engineering & Science, University of KwaZulu-Natal, Westville Campus, P Bag X 54001, Durban, 4000, South Africa; Corresponding author.
Rambabu Gundla
Department of Chemistry, GITAM School of Science, GITAM Deemed to be University, Hyderabad, Telangana, 502329, India; Corresponding author.
Small, strained ring molecules of phenylcyclopropane carboxamide have rigid, defined conformations and unique electronic properties. For these reasons many groups, seek to use these subunits to form biologically active compounds. Herein we report a generally applicable approach for preparing a small cyclopropane ring containing 1-phenylcyclopropane carboxamide derivatives to a wide range of the different aromatic compounds by α-alkylation of 2-phenyl acetonitrile derivatives with 1, 2-dibromo ethane in good yields followed by the conversion of cyano group to acid group by the reaction with concentrated hydrochloric acid. This obtained acid derivative undergoes acid amine coupling with various Methyl 2-(aminophenoxy)acetate to form 1-Phenylcyclopropane Carboxamide. These compounds possess distinct effective inhibition on the proliferation of U937, pro-monocytic, human myeloid leukaemia cell line while these compounds did not show cytotoxic activity on these cells. The structure-activity relationships of these compounds are discussed.
