Synthesis of Novel Bis-imino and Bis-amino Curcuminoids for Evaluation of Their Anticancer and Antibacterial Activity

Abstract

A new set of curcumin analogues with a Schiff base moiety were synthesized from a bis-aldehyde derivative of hydroxybenzylidene cyclohexanone and various alicyclic and aromatic amines. The single crystals of compound 2 (bis-aldehyde), compound 3b (bis-cyclohexylimino derivative), and compound 3c (bis-1-imino piperidyl derivative) were developed. The said bis-imino and bis-amino curcuminoids were tested for anticancer activity against MCF-7 utilizing the conventional MTT assay. These Schiff bases had significantly higher anticancer efficacy than curcumin and methotrexate against MCF-7 cell lines. Compounds 3k, 3b, and 3l have the highest efficacy among all synthesized curcuminoids. The MTT results are in accordance with the binding affinities found by docking the said molecules with HER2 Tyrosine Kinase (HER2-TK). Compound 3b is identified as a promising HER2-TK inhibitor and also shows effective inhibition against Gram-positive bacteria Staphylococcus aureus.

Curcumin‐based bioactive heterocycles derived via multicomponent reactions

“…Curcumin has received great attention over the last two decades as an anticancer agent. [17,[128][129][130] Recent literature revealed that DHPMs exhibited a broad spectrum of anticancer activity. [131,132] The curcumin-based 3,4-DHPMs displayed [72] potential cytotoxicity against Hep-G2 (human hepatocarcinoma), human colorectal carcinoma cell line (HCT-116, human colon carcinoma), and human lung carcinoma cell lines (QG-56).…”

Synthesis, pharmacological evaluation, and in silico study of new 3-furan-1-thiophene-based chalcones as antibacterial and anticancer agents

“…The currently employed methods for breast cancer treatment include prophylactic mastectomy, chemotherapy, radiotherapy, medicines, and gene therapy [ [4] , [5] , [6] ]. However, these methods of treatments are usually associated with pain and considered expensive particularly in countries with low- and middle-income rates [ 7 , 8 ].…”