Study on Anti‐Proliferative Activity in Cancer Cells and Preliminary Structure–Activity Relationship of Pseudo‐Peptide Chiral Thioureas

Abstract

In our previous studies, we have shown that thiourea compounds containing phosphate esters have potent antitumor activity and can be used as a novel strategy for the development of antitumor agents. Herein, a series of novel phosphonate thioureas 5–38 have been synthesized, which were fully characterized by 1H NMR, 13C NMR spectrum, elemental analysis. Three human cancer cell lines (Bcap‐37, BGC‐823, and PC‐3) have been used to investigate these compounds’ antitumor activities. After the summarization of the structure–activity relationships, we found that the variation of R, R1, and R2 in these novel phosphonate thioureas contribute to the antitumor activities. All these SAR‐guided efforts may lead to novel antitumor drugs in the market in the near future.

Phosphonopeptides containing free phosphonic groups: recent advances

“…These peptides exhibited promising antiproliferative activity against several cancer cell lines (BCG-823, A-549, PC-3, Bcap-37 and BCG-823) with compounds 25, 26, 27 and 28 being the most active. 44,45 An addition of diethyl or dimethyl phosphites to aldehydes derived from S-phenylalanyl-S-alanine resulted in diastereomeric mixtures of dipeptidyl 2-amino-1-hydroxyphosphonates (Fig. 8).…”

Thiourea and Guanidine Compounds and Their Iridium Complexes in Drug‐Resistant Cancer Cell Lines: Structure‐Activity Relationships and Direct Luminescent Imaging

“…Thioureas show promise as anticancer drug candidates due to their sulfur atoms, with sulfur itself being a versatile and biologically important element to all living organisms . Thiourea derivatives have been synthesised with an assortment of partnering organic structures and demonstrated to exert anti‐cancer effects in human cancer cell lines from different entities including breast and lung cancer as well as leukaemia …”

“…[24] Thiourea derivatives have been synthesised with an assortment of partnering organic structures and demonstrated to exert anti-cancer effects in human cancer cell lines from different entities including breast and lung cancer as well as leukaemia. [25][26][27]28] We are currently investigating guanidine-and thioureabased molecules as components in advanced organic LED materials through formation of luminescent iridium complexes. [29,30] Iridium complexes themselves are of great interest as potential cancer therapeutics because they generate a 3D scaffold, enabling structural diversity beyond the 'flatter' organic molecules or platinum complexes used in cancer therapy; they offer an opportunity for simultaneous imaging due to their rich and tunable luminescence properties; [31] and they offer an opportunity for photogeneration of singlet oxygen within cells.…”

Conjugation as a Tool in Therapeutics: Role of Amino Acids/Peptides-Bioactive (Including Heterocycles) Hybrid Molecules in Treating Infectious Diseases

“…The compounds containing fluorine groups in the amino acid amide structure showed significant anticancer activity. Authors concluded that the variation of alkyl groups in the novel phosphonate thioureas contribute to their anticancer activity [ 193 ].…”