Antiproliferative Activity of Aminobenzylnaphthols Deriving from the Betti Reaction

Abstract

Two aminobenzylnaphthols, which are representative items of the family of compounds synthesized with the Betti reaction, were investigated as antiproliferative agents against adenocarcinoma human colorectal (Caco-2) and human neuroblastoma (SH-SY5Y) cell lines, using cisplatin as a positive control. A better antiproliferative activity was recorded after 24 h of incubation for the first tested molecule, whereas the other one was more effective after 72 h of incubation. These results support the hypothesis that both of the tested aminobenzylnaphthols could potentially be endowed with a biological activity.

(S,S)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester

“…This nitro-substituted compound will be evaluated for its bio-activity, as previously reported for the unsubstituted derivative [7].…”

“…Our contribution to this topic includes an evaluation of the action of these molecules towards Candida albicans [6], and later an evaluation of antiproliferative activity towards two tumor cell lines [7]. In both papers, Betti aminobenzylnaphthols encompassing an amino acid residue were investigated.…”

A Green Protocol for One‐Pot Pseudo Five‐Component Synthesis of a New Series of Bis‐Betti Bases Via Mannich‐Type Reaction

“…It is also clear that the most important area of application of the non‐racemic aminonaphthols is their use in asymmetric transformations, either as chiral ligands or as chiral auxiliaries [19–22] . Also, some of these products possess biological activity [23–28] . However, in spite of the number of structures reported, it is possible to synthesize and investigate applications of the various structures of these compounds due to their importance.…”

“…[19][20][21][22] Also, some of these products possess biological activity. [23][24][25][26][27][28] However, in spite of the number of structures reported, it is possible to synthesize and investigate applications of the various structures of these compounds due to their importance. In continuation of our previous efforts regarding the synthesis of Betti-base derivatives, [29] we described herein, for the first time an efficient, simple, and environmentally friendly one-pot, pseudo five-component method for the synthesis of a new series of symmetrical bis-Betti base derivatives form 5,5'-methylenebis(thiazol-2-amine), aromatic aldehydes and 2-naphthol in the presence of p-TSA as organocatalyst under solvent-free conditions.…”

Synthesis, Computational, and Anticancer In Vitro Investigations of Aminobenzylnaphthols Derived from 2-Naphtol, Benzaldehydes, and α-Aminoacids via the Betti Reaction

“…In addition, such compounds show stronger cytotoxic and anticancer properties [20,21] compared to derivatives without an amino acid group. However, to the best of our knowledge, there is only one example of testing aminoacid-functionalized Betti base as an antitumor agent [19].…”