Selected Drug-Likeness Properties of 2-Arylidene-indan-1,3-dione Derivatives—Chemical Compounds with Potential Anti-Cancer Activity

Abstract

2-Arylidene-indan-1,3-done derivatives have very different properties, thanks to which they find various applications in science, medicine, and industry. Selected derivatives show antiviral, antibacterial, and anti-inflammatory activity. This paper presents a procedure for the synthesis of a series of indan-1,3-dione derivatives that present antiproliferative activity. The aim of the work was to develop a method of simple synthesis and purification, evaluate the fulfillment of the Lipiński’s and Veber’s rule, and determine the potential scope of application of the obtained series of compounds. The structure of the synthesized compounds was confirmed, and their lipophilicity was determined using experimental and computational methods. Their antiproliferative activity against selected cell lines was tested in accordance with the MTT protocol; the ability to bind to albumin was tested, and the parameters related to the toxicity of substances in silico were determined. The selected compounds which showed antiproliferative activity were strongly bound to albumin and, in most cases, met the Lipiński’s and Veber’s rule. Thus, the obtained results suggest that 2-arylidene-indan-1,3-done derivatives appear to be good candidates for drugs with a potential leading structure for further development.

Lvsiyujins A–G, new sesquiterpenoids, fromCurcuma phaeocaulisValeton root tuber and their preliminary pharmacological property assessment based on ADME evaluation, molecular docking andin vitroexperiments

“…The main difference was that C-1, C-3, C-6, C-9, C-14 and C-15 of 3 were shifted by Δ δ C +3.8, −4.6, −4.6, −5.2, +0.5 and +4.3 ppm, respectively, which was probably due to different stereoscopic structures. The NMR spectrum of 3 closely resembled that of the known compound wenyujin I 24 except that C-10 was substituted by a sulfonic acid group in 3 , which deduced a similar structure for both. This deduction was corroborated by the ROESY and ECD spectra (Fig.…”

“…The isolated compounds were assessed according to Lipinski's ''rule of five'' (molecular weight not more than 500 Dalton; hydrogen bond acceptors r10; hydrogen bond donors o5; and Alog P o 5) and Veber's rule of bioavailability (polar surface area r140 Å, rotatable bonds r10), which has been considered for the evaluation of the positive drug-like properties of any compound. 24,54 The ''ADME/T Descriptor'' module of DS was used to predict aqueous solubility, BBB penetration, CYP2D6 and HIA. These properties were helpful in ascertaining whether the isolated compounds had the potential of druggability.…”

Assessment of Bioavailability Parameters of Mono- and Bistriazole Derivatives of Propynoylbetulin

“…Lipophilicity is connected with other parameters which determine bioavailability. The first rules defining oral availability were described by Lipinski and Veber [67][68][69]. According to Lipinski's rule, lipophilicity should be less than 5.…”

Investigation of the corrosion inhibition potentials of some 2-(4-(substituted)arylidene)-1H-indene-1,3-dione derivatives: density functional theory and molecular dynamics simulation

“…Pluskota et al [21] synthesized some 2-arylideneindan-1,3-dione derivatives and checked their druglike properties [26]. However, the electron-rich structure of these organic systems owing to the presence of π-conjugation and heteroatoms has attracted our group to investigate the corrosion inhibitive potential of these compounds in progress of our research efforts to discover organic molecule with high corrosion inhibition potential.…”