Novel rhodanines with anticancer activity: design, synthesis and CoMSIA study

Abstract

Three different series of some novel N-substituted rhodanines were designed for anticancer activity and prepared from the corresponding dithiocarbamates. The synthesized compounds were analyzed by IR, NMR and MASS to confirm their structures. All the titled compounds were found to be of Z configuration based on NMR spectral analysis. All the synthesized rhodanines were screened for in vitro anticancer activity against MCF-7 breast cancer cells at the concentration of 10µg. Compounds showed moderate to significant cytotoxicity. Amongst them, interestingly, compounds 10, 22 and 33 with cinnamoyl substitution at 5 th position of thiazolidine ring system showed significant activity. Further, we subjected all these compounds for the CoMSIA study to study their 3D quantitative structure activity relationships (3D QSAR). The illustration about the design of novel rhodanines, synthesis, analysis, activity against MCF-7 cells and SAR via CoMSIA study are reported here.

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

“…These aldehydes 3 a-g were then condensed with Rhodanine 4 a and Rhodanine-3-acetic acid 4 b in glacial acetic acid and sodium acetate buffer medium to give final compounds 5 a-g and 6 a-g respectively. Structures of all the target compounds were confirmed by IR, 1 HNMR, 13 CNMR, and mass spectral data.…”

“…[7] Rhodanine is a propitious molecule in the antidiabetic drug discovery program. [8,9] Rhodanine derivatives displayed a wide range of biological activities such as antimicrobial, [10,11] antitubercular, [12] anticancer, [13] antiviral, [14] anti-inflammatory, [15] antimalarial, [16] antioxidant [17] and acetylcholinesterase inhibitor [18] activities. They have emerged as promising motif in antidiabetic drug discovery program and as reported in the literature (Figure 1), Rhodanine derivative 1 showed PPARγ binding activity, [19] 2, 3 as potent α-glucosidase inhibitors, [20,21] and 4displayed aldose reductase inhibitory activity.…”

Design and Synthesis of New CDK2 Inhibitors Containing Thiazolone and Thiazolthione Scafold with Apoptotic Activity

“…The progress of the reactions was determined using TLC aluminum silica gel plates 60 F245. IR, the analysis ( 1 H-NMR, 13 C-NMR and Elemental analyses) were proceeded at the, Cairo University Micro analytical Centre, Egypt. Synthesis of (Z)-5-(Thiophen-2-ylmethylene)-2-thioxothiazolidin-4-one (1).…”

“…[1][2][3][4] Heterocyclic compounds such as 2-thioxothiazolidin-4-ones, pyrimidines and pyrazolines have been widely studied for their importance in medicinal chemistry regarding their wide biological inhibi-tory activities of CDK2/CyclinA. These compounds displayed wide pharmacological activities, including antibacterial, [6][7][8] antiviral, 9) antidiabetic, 10) anticancer, 11) anti-inflammatory, 12) antioxidant, 13) anti-tubercular, 8) anticonvulsant, 14) and cytotoxic activities. [15][16][17][18][19][20][21][22][23][24] Derivatives of pyridine scaffold also were widely used as both fungicides and anticancer drugs.…”

Molecular modeling studies of 1,2,4-triazine derivatives as novel h-DAAO inhibitors by 3D-QSAR, docking and dynamics simulations

“…It has been developed and widely used for anticancer drugs, anti-HCV drugs, antiinammatory drugs and anti-AIDS drugs, [26][27][28][29] but few studies on antipsychotic drugs have been conducted. Moreover, there has never been a study on h-DAAO inhibitors with a simultaneous combination of modeling, prediction, design, molecular docking and dynamics simulation.…”