Design and synthesis of novel 5-aminosalicylate (5-ASA)–4-thiazolinone hybrid derivatives with promising antiproliferative activity

Abdu-Allah, Hajjaj H.M.; Abdel-Moty, Samia G.; El‐Awady, Raafat; El‐Shorbagi, Abdel‐Nasser

doi:10.1016/j.bmcl.2016.02.073

Cited by 22 publications

(20 citation statements)

References 35 publications

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“…Among a plethora of classes and subclasses of heterocyclic cores, 4‐thiazolidinone has attracted a significant interest of the researchers . The presence of three heteroatoms in one core, easy and high yielding synthesis, low to moderate molecular weight (MW), broad range of activities through unique mechanism, and so forth are some of the unique features offered by these five‐membered cores . In the past, we have demonstrated that 4‐thiazolidinones can effectively check the amoebic growth and show moderate anticancer activity in vitro .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Mushtaque¹,

Avecilla

Hafeez

et al. 2019

Journal of Heterocyclic Chem

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Scaffolds containing one or more heteroatoms are ubiquitous in nature and are responsible for almost every biological processes in flora and fauna. The fact that heterocyclic cores have high propensity for biological targets, several nitrogen, oxygen, and sulfur‐containing heterocyclic compounds have been reported in the last few decades. One such intriguing class is 4‐thiazolidinone that exhibit diverse range of pharmacological activities. In the present study, we report synthesis, characterization, molecular docking, and anticancer evaluation of 10 new 4‐thiazolidinone analogues (5–14). One of the compounds (11) was structurally characterized using single crystal X structure. Anticancer evaluation against hepatocellular carcinoma cell line (HepG2) revealed that compound (7) was the most potent (IC50 = 75 μM) while other showed moderate to low activity (85–530 μM). To underpin the druggability and possible modes of action, drug‐likeness was determined and docking studies were carried out against β‐carbonic anhydrase receptor (PDB ID: 3IA). Attempts have also been made to establish a structure–activity relationship of the reported compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Mushtaque¹,

Avecilla

Hafeez

et al. 2019

Journal of Heterocyclic Chem

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“…[ 17,20,39 ] The ( Z ) configuration of the exocyclic C═C bond of the final compounds was confirmed by spectroscopic and X‐ray studies performed for chosen structures and described before. [ 20,22 ] The coexistence of tautomeric forms and syn/anti‐arrangement rotamers for all compounds 1 – 30 is confirmed by a characteristic doubling of signals observed in the 1 Н and 13 С NMR (nuclear magnetic resonance) spectra. [ 20,22 ]…”

Section: Resultsmentioning

confidence: 91%

“…[ 20,22 ] The coexistence of tautomeric forms and syn/anti‐arrangement rotamers for all compounds 1 – 30 is confirmed by a characteristic doubling of signals observed in the 1 Н and 13 С NMR (nuclear magnetic resonance) spectra. [ 20,22 ]…”

Section: Resultsmentioning

confidence: 93%

“…Among 5‐ene‐2‐amino(imino)‐4‐thiazolidinones, a series of active anticancer agents inhibiting the cancer cells' growth was identified in in vitro assays. [ 17–22 ] Moreover, many ligands with a high affinity toward the known anticancer targets were described, for example, integrin α v β 3 antagonists, [ 23 ] inhibitors of CDK1/cyclinB, [ 24,25 ] PPAR antagonists, [ 26 ] estrogen‐related receptor‐α (ERR‐α) modulators, [ 27 ] SHP‐2 inhibitors, [ 28,29 ] PTP1B inhibitors, [ 30 ] DNA‐binding agents (binding with the DNA minor groove involving van der Waals, H‐bonding, and hydrophobic interactions), [ 31 ] and so forth. Some structurally related (5‐aminosalicylate)‐4‐thiazolinone hybrids exhibited strong anticancer effects mainly through DNA induction, which initiated G2/M arrest and apoptosis.…”

Section: Introductionmentioning

confidence: 99%

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5‐Arylidene‐2‐(4‐hydroxyphenyl)aminothiazol‐4(5H)‐ones with selective inhibitory activity against some leukemia cell lines

Subtel’na

Kryshchyshyn‐Dylevych

Jia

et al. 2020

Archiv der Pharmazie

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The data on the pharmacology of 4‐thiazolidinones showed that 5‐ene‐2‐(imino)amino‐4‐thiazolidinones are likely to comprise one of the most promising groups of compounds possessing anticancer properties. A series of 5‐arylidene‐2‐(4‐hydroxyphenyl)aminothiazol‐4(5H)‐ones was designed, synthesized, and studied against 10 leukemia cell lines, including the HL‐60, Jurkat, K‐562, Dami, KBM‐7, and some Ba/F3 cell lines. The structure–activity relationship analysis shows that almost all tested 5‐arylidene‐2‐(4‐hydroxyphenyl)aminothiazol‐4(5H)‐ones were characterized by ІС50 values lower or comparable to that of the control drug chlorambucil. Among the tested compounds, (5Z)‐5‐(2‐methoxybenzylidene)‐ (12), (5Z)‐(2‐ethoxybenzylidene)‐ (21), (5Z)‐5‐(2‐benzyloxybenzylidene)‐ (25), and (5Z)‐5‐(2‐allyloxybenzylidene)‐2‐(4‐hydroxyphenylamino)thiazol‐4(5H)‐ones (28) possessed the highest antileukemic activity at submicromolar concentrations (ІС50 = 0.10–0.95 µM).

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“…5‐Aminosalicylic acid, a benzoic acid containing amino and hydroxyl groups, has traditionally been used in the treatment of inflammatory bowel disease, ulcerated colitis and Crohn's disease . Its Schiff base with salicylaldehyde, 5‐(salicylideneamino)salicylic acid, possesses multiple coordination sites including two phenolic hydroxyl groups, one carboxyl group and one imine group, and can construct a variety of structural modes with metals.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization and cytotoxic activity of triorganotin 5‐(salicylideneamino)salicylates

Liu

Lin

Liu

et al. 2019

Applied Organom Chemis

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Six new triorganotin complexes (1a–1c and 2a–2c) of 5‐(salicylideneamino)salicylic acid, [5‐(3‐X‐2‐HOC6H3CH═N)‐2‐HOC6H3COO]SnR3 (X = H, 1; CH3O, 2; R = Ph, a; Cy, b; CH2C(CH3)2Ph, c), have been synthesized by one‐pot reaction of 5‐aminosalicylic acid, salicylaldehyde and triorganotin hydroxide and characterized using elemental analysis and infrared and NMR (1H, 13C and 119Sn) spectra. The crystal structures of 1a, 1b, 2a·CH3OH, 2b·CH3OH and 2c·CHCl3 have been determined using single‐crystal X‐ray diffraction. In non‐coordinated solvent CDCl3, the tin atoms in the complexes are all four‐coordinated. In the crystalline state, these compounds adopt a four‐ or five‐coordination mode. Complex 1a exhibits a 44‐membered macrocyclic tetrameric structure with trigonal bipyramidal geometry around the tin atoms in which the axial positions are occupied by the oxygen atom of carboxylate group of the ligand and the phenolic oxygen atom from the adjacent ligand. The coordination geometry of tin atom in 1b and 2c·CHCl3 is a distorted tetrahedron shaped by three carbon atoms of alkyl groups and a carboxylate oxygen atom of the ligand. In 2a·CH3OH and 2b·CH3OH, the tin atom has a distorted trans‐C3SnO2 trigonal bipyramidal geometry formed by three alkyl groups, a monodentate carboxylate group and a coordinated methanol molecule. The molecules of 2a·CH3OH and 2b·CH3OH are linked via O─H···O hydrogen bonds into a one‐dimensional supramolecular chain and a centrosymmetric R44(22) macrocycle, respectively. Bioassay results against two human tumor cell types (A549 and HeLa) show the complexes are efficient cytostatic agents and may be explored as potential antitumor drugs.

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Design and synthesis of novel 5-aminosalicylate (5-ASA)–4-thiazolinone hybrid derivatives with promising antiproliferative activity

Cited by 22 publications

References 35 publications

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

5‐Arylidene‐2‐(4‐hydroxyphenyl)aminothiazol‐4(5H)‐ones with selective inhibitory activity against some leukemia cell lines

Synthesis, structural characterization and cytotoxic activity of triorganotin 5‐(salicylideneamino)salicylates

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