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New sets of functionalized thiazolidinone and thiadiazole derivatives were synthesized, and their cytotoxicity was evaluated on HepG2, MCF-7, HTC-116, and WI38 cells. The synthetic approach is based on the preparation of 4-(4-acetamidophenyl)thiosemicarbazide (4) and their thiosemicarbazones 5 a-e, which are converted to the corresponding thiazoldin-4-one compounds 6 a-e upon cyclization with ethyl bromoacetate. The thiadiazole compounds 9 and 12 were obtained by reacting 4-(4-acetamidophenyl)thiosemicarbazide with isothiocyanates and/or ethyl 2-cyano-3,3-bis(methylthio)acrylate, respectively. The thiazolidinone compounds 6 c and 6 e exhibited strong cytotoxicity against breast cancer cells, with an IC 50 (6.70±0.5 μM) and IC 50 (7.51±0.8 μM), respectively, very close to that of doxorubicin (IC 50 : 4.17±0.2 μM). In addition, the anti-cancer properties of the tested thiazolidinone and thiadiazole scaffolds were further explored by the molecular docking program (MOE)-(PDB Code-1DLS). Compounds 5 d, 5 e, 6 d, 6 e, and 7 have the best binding affinity, ranging from -8.5386 kcal.mol -1 to -8.2830 kcal.mol -1 ., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

In this study, novel 3-(phenylamino)thiazolidin-4-one 2 a-d and 3-(phenyl)thiazolidin-4-one 3 a-g derivatives which are having benzimidazole moiety were synthesized and their tyrosinase inhibitory activity were investigated. The structures of the target compounds were elucidated using 1 H/ 13 C-NMR, IR and MS. The structure of 2 b was also characterized using HSQC NMR technique. Among the target compounds, 3 b-g demonstrated stronger tyrosinase inhibitory activity (IC 50 values for 3 b-g ranged from 80.93 to 119.20 μM), compared to the positive control kojic acid (IC 50 : 125.08 μM). With IC 50 value of 80.93 μM, 5-(2-(4-(1H-benzimidazol-1-yl)phenyl)-4-oxothiazolidin-3-yl)-2-methylbenzenesulfonamide 3 g was found to be the most active derivative of the series. Molecular docking studies were conducted to elucidate the binding interactions between compounds and tyrosinase. The MTT assay studies used to determine the cytotoxicity of 3 b-g showed that 3 c, 3 d, 3 f and 3 g were not cytotoxic in the range of 0-200 μM. Considering its tyrosinase inhibitory activity and cytotoxic effect, 3 g exhibits promising potential for further research and development as a novel tyrosinase inhibitor., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Objective: Aim: This study focuses on developing and evaluating five newly created compounds targeting carbonic anhydrase isoforms found in solid tumors. Our primary goal is to create exceptionally potent anti-cancer drugs., Patients and Methods: Materials and Methods: Sulfanilamide, chloroacetyl chloride, Gamma-aminobutyric acid, thionyl chloride, methanol, hydrazine hydrate, aromatic aldehyde derivatives, glacial acetic acid, and thioglycolic acid were used in the chemical synthesis. We performed docking studies using the Molecular Operating Environment software program version 2015.10, and used MTT assay to predict cytotoxic activity., Results: Results: The compounds we developed demonstrated impressive antineoplastic action in both in silico experiments as well as cell line experiments. Their toxicity to normal cells varied significantly, but their efficacy against cancer cells differed significantly from cisplatin. When compared to acetazolamide, each of the produced compounds exhibited significant differences in their effects on MCF7 cells. Based on these findings, synthetic compounds may serve as antineoplastic medications. Including the thiazolidinone ring in these compounds enhanced their affinity for the receptor by binding to multiple crucial amino acids that play a significant role in our target's enzymatic activity and substrate binding., Conclusion: Conclusions: Our synthetic compounds revealed cytotoxicity and inhibitory potencies against carbonic anhydrase. Moreover, they exhibited cytotoxicity.

Cancer is one of the life-threatening diseases accountable for millions of demises globally. The inadequate effectiveness of the existing chemotherapy and its harmful effects has resulted in the necessity of developing innovative anticancer agents. Thiazolidin-4-one scaffold is among the most important chemical skeletons that illustrate anticancer activity. Thiazolidin-4-one derivatives have been the subject of extensive research and current scientific literature reveals that these compounds have shown significant anticancer activities. This manuscript is an earnest attempt to review novel thiazolidin-4-one derivatives demonstrating considerable potential as anticancer agents along with a brief discussion of medicinal chemistry-related aspects of these compounds and structural activity relationship studies in order to develop possible multi-target enzyme inhibitors. Most recently, various synthetic strategies have been developed by researchers to get various thiazolidin-4-one derivatives. In this review, the authors highlight the various synthetic, green, and nanomaterial-based synthesis routes of thiazolidin-4-ones as well as their role in anticancer activity by inhibition of various enzymes and cell lines. The detailed description of the existing modern standards in the field presented in this article may be interesting and beneficial to the scientists for further exploration of these heterocyclic compounds as possible anticancer agents., (© 2023. Crown.)

This study represents the synthetic approaches of a new set of 2-(((3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazono)-5-(aryl)thiazolidin-4-one derivatives 4-22 aiming to obtain new antiproliferative candidates against human cervix carcinoma cells (Hela) of EGFR PK inhibiting potency. The cancer cells represented promising sensitivity towards the compounds 6, 7, 11, 13, 14, 16, 17 more than or equal to that against the reference drug doxorubicin. In addition, the latter compounds were tested as EGFR protein kinase inhibitors. The results revealed that compound 14 showed more significant EGFR PK inhibitory activity than the reference drug erlotinib (IC50; 0.07, 0.08 µM, respectively). Moreover, cell cycle analysis and apoptosis assay were performed for compound 14 proving its ability to cause G1/S phase arrest and apoptosis in Hela cancer cells, in addition to its activation of the caspases-7 and -3. In addition, derivative 14 increased the expression level of p53 and the ratio of Bax/Bcl-2 which confirmed its mode of action. Molecular docking study of 14 was performed to investigate its binding mode of interaction with EGFR PK in the active site with the aim of rationalizing its promising inhibitory activity. Accordingly, compound 14 might be considered as a promising scaffold anticervical cancer chemotherapeutic and deserves further optimization and in-depth biological studies., (Copyright © 2019. Published by Elsevier Inc.)

Aim: To synthesize a series of new thiazolidinone-pyrazole hybrids (5a-o) and assess their anticancer (in vitro and in vivo) and antimicrobial activities., Results: The compounds 5h (against Ehrlich ascites carcinoma cells), 5e and 5i (against the human breast cancer [MDA-MB231] cell line) exhibited potent anticancer activity. All the compounds except 5g and 5e found to be less toxic for the human dermal fibroblast cells. The effective interactions of the compounds in silico with MDM2 exemplified their inhibitory potency. The derivatives also showed moderate antimicrobial activity., Conclusion: The halogen atoms on various positions of the N-arylamino ring played an advantageous role in elevating the potency of the molecules. Thus, these conjugates could be used as a lead for further optimization to achieve promising therapeutics.

Both quinacrine, which contains a 9-aminoacridine scaffold, and thiazolidin-4-one are promising anticancer leads. In an attempt to develop effective and potentially safe anticancer agents, we synthesized 23 novel hybrid compounds by linking the main structural unit of the 9-aminoacridine ring with the thiazolidin-4-one ring system, followed by examination of their anticancer effects against three human breast tumor cell lines and matching non-cancer cells. Most of the hybrid compounds showed good activities, and many of them possessed the preferential killing property against cancer over non-cancer cells. In particular, 3-[3-(6-chloro-2-methoxy-acridin-9-ylamino)-propyl]-2-(2,6-difluoro-phenyl)-thiazolidin-4-one (11; VR118) effectively killed/inhibited proliferation of cancer cells at IC 50 values in the range of 1.2-2.4 μM. Furthermore, unlike quinacrine or cisplatin, compound 11 showed strong selectivity for cancer cell killing, as it could kill cancer cells 7.6-fold (MDA-MB231 vs MCF10A) to 14.7-fold (MCF7 vs MCF10A) more effectively than matching non-cancer cells. Data from flow cytometry, TUNEL and Western blot assays showed that compound 11 kills cancer cells by apoptosis through the down-regulation of Bcl-2 (but not Bcl-X L ) survival protein and up-regulation of Bad and Bax pro-apoptotic proteins. Thus, compound 11 is a highly promising lead for an effective and potentially anticancer therapy., (Copyright © 2017 Elsevier Masson SAS. All rights reserved.)

Design and synthesis of new pyrimidine derivatives clubbed with thiazolidin-4-one from 4-(2-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidin-2-amine and their in vitro anticancer activities were screened at National Cancer Institute (NCI), USA against full NCI 60 cell lines. Compound 2 (NSC: 765735) exhibited remarkable growth inhibition at single dose (10 μM) and encourage chosen for broadcast at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 μM). The compound 2 was found better quality for Lung cancer cell line (HOP-92) by viewing growth inhibition (GI50 0.52) and no cytotoxicity seen (LC50 > 100). Molecular docking study was performed using Maestro 9.0 (Schrodinger Inc. USA) to provide binding mode into binding sites of CDK2. Compound 2 could be used as a lead compound for developing new potential anticancer agents., (Copyright © 2014 Elsevier Masson SAS. All rights reserved.)

A set of novel 5-benzylidene-3-ethyl-2-(2-methyl-3-trifluoromethyl-phenylimino)-thiazolidin-4-one derivatives have been synthesized by Knoevenagel reaction via both conventional as well as non-conventional methods on the synthesized iminothiazolidinone core. In terms of yield and reaction time, the ultrasound mediated Knoevenagel reaction method has proved to be more effective than the conventional approach using heat. The ¹H NMR spectra have been used to deduce the structure of the compounds, while LC-MS, FTIR, and elemental analysis data have also been utilized for better confirmation. Using a 2D NOESY NMR experiment, the stereochemistry of the final compound has been verified. The synthesized benzylidine compounds have been screened for in vitro anticancer potential against Human Hepatoma (Hep-G2) cell line. The compound having p-substituted methoxy group on benzylidine moiety is observed to be the most active against the tested cell line as compared to the rest of the compounds. [ABSTRACT FROM AUTHOR]

Objective: Microbial infections and the cancer are the biggest health concerns now days. It has been reported that 19.3 million new cancer cases and approximately 10 million deaths occurred due to cancer. The pyrimidine and their derivatives have been investigated a lot by the researchers due to their versatile chemotherapeutic effects. The unmet demand for the new antimicrobial and anticancer chemotherapeutic agents and the versatile pharmacological applications of pyrimidine derivatives prompted us to perform the synthesis and biological assessment of some novel 3-(substitued)-6-(substituted)pyrimidin-2-yl)-2-phenylthiazolidin-4-one. Methods: As a part of or investigation to find out some novel antimicrobial and anticancer agents, in this paper we focused on the synthesis of some novel 3-(substitued)-6-(substituted)pyrimidin-2-yl)-2-phenylthiazolidin-4-one derivatives. Additionally, the compounds were screened virtually for the drug likeness properties and characterized by FT-IR and NMR. Antimicrobial and anticancer studies were performed using the methods of disc diffusion, macro dilution and MTT assay. Results and Discussion: The virtual screening results revealed that all the compounds were found under the zone of inhibition for an active drug molecule. It was observed that the analytical data strongly supported the structure of the aimed compounds. Among all the synthesized compounds, the compounds (IX–XII), (XIV–XVI) were possessed very good antimicrobial effects. Some of these members represented even better antimicrobial potential against some specific pathogens. The compound (XII) was observed to be the most active compound of the series against almost all bacterial pathogens. The MTT findings revealed that the compounds (III), (IX), (X), (XII) were possessed similar IC50 to the reference drug doxorubicin. Conclusions: The antimicrobial and anticancer findings were promising and it was believed that further studies with these compounds aiming in vivo analysis will be helpful in producing the novel antimicrobial and anticancer agents. [ABSTRACT FROM AUTHOR]

Herein we report the synthesis and biological evaluation of a new series of thiazolidin-4-one derivatives. The C4 and C5 functionalized, 5-arylidene/alkylidene, 5-bromo, 5-pyridinium, and 4-arylimino analogs of thiazolidine-4-one were prepared efficiently using appropriate synthetic routes and characterized by IR, NMR and Mass spectrometry. Results of antimicrobial evaluation showed that compounds 4 and 8 had significant antibacterial activity comparable to that of the reference drug gentamicin. Compound 5a showed promising antifungal activity compared to amphotericin B as a reference drug. The antitumor activity revealed that compound 4 was the most active analog among the tested series with IC50 values of 28.4 and 12.6 µg/mL against both HCT-116 and HepG-2 cell lines, respectively, compared to standard drug doxorubicin. Results from the biological evaluation, in-silico molecular docking studies, and ADMET analyses confirmed that thiazolidin-4-one is a promising scaffold that can be used to design potential lead compounds for the antibacterial and antitumor agents. [ABSTRACT FROM AUTHOR]

Thiazolidin‐4‐one is a versatile nucleus that has been reported to exhibit a diverse array of biological activities, including anticancer and antimicrobial activities. In the current research study, a series of C2‐(p‐substituted phenyl)‐thiazolidin‐4‐one compounds conjugated with anilines were designed and tested for drug‐likeness behaviour. Subsequently, the designed compounds were synthesized, characterized, and tested for anticancer activity against three cancer cell lines, namely liver (HEP−G2 cells), breast (MDA‐MB‐231), and glioblastoma (U87MG cells), with gemcitabine as the reference positive control drug. Initially, the compounds were tested at 50 micromolar, while the MIC was determined for the selected active compounds. Among the three cell lines, MDA‐MB‐231 showed relatively higher sensitivity towards the tested compounds. Four compounds of the series exhibited comparable or superior cytotoxicity to the reference drug gemcitabine. Particularly, N‐(p‐tolyl)‐2‐(2‐(4‐methoxyphenyl)‐4‐oxothiazolidin‐3‐yl)acetamide (6 d) displayed highest cytotoxicity among the series. The anticancer activity of the selected compounds was also tested against 3D spheroid models, in which compound N‐(4‐chlorophenyl)‐2‐(2‐(4‐methoxyphenyl)‐4‐oxothiazolidin‐3‐yl)acetamide (6 a) induced apoptosis in brain tumour spheroids (MTS). Docking studies of compound 6 d were performed against different targets, namely dihydrofolate reductase, phosphoinositide 3‐kinase, epidermal growth factor receptor, dihydroorotate dehydrogenase, and murine double minute 2, which illustrated inhibition of dihydroorotate dehydrogenase as a possible mechanism of toxicity. The compounds were also evaluated in vitro for antibacterial activity against two bacterial strains (E. coli and P. aeruginosa) and a Candida albicans fungal strain. [ABSTRACT FROM AUTHOR]

Thiazolidin-4-ones is a versatile and privileged nucleus comprising of a five five-membered heterocyclic ring system possessing sulphur heteroatom and a cyclic amide bond. Extensive research and review studies mainly published in the last decade explored the diverse types of biological activities of this nucleus with potential therapeutic applications. Various silent features like drug likeness behaviour, suitability for diversity-oriented synthesis, and its sensitivity toward the redox tumour microenvironment makes it an attractive scaffold for anti-cancer drug discovery. Thiazolidine-2,4-dione and thiazolidine-4-ones are the two classical variants of thiazolidine scaffold, the former is more explored in comparison to thiazolidine-4-one. However, thiazolidine-4-one nucleus is also getting the attention of researchers, evident by the various research studies, mainly published in the last few years. The current comprehensive review focuses on its anti-cancer potential, covering structural diversity and substitution patterns among diverse derivatives containing this nucleus as a core skeleton. This review also gives impetus to the different enzymatic targets, exploited for drug discovery, relative selectivity in cancerous tissue compared to healthy counterpart cells, structure-activity relationship (SAR), and future perspectives for translational research. To generate potential lead candidates with the translational outcome next level studies like pharmacokinetic and metabolic stability are suggested. [ABSTRACT FROM AUTHOR]

A variety of novel thiazolidin‐4‐one himachalene derivatives were designed and synthesized through hetero‐cyclization of thiosemicarbazone analogs that have previously exhibited strong anticancer activity. The synthesized products 2 a–4 f were completely characterized by 1H NMR, 13C NMR, IR, and HRMS and were later submitted for in vitro evaluation of their anticancer activity and cytotoxicity on a panel of four human cancer cell lines (i.eHT‐1080, MCF‐7, A‐549, and MDA‐MB‐231). Most of the evaluated compounds showed potent antiproliferative activities against the four human cancer cell lines with tested IC50 values ranging from 5.25±0.32 to 9.26±0.73 μM. The mechanism of action revealed that compounds 2 b and 4 b induced caspase‐3/7‐activated apoptosis and cell cycle arrest in the G0/G1 stage in HT‐1080 and A‐549 cells. Furthermore, molecular docking studies were conducted to evaluate the binding affinities and the possible binding modes of the top‐performing compounds 2 b and 4 b. This was later supported by Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) analysis predicting their prospective pharmacological profiles. The outcome of this study supports the validity of our strategy and presents 2 b and 4 b as a pattern for the discovery of novel cancer therapeutics. [ABSTRACT FROM AUTHOR]

A library of novel naphthyl bearing 2‐iminothiazolidin‐4‐ones (2‐ITZDs) (2 a–2 q) was designed and synthesized through a facile route involving regioselective heterocyclization of unsymmetrical thioureas (1 a–1 q). The synthesis was achieved at ambient temperature in good to excellent yields under catalyst free conditions. The molecular structures of 2‐ITZDs were elucidated by spectroscopic techniques such as FT‐IR, 1H‐NMR and 13C‐NMR. X‐ray structural data was used to establish the structure (2 o) unequivocally and to define the geometry of exo double bond. The in vitro anticancer activity of 2‐ITZDs (2 a–2 q) was investigated in several human cancer cell lines (A549, LNCap, PC‐3, MDA‐MB‐231, BxPC3, MIA PaCa2). All compounds showed cytotoxicity with IC50 values ranging from 6–23 μM in the tested cancer cell lines except MDA‐MB‐231. Compound 2 k (IC50=7 μM) and the homologous analog 2 q (IC50=6 μM) were found to be equipotent to 2 k and showed moderate cytotoxicity against human breast cell line (DA‐MB‐231). Furthermore, compound 2 k exhibited a medium permeability, enough metabolic stability and no significant inhibition of hERG channel. Compound 2 k inhibited cytochrome P450 activity below 50 % in 1 A2, 3 A4 and 2 C19, but not in 2 C9 and 2D6 at 10 μM. Structure‐activity relationships (SAR) provided useful insights towards this class of compounds and tiled a way to design novel analogues with increased potency. [ABSTRACT FROM AUTHOR]

A series of new antipyrine derivatives containing thiazolidin-4-one ring system were synthesized via the cycloaddition reaction of a series of Schiff bases 1a-e with mercaptoacetic acid under reflux conditions. The structure of the new antipyrine derivatives 2a-e was confirmed by spectral data. In addition, the cytotoxic activity of the target compounds 2a-e was investigated in vitro against breast carcinoma cell line (MCF-7). In general, the bioassay results revealed that the synthesized compounds 2a-e have a promising reducing tumor growth comparison to the normal cells. [ABSTRACT FROM AUTHOR]

A series of 4-(2-(4-substituted phenyl)-4-oxoquinazolin-3(4H)-yl)-N-(2-(4 fluorophenyl)-4-oxo-5- (arylidene)thiazolidin-3-yl) benzamides (VIa-n) have been synthesized by condensation of N-(2-(4- fluorophenyl)-4-oxothiazolidin-3-yl)-4-(4-oxo-2-(4-substituted phenyl)quinazolin 3(4H)-yl)benzamides (Va-b) with various aryl/heteroaryl aldehydes using conventional methodology. All compounds were screened for their in vitro anticancer activity against the human breast cancer cell lines (MCF-7), human lung cancer cell lines (A549) using MTT assay method and doxorubicin is used as standard drug. Compound VId, VIk and VIn showed high potency against A549 cell lines with IC50 values 0.035±0.002 μM, 0.031±0.002 μM and 0.030±0.002 μM respectively compared to 0.023±0.002 μM showed by the standard. However, highest activity against MCF-7 cell lines was exhibited by Va, Vb, VIk and VIn with IC50 values between 0.040 - 0.050 μM. All the remaining compounds showed moderate anticancer activity against both the MCF-7 and A549 cell lines. To understand the interactions with active binding site of receptor, molecular docking study was also performed. [ABSTRACT FROM AUTHOR]

Thiazolidin-4-one derivative 3 was synthesized by the transformation of chloroacetamide derivative 2 with NH4SCN.The condensation of 3 with p-anisaldehyde afforded the corresponding arylidene derivative 4. Also, the alkylation of chloroacetamide derivative 2 with different heterocyclic compounds was investigated. Annulation of 5-amino-3-methylisoxazole ( 1) with α-halocarbonyl compounds 12 and 14 furnished pyrrolo[3,2-d]isoxazole and isoxazolo[5,4-b]azepin-6-one derivatives 13 and 15, respectively, while reaction of 1 with 1-chloro-4-(chloromethyl)benzene gave the monoalkylated product 17. The newly synthesized compounds were screened for their antitumor activity, and the geometry optimizations are in a good agreement with the experimentally observed data. [ABSTRACT FROM AUTHOR]

• The new HER2 inhibitors was synthesized with a thiazolidine-4-one structure. • Compound 7g is the most potent against MCF7 cells with IC 50 values 4.38 µM. • The selectivity of 7g is 9-fold higher than doxorubicin against MCF7 cells. • The in vitro tests were supported by in silico and 7g was found as the most active. In this study, 16 new hybrid compounds 6(a-h) and 7(a-h) were synthesized starting from methylparaben. These new compounds consist of eight 1,2,3-triazole-arylidenehydrazide derivatives and eight 1,2,3-triazole-thiazolidin-4-one derivatives. All compounds were tested against MCF-7 breast cancer cells and MCF10A breast healthy tissue to determine their anti-cancer activity. Molecular docking studies were also carried out against receptor proteins (HER2, EGFR, and VEGFR1) that are related to the growth factor of cancer cells to understand the inhibition mechanism. According to the results of in silico and in vitro activity studies, compounds 6g and 7g were found as the highest selective and active against breast cancer cells. The IC 50 values of compounds 6g and 7g against MCF7 cells were found as 8.48 and 4.38 µM, respectively. In addition, the IC 50 values of compounds 6g and 7g against MCF10A cells were found as 114.80 and 170.60 µM. When comparing the selectivity of the 6g and 7g to the reference drug doxorubicin, 6g and 7g had higher selectivity (13.5 and 39 respectively) compared to doxorubicin (4). The compound 7g also showed activity against cancer cells at lower doses and was found to be safe against healthy cells at high doses. Molecular docking results showed that both 6g and 7g had higher binding scores for all 3 target enzymes and especially for HER2 protein related to breast cancer with binding scores of -8.059 kcal and -9,008 kcal respectively, while doxorubicin had a binding score of -7.854 kcal. According to the results of the in vitro, and in silico study, compound 7g which was synthesized in this study is a promising, potent, and selective anti-cancer drug candidate for the treatment of breast cancer. All the tested compounds were very well characterized by spectroscopic methods and they have at least 95% HPLC purity. [Display omitted] [ABSTRACT FROM AUTHOR]

Abstract: The novel 4-(4-oxo-2-arylthiazolidin-3-yl)benzenesulfonamide derivatives were designed and synthesized for selective carbonic anhydrase IX (CA IX) inhibitory activity with anticancer potential. In the CA inhibition assay, 3f was found to be the most potent and selective inhibitor of CA IX with inhibitory constant (K I) value of 2.2 nM. Among the synthesized compounds, 3f showed IC50 values of 5.03 μg/ml (cisplatin: 6.56 μg/ml), 5.81 μg/ml (cisplatin: 5.85 μg/ml), and 23.93 μg/ml (cisplatin: 2.75 μg/ml) against COLO-205, MDA-MB-231, and DU-145 cell lines, respectively. At IC50, 3f caused cell shrinkage, nuclear condensation, and nuclear fragmentation events characteristic to apoptosis in the Hoechst 33258 and acridine orange-ethidium bromide staining studies of COLO-205 cells. In the Dalton's lymphoma ascites (DLA) solid tumor model 3f decreased tumor volume by 64.83% (cisplatin: 71.62%), while increase in mean body weight was found to be only 4.09% (cisplatin: 3.47%). [Copyright &y& Elsevier]

A series of new benzofuran derivatives 3a-f, 5a-e containing a heterocyclic substituent linked to benzofuran nucleus at C-2 were synthesized as potential antitumor agents. These products were synthesized starting with 2-bromoacetylbenzofuran 1. The structures of all compounds were established on the basis of analytical and spectral data. The synthesized compounds were tested against human liver carcinoma cell line (HEPG2) and all were more potent than the comparative standard (5-flurouracil). Compound 3f was the most active (IC50 = 12.4 μg/mL). [ABSTRACT FROM AUTHOR]

Thiazolidin-4-ones are known to exhibit diverse biological activities such as antimicrobial, anticancer, antidiarrheal, anticonvulsant, antidiabetic, antihistaminic, and antifungal activities. In the present investigation, a series of 2-haloacetamides was prepared by reacting chloroacetyl chloride with amines in dry benzene under reflux conditions. The formed 2-haloacetamides reacted with potassium thiocyanate in refluxing dry acetone to afford new 2-iminothiazolidin-4-ones. The 5-arylidene-2-imino-3 (napthalen-2yl)-thiazolidin-4-ones were prepared by condensing 2-iminothiazolidin-4-ones with substituted benzaldehydes. All the products were characterized by infrared, mass, and 1H and 13C NMR techniques. [ABSTRACT FROM AUTHOR]

Abstract: A series of sulfapyridine-polyhydroxyalkylidene (or arylidene)-imino derivatives (Schiff''s bases) 2a–c and 4a–e were prepared by condensation of 4-amino-N-pyridin-2-ylbenzenesulfonamide (1) with different monosaccharides or with aromatic aldehydes. Treatment of 2a–c with thioglycolic acid led to the formation of the C-nucleosides (3a–c), while treatment of 4a–e with thioglycolic and/or thiosalicylic acids afforded the corresponding 2-arylthiazolidin-4-one or 2-arylbenzothiazin-4-one derivatives 5a–e and/or 6a–e, respectively. Some representative examples of the newly prepared compounds showed considerable cytotoxic effect against breast carcinoma cell line MCF7 and cervix carcinoma cell line HELA in comparison with 5-flurouracil and doxorubicin. AutoDock molecular docking into PTK has been done for lead optimization of the compounds in study as potential PTK inhibitors. [Copyright &y& Elsevier]

Abstract: Some novel 2-aryl-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl] thiazolidin-4-ones were synthesized by the three-component condensation of an amino sugar 1, an aromatic aldehyde 2, and mercaptoacetic acid 3 in the presence of DCC and DMAP at room temperature. Two diastereoisomers 4 and 5 were afforded as the main products in totally isolated yields of 25.4–70%. The reaction was carried out with almost no observed stereoselectivity except in the case of 2c, which showed a moderate stereoselectivity. The structures of the new compounds were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration of the newly generated chiral carbon (C-2) in the thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 5d and the comparison of their corresponding NMR signals. The antitumor (human cervical cancer cells) activity and the inhibition against the glycosidases (α-glucosidase, β-glucosidase, α-amylase) have been evaluated for the new compounds, some of which exhibited antitumor activity. [Copyright &y& Elsevier]