Synthesis and Antimicrobial Evaluation of Some Novel 2-(4-Chlorophenylimino) thiazolidin-4-one Derivatives

B'Bhatt, H.,Sharma, S. Korean Chemical Society 2012 대한화학회지 Vol.56 No.3

A series of 2-(4-chlorophenylimino)-5-((3-(p-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene) thiazolidin-4-one ($\mathbf{3a-h}$) compounds were prepared from the 2-(4-chlorophenylimino) thiazolidin-4-one ($\mathbf{1}$) and 1-phenyl-3-(p-substituted phenyl)-1H-pyrazole-4-carbaldehyde ($\mathbf{2a-h}$). All compounds were characterized by elemental (C, H, N) analysis and spectral (FT-IR, $^1H$ NMR and GC-MS) analysis. These newly synthesized compounds were screened for their antibacterial and antifungal activities. Antimicrobial activity was observed and evaluated against the bacterial strains like Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442) and against the fungal strains like Candida albicans (MTCC 227), Aspergillus niger (MTCC 282) and Aspergillus clavatus (MTCC 1323). All the synthesized compounds were found to possess moderate to excellent antimicrobial activity against above selected strains.

Synthesis and Biological Evaluation of 2-Phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-ones as IKK2 Inhibitors

김희숙,오광석,이병호,추현아,배애님,노은주,남길수 대한화학회 2015 Bulletin of the Korean Chemical Society Vol.36 No.11

In a search for novel molecules to treat inflammatory disorders, we identified several compounds with inhibitory action against the IKK2 enzyme using in silico methods. Based on the virtual hit of compounds 1 and 2, a novel series of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-one derivatives was designed, synthesized, and evaluated for IKK2 inhibitory activity. Among the synthesized derivatives, compounds 17f and 19f showed good IKK2 inhibitory potency, which have 4-carboxaminophenyl on the 2-furan ring and a methoxy group on the phenylimino moiety at the 2-position of the core structure. The most potent compound was 2-(2,4-dimethoxyphenyl)imino-5((5(4-carboxaminophenyl)furan-2-yl)methylene)thiazolidin-4-one (19f, IC50 = 0.94 μM), which represents a synergic effect of the two virtual hit compounds against IKK2. We also identified compounds showing inhibitory activities against interleukin (IL)-17, CCK-8, and tumor necrosis factor-alpha (TNF-α), which are NF-κB-dependent pro-inflammatory cytokine mediators.

Synthesis and in Vitro Antimicrobial Evaluation of Benzothiazole Incorporated Thiazolidin-4-ones Derivatives

Agarwal, Shikha,Agarwal, Dinesh Kumar,Gautam, Naveen,Agarwal, Kshamta,Gautam, Dinesh Chandra Korean Chemical Society 2014 대한화학회지 Vol.58 No.1

In the course of work on new pharmacologically active antimicrobial agents, we have reported the synthesis of a new class of structurally novel derivatives, incorporating two bioactive structures, a benzothiazole and thiazolidin-4-one, to yield a class of compounds having interesting antimicrobial properties. The antimicrobial properties of the synthesized compounds were investigated against bacteria (Staphylococcus aureus and Escherchia coli) and fungi (Candida albicans and Aspergillus niger) using serial plate dilution method. The structure of the synthesized compounds have been established by elemental analysis and spectroscopic data.

Thiadiazole Derivatives as Potential Anticonvulsant Agents

PoojaMullick,SuroorA. Khan,Surajpal Verma,OzairAlam 대한화학회 2011 Bulletin of the Korean Chemical Society Vol.32 No.3

A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR,^(1)HNMR,^(13)C NMR and mass spectral data confirmed the structure of the synthesized compounds. The derivatives of these moieties were evaluated for anticonvulsant activity byMESmodel and neurotoxicity by rotarod method. The synthesized compounds showed good potential for anticonvulsant activity besides this, the compounds also showed neurotoxic effect. It was observed that compounds with OCH_3 at 3, 4 position of phenyl ring [5(a-l)] showed less protection against convulsions as compared to compounds having unsubstituted phenyl ring [4(a-l)].

Synthesis, Characterization and Antimicrobial Activity of New Thiadiazole Derivatives

Pooja Mullick,Suroor A. Khan,Surajpal Verma,Ozair Alam 대한화학회 2010 Bulletin of the Korean Chemical Society Vol.31 No.8

A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data confirmed the structure of the newly synthesized compounds. The derivatives of these moieties were evaluated for antimicrobial activity. Most of the synthesized compounds showed good antimicrobial activity at 200 and 100 μg/mL. Compounds showed most significant antibacterial activity against gram negative test organism Escherichia coli and most significant antifungal activity against test organisms Aspergillus niger and Candida albicans. It was observed that compounds with OCH3 at 3, 4 position of phenyl ring [5(a-l)] were more potent against microbes as compared to compounds having unsubstituted phenyl ring [4(a-l)].

Synthesis, Characterization and Antimicrobial Activity of New Thiadiazole Derivatives

Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair Korean Chemical Society 2010 Bulletin of the Korean Chemical Society Vol.31 No.8

A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, $^1H$ NMR, $^{13}C$ NMR and mass spectral data confirmed the structure of the newly synthesized compounds. The derivatives of these moieties were evaluated for antimicrobial activity. Most of the synthesized compounds showed good antimicrobial activity at 200 and $100\;{\mu}g/mL$. Compounds showed most significant antibacterial activity against gram negative test organism Escherichia coli and most significant antifungal activity against test organisms Aspergillus niger and Candida albicans. It was observed that compounds with $OCH_3$ at 3, 4 position of phenyl ring [5(a-l)] were more potent against microbes as compared to compounds having unsubstituted phenyl ring [4(a-l)].

Thiadiazole Derivatives as Potential Anticonvulsant Agents

Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair Korean Chemical Society 2011 Bulletin of the Korean Chemical Society Vol.32 No.3

A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, $^1H$ NMR, $^{13}C$ NMR and mass spectral data confirmed the structure of the synthesized compounds. The derivatives of these moieties were evaluated for anticonvulsant activity by MES model and neurotoxicity by rotarod method. The synthesized compounds showed good potential for anticonvulsant activity besides this, the compounds also showed neurotoxic effect. It was observed that compounds with $OCH_3$ at 3, 4 position of phenyl ring [5(a-l)] showed less protection against convulsions as compared to compounds having unsubstituted phenyl ring [4(a-l)].

Zn2+ PVC-based Membrane Sensor Based on 3-[(2-Furylmethylene)amino]-2-thioxo-1,3-thiazolidin-4-one

Mohammad Reza Ganjali*,Hassan Ali Zamani,Parviz Norouzi,Mehdi Adib,Morteza Rezapour,Mohammad Aceedy 대한화학회 2005 Bulletin of the Korean Chemical Society Vol.26 No.4

The 3-[(2-furylmethylene)amino]-2-thioxo-1,3-thiazolidin-4-one (FTT) was used as an excellent ionophore in construction of a Zn2+ PVC-based membrane sensor. The best performance was obtained with a membrane composition of 30% poly(vinyl chloride), 62% nitrobenzen (NB), 3% FTT and 5% sodium tetraphenyl borate (TBP). This membrane sensor shows very good selectivity and sensitivity towards Zn2+ over a wide variety of cations, including alkali, alkaline earth, transition and heavy metal ions. The membrane sensor revealed a great enhancement in selectivity coefficients for Zn2+ ions, in comparison to the previously reported Zn2+ membrane sensors. Theoretical studies also showed the selective interaction of TFF and Zn2+ ions. The proposed membrane sensor exhibits a Nernstian behavior (with slope of 29.3 ± 0.3 mV per decade) over a wide concentration range (1.0´106-1.0´102) with a detection limit of 8.5´107 M (52 ng mL1). It shows relatively fast response time, in the whole concentration range (< 20 s), and can be used for at least 10 weeks in a pH range of 3.0-7.0. The proposed membrane sensor was successfully used in direct determination of Zn2+ ions in wastewater of industrial zinc electroplating companies, and also as an indicator electrode in titration with EDTA.

Zn²⁺ PVC-based Membrane Sensor Based on 3-[(2-Furylmethylene)amino]-2-thioxo-1,3-thiazolidin-4-one

Ganjali, Mohammad Reza,Zamani, Hassan Ali,Norouzi, Parviz,Adib, Mehdi,Rezapour, Morteza,Aceedy, Mohammad Korean Chemical Society 2005 Bulletin of the Korean Chemical Society Vol.26 No.4

The 3-[(2-furylmethylene)amino]-2-thioxo-1,3-thiazolidin-4-one (FTT) was used as an excellent ionophore in construction of a $Zn^{2+}$ PVC-based membrane sensor. The best performance was obtained with a membrane composition of 30% poly(vinyl chloride), 62% nitrobenzen (NB), 3% FTT and 5% sodium tetraphenyl borate (TBP). This membrane sensor shows very good selectivity and sensitivity towards $Zn^{2+}$ over a wide variety of cations, including alkali, alkaline earth, transition and heavy metal ions. The membrane sensor revealed a great enhancement in selectivity coefficients for $Zn^{2+}$ ions, in comparison to the previously reported $Zn^{2+}$ membrane sensors. Theoretical studies also showed the selective interaction of TFF and $Zn^{2+}$ ions. The proposed membrane sensor exhibits a Nernstian behavior (with slope of 29.3 ${\pm}$ 0.3 mV per decade) over a wide concentration range (1.0 ${\times}$ $10^{-6}$-1.0 ${\times}$ $10^{-2}$) with a detection limit of 8.5 ${\times}$ $10^{-7}$ M (52 ng mL$^{-1}$). It shows relatively fast response time, in the whole concentration range ($\lt$ 20 s), and can be used for at least 10 weeks in a pH range of 3.0-7.0. The proposed membrane sensor was successfully used in direct determination of $Zn^{2+}$ ions in wastewater of industrial zinc electroplating companies, and also as an indicator electrode in titration with EDTA.