154617-50-2Relevant academic research and scientific papers
Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms
Eldehna, Wagdy M.,Taghour, Mohammed S.,Al-Warhi, Tarfah,Nocentini, Alessio,Elbadawi, Mostafa M.,Mahdy, Hazem A.,Abdelrahman, Mohamed A.,Alotaibi, Ohoud J.,Aljaeed, Nada,Elimam, Diaaeldin M.,Afarinkia, Kamyar,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
, p. 531 - 541 (2022/01/13)
Different 2,4-thiazolidinedione-tethered coumarins 5a–b, 10a–n and 11a–d were synthesised and evaluated for their inhibitory action against the cancer-associated hCAs IX and XII, as well as the physiologically dominant hCAs I and II to explore their selec
Design and synthesis of 4′-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methyl)biphenyl-2-carbonitrile analogs as bacterial peptide deformylase inhibitors
Khan, Firoz A. Kalam,Patil, Rajendra H.,Shinde, Devanand B.,Sangshetti, Jaiprakash N.
, p. 938 - 944 (2016/11/11)
Herein, we report the synthesis and screening of 4′-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methyl)biphenyl-2-carbonitrile analogs 11(a–j) as bacterial peptide deformylase (PDF) enzyme inhibitors. The compounds 11b (IC50 value?=?139.28?μm), 11g (IC50 value?=?136.18?μm), and 11h (IC50 value?=?131.65?μm) had shown good PDF inhibition activity. The compounds 11b (MIC range?=?103.36–167.26?μg/mL), 11g (MIC range?=?93.75–145.67?μg/mL), and 11h (MIC range?=?63.61–126.63?μg/mL) had also shown potent antibacterial activity when compared with standard ampicillin (MIC range?=?100.00–250.00?μg/mL). Thus, the active derivatives were not only PDF inhibitors but also efficient antibacterial agents. To gain more insight on the binding mode of the compounds with PDF enzyme, the synthesized compounds 11(a–j) were docked against PDF enzyme of Escherichia coli and compounds exhibited good binding properties. The results suggest that this class of compounds has potential for development and use in future as antibacterial drugs.
Tetrabutylammonium bromide and K 2CO 3: An eco-benign catalyst for the synthesis of 5-Arylidene-1,3-Thiazolidine-2,4-diones via Knoevenagel condensation
Durai Ananda Kumar,Swathi,Navatha,Subrahmanyam,Satyanarayana
, p. 105 - 115 (2015/10/20)
Phase-Transfer catalyzed, energy-efficient and facile synthesis of 5-Arylidene-1,3-Thiazolidine-2,4-diones was developed. Three independent variables (temperature, bases and phase-Transfer catalyst (PTC)) were screened through one-factor-At-A time (OFAT) study. The optimum reaction conditions suggested by the OFAT analysis were the use of tetrabutylammonium bromide (8mol%) and potassium carbonate (1mmol) for the reaction at 100°C. The nitrogen of PTC stabilizes carbonyl groups of thiazolidine-2,4-dione (TZD). The active methylene hydrogen of TZD forms potassium salt with potassium carbonate and generates 5-Arylidene-1,3-Thiazolidine-2,4-diones (1-16) through nucleophilic attack on the carbonyl carbon of arylaldehydes. The prominent advantages of this new process are economic viability, shorter reaction time (15min), simple product isolation (non-chromatographic method), good to excellent yields (78-96%) and solvent-free conditions.
Sonochemistry: A good, fast and clean method to promote the synthesis of 5-arylidene-2,4-thiazolidinediones
Drawanz, Bruna B.,Ribeiro, Camila S.,Masteloto, Hellen G.,Neuenfeldt, Patrícia D.,Pereira, Claudio M.P.,Siqueira, Geonir M.,Cunico, Wilson
, p. 1615 - 1617 (2014/06/09)
The efficient synthesis of sixteen 5-arylidene-2,4-thiazolidinediones by aldol condensation reaction of 2,4-thiazolidinedione, mono- and di-substituted arenealdehydes and KOH using ultrasound irradiation is reported. The desired compounds were obtained in
A convenient synthesis of 5-benzylidenethiazolidine-2, 4-diones under microwave irradiation without solvent
Yang, De-Hong,Chen, Zhen-Chu,Chen, Song-Ying,Zheng, Qin-Guo
, p. 330 - 331 (2007/10/03)
A series of 5-benzylidenethiazolidine-2,4-diones was synthesised by the Knoevenagel condensation of aromatic aldehydes with thiazolidine-2,4-dione in the presence of catalytic amounts of piperidine and acetic acid under microwave irradiation without solvent in good yields.
