790-04-5Relevant academic research and scientific papers
Synthesis of 2-iminothiazolidin-4-ones using guanine functionalized SBA-16 as a solid base catalyst
Gupta, Radha,Pathak, Devendra Deo
, (2021/11/08)
The first example of a one-pot three-component tandem annulation approach is described for the synthesis of 2-iminothiazolidin-4-ones by the reaction of aromatic/aliphatic amines, aryl isothiocyanates, and ethyl bromoacetate, catalysed by guanine-functionalized SBA-16, [SBA-16@G], as an efficient and recyclable heterogeneous solid base catalyst. The methodology is simple and offers a broad-substrate scope under mild reaction conditions.
Targeting tubulin polymerization and DNA binding of 4-thiazolidinone-umbelliferone hybrids: synthesis and cytotoxicity evaluation
Ambatwar, Ramesh,Kadagathur, Manasa,Kiranmai, Gaddam,Nagendra Babu, Bathini,Nagesh, Narayana,Nunewar, Saiprasad N.,Shankaraiah, Nagula,Sigalapalli, Dilep Kumar,Tangellamudi, Neelima D.,Tokala, Ramya,Tripura, Chaturvedula
, p. 18908 - 18923 (2021/10/26)
The discovery of a series of combretastatin A-4 inspired novel molecular hybrids of 4-thiazolidinone-umbelliferone as prominent cytotoxic agents is reported. Representative compounds exhibited potent anti-proliferative activities against four human cancer cell lines (A549, MDA-MB-231, THP-1 and HL-60). Amongst the compounds tested,7qshowed the highest potency against A549 cells with an IC50value of 0.96 ± 1.09 μM and a selectivity index of 51.7. The flow cytometric analysis of compound7qtreated A549 cells showed apoptosis induction by the annexin-v/PI dual staining assay and the effect of7qon different phases of the cell cycle was also analyzed. Target based studies demonstrated inhibition of tubulin polymerization by7qat an IC50value of 2.65 ± 0.47 μM and its effective binding with CT-DNA. Further, molecular modelling studies revealed that7qhas a prominent binding affinity towards the α/β-tubulin receptor with remarkable protein-ligand interactions and binding energy.
Visible Light-Promoted Three-Component Tandem Annulation for the Synthesis of 2-Iminothiazolidin-4-ones
Guo, Wei,Zhao, Mingming,Tan, Wen,Zheng, Lvyin,Tao, Kailiang,Liu, Lingxiu,Wang, Xinyu,Chen, Deliang,Fan, Xiaolin
, p. 1402 - 1413 (2018/02/10)
Described is a visible light-promoted three-component tandem annulation of amines, aryl/alkyl isothiocyanates, and α-bromoesters to form 2-iminothiazolidin-4-ones in the absence of metal and photocatalyst at room temperature. This [1 + 2 + 2] cyclization strategy involves visible light-promoted C-S/C-N bond formation and features a powerful approach to the synthesis of 2-iminothiazolidin-4-ones with broad substrate scope, excellent functional group tolerance, mild reaction conditions, step-economy, and simple operation, which also has potential applications in the pharmaceutical industry. UV-vis spectroscopy indicates that an in situ-generated H-bonding electron donor-acceptor (EDA) complex probably acts as the photocatalyst, facilitating the reaction process.
Novel thiazolidinone/thiazolo[3,2-a] benzimidazolone-isatin conjugates as apoptotic anti-proliferative agents towards breast cancer: One-pot synthesis and in vitro biological evaluation
El-Naggar, Mohamed,Eldehna, Wagdy M.,Almahli, Hadia,Elgez, Amr,Fares, Mohamed,Elaasser, Mahmoud M.,Abdel-Aziz, Hatem A.
, (2018/06/18)
In connection with our research program on the development of new isatin-based anticancer candidates, herein we report the synthesis of two novel series of thiazolidinone-isatin conjugates (4a–n) and thiazolo[3,2-a]benzimidazolone-isatin conjugates (7a–d), and in vitro evaluation of their antiproliferative activity towards two breast cancer cell lines; triple negative MDA-MB-231, and MCF-7. Compounds 4m and 7b emerged as the most active congeners against MDA-MB-231 cells (IC50 = 7.6 ± 0.5 and 13.2 ± 1.1 μM, respectively). Compounds 4m and 7b were able to provoke apoptosis in MDA-MB-231 cells, evidenced by the up-regulation of Bax and down-regulation of Bcl-2, besides boosting caspase-3 levels. Hybrid 4m induced a fourfold increase in the percentage of cells at Sub-G1, with concurrent arrest in G2-M phase by 2.5-folds. Furthermore, hybrid 4m resulted in a sixfold increase in the percentage of annexin V-FITC positive apoptotic MDA-MB-231 cells as compared with the control. Moreover, the cytotoxic activities of the active conjugates were assessed towards two nontumorigenic cell lines (breast MCF-10A and lung WI-38) where both conjugates 4m and 7b displayed mean tumor selectivity index: 9.6 and 13.9, respectively. Finally, several ADME descriptors were predicted for the active conjugates via a theoretical kinetic study.
Novel non-peptidic small molecule inhibitors of secreted aspartic protease 2 (SAP2) for the treatment of resistant fungal infections
Dong, Guoqiang,Liu, Yang,Wu, Ying,Tu, Jie,Chen, Shuqiang,Liu, Na,Sheng, Chunquan
, p. 13535 - 13538 (2019/01/05)
Targeting secreted aspartic protease 2 (SAP2), a kind of virulence factor, represents a new strategy for antifungal drug discovery. In this report, the first-generation of small molecule SAP2 inhibitors was rationally designed and optimized using a structure-based approach. In particular, inhibitor 23h was highly potent and selective and showed good antifungal potency for the treatment of resistant Candida albicans infections.
Synthesis, crystal structure and biological evaluation of 5-arylidine derivatives of 3-phenyl-2-(phenylimino)thiazolidin-4-one
Haroon, Muhammad,Akhtar, Tashfeen,Tahir, Muhammad Nawaz,Ali, Imran,Hameed, Shahid
, p. 614 - 618 (2017/11/06)
Summary: Arylidene derivatives of 3-phenyl-2-(phenylimino)thiazolidin-4-ones are prepared by its condensation with respective aromatic aldehydes. The structures of synthesized compounds are established using FTIR, 13C-NMR, 1H-NMR, mass spectrometry. The s
Substituted thiazole ketones secreted aspartic protease inhibitors and its preparation method
-
, (2017/08/31)
The invention relates to a substituted thiazole ketones secretory aspartic protease inhibitor and a preparation method thereof, and particularly provides a novel thiazole ketones compound. The general structural formula of the novel thiazole ketones compound is shown as follows. The thiazole ketones compound is high in Sap2 enzyme inhibiting activity and nematode and mouse in-vivo antifungal activity, and has good antifungal medicine combination effect on fluconazole resistant bacteria, thereby being capable of being used for preparing medicine for preventing fungal infection or being combined with existing antifungal medicine. A new approach is created for deeply studying and developing novel antifungal medicine.
An Environment-friendly Synthesis of 2,3-Disubstituted-2-iminothiazoline-4-ones
Meng, Ge,Zheng, Meilin,Dong, Mengshu,Wang, Mei,Zheng, Aqun,Guo, Zengjun
, p. 588 - 594 (2016/04/19)
A series of 2,3-substituted-2-iminothiazoline-4-ones derivatives have been synthesized via an improved method including an auto-catalyzed reaction. This method avoided using any extra catalyst except for the reaction material. This method has been successful in both the aromatic substituted 2-iminothiazolines and the alkyl substituted 2-iminothiazolines. The special product with a hydroxyl group on the 2-iminogroup of 1,3-thiazoline-4-ones has also been obtained unexpectedly. The possible mechanism has been proposed for the special process of dealkylation and hydroxylation. This method offered a special way to afford the 2-hydroxyimino-substituted thiazoline-4-one derivatives in an efficient and eco-friendly way. The mechanism of the transformation under acid condition has also been proposed.
Design and synthesis of new potent PTP1B inhibitors with the skeleton of 2-substituted imino-3-substituted-5-heteroarylidene-1,3-thiazolidine-4-one: Part I
Meng, Ge,Zheng, Meilin,Wang, Mei,Tong, Jing,Ge, Weijuan,Zhang, Jiehe,Zheng, Aqun,Li, Jingya,Gao, Lixin,Li, Jia
supporting information, p. 756 - 769 (2016/08/18)
A new series of 2-substituted imino-3-substituted-5- heteroarylidene-1,3-thiazolidine-4-ones as the potent bidentate PTP1B inhibitors were designed and synthesized in this paper. All of the new compounds were characterized and identified by spectra analysis. The biological screening test against PTP1B showed that some of these compounds have the positive inhibitory activity against PTP1B. The activity of the compounds with 5-substituted pyrrole on 5-postion of 1,3-thiazolidine-4-one are more potent than that of those compounds with 5-substituted pyridine group. Compound 14b, 14h and 14i showed IC50values of 8.66?μM, 6.83?μM and 6.09?μM against PTP1B, respectively. Docking analysis of these active compounds with PTP1B showed the possible interaction modes of these biheterocyclic compounds with the active sites of PTP1B. The inhibition tests against oncogenetic CDC25B were also conducted on this set of compounds to evaluate the selectivity and possible anti-neoplastic activity. Compound 14b also showed the lowest IC50of 1.66?μM against CDC25B among all the possible inhibitors, including 14g, 14h, 14i and 15c. Some pharmacological parameters including VolSurf, steric and electric descriptors of all the compounds were calculated to give some hints about the relative relationship with the biological activity. The result of this study might give some light on designing the possible anti-cancer drugs targeting at phosphatases. The most active compound 14i might be used as the lead compound for further structure modification of the new low molecular weight PTP1B inhibitors with the N-containing heterocyclic skeleton.
Synthesis of some 3,5-disubstituted phenyl-5,6-dihydrofuro[2,3-d]thiazol-2(3H)-ylidene) imines as potential pesticides
Tiwari, Shailendra,Singh, Kamal Pratap,Ahmad, Akeel
, p. 1007 - 1012 (2017/11/10)
A new series of novel 3,5-disubstituted phenyl-5,6-dihydrofuro[2,3-d]thiazol-2(3H)-ylidene) imines have been synthesized from a common intermediate, in good yield. These compounds have been screened for their herbicidal activities against èchinochloa oryzicola, Echinochloa crus-galli, Oryza sativa, Glycine max and antifungal activities against Aspergillus Niger and Pyricularia oryzae whereas for antimicrobial activities, they have been screened against Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis and Bacillus pumilus.
