thiazole derivatives
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Author(s):  
Neeharika Yamsani ◽  
Raja Sundararajan

Aim: The study aims to design & synthesize novel thiazole derivatives as potent antitubercular agents with minimal side effects. Background: The emergence and rapid spread of multi-drug resistant infectious microbial flora embracing a variety of bacterial as well as mycobacterium strains are causing a threat to public health worldwide. Objective: Owing to the importance, we designed compounds with thiazole functionality coupled with Schiff base and thiosemicarbazide, predicted the molecular properties and antitubercular potency of designed compounds by the in-silico method, and synthesized fifteen novel thiazole analogs, characterized and tested in vivo antitubercular, antibacterial and antioxidant potencies. Methods: Molinspiration online tool was used to predict the molecular properties and molecular docking was used to predict the antitubercular potency. FT-IR, 1H-NMR, 13C-NMR, Mass spectroscopy and bases of elemental analysis are employed to confirm the structure of compounds. 10-Fold serial dilution method, agar streak dilution test and DPPH radical scavenging methods are used to estimate antitubercular, antibacterial and antioxidant potency of title analogs, respectively. Results: Multi-step synthesis was used to synthesize a variety of novel thiazole derivatives coupled with Schiff base and thiosemicarbazide. Synthesized title compounds displayed a varying degree of antitubercular, antibacterial and antioxidant activities (mild to good). The title compounds possessing deactivating group exhibited superior activities than activating group, while unsubstituted analogs displayed intermediate activities. In addition, para-substituted analogs showed slightly higher activity than the corresponding meta substituted analogs. Conclusion: Among fifteen tested title compounds, the potent compound of this series was found to be 1-(4-nitrobenzylidene)-4-(4-(4-methoxyphenyl)thiazol-2-yl)thiosemicarbazide (BTS14), which might be extended as a novel class of antitubercular and antibacterial agents.


2022 ◽  
Vol 19 ◽  
Author(s):  
Entesar A. Hassan ◽  
Salem E. Zayed ◽  
Al-Hassan S. Mahdy ◽  
Ahmed M. Abo-Bakr

Background: A series of new pyrimidines and thiazoles containing camphor moiety were synthesized under both conventional and microwave irradiation techniques. Methods: The condensation of camphor either with aminoguanidine or thiosemicarbazide gives the camphor hydrazine carboximidiamide 2 and the camphor thiosemicarbazone 3, respectively. Refluxing of 3 with chloroacetonitrile afforded the camphor thiazol-4-imine 4. Compounds 2 and 4 were used as precursors for the synthesis of target products. Results: The reaction of 2 with different species such as arylidene malononitrile, acetylacetone, and ethyl acetoacetate gave the corresponding camphor pyrimidine derivatives 5a,b-7 while refluxing of compound 4 with different reagents e.g. aldehydes, isatin, ninhydrin, acetic anhydride, benzene sulphonyl chloride, and p-nitro-benzoyl chloride afforded the camphor thiazole derivatives 8a-d-13, respectively. Conclusion: A comparison between the conventional way and the eco-friendly microwave irradiation method occurred in the synthesis of the same compounds, which the latter was more efficient. The elemental analysis, FT-IR, 1H NMR, 13C NMR, and Mass spectra confirm the structures of the obtained new compounds. The potential use of some selected derivatives as antimicrobial agents was investigated and gave promising results


2022 ◽  
Vol 517 ◽  
pp. 112022
Author(s):  
Peng-Wei Zhu ◽  
Yan-Tong Yang ◽  
Yang Li ◽  
Jie Zhu ◽  
Lei Wu

2022 ◽  
pp. 132374
Author(s):  
Karthik Rajagopal ◽  
Saravanan Dhandayutham ◽  
Manivannan Nandhagopal ◽  
Mathivanan Narayanasamy ◽  
Mohamed I Elzagheid ◽  
...  

Author(s):  
Rafat M. Mohareb ◽  
Maher H. E. Helal ◽  
Sara S. Mohamed ◽  
Amira E. M. Abdallah

Background: Many tetrahydrobenzo[d]thiazole derivatives were considered as the most important class of heterocyclic compounds due to their biological applications. There are many drugs known in the market containing the thiazole moiety which is responsible for the high drug activity. Objective: This work aimed to produce novel heterocyclic compounds such as pyrazole, isoxazole, thiophene, chromeno[7,8-d]thiazole, and thiazolo[4,5-h]quinoline derivatives. The newly synthesized heterocyclic compounds were evaluated against anticancer cell lines followed by c-Met enzymatic activity and tyrosine kinases inhibition for the most active compounds. Methods: In this work, the 3-phenyl-2-thioxo-2,3,5,6-tetrahydrobenzo[d]thiazol-7(4H)-one (3) was synthesized through the reaction of cyclohexane-1,3-dione with phenyl isothiocyanate and elemental sulfur. Compound 3 showed interesting activity toward some chemical reagents producing new heterocyclic compounds that can’t be obtained through another way. The newly synthesized compounds were evaluated towards the six cancer cell lines. The most active compounds were selected and tested toward c-Met enzyme by taking foretinib as the positive control. Also, the inhibitions toward the PC-3 cell line using the reference SGI-1776 were measured. Finally, the inhibitions towards the five tyrosine kinases were also tested. Results: The synthesized quinoline and chromene derivatives were evaluated toward c-Met enzyme using foretinib as the positive control the obtained results showed that twelve compounds exhibited IC50 values less than 1.30 nM. On the other hand, sixteen compounds showed higher inhibitions than the reference SGI-1776 (IC50 4.86 nM) toward the PC-3 cell line. Conclusion: Novel, heterocyclic compounds were synthesized with a high impact of biological activities. All synthesized compounds were screened for their anti-proliferative effect and most of them revealed high potent effects. In addition, the c-Met and prostate cancer cell line PC-3 inhibitions for the most active compounds showed that these compounds exhibited high inhibitions. Anti-proliferative activity of selected compounds toward cancer cell lines classified according to the disease showed that most compounds exhibited high inhibitions.


Molecules ◽  
2021 ◽  
Vol 27 (1) ◽  
pp. 74
Author(s):  
Dovilė Malūkaitė ◽  
Birutė Grybaitė ◽  
Rita Vaickelionienė ◽  
Giedrius Vaickelionis ◽  
Birutė Sapijanskaitė-Banevič ◽  
...  

Rapidly growing antimicrobial resistance among clinically important bacterial and fungal pathogens accounts for high morbidity and mortality worldwide. Therefore, it is critical to look for new small molecules targeting multidrug-resistant pathogens. Herein, in this paper we report a synthesis, ADME properties, and in vitro antimicrobial activity characterization of novel thiazole derivatives bearing β-amino acid, azole, and aromatic moieties. The in silico ADME characterization revealed that compounds 1–9 meet at least 2 Lipinski drug-like properties while cytotoxicity studies demonstrated low cytotoxicity to Vero cells. Further in vitro antimicrobial activity characterization showed the selective and potent bactericidal activity of 2a–c against Gram-positive pathogens (MIC 1–64 µg/mL) with profound activity against S. aureus (MIC 1–2 µg/mL) harboring genetically defined resistance mechanisms. Furthermore, the compounds 2a–c exhibited antifungal activity against azole resistant A. fumigatus, while only 2b and 5a showed antifungal activity against multidrug resistant yeasts including Candida auris. Collectively, these results demonstrate that thiazole derivatives 2a–c and 5a could be further explored as a promising scaffold for future development of antifungal and antibacterial agents targeting highly resistant pathogenic microorganisms.


2021 ◽  
Vol 68 (4) ◽  
pp. 990-996
Author(s):  
Mohamed A. Salem ◽  
Samir Y. Abbas ◽  
Marwa A. M. Sh. El-Sharief ◽  
Mohamed H. Helal ◽  
Moustafa A. Gouda ◽  
...  

One of the best ways to design new biocidal agents is synthesizing hybrid molecules by combining two or more bioactive moieties in a single molecular scaffold. So, new series of pyrroles bearing a thiazole moiety were synthesized using 1-methyl-1H-pyrrole-2-carbaldehyde thiosemicarbazones 1a–c. Cyclization of thiosemicarbazone derivatives 1a–c with ethyl chloroacetate, ethyl 2-chloropropanoate, chloroacetone and phenacyl bromide afforded the corresponding thiazolidin-4-ones 2a–c, 5-methylthiazolidin-4-ones 3a–c, 4-methyl-2,3-dihydrothiazoles 4a–c, and 4-phenyl-2,3-dihydrothiazoles 5a–c, respectively. The antimicrobial activity of the new thiazole derivatives was evaluated.


Author(s):  
Abhishek Kumar ◽  
Pankaj Kumar ◽  
Aravinda Pai

Synthesis and screening of a series of new coumarin derivatives coupled with thiazole are performed for their antimicrobial properties. A series of new thiazolyl coumarin derivatives were synthesized upon refluxing 3-bromoaceytl coumarin, substituted benzaldehyde and thiosemicarbazide in the presence of glacial acetic acid. Substituted 3-acetyl coumarin undergoes bromination in the presence of bromine and chloroform to form 3-Bromoaceytl coumarin. The thiazolyl coumarin derivatives were characterized based on IR, 1H NMR, and Mass spectral data. The docking studies have been carried out against the enzyme DNA gyrase (1KZN). Compound SCT 2 showed the highest docking score -5.662 compared to other compounds. The final synthesized compounds were screened for their antibacterial activity by tube dilution method. Compound SCT 1 and SCT 2 showed significant antibacterial activity with minimum inhibitory concentration of 12.5µg/ml and 6.25µg/ml, respectively, compared to standard Cephalosporin. The MIC results suggest that compounds SCT 1 and SCT 2 showed promising antibacterial activity. So these compounds are interesting lead molecules for further synthesis as antimicrobial agents. 


Author(s):  
. Isha ◽  
Neetu Sachan

Aims: To synthesize thiazole derivatives and evaluate their therapeutic potential to continue our quest for new antibacterial and antioxidant drugs. Place and Duration of Study: Institute of Pharmaceutical Research, GLA University, Mathura, Uttar Pradesh, between January 2021 and July 2021. Methodology: The target compounds in this investigation were synthesized in the search for new molecules having antioxidant and antimicrobial activity. Physicochemical and spectroanalytical studies validated the derivatives molecular structures. Antioxidant and antimicrobial properties of the synthesized molecules were evaluated in vitro using the DPPH and tube dilution methods, respectively. Results: The majority of the synthesized derivatives displayed antioxidant and antimicrobial activity. The efficacy of the derivatives varied based upon the substituent. Compound 7c exhibited significant antioxidant and antibacterial activity, according to the results of the study. Conclusion: Our results showed the antioxidant and antibacterial properties of novel thiazole compounds, implying the probability of their utilization in the development of new therapeutics.


2021 ◽  
Vol 15 (4) ◽  
pp. 37-48
Author(s):  
M. V. Popovych ◽  
◽  
Ya. R. Shalai ◽  
S. M. Mandzynets ◽  
N. E. Mitina ◽  
...  

Background. Previous studies have shown a pronounced cytotoxic effect of thiazole derivatives in combination with polymeric carriers on tumor cells. At the same time, the derivatives were not cytotoxic against non-cancerous cells in vitro. It was shown that thiazole derivatives at concentrations of 10 and 50 μM affected the prooxidant and antioxidant systems of lymphoma cells in vitro. The aim of this work was to study the effect of the complex of thiazole derivative N-(5-benzyl-1,3-thiazol-2-yl)-3,5-dimethyl-1-benzofuran-2-carboxamide (BF1) in combination with polymeric carriers poly(VEP-co-GMA)-graft-mPEG (Th1), poly(PEGMA) (Th3) and poly(PEGMA-co-DMM) (Th5) on the antioxidant defense system of the NK/Ly cell in vitro. Materials and Methods. The experiments were performed on white wild-type male mice with grafted NK/Ly lymphoma. Tumor cells were inoculated into mice intraperitoneally. Ascites was drained from the abdominal cavity of anaesthetized mice with a sterile syringe on the 7th-10th day after inoculation. Investigated compounds BF1, BF1 + Th1 (Th2, Th12), BF1 + Th3 (Th4, Th14), BF1 + Th5 (Th6, Th16) at a final concentration of 10 μM were added to the lymphoma samples and incubated for 10 min; the activity of antioxidant enzymes was determined according to the techniques described previously. Results. It was found that all the studied complexes based on thiazole derivative BF1 and polymeric carriers poly (VEP-co-GMA)-graft-mPEG (Th2, Th12), poly (PEGMA) (Th4, Th14) and poly (PEGMA-co-DMM) (Th6, Th16) at a concentration of 10 μm increased the activity of SOD, while the activity of CAT and GPX were reduced compared to control. Complexes Th2, Th12 and Th4 increased the significance of the BF1 influence on lymphoma cells from P <0.05 to P <0.01. Pure polymeric carriers did not affect the level of the antioxidant defense system enzymes. Conclusions. Thus, it was found that the polymeric carriers in combination with thiazole derivative BF1 increased the significance of thiazole derivative BF1 influence on the activity of the antioxidant defense system of lymphoma cells, while pure polymeric carriers did not affect the activity of SOD, CAT or GPX. The results of this work can be used for further studies of complexes of thiazole derivative and PEG-containing polymeric carriers as potential antitumor drugs.


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