Synthesis, Antimicrobial and Anticancer Evaluations of Novel Thiazoles Incorporated Diphenyl Sulfone Moiety

Shaaban, Mohamed R.; Farghaly, Thoraya A.; Alsaedi, Amani M. R.

doi:10.1080/10406638.2020.1837887

Cited by 16 publications

(8 citation statements)

References 36 publications

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“…Furthermore, several previous studies of compounds containing thiazole moiety proved the effectiveness of these compounds as anticancer drugs [36][37][38][39][40]. The scenario of cancer is one of the most important in medicinal chemistry, while thiazoles are very important in treating cancers.…”

Section: Plos Onementioning

confidence: 99%

“…13 C NMR (CDCl 3 ): 26.7 (CH 2 ), 28.3 (CH 2 ), 122.9, 125.7, 128.9, 130.8, 135.8, 150.4, 156.5, 178.7 (C = S). MS(m/z): 285 (M + +2, 29), 284 (M + +1, 6), 283 (M + , 27), 268 (15), 266 (14), 129 (10), 115 (67), 102 (31), 90 (8), 89 (42), 76 (39), 60 (100). Elemental Analysis (%): (C 10 H 10 BrN 3 S; Mwt: 284.18) Calc.…”

Section: Synthesis Of 2-(5-bromo-23-dihydro-1h-inden-1-ylidene)hydraz...mentioning

confidence: 99%

“…6, 130.6, 130.7, 137.3, 137.6, 150.7, 169.6. Mass (m/z): 400 (M + +2, 22), 398 (M + , 44), 190 (51), 162 (10), 148(100), 129 (29), 115 (52), 102 (39), 89 (20), 75 (10). MS(m/z): 399(M + +2, 88), 397 (M + +1, 87), 339 (M+, 4), 289(5), 190 (51), 174 (9), 162 (10), 148(100), 135 (10), 129 (29), 115 (53), 102 (38), 91 (25), 77 (18), 63 (15), 51 (11)…”

Section: N-(5-bromo-indan-1-ylidene)-n'-(4-p-tolyl-thiazol-2-yl)-hydr...unclassified

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Indenyl-thiazole and indenyl-formazan derivatives: Synthesis, anticancer screening studies, molecular-docking, and pharmacokinetic/ molin-spiration properties

2023

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Two new series of thiazole and formazan linked to 5-Bromo-indan were synthesized, and their structures were assured based on all possible analytical techniques. The size of the tested derivatives was calculated from the XRD technique and found five derivatives 3, 10a, 14a, 15, and 16 on the nanosized scale. The two series were tested for their efficacy and toxicity as anti-colon and stomach cancers. Derivative 10d showed activity more than the two reference drugs used in the case of SNU-16. Surpislly, in the case of COLO205, five derivatives 4, 6c, 6d, 6e, and 10a are better than the two benchmarks used, and two derivatives, 14a and 14b more potent than cisplatin. All potent derivatives showed a strong fit with the active site of the two tested proteins (gastric cancer (PDB = 2BID) and colon cancer (PDB = 2A4L)) in the molecular docking study. The Pharmacophore and ADME studies of the new derivatives showed that most derivatives revealed promising bioactivity, which indicates the drug-likeness properties against kinase inhibitors, protease, and enzyme inhibitors. In addition, the ProTox-II showed that the four compounds 10d, 16, 6d, and 10a are predicted to have oral LD50 values ranging from 335 to 3500 mg/kg in a rat model with (1 s,4 s)-Eucalyptol bearing the highest values and quercetin holding the lowest one.

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Section: Plos Onementioning

confidence: 99%

Section: Synthesis Of 2-(5-bromo-23-dihydro-1h-inden-1-ylidene)hydraz...mentioning

confidence: 99%

Section: N-(5-bromo-indan-1-ylidene)-n'-(4-p-tolyl-thiazol-2-yl)-hydr...unclassified

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Indenyl-thiazole and indenyl-formazan derivatives: Synthesis, anticancer screening studies, molecular-docking, and pharmacokinetic/ molin-spiration properties

2023

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“…1), a thiazole derivative developed by GlaxoSmithKline as a potent and selective B-RAFV600E inhibitor, was approved by FDA in 2013 for the treatment of B-RAFV600E-driven tumors. 19 In the light of these facts and in continuation of our effort toward the discovery of potent anticancer agents, [24][25][26][27][28][29][30][31][32][33][34][35][36] herein, novel thiazole derivatives were designed and synthesized as potent B-RAFV600E kinase inhibitors with potential anticancer activities, based on the clinically-approved B-RAFV600E inhibitor, dabrafenib. The design of our target compounds is illustrated in Fig.…”

Section: Introductionmentioning

confidence: 99%

“…In the light of these facts and in continuation of our effort toward the discovery of potent anticancer agents, 24–36 herein, novel thiazole derivatives were designed and synthesized as potent B-RAFV600E kinase inhibitors with potential anticancer activities, based on the clinically-approved B-RAFV600E inhibitor, dabrafenib. The design of our target compounds is illustrated in Fig.…”

Section: Introductionmentioning

confidence: 99%

Novel thiazole derivatives incorporating phenyl sulphonyl moiety as potent BRAFV600E kinase inhibitors targeting melanoma

et al. 2022

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Microwave‐assisted solvent‐free synthesis of some novel thiazole‐substituted thiosemicarbazone analogues: antimicrobial and anticancer studies

Hossan

2023

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The increased resistance to antibiotics has compelled researchers to devise novel active compounds targeting multidrug‐resistant pathogenic microorganisms. A series of thiosemicarbazone derivatives were synthesized by reacting thiosemicarbazide with 2‐aryl‐4‐formylthiazole, 2‐aryl‐5‐formyl‐4‐methylthiazole, and/or 5‐acetyl‐2‐aryl‐4‐methylthiazole compounds. These thiosemicarbazone‐based thiazole adducts were evaluated for their inhibitory activities against tuberculosis H37Ra and Bovis BCG mycobacteria. Their cytotoxicity was assessed against two cancer cell lines: colonic carcinoma (HCT‐116) and cervical cancer (HeLa). Notably, these thiosemicarbazones exhibited minimal cytotoxic effects on these cell lines even at their highest concentrations. Furthermore, the prepared thiosemicarbazone derivatives demonstrated significant antimicrobial efficacy against Bacillus subtilis and Staphylococcus aureus (gram‐positive bacterial pathogens) as well as Escherichia coli and Pseudomonas fluorescens (gram‐negative bacterial pathogens). While most of the prepared thiosemicarbazone derivatives exhibited moderate activity against Candida albicans (a fungal strain), their performance was notable. The thiosemicarbazone‐based thiazole adducts were also successfully synthesized using a solvent‐free approach under microwave irradiation. Compared with conventional reflux methods, the microwave‐assisted technique yielded high thiazole yields within just 5 minutes, obviating the need for catalysis. This study signifies significant strides toward the rational design of more potent antimycobacterial agents.

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Synthesis, Antimicrobial and Anticancer Evaluations of Novel Thiazoles Incorporated Diphenyl Sulfone Moiety

Cited by 16 publications

References 36 publications

Indenyl-thiazole and indenyl-formazan derivatives: Synthesis, anticancer screening studies, molecular-docking, and pharmacokinetic/ molin-spiration properties

Indenyl-thiazole and indenyl-formazan derivatives: Synthesis, anticancer screening studies, molecular-docking, and pharmacokinetic/ molin-spiration properties

Novel thiazole derivatives incorporating phenyl sulphonyl moiety as potent BRAFV600E kinase inhibitors targeting melanoma

Microwave‐assisted solvent‐free synthesis of some novel thiazole‐substituted thiosemicarbazone analogues: antimicrobial and anticancer studies

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