Synthesis, Molecular Docking and Anticancer Evaluation of New Arylazothiazoles

Sobhi, M. Gomha; Farghaly, Thoraya A.; Nadia, T Alqurashi; Hanaa, Y Abdou; Eman, Kamal

doi:10.2174/1570179414666161116123839

Cited by 8 publications

(6 citation statements)

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“…It seems that the presence of a chlorophenyl substitution at phenyl hydrazine moiety at the 2nd position (71c, 70c) is favorable for anticancer activity, while the arylazo Gomha et al [111] synthesized a series of arylazothiazoles (Figure 26) and evaluated their in vitro growth activity against hepatocellular (HepG2) and colorectal (HCT-116) carcinoma cell lines by colorimetric MTT assay with 5-fluorouracil and cisplatin as reference drugs. The study revealed that in general, all compounds showed moderate to good activity against both cell lines Compounds 70a, 70b, 70c, 71c, and 72c (Figure 27) with IC 50 values ranging from 4.9 to 9.3 µM showed the highest activity among all compounds tested against hepatocellular (HepG2) carcinoma cells, with 72c (IC 50 = 4.9 ± 0.5 µM) being even more potent than cisplatin (IC 50 = 6.9 ± 0.7 µM).…”

Section: Thiazole Derivatives As Anticancer Agentsmentioning

confidence: 99%

Thiazole Ring—A Biologically Active Scaffold

2021

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Background: Thiazole is a good pharmacophore nucleus due to its various pharmaceutical applications. Its derivatives have a wide range of biological activities such as antioxidant, analgesic, and antimicrobial including antibacterial, antifungal, antimalarial, anticancer, antiallergic, antihypertensive, anti-inflammatory, and antipsychotic. Indeed, the thiazole scaffold is contained in more than 18 FDA-approved drugs as well as in numerous experimental drugs. Objective: To summarize recent literature on the biological activities of thiazole ring-containing compounds Methods: A literature survey regarding the topics from the year 2015 up to now was carried out. Older publications were not included, since they were previously analyzed in available peer reviews. Results: Nearly 124 research articles were found, critically analyzed, and arranged regarding the synthesis and biological activities of thiazoles derivatives in the last 5 years.

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Section: Thiazole Derivatives As Anticancer Agentsmentioning

confidence: 99%

Thiazole Ring—A Biologically Active Scaffold

2021

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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%

“…1, 128.5, 130.3, 137.7, 148.6, 155.5. MS(m/z): 225 (M + , 2), 208 (13), 143 (7), 129 (37), 115 (100), 113 (10), 102 (40), 89 (20), 83 (14), 77 (15), 75 (17), 71 (20), 63 (24), 57 (32), 55 (27). Elemental Analysis (%): (C 9 H 9 BrN 2 ; Mwt: 225.09) Calc.…”

Section: Synthesis Of (5-bromo-indan-1-ylidene)-hydrazine (4)mentioning

confidence: 99%

“…The method for synthesis of derivatives 6a-e, 10a-d, 14a, b, 15, and 16 as illustrated in Fig 2. PLOS ONE (M + , 3), 439 (5), 129 (19), 115 (53), 106 (18), 102 (20), 91 (100), 78 (10), 77 (27), 65 (24), 51 (7) (5), 129 (22), 115 (58), 106 (18), 102 (20), 91 (100), 77 (26), 65 (20), 51 (8) (5), 139 (6), 129 (34), 115 (100), 111 (92), 102 (37), 99 (29), 95 (5), 89 (20), 77 (14), 75 (36), 67 (37), 63 (27), 57 (7), 55 (7), 51 (11) (2), 210 (3), 141 (5), 129 (34), 115 (96), 111 (100), 102 (38), 99 (29), 89 (19), 77 (11), 75 (33), 71 (14), 67 (32), 63 (22), 51 (9) 12), 383 (24), 210 (4), 176 (45), 148 (9), 134 (100), 121 (12)<...…”

Section: The Reaction Of 2-(5-bromo-23-dihydro-1h-inden-1-ylidene)hyd...mentioning

confidence: 99%

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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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“…Therefore, the development of anticancer molecules remains actual and is the fastest growing category in pharmacology. A better understanding of the biology of carcinogenesis may lead to the development of novel promising antineoplastic molecules, and thiazoles are among them [ 7 , 8 , 9 ]. Based on the reported research, it may be concluded that small thiazole-containing molecules utilize different mechanisms of blocking cancer cells growth via inhibition of the activity of the MMP [ 10 ], Bcl-2 [ 11 ], HDACs [ 12 ], STAT3 [ 13 ], HEC1 regulatory proteins [ 14 ], and targeting the VHL tumor suppressor gene [ 15 ] ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Development of Novel Pyridine-Thiazole Hybrid Molecules as Potential Anticancer Agents

et al. 2022

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Novel pyridine-thiazole hybrid molecules were synthesized and subjected to physico-chemical characterization and screening of their cytotoxic action towards a panel of cell lines derived from different types of tumors (carcinomas of colon, breast, and lung, glioblastoma and leukemia), and normal human keratinocytes, for comparison. High antiproliferative activity of the 3-(2-fluorophenyl)-1-[4-methyl-2-(pyridin-2-ylamino)-thiazol-5-yl]-propenone 3 and 4-(2-{1-(2-fluorophenyl)-3-[4-methyl-2-(pyridin-2-ylamino)-thiazol-5-yl]-3-oxopropylsulfanyl}-acetylamino)-benzoic acid ethyl ester 4 was revealed. The IC50 of the compound 3 in HL-60 cells of the acute human promyelocytic leukemia was 0.57 µM, while in the pseudo-normal human cell lines, the IC50 of this compound was >50 µM, which suggests that the compounds 3 and 4 might be perspective anticancer agents. The detected selectivity of the derivatives 3 and 4 for cancer cell lines inspired us to study the mechanisms of their cytotoxic action. It was shown that preincubation of tumor cells with Fluzaparib (inhibitor of PARP1) reduced the cytotoxic activity of the derivatives 3 and 4 by more than twice. The ability of these compounds to affect DNA nativity and cause changes in nucleus morphology allows for the suggestion that the mechanism of action of the novel pyridine-thiazole derivatives might be related to inducing the genetic instability in tumor cells.

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Synthesis, Molecular Docking and Anticancer Evaluation of New Arylazothiazoles

Cited by 8 publications

References 0 publications

Thiazole Ring—A Biologically Active Scaffold

Thiazole Ring—A Biologically Active Scaffold

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

Development of Novel Pyridine-Thiazole Hybrid Molecules as Potential Anticancer Agents

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