Thiophene-based derivatives as anticancer agents: An overview on decade’s work

Archna,; Pathania, Shelly; Chawla, Pooja

doi:10.1016/j.bioorg.2020.104026

Cited by 97 publications

(59 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Coupling of 17 with 3-acetyl-3-oxo-N-phenylbutanethioamide (19), [42] obtained from the addition 2,4-pentanedione (18) to phenyl isothiocyanate in DMF containing potassium hydroxide at room temperature followed by acidification with diluted HCl, in buffered ethanolic sodium acetate solution proceeded smoothly following the Japp-Klingemann reaction and affected acetyl cleavage to produce butanethioamide derivative 20 (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

“…[16] On the other hand, the antiproliferative carbazole derivative EHop-016 acts as Rac1 inhibitor. [17] Besides carbazoles, thiophene, [18][19][20] 1,3-thiazole [21][22][23] and 1,3,4-thiadiazole [24][25][26] derivatives are acquiring a lot of interest as central cores in drug design and in particular as promising templates for the development of new and more efficient anticancer agents that can solve or at least minimize major problems such as drug resistance, toxicity, or other adverse side effects.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

2020

View full text Add to dashboard Cite

In continuation to our efforts to discover new powerful antitumor agents, a series of new carbazole-based thiazole, thiophene, and 1,3,4-thiadiazole derivatives were conveniently synthesized, spectrally characterized, and mechanistically discussed. The synthetic strategy involves the cyclization reactions of two easily attainable commencing materials, N-(9-ethylcarbazol-3-yl)-2-cyanoacetamide (1) and 2-((9-ethylcarbazol-3yl)hydrazono)-3-oxo-N-phenylbutanethioamide (20), with αchlorocarbonyl reagents, α-chloronitrile, and hydrazonoyl chlorides in a basic medium. They were also assessed against three human tumor cell lines (HCT-116, HepG-2, and MCF-7) and one non-tumor human cell line (REP1) for their in vitro antitumor activity. The results demonstrated that seven carbazoles 4, 15 a, 15 b, 15 d, 20, 22 b, and 29 a had high antitumor activity, having IC 50 values in the range 5.24-9.70 μM. The most potent carbazoles 15 b, 20 and 22 b inhibited the growth of all tested tumor cell lines and did not display human toxicity.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

2020

View full text Add to dashboard Cite

show abstract

“…Treatment of 2-cyano-2-phenylthiocarbamoylacetanilide (1) [35] with ethyl 4-chloroacetoacetate, in boiling ethanol, and triethylamine, [36] produced ethyl 3-(3-amino-5-(phenylamino)-4-(phenylcarbamoyl)thiophen-2-yl)-3oxopropanoate (2) in 82% yield (Scheme 1). The reaction may start through nucleophilic displacement of chlorine from ethyl 4-chloroacetoacetate by sulfur nucleophile of thiocarbamoyl compound 1 giving intermediate (A), which underwent nucleophilic addition of methylene group (C-4) on the nitrile function forming the intermediate (B).…”

Section: Chemistrymentioning

confidence: 99%

“…Substituted thiophenes have been utilized as key structural units in significant bioactive pharmacophores, [1,2] and also as important building blocks in organic and medicinal chemistry. [3][4][5] Several thiophene-based compounds have been synthesized to screen their biological activities such as antimicrobial, [6][7][8] cytotoxic, [9,10] antiinflammatory, [11] anti-arrhythmic, [12] and antidepressant [13] agents.…”

Section: Introductionmentioning

confidence: 99%

Convenient synthesis and anticancer evaluation of novel pyrazolyl‐thiophene, thieno[3,2‐b]pyridine, pyrazolo[3,4‐d]thieno[3,2‐b]pyridine and pyrano[2,3‐d]thieno[3,2‐b]pyridine derivatives

Masaret

2021

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The newly synthesized 3-(3-amino-5-(phenylamino)-4-(phenylcarbamoyl) thiophen-2-yl)-3-oxopropanoate was utilized as a precursor for the synthesis of pyrazolyl-thiophene derivative, which undergoes cyclization upon treatment with benzaldehyde derivatives to provide pyrazolo [3,4-d]thieno[3,2-b]pyridines. Basic treatment of pyrazolyl-thiophene derivative with phenyl isothiocyanate followed by subsequent addition of chloroacetone and/or ethyl bromoacetate yielded the thiazolylidene-pyrazolyl thiophenes. In addition, the building block 3-(3-amino-5-(phenylamino)-4-(phenylcarbamoyl)thiophen-2-yl)-3-oxopropanoate was converted into the corresponding thieno[3,2-b] pyridine compounds through its reactions with (DMF-DMA) and/or heating in sodium ethoxide. Moreover, the reaction of 7-hydroxy-5-oxo-N-phenyl-2-(phenylamino)-4,5-dihydrothieno[3,2-b]pyridine-3-carboxamide with 2-arylidenemalononitrile produced the new annulated pyrano[2,3-d]thieno[3,2-b]pyridines. The prepared thiophene-based compounds were evaluated against HepG2, PC3, and MCF-7 cancer cells, and normal fibroblast cell (WI38). The pyrazolo [3,4-d]thieno[3,2-b]pyridine and pyrano [2,3-d]thieno[3,2-b]pyridine compounds substituted with chlorophenyl group presented promising cytotoxic activities against HepG2 cancer cell line without any human toxicity. Docking study for the synthesized thiophene compounds delivered valuable insights about the binding interactions with the crystal structure of NS5B enzyme with PDB ID (4TLR).

show abstract

“…Thiophene derivatives have been identified as anti-cancer agents for several years and exhibit their influence via different cancer pathways. 8–13 Thiazole-containing drugs, on the other hand, have demonstrated their involvement in a variety of commercially available anti-cancer medications, such as tiazofurin (inhibitor of IMP dehydrogenase), 14 dasatinib (Bcr-Abl tyrosine kinase inhibitor), 15 dabrafenib (inhibitor of enzyme B-RAF), 16 ixabepilone (stabilization of microtubules), 17 and epothilone (inhibition of microtubule function) 18 ( Figure 1 ). Thiazole-containing compounds depict anticancer activity profile through diverse mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Thiazole-Based Thiosemicarbazones: Synthesis, Cytotoxicity Evaluation and Molecular Docking Study

Gomha

Abdelhady

Hassain

et al. 2021

DDDT

View full text Add to dashboard Cite

Introduction Hybrid drug design has developed as a prime method for the development of novel anticancer therapies that can theoretically solve much of the pharmacokinetic disadvantages of traditional anticancer drugs. Thus a number of studies have indicated that thiazole-thiophene hybrids and their bis derivatives have important anticancer activity. Mammalian Rab7b protein is a member of the Rab GTPase protein family that controls the trafficking from endosomes to the TGN. Alteration in the Rab7b expression is implicated in differentiation of malignant cells, causing cancer. Methods 1-(4-Methyl-2-(2-(1-(thiophen-2-yl) ethylidene) hydrazinyl) thiazol-5-yl) ethanone was used as building block for synthesis of novel series of 5-(1-(2-(thiazol-2-yl) hydrazono) ethyl) thiazole derivatives. The bioactivities of the synthesized compounds were evaluated with respect to their antitumor activities against MCF-7 tumor cells using MTT assay. Computer-aided docking protocol was performed to study the possible molecular interactions between the newly synthetic thiazole compounds and the active binding site of the target protein Rab7b. Moreover, the in silico prediction of adsorption, distribution, metabolism, excretion (ADME) and toxicity (T) properties of synthesized compounds were carried out using admetSAR tool. Results The results obtained showed that derivatives 9 and 11b have promising activity (IC 50 = 14.6 ± 0.8 and 28.3 ± 1.5 µM, respectively) compared to Cisplatin (IC 50 = 13.6 ± 0.9 µM). The molecular docking analysis reveals that the synthesized compounds are predicted to be fit into the binding site of the target Rab7b. In summary, the synthetic thiazole compounds 1–17 could be used as potent inhibitors as anticancer drugs. Conclusion Promising anticancer activity of compounds 9 and 11 compared with cisplatin reference drug suggests that these ligands may contribute as lead compounds in search of new anticancer agents to combat chemo-resistance.

show abstract

Thiophene-based derivatives as anticancer agents: An overview on decade’s work

Cited by 97 publications

References 52 publications

Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

Convenient synthesis and anticancer evaluation of novel pyrazolyl‐thiophene, thieno[3,2‐b]pyridine, pyrazolo[3,4‐d]thieno[3,2‐b]pyridine and pyrano[2,3‐d]thieno[3,2‐b]pyridine derivatives

Thiazole-Based Thiosemicarbazones: Synthesis, Cytotoxicity Evaluation and Molecular Docking Study

Contact Info

Product

Resources

About