Design and Synthesis of New 4-(3,4,5-Trimethoxyphenyl)Thiazole–Pyrimidine Derivatives as Potential Antiproliferative Agents

El-Damasy, Ashraf K.; Jin, Heewon; Sabry, Mohamed; Kim, Hyun Ji; Alanazi, Mohammed M.; Seo, Seon Hee; Bang, Eun‐Kyoung; Keum, Gyochang

doi:10.3390/medicina59061076

Cited by 4 publications

(3 citation statements)

References 35 publications

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“…[74] The prediction data for the new 3 20) indicated drug-resembling properties and ability to target protein kinases. [75] The structures found with the Z configuration serve as pivotal building blocks in organic synthesis as active synthons and are also prevalent in biologically active natural products. This led Al-Warhi et al, to synthesize two distinct series of novel thiazole-based analogs from the initial materials hydrazine carbothioamide derivatives characterized by the Zconfiguration.…”

Section: Thiazole Derivatives As Anticancer Agentsmentioning

confidence: 99%

Anticancer Potential of the S‐Heterocyclic Ring Containing Drugs and its Bioactivation to Reactive Metabolites

Maji,

Debnath,

Panda

et al. 2024

Chemistry & Biodiversity

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Sulfur‐containing heterocyclic derivatives have been disclosed for binding with a wide range of cancer‐specific protein targets. Various interesting derivatives of sulfur‐containing heterocyclics such as benzothiazole, thiazole, thiophene, thiazolidinedione, benzothiophene, and phenothiazine, etc have been shown to inhibit diverse signaling pathways implicated in cancer. Significant progress has also been made in molecular targeted therapy against specific enzymes such as kinase receptors due to potential binding interactions inside the ATP pocket. Sulfur‐containing heterocyclic ring metal complexes i.e., benzothiazole, thiazole, thiophene, benzothiophene and phenothiazines are among the most promising active anticancer compounds. However, sulfur heteroaromatic rings, particularly thiophene, are of high structural alert due to their metabolism to reactive metabolites. The mere presence of a structural alert itself does not determine compound toxicity therefore, this review focuses on some specific findings that shed light on factors influencing the toxicity. In the current review, synthetic strategies of introducing the sulfur core ring in the synthesized derivatives are discussed with their structure‐activity relationships to enhance our understanding of toxicity mechanisms and develop safer therapeutic options. The sulfur‐containing marketed anticancer drugs included in this review direct the synthesis of novel compounds and will help in the development of potent, safer sulfur‐based anticancer drugs in near future.

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Section: Thiazole Derivatives As Anticancer Agentsmentioning

confidence: 99%

Anticancer Potential of the S‐Heterocyclic Ring Containing Drugs and its Bioactivation to Reactive Metabolites

Maji,

Debnath,

Panda

et al. 2024

Chemistry & Biodiversity

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show abstract

“…The thiazole ring is very useful in terms of biological activity. There is a lot of literature information showing its anticancer and antifungal activity [10–17] . In addition to this information, there is also a study using the thiazole ring as a VEGFR‐2 inhibitor [18] .…”

Section: Introductionmentioning

confidence: 99%

“…There is a lot of literature information showing its anticancer and antifungal activity. [10][11][12][13][14][15][16][17] In addition to this information, there is also a study using the thiazole ring as a VEGFR-2 inhibitor. [18] When docking studies are examined, the interaction of the thiazole ring with Asp1046, which is an important amino acid for the enzyme, shows the potential of the ring to inhibit VEGFR-2.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Imidazole‐2,3‐dihydrothiazole Compounds as VEGFR‐2 Inhibitors and Their Support with in Silico Studies

Osmaniye,

Bozkurt,

Kurban

et al. 2023

Chemistry & Biodiversity

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When the structure of VEGFR inhibitors is examined, it is seen that it consists of 4 pharmacophoric parts. In the light of this information, within the scope of this study, new 2‐((1‐(4‐(1H‐imidazol‐1‐yl)phenyl)ethylidene)hydrazineylidene)‐3‐ethyl‐4‐(substitutephenyl)‐2,3‐dihydrothiazole derivatives were synthesized. Structure determinations of the synthesized derivatives were made using spectroscopic methods. Firstly, the resulting compounds (4a‐4l) were subjected to the 24‐hour MTT test against MCF7, HepG2 and NIH3T3 cells. According to the MTT test results, compound 4h showed activity with IC50=4.566±0.246 µM and compound 4k with IC50=4.537±0.463 µM against HepG2 cell line. The antifungal activities and biofilm inhibition percentages of all compounds against infection problems that may develop in patients receiving chemotherapy were investigated. Compounds 4h and 4k which are active in the MTT test were tested for inhibition of VEGFR‐2 enzymes. Compound 4h displayed VEGFR‐2 inhibition with IC50=0.066±0.002 µM value; compound 4k did not show enzyme inhibition with an IC50>10 µM. Molecular docking studies were performed with two compounds (4k and 4h) and sorafenib to understand the dramatic difference for VEGFR‐2 inhibition. Molecular dynamics studies were performed with using 4h‐4ASE complex and both stability (RMSD, RMSF, Rg) and interaction potentials of the complex were analyzed and presented.

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The trimethoxyphenyl (TMP) functional group: a versatile pharmacophore

Langarizadeh,

Ameri,

Tavakoli

et al. 2023

Med Chem Res

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Design and Synthesis of New 4-(3,4,5-Trimethoxyphenyl)Thiazole–Pyrimidine Derivatives as Potential Antiproliferative Agents

Cited by 4 publications

References 35 publications

Anticancer Potential of the S‐Heterocyclic Ring Containing Drugs and its Bioactivation to Reactive Metabolites

Anticancer Potential of the S‐Heterocyclic Ring Containing Drugs and its Bioactivation to Reactive Metabolites

Synthesis of Imidazole‐2,3‐dihydrothiazole Compounds as VEGFR‐2 Inhibitors and Their Support with in Silico Studies

The trimethoxyphenyl (TMP) functional group: a versatile pharmacophore

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