Application and synthesis of thiazole ring in clinically approved drugs

Niu, Zhen-Xi; Wang, Yatao; Zhang, Shengnan; Li, Yan; Chen, Xiaobing; Wang, Saiqi; Liu, Hong‐Min

doi:10.1016/j.ejmech.2023.115172

Cited by 43 publications

(19 citation statements)

References 96 publications

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“…[17] Additionally, it can be found in cefotaxime (a), the most important broad spectrum antibiotics. [18] Sulfathiazole (b) and other compounds containing thiazoles are used as antimicrobials, [19] dasatinib (c) is used to treat metastatic melanoma, [20] nitazoxanide (d) as an antiprotozoal, [21] ritonavir (e) is used as an antiviral, [22] tiazofurin (f) act as antineoplastic, [23] abafungin (g) is used as an antifungal, [24] and nizatidine (h) as an antihistaminic [25] (Figure 1 Medications for diabetes known as glucosidase inhibitors are used to treat type II diabetes in order to prevent postprandial hyperglycemia. [26,27] A metabolic condition known as diabetes mellitus type II has been defined by high blood glucose levels in the presence of insulin resistance and a relative insulin shortage.…”

Section: Introductionmentioning

confidence: 99%

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Ullah,

Alam,

Zainab

et al. 2024

ChemistrySelect

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This research work is based on synthesis of eleven novel thiazole derivatives (3 a‐k) of thiophene carbaldehyde. All the synthesized compounds were successfully synthesized, characterized by 1H‐NMR and EI‐MS spectroscopic techniques and finally subjected for their in vitro α‐glucosidase inhibitory activity. Seven derivatives 3 i (IC50=10.21±1.84 μM), 3 b (IC50=11.14±0.99 μM), 3 f (IC50=13.21±2.76 μM), 3 h (IC50=14.21±0.31 μM), 3 k (IC50=15.21±1.02 μM), 3 e (IC50=16.21±1.32 μM), and 3 c (IC50=18.21±1.89 μM), in the series displayed excellent inhibitory potential better than the standard acarbose. However, two compounds 3 g (IC50=33.21±1.99 μM) and 3 d (IC50=42.31±2.12 μM) showed significant activity while two compounds 3 j and 3 a were found less active with IC50 values of 82.31±0.31 and 88.36±1.21 μM respectively. Additional research revealed that the compounds are not exhibiting any cytotoxic effects. The molecular docking study of these derivatives showed their good binding potential for α‐glucosidase active site with excellent interactions and docking scores.

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Section: Introductionmentioning

confidence: 99%

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Ullah,

Alam,

Zainab

et al. 2024

ChemistrySelect

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“…The thiazole molecule has played a significant role as a heterocycle in chemistry for many years. [42] The π (pi) electrons in the thiazole ring, made up of sulphur and nitrogen, can shift from one bond to another, providing the nucleus with aromatic ring properties. [43] Due to its aromaticity, the ring has numerous reactive sites where reactions like nucleophilic, oxidative, donor-acceptor, and others can occur.…”

Section: Incredibility Of Thiazole In Past Yearsmentioning

confidence: 99%

“…Thiazole derivatives can be thoroughly examined as preferred scaffolds for designing and synthesizing novel molecules with enhanced biological activity. [42,55] Some of the FDA-approved thiazole-containing drugs have been mentioned in Figure 3.…”

Section: -100mentioning

confidence: 99%

Thiazole Heterocycle: An Incredible and Potential Scaffold in Drug Discovery and Development of Antitubercular Agents

Bhanwala,

Gupta,

Chandrakar

et al. 2023

ChemistrySelect

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In 2020, 15 million people were diagnosed with tuberculosis (TB), and 2.4 million died. Additionally, the TB situation is worse with multidrug resistance (MDR) and extended‐drug resistance (XDR)‐TB. Research into innovative anti‐tubercular drugs with improved MDR‐TB activity, lower toxicity, and shorter therapy duration is crucial for solving this issue. Fortunately, numerous novel potential anti‐tubercular candidates are currently under clinical trials. Most of these candidates have five‐membered rings and are most likely effective against sensitive and resistant strains. This review discusses current developments in the five‐membered heterocyclic thiazole ring, emphasizing its anti‐tubercular properties, toxicity, structure‐activity relationship, and mechanism of action. Thiazole ring has a wide range of biological activities and thus gained much synthetic interest. Due to the popularity of thiazole as an anti‐tubercular moiety, it combined with other medicinally active chemical functionality and nuclei to design and synthesize novel hybrid analogues with maximum activity and minimal toxicity. In this review we have done the literature survey of the past 10 years, and compiled the structural and functional studies of thiazole as an anti‐tubercular agent with its potent chemical entities showing prominent pharmacological action.

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“…As highly valuable structural units, thiocyanate (SCN) and thiazole are widely found in natural products and bioactive molecules (Scheme a). , They are also unique scaffolds that readily form sulfur- and nitrogen-containing compounds . Various classical methods have also been developed to construct thiazoles, such as Andreasch, Asinger, Cook–Heilbron, Hantzsch and Wohl–Marckwald thiazole synthesis, – and so forth.…”

Section: Introductionmentioning

confidence: 99%

Switchable Nucleophilic Site Enables Expedient Synthesis of CF₃-Containing Thiazoles and Allenes from 1,3-Enynes

Li,

Yang

et al. 2023

ACS Catal.

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Typically, trimethylsilyl isothiocyanate (TMSNCS) is used as a nucleophilic thiocyanate building block ( − S−C�N) that reacts with various electrophiles. However, it has been less explored as a source of isothiocyanates ( − N�C�S), which can usually be converted by thermal isomerization of allyl or propargyl thiocyanates. Achieving a method with precise site control is even more challenging. Here, we demonstrate an approach that uses metal catalysts to control switchable nucleophilic sites and provide a strategy to construct CF 3 -containing thiazoles and allenes via the multicomponent reaction of 1,3-enynes, TMSNCS, and electrophilic trifluoromethyl reagent. In the presence of inexpensive Fe(III) or Cu(II) catalysts, the current reaction is practical and convenient, compatible with various substrates bearing sensitive functional groups that can be readily transferred to more complex scaffolds. The biological evaluation showed that two of the developed CF 3 -containing thiazoles exhibited dramatic inhibitory activities for three human cancer cell lines beyond those of 5fluorouracil. Both compounds increased the level of reactive oxygen species in MCF-7 cells, which is believed to be an early step in tumor cell apoptosis.

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Application and synthesis of thiazole ring in clinically approved drugs

Cited by 43 publications

References 96 publications

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Thiazole Heterocycle: An Incredible and Potential Scaffold in Drug Discovery and Development of Antitubercular Agents

Switchable Nucleophilic Site Enables Expedient Synthesis of CF₃-Containing Thiazoles and Allenes from 1,3-Enynes

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Application and synthesis of thiazole ring in clinically approved drugs

Cited by 43 publications

References 96 publications

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Investigating Novel Thiophene Carbaldehyde Based Thiazole Derivatives as Potential Hits for Diabetic Management: Synthesis, In Vitro and In Silico Approach

Thiazole Heterocycle: An Incredible and Potential Scaffold in Drug Discovery and Development of Antitubercular Agents

Switchable Nucleophilic Site Enables Expedient Synthesis of CF3-Containing Thiazoles and Allenes from 1,3-Enynes

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Switchable Nucleophilic Site Enables Expedient Synthesis of CF₃-Containing Thiazoles and Allenes from 1,3-Enynes