Synthesis of <i>C</i>-Pseudonucleosides Bearing Thiazolidin-4-one as a Novel Potential Immunostimulating Agent

Chen, Hua; Yin, Qingmei; Li, Chunxiao; Wang, Enkai; Gao, Fang; Zhang, Xiaobo; Yin, Zhi Kui; Wei, Sinan; Li, Xiaoliu; Mao, Meng; Zhang, Pingzhu; Li, Na; Zhang, Jinchao

doi:10.1021/ml200155k

Cited by 20 publications

(7 citation statements)

References 25 publications

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“…As demonstrated in Figure 1, there are several thiazolidine ring containing approved drugs available in market such as Ralitoline ( A , antiepileptic), Teneligliptin ( B , anti‐diabetic), Etozoline ( C , diuretic), Penicillins ( D , antibiotic), Epalrestat ( E , diabetic neuropathy). In addition, thiazolidines are reported as influenza neuraminidase inhibitor, 21 tyrosyl‐DNA phosphodiesterase I inhibitor, 22 S1P1 receptor antagonists, 23 prodrugs as cystinosis, 24 and also act as immuno‐stimulating agents 25 …”

Section: Introductionmentioning

confidence: 99%

Identification of novel inhibitors for Prp protein of Mycobacterium tuberculosis by structure based drug design, and molecular dynamics simulations

et al. 2022

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In this study, we assess the effective inhibition of a series of thiazolidine derivatives (1a–1q) were adopting structure‐based drug design. Thiazolidine is a five‐membered ring structure with thioether and amino groups at positions 1 and 3. Although, thiazolidine may bind to a wide range of protein targets, it is a major heterocyclic core in medicinal chemistry. Different scoring utilities including AutoDock Vina, Glide, and MM/GBSA analysis were performed to commensurate the improvement of screening progress. The evaluated binding affinities were validated by molecular dynamics simulations over a period of 20 ns for the interactions between the Mycobacterium tuberculosis protein PrpR with three novel scaffolds (1b, 1j, and 1k). All the scaffolds exhibited distinct stable interactions with the significant residues like Arg169, Arg197, Tyr248, Arg308, and Gly311 respectively. Further, the inhibitory activities of scaffolds were predicted and evaluated by machine learning based algorithm to rank the above proposed compounds. This study reveals the potential of 1k and 1j as effective inhibitor candidates for the treatment of tuberculosis.

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Section: Introductionmentioning

confidence: 99%

Identification of novel inhibitors for Prp protein of Mycobacterium tuberculosis by structure based drug design, and molecular dynamics simulations

et al. 2022

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“…Heterocycles are an important framework for the development of new drugs, especially S-containing heterocycles which have been found to have the ability to induce apoptosis of various cells [ 16 ]. Thiazolidine drugs containing N and S atoms can exert drug effects through various mechanisms of action, such as inhibiting neuraminidase of influenza A virus [ 17 ], inhibiting protein synthesis [ 18 ], accelerating cell apoptosis [ 16 , 19 ], enhancing antioxidant capacity [ 7 ], immune stimulation [ 20 ], etc. Some thiazolidine-4-carboxylic acid derivatives can also oxidatively cleave DNA and interact with metal ions [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents

et al. 2021

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Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by 1H-NMR, 13C-NMR, and HRMS techniques. The antiviral and antifungal activities of cysteine and its derivatives were evaluated in vitro and in vivo. The results of anti-TMV activity revealed that all compounds exhibited moderate to excellent activities against tobacco mosaic virus (TMV) at the concentration of 500 μg/mL. The compounds cysteine (1), 3–4, 7, 10, 13, 20,23, and 24 displayed higher anti-TMV activities than the commercial plant virucide ribavirin (inhibitory rate: 40, 40, and 38% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively), especially compound 3 (inhibitory rate: 51%, 47%, and 49% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity emerged as a new antiviral candidate. Antiviral mechanism research by TEM exhibited that compound 3 could inhibit virus assembly by aggregated the 20S protein disk. Molecular docking results revealed that compound 3 with higher antiviral activities than that of compound 24 did show stronger interaction with TMV CP. Further fungicidal activity tests against 14 kinds of phytopathogenic fungi revealed that these cysteine derivatives displayed broad-spectrum fungicidal activities. Compound 16 exhibited higher antifungal activities against Cercospora arachidicola Hori and Alternaria solani than commercial fungicides carbendazim and chlorothalonil, which emerged as a new candidate for fungicidal research.

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“…In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase I [33] and influenza neuraminidase [34], pro-drugs for the treatment of cystinosis [35], radioprotective against γ-irradiation [36] and as S1P1 receptor agonists [37,38] has also been reported. They are also used in peptide and protein modification [39], protein chemical synthesis [40], as activators to innate immunity [41] and also act as immunostimulating agents [42]. These derivatives are also involved in various syntheses as synthetic precursors, potential biomarkers for oxidative stress and formaldehyde exposure [43], heterogeneous catalysts [44,45], free radicals, superoxide anion radical and hydroxyl radical scavengers [46][47][48], inducible nitric oxide synthase (iNOS) inhibitors [49], to construct non-fullerene small molecules [50] and on and on.…”

Section: Introductionmentioning

confidence: 99%

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

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In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

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Synthesis of C-Pseudonucleosides Bearing Thiazolidin-4-one as a Novel Potential Immunostimulating Agent

Cited by 20 publications

References 25 publications

Identification of novel inhibitors for Prp protein of Mycobacterium tuberculosis by structure based drug design, and molecular dynamics simulations

Identification of novel inhibitors for Prp protein of Mycobacterium tuberculosis by structure based drug design, and molecular dynamics simulations

Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

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