Design and synthesis of new potent PTP1B inhibitors with the skeleton of 2-substituted imino-3-substituted-5-heteroarylidene-1,3-thiazolidine-4-one: Part I

Meng, Guangrong; Zheng, Meilin; Wang, Mei; Tong, Jing; Ge, Weijuan; Zhang, Jiehe; Zheng, Anqing; Li, Jingya; Gao, Lixin

doi:10.1016/j.ejmech.2016.05.060

Cited by 30 publications

(12 citation statements)

References 64 publications

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“…IR spectra were recorded on a Nicolet FT-IR 360 spectrophotometer (Thermo Scientific, Waltham, MA, USA). 1 H-NMR and 13 C-NMR spectra were determined on a Bruker AM-400 (400 MHz) spectrometer (Brucker Company, Fällanden, Switzerland) with tetramethylsilane (TMS) as an internal standard. Chemical shifts are reported in δ.…”

Section: Methodsmentioning

confidence: 99%

“…This method offers an alternative way to provide 2,3-diethyl-2,3-dihydro-1,3-thiazole (1a) instead of the traditional two-step method from disubstituted thioureas and β-keto ester derivatives (Scheme 2). As part of our recent studies on the new biological heterocyclic compounds [12,13], we now report a successful simple procedure to synthesize 1a from ethyl acetoacetate (2a), NBS, and N,N′-diethylthiourea (4a). While 1a shares a similar structure with the reported analogues [8], it was still reported for the first time by our research group in this paper.…”

Section: Introductionmentioning

confidence: 99%

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3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester

Meng

Mei

Cheng

et al. 2016

Molbank

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An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N -diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method is facile. The work-up procedure is easy and gives the pure target compound under milder reaction conditions in a relatively high yield of 75%.Abstract: An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method is facile. The work-up procedure is easy and gives the pure target compound under milder reaction conditions in a relatively high yield of 75%.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester

Meng

Mei

Cheng

et al. 2016

Molbank

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“…Meng et al [81] synthesized 2-substituted imino-3-substituted-5heteroarylidene-1,3-thiazolidine-4-ones 57 as the potent bidentate PTP1B inhibitor. Biological screening test against PTP1B revealed that most of these compounds have positive inhibitory activity against PTP1B.…”

Section: Density Functional Theory (Dft) Review Of Thiazolidinonementioning

confidence: 99%

Green Synthesis, Biological Evaluation and DFT Calculations of Thiazolidinone Derivatives – A Review

P¹,

M²,

Santhanalakshmi³

et al. 2019

Asian J Pharm Clin Res

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In the new millennium, we have novel biological targets which are defined at the molecular level, which have incredible success in comprehending human illness. On the other hand, the drug design processes are largely including pharmaceutical research study, scientific intuition, reaction and expertise to drive. Final thoughts attracted from this analysis can perform crucial function shaping the way our team believe concerning existing as well as future projects. With its origins rooted in natural synthesis as well as medicinal chemistry, heterocyclic compounds are existed themselves as a fundamental department of organic chemistry. IUPAC defined “cyclic compounds possessing ring members with atoms of at least two distinct elements" 1. Heterocyclic ring structures are core substances made up of components aside from carbon, where one of the most usual substituents is oxygen, nitrogen as well as sulphur 2, 3. According to the heteroatom(s) existing in the ring structure, heterocyclic could be recorded as oxygen, nitrogen or sulfur based and within each and every class of compound is based on the size of the ring structure, determined by the total number of atoms 4. The type and size of the ring structures, as one with the substituent groups of the core scaffold, impact is strongly on the physico-chemical properties 5. Heating responses with conventional devices, such as oil bath and also home heating mantles, are not only slow, yet additionally it produces a hot surface area on the reaction vessel where reagents, items and substrates are frequently disintegrate after at some time. Microwave power alternatively, is brought right into the chemical reactor from another location and travels through the walls of the response vessel, warming the catalysts and solvents directly. Microwave dielectric heating drives chain reactions by manipulating the benefit of the potential of some solids and liquids to change electromagnetic radiation into warm. Recently, a new technique has actually concerned the leading edge of chemical investigation, that is, microwave dielectric heating. In a similar method to the introduction of the isomantle, this technical advancement will no question need an adjustment in the drug store's mind set. In the future, the drug store will make use of fast blasts of microwave power to heat and also increase chemical reactions, as opposed to an alternate application in the very first circumstances for the mantle or hot plate. High-speed synthesis with microwaves has actually attracted a significant quantity of rate of interest in most recent years 6. Considering that, the very first reports on the usage of microwave home heating by Gedye and also Giguere / Majetich groups in speeding up organic chemical conversion in 1986, far more than 2,000 write-ups have been released in the area of Microwave Assisted Organic Synthesis 7, 8.

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“…[8][9][10][11][12][13] Furthermore, some of them were reported to possess antiviral, 14) antidiabetic, 15,16) antiinflammatory 17,18) and antimalarial 19) activities. Moreover, various substituted rhodanines were found to be anti-tubercular, 20,21) antiproliferative agent against human colon cancer, 22) anti-human immunodeficiency virus (HIV), [23][24][25][26][27] cyclooxygenase (COX-2) inhibitors, 28) potent PTP1B inhibitors, 29) antiglioma and cytotoxicity. 30) Additionally, rhodanine-based molecules have been popular as small molecule inhibitors of numerous targets such as Hepatitis C virus NS3 protease, 31) β-lactamase, 32) uridine diphospho-N-acetylmuramate/L-alanine ligase, 33) cathepsin D 34) and c-Jun N-terminal kinase (JNK)stimulating phosphatase-1 (JSP-1), 35) while some of rhodanine derivatives are used for the analysis of certain noble metal ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, <i>in-Vitro</i> Cytotoxicity and Antimicrobial Evaluations of Some Novel Thiazole Based Heterocycles

El-Mawgoud

2019

Chem. Pharm. Bull.

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Condensation of rhodanine (1) with pyrazol-3(2H)-one derivatives (2a-f) gave 5-substituted-2-thioxo-1,3thiazolidin-4-one derivatives (3a-f). Reaction of compound (1) with 2-arylmethylidene-malononitrile (4a-d) yielded the unexpected derivatives (5a-d). The latter compounds were subjected to cyclization reactions with malononitrile under different basic conditions, hydroxylamine hydrochloride and/or thiourea to furnish the fused thiazole derivatives (6a-d) and (8-10a-d). Coupling of (1) with diazotized aromatic amines (11a-c) in pyridine afforded the arylhydrazones (12a-c). Fusion of latter compounds with malononitrile afforded the thiazolopyridazine derivatives (13a-c). The structures of the newly synthesized compounds were elucidated via spectral data and elemental analyses. The in-vitro cytotoxic activity of compounds (3a-f) against the cell line MCF-7 was evaluated. Also, the synthesized products were investigated for their antibacterial and antifungal activities against six standard organisms including the G bacteria, Staphylococcus aureus and Bacillus subtilis, G bacteria, Escherichia coli and Proteus vulgaris in addition to fungi, Candida albicans and Aspergillus flavus.

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Design and synthesis of new potent PTP1B inhibitors with the skeleton of 2-substituted imino-3-substituted-5-heteroarylidene-1,3-thiazolidine-4-one: Part I

Cited by 30 publications

References 64 publications

3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester

3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester

Green Synthesis, Biological Evaluation and DFT Calculations of Thiazolidinone Derivatives – A Review

Synthesis, <i>in-Vitro</i> Cytotoxicity and Antimicrobial Evaluations of Some Novel Thiazole Based Heterocycles

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