Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity

Wei, Meng-Xue; Feng, Lei; Li, Xueqiang; Zhou, Xuezhang; Shao, Zhihui

doi:10.1016/j.ejmech.2009.03.023

Cited by 65 publications

(24 citation statements)

References 27 publications

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“…The heterocyclic compounds have broad applications including the treatment of hypertension, bacterial and HIV infections, allergies and as antibiotics and ligands for estrogen receptors 3,4 . Beside, these compounds have used as inhibitors against fructose 1,6-bisphosphatase 5 , tumor-associated carbonic anhydrase isoforms hCA IX and hCA XII 6 , sphingosine kinase 7 and evaluation of in vitro anticancer activity 8 . The carbonic anhydrases (CAs, EC 4.2.1.1) are superfamily of metalloenzymes present in Archaea, prokaryotes and eukaryotes, and in all life kingdoms with five genetically distinct families described in various organisms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II

Kilicaslan

Arslan

Ruya

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Sulfonamide-bearing thiazole compounds were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase I and II were evaluated. Human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of the 12 synthesized sulfonamide (5a-l) on the hydratase and esterase activities of these isoenzymes (hCA-I and hCA-II) were studied in vitro. In relation to these activities, the inhibition equilibrium constants (Ki) were determined. The results showed that all the synthesized compounds inhibited the CA isoenzyme activity. Among them 5b was found to be the most active (IC 50 ¼ 0.35 mM; Ki: 0.33 mM) for hCA I and hCA II.

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II

Kilicaslan

Arslan

Ruya

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The standard statistical thermodynamic functions such as heat capacity (C), entropy (S) and enthalpy changes (ΔH) heat capacity (C 0 p,m), entropy (S 0 m), and enthalpy changes (H 0 m) for the title compound were obtained on the basis of vibrational analysis, using DFT-B3LYP/6-31G(d.p) method and listed in Table 10. From Table 10, it can be observed that these thermodynamic functions increase with temperature ranging from 100 to 1000 K due to the fact that the molecular vibrational intensities increase with temperature [Wei et al 2009]. The correlation equations between heat capacity, entropy, enthalpy changes and temperatures are fitted by quadratic formulas.…”

Section: Thermodynamic Propertiesmentioning

confidence: 99%

Synthesis, spectral characterization (FT-IR and NMR) and DFT (Conformational analysis, molecular structure, HOMO-LUMO, UV-vis, NLO) computational studies on 2,2â€™-((1E,1â€™E)-phenazine-2,3 dilbis(azanylylidene))bis(methanyly- lidene))diphenol

Prabhakaran¹,

Rajaraman

et al. 2017

IJAC

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A new Schiff base was synthesized for the first time by the phenazine-2,3-diamine and 2-hydroxy benzaldedye in ethanol (1:1). The structure of Schiff bases was experimentally characterized by using UV-vis, IR, 1H NMR and 13C NMR spectroscopic methods. Further, the synthesized compound was subjected to DFT for better understanding of the molecular architecture and optoelectronic properties. The optimized geometric parameters supported the available experimental values. The Mulliken and MEP analyses are utilized to identify reactive sites of title molecule. The energetic behaviors of compound 3 in hexane, chloroform, methanol solvents and gas phase were examined using by time-dependent DFT (TD-DFT) method by applying the polarizable continuum model (PCM). The calculated ΔE energies exposed that charge transfer takes place within the molecule. In addition to the polarizability and hyperpolarizability have been calculated which exhibit that compounds possess non-linear optical nature.

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“…Since molecules in nature have a tendency to be found in their lowest energy form, the final configuration should also be of low energy [6]. Understanding these properties is crucial in the ration al design of potent inhibitors.…”

Section: Introductionmentioning

confidence: 99%

“…Many piperidin-4-one scaffold containing compounds are biological activities like antiviral [1,2], antitumor [3], anti-inflammatory [4], central nervous system [5], anticancer [6] and antibacterial activity [7]. Inspired by the growing importance of piperidin-4-one heterocyclic rings and the wide range of biological importance of heterocycles containing piperidin-4-one framework, we have devised a synthesis for the construction of piperidin-4-one ring systems incorporating a hydrazone framework with oxygen heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure-based molecular design of some novel (E)-N’-(3,3-dimethyl-2,6-diarylpiperidin-4-ylidene) -4-methoxybenzohydrazide as DNA gyrase inhibitors

Sundaraselvan¹,

Quine²

2016

Int. J. Curr. Res. Chem. Pharm. Sci

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A novel series of (E)-N'-(3,3-dimethyl-2,6-diarylpiperidin-4-ylidene)-4-methoxybenzohydrazide (DMMs) derivatives have been designed, synthesized by using FT-IR, 1 H, 13 C NMR and Mass spectral studies. The antibacterial activity of the DMMs evaluated against different bacteria viz. Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Streptococcus pyogenes. Among them, compounds 10 and 11 were found to be the most potent than the others. Different docking programs (Auto-Dock and molecular docking server) have been used to assess the accuracy of virtual screening methods against DNA gyrase target. An analysis provides us which functions perform well and feasibility of two docking approaches. In connection with these efforts we conclude that Auto Dock program gives us more accuracy and scoring reliability of the selected docking approaches. From these results, we report analogue 10 and 11 as promising candidates for the discovery of well-balanced compounds.

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Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity

Cited by 65 publications

References 27 publications

Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II

Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II

Synthesis, spectral characterization (FT-IR and NMR) and DFT (Conformational analysis, molecular structure, HOMO-LUMO, UV-vis, NLO) computational studies on 2,2â€™-((1E,1â€™E)-phenazine-2,3 dilbis(azanylylidene))bis(methanyly- lidene))diphenol

Synthesis, Structure-based molecular design of some novel (E)-N’-(3,3-dimethyl-2,6-diarylpiperidin-4-ylidene) -4-methoxybenzohydrazide as DNA gyrase inhibitors

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