Synthesis, molecular docking and biological evaluation of 3-arylfuran-2(5H)-ones as anti-gastric ulcer agent

Wang, Xudong; Wei, Wei; Wang, Pengfei; Yi, Li-Cheng; Shi, Wei-Kang; Xie, Yong-Xiang; Wu, Lang-Zhou; Tang, Nian; Zhu, Liang-Song; Peng, Jia; Liu, Chan; Li, Xianhui; Tang, Shi; Xiao, Zhu‐Ping; Zhu, Hai‐Liang

doi:10.1016/j.bmc.2015.05.026

Cited by 27 publications

(11 citation statements)

References 36 publications

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“…H. pylori (ATCC 43504; American Type Culture Collection, Manassas, VA) was grown in Brucella broth supplemented with 10% sheep sterile and defibrinated blood for 24 h at 37 C under microaerobic conditions (5% O 2 , 10% CO 2 , and 85% N 2 ), as our previously described literature 13,14 .…”

Section: Bacteriamentioning

confidence: 99%

“…Novel urease inhibitors with high potency are urgently needed. We therefore have focussed our efforts on this field for several years, and some potent urease inhibitors with structural diversity were reported such as catechols, diarylethylenes, flavonoids, arylamides, and hydroxamic acids [11][12][13][14][15] .…”

Section: Introductionmentioning

confidence: 99%

“…-112.1 C,1 H NMR (600 MHz, CDCl 3 ) d (ppm): 3.71 (s, 2H, CH 2 ); 7.28 (d, J ¼ 6.8 Hz, 2H, Ar); 7.35 (t, J ¼ 7.3 Hz, 1H, Ar); 7.39 (t, J ¼ 7.3 Hz, 2H, Ar); 7.44 (s, 1H, NH 2 ); 9.29 (s, 1H, NH 2 ); 9.88 (s, 1H, NH);13 C NMR (150 MHz, CDCl 3 ): 43.97; 128.06; 129.22; 129.38; 132.19; 171.72; 182.01; MS (ESI) m/z 195 (M þ H) þ ; Anal. Calcd for C 9 H 10 N 2 OS: C, 55.65; H, 5.19; N, 14.42; S, 16.51; found: C, 55.…”

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confidence: 99%

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N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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A urease inhibitor with good in vivo profile is considered as an alternative agent for treating infections caused by urease-producing bacteria such as Helicobacter pylori. Here, we report a series of N-monosubstituted thioureas, which act as effective urease inhibitors with very low cytotoxicity. One compound (b19) was evaluated in detail and shows promising features for further development as an agent to treat H. pylori caused diseases. Excellent values for the inhibition of b19 against both extracted urease and urease in intact cell were observed, which shows IC 50 values of 0.16 ± 0.05 and 3.86 ± 0.10 mM, being 170-and 44fold more potent than the clinically used drug AHA, respectively. Docking simulations suggested that the monosubstituted thiourea moiety penetrates urea binding site. In addition, b19 is a rapid and reversible urease inhibitor, and displays nM affinity to urease with very slow dissociation (k off ¼1.60 Â 10 À3 s À1 ) from the catalytic domain.

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Section: Bacteriamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…2-( O -tolyl) acetic acid (0.15 g, 1 mmol) was dissolved in 15 mL of methanol, slowly add 2–3 drops of concentrated sulfuric acid, then refluxing for 8 h and monitored by TLC, after the reaction is completed, the solvent methanol was removed by rotary evaporation, 30 mL of water was added to the residue and stirred, extracted three times with ethyl acetate, washed with water, dried and concentrated to give compound 5a . The obtained compound 5a was placed in a round bottom flask, and 1.2 eq of methyl glycolate, 20 mL of tetrahydrofuran, and 2.2 eq of potassium t-butoxide were added, refluxing and stirring the reaction and monitored by TLC, after the reaction is completed, 50 mL of water was added to the residue and stirred, adjust the pH of the solution to 5–6, then extracted three times with ethyl acetate, washed with water, dried and concentrated to obtain key lactone intermediates II ( 6a ) [10,11,12,13,14].…”

Section: Methodsmentioning

confidence: 99%

“…3-Aryl-4-hydroxy-2(5 H )-furanone belongs to the class of natural butenolides, and the core structure of these compounds is a five-membered lactone ring unit, and which is not only a structural fragment contained in many natural products [7,8] but also the core structure of insecticides [9]. As shown in Figure 1, many natural products such as ascorbic acid (vitamin C) and pulvinic acid possess the β-keto-γ-butyrolactone motif, and a lot of butenolide compounds containing this moiety have anti-tumor, anti-inflammatory, antioxidant and other biological activities [10,11,12,13,14,15,16,17]. Studies have shown that in the process of bacterial cell wall synthesis, these butenolide derivatives can inhibit the activity of Mur enzyme to achieve antibacterial action, so it is an antibacterial lead compound with research and development potential [18,19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bio-Evaluation of Natural Butenolides-Acrylate Conjugates

et al. 2019

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A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L−1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

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Regio‐ and Stereoselective Oxidation of Styrene Derivatives to Arylalkanoic Acids via One‐Pot Cascade Biotransformations

Zhou

Seet

et al. 2017

Adv Synth Catal

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Green and selective oxidation methodsa re highly desired in chemical synthesisa nd manufacturing. In this work, we have developedabiocatalytic method for the regio-and stereoselective oxidation of styrene derivatives into arylacetic and( S)-2-arylpropionic acids via ao ne-pot epoxidation-isomerization-oxidation sequence.T his was done via the engineering of Escherichia coli (StyABC-EcALDH)c oexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI) and aldehyde dehydrogenase (EcALDH)a sa na ctive and easily available wholecell catalyst. Regioselective oxidation of styrene and 11 substituted styrenes using the E. coli cells wasperformed in ao ne-pot set-up,p roducing 12 phenylacetic acids in bothh igh conversion and high yield. Engineering of E. coli (StyABC-ADH9v1) coexpressing SMO,S OI andA DH9v1 (a mutated alcohol dehydrogenase) led to biocatalystsc apable of regio-and stereoselective oxidation of a-methylstyrene derivatives to the corresponding chiral acids.O ne-pot asymmetric synthesis of 4( S)-2-arylpropionic acids was achieved in good conversion and excellent ee with the E. coli cells.T his is an ew type of asymmetric alkene oxidation to give chiral acids with no chemical counterpart thus far. Thec ascade bio-oxidation operates under mild conditions,u ses molecular oxygen, exhibitsv ery high regio-and enantioselectivity,a nd gives high conversion, thus providing ag reena nd efficientm ethod for the synthesiso fa rylacetic acids and (S)-2-arylpropionic acids directly from easily available styrenes.

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Synthesis, molecular docking and biological evaluation of 3-arylfuran-2(5H)-ones as anti-gastric ulcer agent

Cited by 27 publications

References 36 publications

N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

Synthesis and Bio-Evaluation of Natural Butenolides-Acrylate Conjugates

Regio‐ and Stereoselective Oxidation of Styrene Derivatives to Arylalkanoic Acids via One‐Pot Cascade Biotransformations

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