Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors

Menteşe, Emre; Yılmaz, Fatih; Emirik, Mustafa; Ülker, Serdar; Kahveci, Bahittin

doi:10.1016/j.bioorg.2017.12.023

Cited by 55 publications

(35 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The crystal structure of JBU was retrieved from the Protein Data Bank using PDBID 3LA4 . The docking procedures were performed as described in our previous articles . The compounds 10a , 10b , and 10d showed better docking scores ranging from −7.38 to −9.11 kJ/mol than the standard inhibitors acetohydroxamic acid (−6.93 kJ/mol) and thiourea (−3.71 kJ/mol) in Table .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Menteşe

Akyüz

Yılmaz

et al. 2018

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

A new series of quinazolinone hybrid molecules containing coumarin, furan, 1,2,4triazole and 1,2,4-thiadiazole rings was designed, synthesized, and screened for their urease inhibition activities. All newly synthesized compounds showed outstanding urease inhibitory potentials with IC 50 values ranging between 1.26 ± 0.07 and 7.35 ± 0.31 μg/mL. Among the series, coumarin derivatives (10a-d) exhibited the best inhibitory effect against urease in the range of IC 50 = 1.26 ± 0.07 to 1.82 ± 0.10 μg/mL, when compared to standard urease inhibitors such as acetohydroxamic acid and thiourea (IC 50 = 21.05 ± 0.96 and 15.08 ± 0.71 μg/mL, respectively). Molecular docking studies were also performed to analyze the binding mode of compound 10b, and supported the experimental results. K E Y W O R D S coumarin, furan, molecular docking, quinazolin-4(3H)-one, thiadiazole, triazole, urease inhibition

show abstract

Section: Resultsmentioning

confidence: 99%

“…1,3,4‐Oxadiazole, furan, 1,3,4‐triazoles and 1,3,4‐thiadiazoles are the common and useful structural core in medicinal chemistry for designing new drug candidates. Compounds containing these moieties have been evaluated against a broad spectrum of pharmacological activities …”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Menteşe

Akyüz

Yılmaz

et al. 2018

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

show abstract

“…In order to determine the cupric ions (Cu 2+ ) reducing ability of the synthesized compounds was determined according to the literature (19,20,21). The standard curve was linear between 32 mM and 1.25 mM trolox (r 2 =0.9989).…”

Section: Cupric Reducing Antioxidant Capacity (Cuprac) Assaymentioning

confidence: 99%

Synthesis of Some New Benzimidazole Derivatives Containing Chlorine and Investigation of Their Antioxidant and Anti-urease Activities

Karaali

2018

Journal of the Turkish Chemical Society Section A: Chemistry

View full text Add to dashboard Cite

In this work, the synthesis of a 2-substituted benzimidazole compound containing chlorine (1) was carried out and then converted to the ester (2) and hydrazide (3) derivatives respectively. In the next steps, the hydrazide compound (3) was reacted with the appropriate reagents to give the thiadiazole (8-10) and triazole (11-13) derivatives. Synthesis of the compound 4 was carried out as a result of the interaction of the ester derivative compound (2) with morpholine. The structures of all new synthesized compounds were determined by FT-IR, 1 H NMR, 13 C NMR and elemental analysis spectroscopic methods. Also, the antioxidant and urease enzyme inhibition properties of these compounds were also investigated.

show abstract

“…The rigid aromatic system that present in the structure of benzimidazole gives rise to specific spectroscopic which makes it an active probe for nucleic acids. Recently, benzimidazole and its derivatives have attained considerable attention due to their potential applications as antiulcer (omeprazole), tubulin polymerization inhibitor, antihypertensive, antifungal, anticancer, anthelmintic, antibacterial, cytotoxicity, antimicrobial, anti‐inflammatory, antitumor, Trypanosomacruzi (Tc) infection, histamine‐H3 antagonist, antioxidant, gastro protective and anti‐parasitic, DNA binding and DNA‐encoded library (DEL) technology, enzyme inhibition, Alzheimer disease (AD) and HIV‐1 induced inhibitor for cytopathic activity. Furthermore, these derivatives have been employed as organic ligands, corrosion science, functional materials, catalysis, chemosensing, fluorescence signaling, self‐aggregation and dye sensitized solar cells (DSSCs) …”

Section: Introductionmentioning

confidence: 99%

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Rafiq

Khalid

Tahir

et al. 2019

Applied Organom Chemis

View full text Add to dashboard Cite

Present study advocates the joint experimental and computational studies of two potent benzoimidazole-based hydrazones with chemical formula C 23 H 18 F 2 N 4 O (5a) and C 25 H 22 FN 5 O 3 (5b). Both 5a and 5b were synthesized and resolved into their crystal structures using SC-XRD for the assessment of bond lengths, bond angles, unit cells and space groups. The structures of 5a and 5b were chemically characterized using infrared (FT-IR), UV-Visible, nuclear magnetic resonance ( 1 H-NMR and 13 C-NMR), EIMS and elemental analysis. DFT at M06-2X/6-31G(d,p) level of theory was performed to get optimized structures and countercheck the experimental findings. Overall, DFT findings show excellent concurrence with the experimental data which confirms the purity of both compounds. FMO, NBO analysis, MEP surfaces and nonlinear optical (NLO) properties were explored at same level of theory. UV-Vis analysis at TDDFT/M06-2X/6-31G(d,p) level of theory showed that 5b is red shifted with λ max 331.69 nm as compared to 5a with λ max 240.25 nm. Global reactivity parameters were estimated using energy of FMOs indicated the greater harness value than the softness values of 5a and 5b. NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper conjugative interactions are pivotal cause for the existence of 5a and 5b in the solid-state. NLO results of 5a and 5b were observed better than standard molecule recommended the NLO activity of said molecules for optoelectronic applications. Highlights• Two novel benzoimidazole-based hydrazones were synthesized.• XRD, NMR, FT-IR, UV-Vis, EIMS and elemental analysis were performed for the characterization.

show abstract

Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors

Cited by 55 publications

References 44 publications

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Synthesis of Some New Benzimidazole Derivatives Containing Chlorine and Investigation of Their Antioxidant and Anti-urease Activities

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Contact Info

Product

Resources

About