Synthesis and antimicrobial activity of cholic acid hydrazone analogues

Rasras, Anas J.; Al‐Tel, Taleb H.; Al‐Aboudi, Amal; Al‐Qawasmeh, Raed A.

doi:10.1016/j.ejmech.2010.02.006

Cited by 100 publications

(73 citation statements)

References 29 publications

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“…The hydrazone molecules display trans configurations about the C=N double bonds. The bond lengths are within normal ranges [15][16][17], and are comparable to those observed in (1). The C7=N1 and C25=N3 bond lengths are 1.272(5) and 1.269(5) Å , respectively, confirming them as double bonds.…”

Section: Resultssupporting

confidence: 54%

“…IR spectra were recorded on an IR-408 Shimadzu 568 spectrophotometer. The [1]HNMR spectra were recorded on Bruker AVANCE 400 MHz spectrometer with tetramethylsilane as the internal reference. X-ray diffraction was carried out on a Bruker SMART 1000 CCD area diffractometer.…”

Section: Methodsmentioning

confidence: 99%

“…In the last few years, hydrazone derivatives have been proved to have interesting biological activities such as antibacterial, antifungal, and antitumor [1][2][3][4][5]. Hydrazone compounds bearing NNO donor atoms have also been introduced to coordination chemistry [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Characterization and Crystal Structures of 3-Hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate and 3-Hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate

2012

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Two hydrazone compounds, 3-hydroxy-N 0 -[methyl (2-pyridyl)methylene]-2-naphthohydrazide monohydrate (1), and 3-hydroxy-N 0 -(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate (2), have been prepared and characterized by elemental analysis, IR spectra, 1 HNMR spectra, and X-ray single crystal structural determination. Compound (1) crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 11.072(2) Å , b = 12.017(2) Å , c = 23.753(3) Å , b = 95.710(2)°, V = 3144.7(9) Ǻ 3 , Z = 8, R 1 = 0.0780, and wR 2 = 0.1465. Compound (2) crystallizes in the triclinic space group P-1 with unit cell dimensions a = 7.601(2) Å , b = 16.522(4) Å , c = 17.048(3) Å , a = 92.516(11)°, b = 96.726(12)°, c = 94.117(12)°, V = 2117.8(8) Ǻ 3 , Z = 4, R 1 = 0.0490, and wR 2 = 0.1012. The hydrazone molecules in the compounds adopt trans configurations about the C=N double bonds. The crystal structures of the compounds are stabilized by intermolecular hydrogen bonds and pÁÁÁp stacking interactions.

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Section: Resultssupporting

confidence: 54%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Characterization and Crystal Structures of 3-Hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate and 3-Hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate

2012

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“…Aryloxyacetic acid hydrazide [13] having promising antibacterial activity against some bacterial strains (Abdel-Wahab et al, 2012). Cholic acid based hydrazones [14] showed antibacterial activity against Escherichia faecalis and E. coli (Rasras et al, 2010). Anthraquinone based hydrazones [15] showed promising bacteriostatic activity against P. auriginosa (Gouda et al, 2010).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Pharmacologically potentials of hydrazonone containing compounds: a promising scaffold

Asif

2014

International Journal of Advanced Chemistry

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“…Various hydrazones have been shown to be strong antimicrobial, anti-inflammatory and antifungal agents [13,14] . The antimicrobial agents, (3α,5β,7α,12α)-3,7,12-trihydroxy-N-[(1E)-4-chlorophenylmethylene] cholan-24-hydrazide were introduced recently by our group [15] . The supe- Inspired by the diverse bioactivities of molecules containing adamantane and hydrazide moieties, and as a continuation of our work on new cholinergic inhibitors [16] , we designed new hybrid compounds containing both moieties and tested their ability to inhibit acetylcholinesterase and butyrylcholinesterase.…”

Section: Introductionmentioning

confidence: 99%

In-silico identification of the binding mode of synthesized adamantyl derivatives inside cholinesterase enzymes

et al. 2015

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Aim: To investigate the binding mode of synthesized adamantly derivatives inside of cholinesterase enzymes using molecular docking simulations. Methods: A series of hybrid compounds containing adamantane and hydrazide moieties was designed and synthesized. Their inhibitory activities against acetylcholinesterase (AChE) and (butyrylcholinesterase) BChE were assessed in vitro. The binding mode of the compounds inside cholinesterase enzymes was investigated using Surflex-Dock package of Sybyl7.3 software. Results: A total of 26 adamantyl derivatives were synthesized. Among them, adamantane-1-carboxylic acid hydrazide had an almost equal inhibitory activity towards both enzymes, whereas 10 other compounds exhibited moderate inhibitory activity against BChE. The molecular docking studies demonstrated that hydrophobic interactions between the compounds and their surrounding residues in the active site played predominant roles, while hydrophilic interactions were also found. When the compounds were docked inside each enzyme, they exhibited stronger interactions with BChE over AChE, possibly due to the larger active site of BChE. The binding affinities of the compounds for BChE and AChE estimated were in agreement with the experimental data. Conclusion:The new adamantly derivatives selectively inhibit BChE with respect to AChE, thus making them good candidates for testing the hypothesis that BChE inhibitors would be more efficient and better tolerated than AChE inhibitors in the treatment of Alzheimer's disease.

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Synthesis and antimicrobial activity of cholic acid hydrazone analogues

Cited by 100 publications

References 29 publications

Synthesis, Characterization and Crystal Structures of 3-Hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate and 3-Hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate

Synthesis, Characterization and Crystal Structures of 3-Hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate and 3-Hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate

Pharmacologically potentials of hydrazonone containing compounds: a promising scaffold

In-silico identification of the binding mode of synthesized adamantyl derivatives inside cholinesterase enzymes

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