28918-16-3Relevant academic research and scientific papers
Spectroscopic investigations and molecular docking study of 3-(1H-imidazol-1-yl)-1-phenylpropan-1-one, a potential precursor to bioactive agents
Al-Alshaikh, Monirah A.,Mary, Y. Sheena,Panicker, C.Yohannan,Attia, Mohamed I.,El-Emam, Ali A.,Alsenoy, C.Van
, p. 131 - 138 (2016)
The optimized molecular structure, vibrational wavenumbers, corresponding vibrational assignments of 3-(1H-imidazol-1-yl)-1-phenylpropan-1-one have been investigated theoretically and experimentally. The calculated geometrical parameters of the title comp
Structural, spectroscopic, Hirshfeld surface and charge distribution analysis of 3-(1H-imidazole-1-yl)-1-phenylpropan-1-ol complemented by molecular docking predictions: An integrated experimental and computational approach
Almutairi, Maha S.,Jayasheela,Periandy,Al-Ghamdi, Alwah R.,Sebastian,Xavier,Kadi, Adnan A.,Abdelhameed,Attia, Mohamed I.
, p. 578 - 591 (2019)
The optimized structure of title compound 3-(1H-imidazole-1-yl)-1-phenylpropan-1-ol (3HIP) was predicted according to the density functional theory (DFT) using the B3LYP method with 6-311G (d,p) basis set. Computed structural parameters of 3HIP were compared with X-ray diffraction data. Recorded and computed wavenumbers were assigned according to the total energy distribution (TED) using VEDA software. The natural bond orbital (NBO) analysis was used to characterize intramolecular rehybridization and delocalization of the electron density within the title molecule. Predictions of the NMR (1H and 13C) chemical shift assignments obtained by applying the gauge including atomic orbital (GIAO) approach were consistent with the corresponding experimental values. Ultraviolet-visible spectra of the title compound were simulated and validated experimentally. A molecular electrostatic potential (MEP) diagram visualized the electrophilic and nucleophilic sites of the 3HIP molecule. Hirshfeld surface analysis assessed the potential interactions of each atom inside the 3HIP molecule. Moreover, molecular docking analysis simulated the potential binding site pose of 3HIP within the active site of its target protein. The resulting 3HIP–target protein model can provide guidance for the development of new potent antifungal treatments.
Spectroscopic (FT-IR, FT-Raman, UV, 1H and 13C NMR) profiling and theoretical calculations of (2E)-2-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]hydrazinecarboxamide: An anticonvulsant agent
Haress, Nadia G.,Govindarajan, Munusamy,Al-Wabli, Reem I.,Almutairi, Maha S.,Al-Alshaikh, Monirah A.,Al-Saadi, Abdulaziz A.,Attia, Mohamed I.
, p. 219 - 232 (2016)
Vibrational characteristics of the anticonvulsant agent, (2E)-2-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]hydrazinecarboxamide ((2E)-IPHC) have been investigated. The computational data are obtained by adopting ab initio Hartree-Fock (HF) and DFT/B3LYP/6-31 + G(d,p) methods. The most stable conformer is identified by a potential energy scan. The optimized geometrical parameters indicated that the overall symmetry of the most stable conformer is CS. Atoms in molecules (AIM) analysis is contained out and the chemical bondings between the atoms are as characterized. Mulliken atomic charges and simulated thermo-molecular (heat capacity and enthalpy) characteristics of the (2E)-IPHC molecule also have been analyzed. The magnitude of the molecular electrostatic potential (MEP) of oxygen, hydrogen, and nitrogen atoms as well as phenyl and imidazole rings in the title molecule were investigated along with their contribution to the biological activity. The energy gap between HOMO and LUMO orbitals has been found to be 5.1334 eV in the gaseous phase. Excitation energies, oscillator strength and wavelengths were computed by the time-dependent density function theory (TD-DFT) approach. Predicted wavenumbers have been assigned and they are consistent with the experimental values. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of the (2E)-IPHC molecule were computed by the gauge independent atomic orbital (GIAO) method and were compared with the experimental results.
Design and synthesis of Mannich base-type derivatives containing imidazole and benzimidazole as lead compounds for drug discovery in Chagas Disease
Atherton, Richard L.,Kelly, John M.,Olmo, Francisco,Sanz-Serrano, Julen,Alcolea, Verónica,Beltran-Hortelano, Iván,Pérez-Silanes, Silvia,Rubio-Hernández, Mercedes
, (2021/07/14)
The protozoan parasite Trypanosoma cruzi is the causative agent of Chagas disease, the most important parasitic infection in Latin America. The only treatments currently available are nitro-derivative drugs that are characterised by high toxicity and limited efficacy. Therefore, there is an urgent need for more effective, less toxic therapeutic agents. We have previously identified the potential for Mannich base derivatives as novel inhibitors of this parasite. To further explore this family of compounds, we synthesised a panel of 69 new analogues, based on multi-parametric structure-activity relationships, which allowed optimization of both anti-parasitic activity, physicochemical parameters and ADME properties. Additionally, we optimized our in vitro screening approaches against all three developmental forms of the parasite, allowing us to discard the least effective and trypanostatic derivatives at an early stage. We ultimately identified derivative 3c, which demonstrated excellent trypanocidal properties, and a synergistic mode of action against trypomastigotes in combination with the reference drug benznidazole. Both its druggability and low-cost production make this derivative a promising candidate for the preclinical, in vivo assays of the Chagas disease drug-discovery pipeline.
Spectral characterization, computed frequencies analysis and electronic structure calculations on (1E)–N-hydroxy-3-(1H-imidazol-1-yl)-1-phenylpropan-1-imine: An oxime-bearing precursor to potential antifungal agents
Al-Wabli, Reem I.,Govindarajan, Munusamy,Almutairi, Maha S.,Attia, Mohamed I.
, p. 264 - 279 (2018/11/23)
(1E)–N-Hydroxy-3-(1H-imidazol-1-yl)-1-phenylpropan-1-imine (H3IPI) is a precursor to potential antifungal agents and was subjected to experimental and simulated spectroscopic (UV, FT-IR, FT-Raman as well as 1H and 13C NMR) characterization. Density functional theory, Hartree-Fock fundamental wavenumbers and intensity of the modes are interpreted with the aid of structure optimizations and normal force field computations. The complete wavenumbers assignments of H3IPI were made on the basis of potential energy distribution of each vibrational mode. The electronic and excited state properties have been determined by time dependent-density functional theory method. The responsiveness parameters as chemical potential, global hardness, and electrophilicity index have also been calculated. The scaled B3LYP/6–311++G (d,p) calculations showed better coincidence with the experimental findings of H3IPI over the other computation method. Molecular electrostatic potential and thermodynamic properties of the title compound were also investigated. In addition, Mulliken and natural charges distribution, non-linear optics properties as well as natural bond orbital analysis of the title molecule were calculated and interpreted. Theoretical calculations of the NMR chemical shifts of H3IPI were carried out through GIAO method at B3LYP/6–311++G (d,p) level and the results were compared with the experimental values.
Synthesis, single crystal X-ray analysis, and antifungal profiling of certain new oximino ethers bearing imidazole nuclei
Al-Wabli, Reem I.,Al-Ghamdi, Alwah R.,Ghabbour, Hazem A.,Al-Agamy, Mohamed H.,Attia, Mohamed I.
, (2017/11/20)
Fungal infections threaten human health, particularly in immune-compromised patients worldwide. Although there are a large number of antifungal agents available, the desired clinical attributes for the treatment of fungal infections have not yet been achieved. Azoles are the mainstay class of the clinically used antifungal agents. In the current study, the synthesis, spectroscopic characterization, and antifungal activity of certain new oximino ethers Va-n bearing imidazole nuclei are reported. The (E)-configuration of the imine double bond of the synthesized compounds Va-n has been confirmed via single crystal X-ray analysis of compound Vi as a representative example of this class of compounds. The molecular structure of compound Vi was crystallized in the monoclinic, P21/c, a = 18.7879(14) ?,β= 5.8944(4) ?, c = 16.7621(12) ?3,β= 93.063(3)β V = 1855.5(2) ?3, Z = 4. The in vitro antifungal activity of the synthesized compounds Va-n were evaluated using diameter of the inhibition zone (DIZ) and minimum inhibitory concentration (MIC) assays against different fungal strains. Compound Ve manifested anti-Candida albicans activity with an MIC value of 0.050 μmol/mL, being almost equipotent with the reference antifungal drug fluconazole (FLC),while compounds Vi and Vn are the most active congeners against Candida parapsilosis, being equipotent and about twenty-three times more potent than FLC with an MIC value of 0.002 μmol/mL. The results of the current report might support the development of new potent and safer antifungal azoles.
In vitro anti-Candida activity of certain new 3-(1H-Imidazol-1-yl)propan-1- one oxime esters
Attia, Mohamed I.,Zakaria, Azza S.,Almutairi, Maha S.,Ghoneim, Soraya W.
, p. 12208 - 12221 (2013/11/06)
Anti-Candida activities of certain new oximes 4a-d and their respective aromatic esters 5a-l are reported. The tested compounds 4a-d and 5a-l exhibited better anti-Candida profiles than fluconazole. Compound 5j, namely (E)-3-(1H-imidazol-1-yl)-1- phenylpropan-1-one O-4-chlorobenzoyl oxime emerged as the most active congener, with a MIC value of 0.0054 μmol/mL being more potent than both fluconazole (MIC > 1.6325 μmol/mL) and miconazole (MIC value = 0.0188 μmol/mL) as a new anti-Candida albicans agent.
Design and synthesis of 3-(azol-1-yl)phenylpropanes as microbicidal spermicides for prophylactic contraception
Kumar, Lalit,Sarswat, Amit,Lal, Nand,Jain, Ashish,Kumar, Sumit,Kiran Kumar,Maikhuri, Jagdamba P.,Pandey, Atindra K.,Shukla, Praveen K.,Gupta, Gopal,Sharma, Vishnu L.
supporting information; experimental part, p. 176 - 181 (2011/02/27)
We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60 s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 μg/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 μg/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive.
Synthesis and anti-candida potential of certain novel 1-[(3-substituted-3- phenyl)propyl]-1H-imidazoles
Aboul-Enein, Mohamed Nabil,El-Azzouny, Aida Abd El-Sattar,Attia, Mohamed Ibrahim,Saleh, Ola Ahmed,Kansoh, Amany Lotfy
scheme or table, p. 794 - 801 (2012/03/10)
The synthesis and anti-Candida activity of 1-[(3-aroyloxy-3-phenyl)propyl]- 1H-imidazoles 5a-f and 1-[(3-alkyl/aralkyl/phenyl-3-phenyl)propan-3-ol]-1H- imidazoles 5g-j are reported. The influence of the ester formation and different substitutions on the anti-Candida activity of the alcohol 4 was investigated. Among the newly developed bioactive chemical entities, compounds 5b and 5c displayed minimum inhibitory concentrations (MICs) against Candida albicans and Candida pseudotropicales comparable to that of tioconazole and more potent than miconazole. The target compounds 1-[(3-aroyloxy-3-phenyl)propyl]-1H-imidazoles 5a-f were obtained in four steps starting from acetophenone 1 whereas 1-[(3-alkyl/aralkyl/phenyl-3-phenyl)propan-3-ol]-1H-imidazoles 5g-j were synthesized in three steps. Compounds 5b and 5c showed anti-Candida activity comparable to tioconazole and were more potent than miconazole. Copyright
Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents
Bhandari, Kalpana,Srinivas, Nagarapu,Marrapu, Vijay K.,Verma, Aditya,Srivastava, Saumya,Gupta, Suman
body text, p. 291 - 293 (2010/04/05)
A series of aryloxy alkyl/aryl alkyl imidazoles were synthesized and evaluated in vitro as antileishmanials against Leishmania donovani. All the 19 compounds exhibited 94-100% inhibition at 10 μg/mL against promastigotes and 12 compounds exhibited high in
