835-93-8Relevant academic research and scientific papers
Synthesis and spectroscopic identification of certain imidazole-semicarbazone conjugates bearing benzodioxole moieties: New antifungal agents
Al-Wabli, Reem I.,Al-Ghamdi, Alwah R.,Ghabbour, Hazem A.,Al-Agamy, Mohamed H.,Attia, Mohamed I.
, (2019)
During the last three decades the extent of life-threatening fungal infections has increased remarkably worldwide. Synthesis and structure elucidation of certain imidazole-semicarbazone conjugates 5a–o are reported. Single crystal X-ray analysis of compound 5e unequivocally confirmed its assigned chemical structure and the (E)-configuration of its imine double bond. Compound 5e crystallized in the triclinic system, P-1, a = 6.3561 (3) ?, b = 12.5095 (8) ?, c = 14.5411 (9) ?, α = 67.073 (4)?, β = 79.989 (4)?, γ =84.370 (4)?, V = 1048.05 (11) ?3, Z = 2. In addition, DIZ and MIC assays were used to examine the in vitro antifungal activity of the title conjugates 5a–o against four fungal strains. Compound 5e, bearing a 4-ethoxyphenyl fragment, showed the best MIC value (0.304 μmol/mL) against both C. tropicalis and C. parapsilosis species, while compounds 5c (MIC = 0.311 μmol/mL), 5k, and 5l (MIC = 0.287 μmol/mL) exhibited the best anti-C. albicans activity.
Synthesis, x-ray single crystal structure, molecular docking and DFT computations on N-[(1E)-1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl) propylidene]-hydroxylamine: A new potential antifungal agent precursor
Al-Wabli, Reem I.,Al-Ghamdi, Alwah R.,Ghabbour, Hazem A.,Al-Agamy, Mohamed H.,Monicka, James Clemy,Joe, Issac Hubert,Attia, Mohamed I.
, (2017)
Mycoses are serious health problem, especially in immunocompromised individuals. A new imidazole-bearing compound containing an oxime functionality was synthesized and characterized with different spectroscopic techniques to be used for the preparation of new antifungal agents. The stereochemistry of the oxime double bond was unequivocally determined via the single crystal X-ray technique. The title compound 4, C13H13N3O3·C3H8O, crystallizes in the monoclinic space group P21 with a = 9.0963(3) ?, b = 14.7244(6) ?, c = 10.7035(4) ?, β = 94.298 (3)°, V = 1429.57(9) ?3, Z = 2. The molecules were packed in the crystal structure by eight intermolecular hydrogen bond interactions. A comprehensive spectral analysis of the title molecule 4 has been performed based on the scaled quantum mechanical (SQM) force field obtained by density-functional theory (DFT) calculations. A molecular docking study illustrated the binding mode of the title compound 4 into its target protein. The preliminary antifungal activity of the title compound 4 was determined using a broth microdilution assay.
(2E)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-N-(4-methoxyphenyl)hydrazinecarboxamide: Synthesis, crystal structure, vibrational analysis, DFT computations, molecular docking and antifungal activity
Al-Wabli, Reem I.,Al-Ghamdi, Alwah R.,Primsa,Ghabbour, Hazem A.,Al-Agamy, Mohamed H.,Joe, I. Hubert,Attia, Mohamed I.
, p. 121 - 130 (2018)
Fungal infections are a growing health threat to mankind. The development of novel potent antifungal agents is a challenge to overcome the resistance to the available antifungal medications. The current report focuses on the synthesis and spectroscopic characterization of a new imidazole-bearing antifungal agent. The vibrational characteristics of the title compound are explored using Fourier transform infrared and Raman spectroscopy with the aid of density functional theory. Highest occupied and lowest unoccupied molecular orbital investigations and natural bond orbital analysis of the title molecule are performed to investigate the possible intermolecular delocalisation or hyper-conjugation, and the possible interactions with the target protein. Single crystal X-ray analysis confirms the assigned (E)-configuration of the imine double bond structure of the title compound. The molecular structure of the title compound is crystallised in a monoclinic space group, namely, P21/c, a = 10.7007 (4) ?, b = 7.3072 (3) ?, c = 24.9088 (8) ?, β = 97.178 (2)°, V = 1932.41 (12) ?3 and Z = 4. The antifungal potential of the title compound is in vitro assessed against four fungal strains. In addition, molecular docking of the title molecule predicts its binding orientation in the active site of the target protein.
Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
Abonia, Rodrigo,Garay, Alexander,Castillo, Juan C.,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Butassi, Estefanía,Zacchino, Susana
, (2018/03/09)
Two practical and efficient approaches have been implemented as alternative procedures for the synthesis of naftifine and novel diversely substituted analogues 16 and 20 in good to excellent yields, mediated by Mannich-type reactions as the key step of the processes. In these approaches, theγ-aminoalcohols 15 and 19 were obtained as the key intermediates and their subsequent dehydration catalyzed either by Br?nsted acids like H2SO4 and HCl or Lewis acid like AlCl3, respectively, led to naftifine, along with the target allylamines 16 and 20. The antifungal assay results showed that intermediates 18 (bearing both a β-aminoketo- and N-methyl functionalities in their structures) and products 20 were the most active. Particularly, structures 18b, 18c, and the allylamine 20c showed the lowest MIC values, in the 0.5-7.8 μg/mL range, against the dermatophytes Trichophyton rubrum and Trichophyton mentagrophytes. Interesting enough, compound 18b bearing a 4-Br as the substituent of the phenyl ring, also displayed high activity against Candida albicans and Cryptococcus neoformans with MIC80 = 7.8 μg/mL, being fungicide rather than fungistatic with a relevant MFC value = 15.6 μg/mL against C. neoformans.
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.
Evaluation of acrylophenones and related bis-Mannich bases against murine P388 leukemia
Dimmock, Jonathan R.,Patil, Shirish A.,Leek, Donald M.,Warrington, Robert C.,Fang, Wei D.
, p. 545 - 552 (2007/10/02)
2-Dimethylaminomethyl-1-(4-methoxyphenyl)-prop-2-en-1-one hydrochloride (IIa) was shown to have potent activity against P388 cells in vitro, whereas in vivo examination of this derivative and related acrylophenone hydrochlorides revealed little activity a
