5653-60-1Relevant academic research and scientific papers
Development of Imidazoline-2-one Derivatives as Potential Antifungal and Anthelminthic Agents: in silico and in vitro Evaluation
Chilamakuru, Naresh Babu,Mallela, Vijaya Jyothi,Peraman, Ramalingam,Shaik, Shakir Basha,Simham, Venu,Singirisetty, Triveni
, p. 423 - 433 (2021/11/24)
Based on appropriate values of synthetic accessibility concerning from ADMET properties and docking scores by docking against proteins 3OZU and 1OJ0, a series of 4,5-diphenyl-1H-imidazol-2-ones (I1?15) were synthesized. The key intermediate, 2-hydroxy-1,2-disubstitutedethanones (E1?15) were prepared by benzoin condensation using 2:1 ratio of aromatic aldehydes and thiamine in the presence of alkali. Further, these cyclized ethanones (E1?15) were treated with urea to yield 4,5-diphenyl-1H-imidazol-2-one derivatives (I1?15) and were characterized by IR,1H NMR, Mass spectra, and CHNO analysis. The synthesized compounds were screened for their anthelmintic potential on Pheretima Posthuma along with standard albendazole, and antifungal activity (minimum inhibitory concentration method) on Candida albicans and Aspergillus niger along with standard miconazole. The results revealed that among all the tested compounds I3, I4, and I7 show considerable synthetic accessibility, docking scores, anthelminthic, and antifungal activity.
(±)Methanodibenzodiazocine tethered [C-H]δ+ functional site: Study towards benzoin condensation and Baylis-Hillman reactions
Sathyanarayana, Arruri,Prabusankar, Ganesan
, p. 821 - 831 (2015/08/06)
Abstract New heterocyclic ring systems consisting of (±) methanodibenzodiazocine and imidazolium/ benzimidazolium salts were synthesized in very good yield. Subsequently, these halide salts were subjected to the anion exchange reaction with KPF6 to yield the corresponding azolium salts in excellent yield. The possible applications of these newly prepared salts were investigated in homogeneous catalysis. Remarkable changes in the catalytic activity were observed by varying the bulkiness of N-substituent at imidazole. Catalytic activity of these newly prepared salts was tested for the benzoin condensation reaction. Exclusive formation of benzoin products were observed in good yield. Similarly, the dimerization of cyclohexen-1-one to Baylis-Hillman type product, 2-(3-oxocyclohexyl)-2-cyclohexen-1-one was studied. [Figure not available: see fulltext.]
Design, synthesis, cytotoxic evaluation and tubulin inhibitory activity of 4-aryl-5-(3,4,5-trimethoxyphenyl)-2-alkylthio-1H-imidazole derivatives
Assadieskandar, Amir,Amini, Mohsen,Ostad, Seyed Nasser,Riazi, Gholam Hossein,Cheraghi-Shavi, Tayebe,Shafiei, Bentolhoda,Shafiee, Abbas
, p. 2703 - 2709 (2013/06/27)
A new series of 4-aryl-5-(3,4,5-trimethoxyphenyl)-2-alkylthio-1H-imidazoles were synthesized and their cytotoxic activities in vitro against four different cell lines (HT-29, MCF-7, NIH-3T3, AGS) were evaluated. Compound 6g bearing 3,4,5-trimethoxyphenyl moiety on ring A and 4-methoxy substituent on ring B displayed potent cytotoxic activity against all cell lines. Flow cytometry analysis and microtubule polymerization assay confirmed that cytotoxic activities of this compound were related to inhibitory effect against microtubules polymerization. Molecular modeling studies revealed that compound 6g could strongly bind to the colchicine binding site of α,β-tubulin through hydrogen bond interactions with Thrα179 and Cysβ241.
Catalytic action of azolium salts. VI. Preparation of benzoins and acyloins by condensation of aldehydes catalyzed by azolium salts
Miyashita,Suzuki,Iwamoto,Higashino
, p. 2633 - 2635 (2007/10/02)
Benzoins 4 (2-hydroxyethanones substituted with aryl groups at the 1- and 2-positions) were prepared by self-condensation of aromatic aldehydes 3 using catalytic amounts of azolium salts 1 and 2 in excellent yields. 1,3-Dimethylbenzimidazolium iodide (2) was an effective catalyst for the preparation of acyloins 6 (2-hydroxyethanones substituted with alkyl groups at the 1- and 2-positions) by self-condensation of aliphatic aldehydes 5. On the other hand, an attempt at the condensation of hexanal (5d) catalyzed by 1,3-dimethylimidazolium iodide (1) failed to yield the acyloin 6d, and instead the aldol-type condensed product 8d was obtained.
Discotic Liquid Crystals of Transition Metal Complexes 11: The First ?-Acceptor in Discotic Columnar Liquid Crystals Obtained from Octasubstituted Bis(diphenylethane-1,2-dithiolene)nickel Complexes
Ohta, Kazuchika,Hasebe, Hiroshi,Ema, Hiroshi,Moriya, Mitsuo,Fujimoto, Tetsuya,Yamamoto, Iwao
, p. 21 - 32 (2007/10/02)
Disk-like complexes, bisnickel (n-alkyl = n-hexyl, n-octyl) and bisnickel have been synthesized and characterized.It was found that n-decyloxy derivative exhibits a hexagonal discordered columnar (Dhd) mesophase while n-alkyl derivatives are not discotic liquid crystals but isotropic liquids at room temperature.The half-wave potentials for reduction of these complexes is -0.04 - -0.06 V. n-Decyloxy derivative is the first ?-acceptor in discotic columnar liquid crystals.
Studies on Hydrobenzoins: Preparation, Crystal Structure and Stability of Borate Complexes
Karlsson, Olov,Lundquist, Knut,Stomberg, Rolf
, p. 617 - 624 (2007/10/02)
The meso and racemic forms of hydrobenzoin , hydroanisoin and hydroveratroin have been prepared by reduction of the corresponding benzoins by sodium tetrahydridoborate and by the borane-dimethyl sulfide complex.The meso and racemic forms could be separated by ion exchange chromatography on an anion exchanger, using a borate solution as the eluent.Borate complexes of the racemic forms were more stable than those of the corresponding meso forms.Hydrobenzoins are useful as model compounds in connection with studies of acid-catalysed reactions and microbial degradation of lignins.The crystal structures of the meso forms of hydroanisoin and hydroveratroin have been determined from single-crystal X-ray diffraction data. meso-Hydroanisoin crystallizes in the space group P21/c with a = 15.269(6), b = 5.035(2), c = 9.198(4) Angstroem, β = 98.75(3) deg and Z = 2.Full-matrix least-squares refinement of 127 structural parameters gave R = 0.039 for 1047 observed 3?(I)> reflections. meso-Hydroveratroin crystallizes in the space group P21/n with a = 8.185(2), b = 12.605(3), c = 8.414(2) Angstroem, β = 109.74(2) deg and Z = 2.Full-matrix least-squares refinement of 153 structural parameters gave R = 0.036 for 1086 3?(I)> reflections.
