88951-63-7

Upstream product

• 22666-84-8 4-hydroxybenzaldehyde sodium salt 
• 3289-75-6 2-chloro-N-(4-chlorophenyl)acetamide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 106-47-8 4-chloro-aniline 
• 51264-69-8 ethyl 2-(4-formylphenoxy)acetate 

Downstream Products

• 88951-36-4 4-(p-chlorophenylcarbamoylmethoxy)benzylidene-p'-butoxyaniline 
• 88951-35-3 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-propoxy-phenylimino]-methyl}-phenoxy)-acetamide 
• 88951-37-5 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-pentyloxy-phenylimino]-methyl}-phenoxy)-acetamide 
• 88951-40-0 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-octyloxy-phenylimino]-methyl}-phenoxy)-acetamide 
• 88951-41-1 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-nonyloxy-phenylimino]-methyl}-phenoxy)-acetamide 
• 88951-33-1 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-methoxy-phenylimino]-methyl}-phenoxy)-acetamide 
• 1266715-50-7 (Z)-N-(4-chlorophenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide 
• 358763-17-4 N-(4-chlorophenyl)-2-(4-((2,4,6-trioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide 
• 359426-22-5 N-(4-chlorophenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide 
• 88951-34-2 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-ethoxy-phenylimino]-methyl}-phenoxy)-acetamide 
• 88951-62-6 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-hydroxy-phenylimino]-methyl}-phenoxy)-acetamide 
• 88951-38-6 N-(4-Chloro-phenyl)-2-(4-{[(E)-4-hexyloxy-phenylimino]-methyl}-phenoxy)-acetamide 

Relevant academic research and scientific papers

Chitosan and functionalized graphene oxide nanocomposite as a novel and highly efficient catalyst for production of bis-coumarins under solvent-free conditions

Chitosan and functionalized graphene oxide nanocomposite was used as efficient, sustainable, and recyclable catalyst in the production of bis-coumarins using 4-hydroxycoumarin and aromatic aldehydes under solvent-free conditions. Chitosan was first functi

The possible effect of microRNA-155 (miR-155) and BACE1 inhibitors in the memory of patients with down syndrome and Alzheimer's disease: Design, synthesis, virtual screening, molecular modeling and biological evaluations

MiR-155 plays main roles in several physiological and pathological mechanisms, such as Down syndrome (DS), immunity and inflammation and potential anti-AD therapeutic target. The miR-155 is one of the overexpressed miRNAs in DS patients that contribute directly and indirectly to the onset or progression of the DS. Since the miR-155 can simultaneously reduce the translation of several genes at post-transcriptional levels, targeting the miR-155 might set the stage for the treatment of DS. One of the rational strategies in providing therapeutic interventions in this respect is to design and develop novel small molecules inhibiting the miR-155 function or biogenesis or maturation. In the present study, we aim to introduce small molecule compounds with the potential to inhibit the generation of the selectively miR-155 processing by employing computational drug design approaches, as well as in vitro studies. We designed and synthesized a novel series of imidazo[1,2-a]pyridines derivatives as new nonpeptic candidates for the treatment of DS with AD. The designed compounds were investigated for their BACE1 and miR-155 binder inhibitory potential in vitro and in cell. In addition, we present a systematic computational approach that includes 3 D modeling, docking-based virtual screening, and molecular dynamics simulation to identify Small - molecule inhibitors of pre-miR-155 maturation. To confirm the inhibitory potential of compound 8k on miR-155 maturation, qRT- PCR was performed. All our results confirm that compound 8k, in addition to being a good inhibitor of BACE1, can also be a good inhibitor of miR-155. Communicated by Ramaswamy H. Sarma.

Synthesis, in vitro and in silico enzymatic inhibition assays, and toxicity evaluations of new 4,5-diphenylimidazole-N-phenylacetamide derivatives as potent α-glucosidase inhibitors

α-Glucosidase is responsible for glucose release of oligosaccharides and disaccharides in the intestine and increase postprandial hyperglycemia. Inhibition of this enzyme is a beneficial therapeutic method for glycemic control in diabetes. This study deals with the design and synthesis of 4,5-diphenylimidazole-N-phenylacetamide derivatives 7a–l and the screen of these compounds for their potential for α-glucosidase inhibition. All the synthesized compounds exhibited superior α-glucosidase inhibition (IC50 = 90.0–598.5 μM) as compared to standard inhibitor acarbose (IC50 = 750.0 μM). In contrast, these compounds were inactive against α-amylase. Among the synthesized compounds, compound 7h was the most potent inhibitor of this library and was a competitive inhibitor into α-glucosidase with Ki value = 86.3 μM. Docking study of the most potent compounds was performed to evaluate the binding interactions of these compounds with the active site of enzyme and to determine of binding energies of ligand–enzyme complexes. The results of this in silico study are in complete agreement with the results obtained from in vitro α-glucosidase inhibition assay. Docking study of the most potent compound demonstrated that it interacted with important residues in the active site of α-glucosidase. In vitro cytotoxic activity of the most potent compounds and in silico druglikeness/ADME/toxicity study of these compounds were evaluated.

Design, synthesis, and α-glucosidase-inhibitory activity of phenoxy-biscoumarin–N-phenylacetamide hybrids

Thirteen new phenoxy-biscoumarin–N-phenylacetamide derivatives (7a–m) were designed based on a molecular hybridization approach as new α-glucosidase inhibitors. These compounds were synthesized with high yields and evaluated in vitro for their inhibitory activity against yeast α-glucosidase. The obtained results revealed that a significant proportion of the synthesized compounds showed considerable α-glucosidase-inhibitory activity in comparison to acarbose as a positive control. Representatively, 2-(4-(bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)phenoxy)-N-(4-bromophenyl)acetamide (7f), with IC50 = 41.73 ± 0.38 μM against α-glucosidase, was around 18 times more potent than acarbose (IC50 = 750.0 ± 10.0 μM). This compound was a competitive α-glucosidase inhibitor. Molecular modeling and dynamic simulation of these compounds confirmed the obtained results through in vitro experiments. Prediction of the druglikeness/ADME/toxicity of the compound 7f and comparison with the standard drug acarbose showed that the new compound 7f was probably better than the standard drug in terms of toxicity.

Production, characterization, and application of a novel chitosan-g-maleic anhydride and modified graphene oxide nanocomposite, supported methane sulfonic acid, for efficient synthesis of 1-(benzothiazolylamino) methyl-2-naphtols

An exceptionally productive and sustainable procedure is described in this paper to fabricate 1-(benzothiazolylamino) methyl-2-naphthols using a novel green nanocomposite of chitosan and diethylenetriamine-modified graphene oxide, supported methanesulfoni

Synthesis and cytotoxic evaluation of some 2-{4-[(2-oxo-1,2-dihydro-3h-indol-3-ylidene)methyl] phenoxy}-n-phenylacetamide

A series of 2-oxindole derivatives were synthesized and evaluated for cytotoxic activity against different human and murine cancer cell lines and cancer chemopreventive activity. Among the tested compounds VS-06, 08, 12 and 17 displayed cytotoxic activity in the range of 5.0 to 8.5 μM against human T-lymphocyte cells (CEM). Results showed that molecules with electron withdrawing substituent at 4 position of N-phenylacetamide group exhibited an increase in activity against the human tumor cell line CEM. The cancer chemopreventive effect of VS-01 (IC50 = 451 nM) displayed equipotent activity in comparison to standard oleanolic acid (IC50 = 449 nM).

Targeting quorum sensing by designing azoline derivatives to inhibit the N-hexanoyl homoserine lactone-receptor CviR: Synthesis as well as biological and theoretical evaluations

To counteract bacterial resistance, we investigated the interruption of quorum sensing mediated by non-classical bioisosteres of the N-hexanoyl homoserine lactone with an azoline core. For this purpose, a set of selected 2-substituted azolines was synthesized, establishing the basis for a new protocol to synthesize 2-amino imidazolines. The synthesized compounds were evaluated as inhibitors of violacein production in Chromobacterium violaceum. Theoretical studies on bioisostere-protein interactions were performed using CviR. The results show that some azolines decreased violacein production, suggesting an antiquorum sensing profile against Gram-negative bacteria. Docking and molecular dynamic simulations together with binding free energy calculations revealed the exact binding and inhibitory profiles. These theoretical results show relationship with the in vitro activity of the azoline series.

Synthesis and biological evaluation of novel 5-benzylidenethiazolidine-2,4- dione derivatives for the treatment of inflammatory diseases

Twenty-two compounds based on thiazolidine-2,4-dione moiety were synthesized and evaluated for the inhibitory potency on the production of nitric oxide (NO), inducible nitric oxide synthase (iNOS) activity, and the generation of prostaglandin E2 (PEG2). (Z)-N-(3-Chlorophenyl)-2-(4- ((2,4-dioxothiazolidin-5-ylidene) methyl) phenoxy) acetamide (3I), superior to the commercial anti-inflammatory drug indomethacin, significantly inhibited iNOS activity (IC50 = 8.66 μM), iNOS-mediated NO, and cyclooxygenase (COX)-2-derived PGE2 production (IC50 = 4.16 and 23.55 μM, respectively) on lipopolysaccharide (LPS)-induced RAW 264.7 cells. Docking study revealed that 3I was perfectly docking into the active site of murine iNOS and suppressed the expression of iNOS protein as evidenced by Western blot analysis. At the dose of 50 mg/kg, oral administration of 3I possessed protective properties in both carrageenan-induced paw edema and adjuvant-induced arthritis rat models.

Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease

Forty-four barbituric acid or thiobarbituric acid derivatives were synthesized and evaluated for their effects on adipogenesis of 3T3-L1 adipocytes by measuring the expression of adiponectin in vitro. Four compounds (3a, 3o, 3s, 4t) were found to increase the expression of adiponectin and lower the leptin level in 3T3-L1 adipocytes at respective concentration of 10 μM. Among them, 3s showed the most efficacious. Oral administration of 3s effectively reduced body weight, liver weight, and visceral fat and regulated serum levels of biochemical markers in the high-fat/diet-induced Wistar rats. Histopathological evaluation of liver sections by Oil Red O and H&E staining confirmed 3s as a potent, orally active molecule for reducing fat deposition against non-alcoholic fatty liver disease.

SYNTHESIS OF SOME HALOGEN DERIVATIVES OF SCHIFF BASES AND INVESTIGATION OF THEIR MESOMORPHOUS CHARACTERISTICS

4-(p-Halogenophenylcarbamoylmethoxy)benzylidene-p'-alkoxyanilines, which posses the characteristics of nematic and smectic liquid crystals, were synthesized by the reaction of halogen-substituted chloroacetanilides, p-hydroxybenzaldehyde, and p-alkoxyanilines.The introduction of a chlorine atom into the benzene ring leads to a reduction in the thermal stability of the smectic meso phase.