10.1016/j.bmc.2008.06.002
The research focuses on the synthesis and biological evaluation of new disubstituted analogues of 6-methoxy-3-(30,40,50-trimethoxybenzoyl)-1H-indole (BPR0L075), which are potential antivascular agents. The study aims to design and synthesize several new disubstituted analogues of BPR0L075 and assess their biological activities as inhibitors of tubulin polymerization, cytotoxic agents against B16 melanoma cells, and their ability to induce morphological changes in endothelial cells (EA.hy 926), indicative of potential antivascular activity. Key compounds synthesized include 7-hydroxy-6-methoxy-3-(3,40,5-trimethoxybenzoyl)-1H-indole (13) and its 7-O-mesylate derivative 28. The experiments involved various chemical reactions using reagents such as phenylsulfonyl chloride, bromoacetaldehyde diacetal, and 3,4,5-trimethoxybenzoylchloride, among others, and analytical techniques employed included NMR, IR, MS, and HRMS to characterize the synthesized compounds. The biological activities were evaluated through tubulin-binding assays, cytotoxicity testing in murine B16 melanoma cells, and assessments of endothelial cell morphology changes.
10.1007/s00044-019-02440-3
This research endeavored to synthesize and evaluate new phenylsulfamoyl carboxylic acids for their antimicrobial, antioxidant, and molecular docking properties. The study aimed to develop compounds with potent pharmacological activities and to assess their efficacy against various microorganisms and oxidative stress conditions. The synthesis involved the reaction of amino acids with benzenesulfonyl chloride in an aqueous base medium, yielding compounds 4a–4g. These compounds were then characterized using various analytical techniques and tested for their biological activities. The results indicated that compounds 4c, 4d, 4e, and 4g exhibited superior in vitro antibacterial and antifungal activities compared to the standard drug Ofloxacin, while compound 4e showed the most excellent antioxidant activity. Molecular docking studies revealed that these compounds had significant interactions with various disease-related targets, suggesting their potential as effective antibacterial, antifungal, antioxidant, antitrypanosome, and antimalaria agents. The research concluded that the synthesized phenylsulfamoyl carboxylic acids hold promise as potent agents in medicinal chemistry.
10.1021/jo00064a043
The study focuses on the synthesis and conformational analysis of a quinoline derivative (1), which is an orally active inhibitor of 5-lipoxygenase and a leukotriene antagonist. The key chemicals involved include 2-(chloromethyl)quinoline (4) and the substituted phenol 12, which are coupled in the final step to form the target compound. The phenol derivative 12 is synthesized from m-hydroxyacetophenone (8) through an aldol condensation with n-butyraldehyde, yielding an intermediate that is subsequently reduced to 12. The synthesis of 2-(chloromethyl)quinoline (4) involves converting quinaldine (2) to its N-oxide monohydrate (3) and then reacting it with benzenesulfonyl chloride. The final coupling of 4 and 12 is performed in DMF with anhydrous potassium carbonate as a base, yielding the desired compound 1 in high purity. The study also includes an X-ray crystallographic analysis and molecular mechanics computations to elucidate the conformation of the synthesized compound, revealing a structure where the quinoline and benzenoid rings are nearly perpendicular, providing insights into its potential therapeutic applications.
10.1080/00397919208021343
The research aimed to develop a strategy for synthesizing optically active ring-A methoxylated indole alkaloids, specifically targeting the preparation of 1-benzenesulfonyl-6-methoxy-D(+)-tryptophan ethyl ester (16). This amino ester is crucial for the synthesis of Alstonia bisindole alkaloids, such as macralstonine, which exhibit potent hypotensive properties. The researchers employed the Moody azide/Schollkopf chiral auxiliary protocol to achieve the stereospecific synthesis of the target compound. Key chemicals used in the research included methyl azidoacetate, 4-methoxybenzaldehyde, benzenesulfonyl chloride, sodium borohydride, and various reagents for specific reactions like formylation and decarboxylation. The study successfully synthesized the desired compound in high yield, demonstrating the feasibility of the chosen synthetic route. The findings open avenues for the synthesis of other biologically active indole alkaloids, highlighting the potential for further exploration in the field of natural product synthesis.
10.1081/SCC-120003160
The research focuses on the synthesis of a new series of 2-(5-aryl-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles, compounds that possess both 5-aryl-2-furoyl and 1,3,4-thiadiazole moieties. These compounds are of interest due to their potential biological activities, such as antimicrobial, analgesic, and anti-inflammatory properties. The synthesis was achieved through the reaction of 5-aryl-2-furoic acids with phenylsulfonyl chloride and 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles under phase transfer catalysis, utilizing polyethylene glycol-400 (PEG-400) as a catalyst in acetonitrile. The intermediates, 5-aryl-2-furoyl phenylsulfonates, were then treated with 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles to afford the desired products in excellent yield. The synthesized compounds were characterized using IR spectroscopy, 1H NMR spectroscopy, and elemental analysis, with the IR spectra showing a strong carbonyl absorption and the 1H NMR spectra displaying peaks for NH and CH2 groups. The elemental composition was also confirmed through these analyses, aligning with the calculated values for carbon, hydrogen, and nitrogen.
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