75849-15-9Relevant academic research and scientific papers
Biological evaluation and synthesis of new pyrimidine-2(1H)-ol/-thiol derivatives derived from chalcones using the solid phase microwave method
Fandakli, Seda,Kahriman, Nuran,Yücel, Tayyibe Beyza,Alpay Karaoglu, ?engül,Yayli, Nurettin
, p. 520 - 535 (2018/06/08)
Twenty-five new hydroxy- and methoxy-substituted 4,6-diarylpyrimidin-2(1H)-ol (20–34) and 4,6-diarylpyri-midine-2(1H)-thiol derivatives (35–44) were synthesized from the reaction of the corresponding 1,3-diaryl-2-propene-1-one compounds (1–19) with urea or thiourea using the solid-phase microwave method. All the new synthetic compounds (20–44) were evaluated with regard to their α-glucosidase activity. However, only compounds 22–25, 27, 31, 34, 35, 37, and 40 exhibited a greater inhibitory effect than standard acarbose. The IC50 values of the active compounds ranged between 2.36 and 13.34 μM. The 25 new compounds were also screened for their in vitro pancreatic lipase activity and compounds 20–27 and 35–39 were found to be active. Of these compounds 26, 27, and 39 exhibited the best antilipase activities at concentrations of 0.40 ± 0.06, 0.26 ± 0.07, and 0.29 ± 0.026 μM. All the new compounds (20–44) were evaluated for their in vitro antimicrobial activity for nine test microorganisms. Compounds 20–24 and 35–39 were determined to possess a significant broad spectrum against the gram-positive bacteria Escherichia faecalis, Staphylococcus aureus, and Bacillus cereus among the tested bacterial agents. Compounds 20–24 and 35–39 exhibit the best activity against Mycobacterium smegmatis, with minimum inhibitory concentrations of 62.5–500 μg/mL, indicating their potential use as antituberculous agents.
Triaryl Pyrazole Toll-Like Receptor Signaling Inhibitors: Structure–Activity Relationships Governing Pan- and Selective Signaling Inhibitors
Pollock, Julie A.,Sharma, Naina,Ippagunta, Sirish K.,Redecke, Vanessa,H?cker, Hans,Katzenellenbogen, John A.
, p. 2208 - 2216 (2018/09/25)
The immune system uses members of the toll-like receptor (TLR) family to recognize a variety of pathogen- and host-derived molecules in order to initiate immune responses. Although TLR-mediated, pro-inflammatory immune responses are essential for host defense, prolonged and exaggerated activation can result in inflammation pathology that manifests in a variety of diseases. Therefore, small-molecule inhibitors of the TLR signaling pathway might have promise as anti-inflammatory drugs. We previously identified a class of triaryl pyrazole compounds that inhibit TLR signaling by modulation of the protein–protein interactions essential to the pathway. We have now systematically examined the structural features essential for inhibition of this pathway, revealing characteristics of compounds that inhibited all TLRs tested (pan-TLR signaling inhibitors) as well as compounds that selectively inhibited certain TLRs. These findings reveal interesting classes of compounds that could be optimized for particular inflammatory diseases governed by different TLRs.
Design, synthesis, and antiviral activities of 1,5-benzothiazepine derivatives containing pyridine moiety
Li, Tianxian,Zhang, Jian,Pan, Jianke,Wu, Zengxue,Hu, Deyu,Song, Baoan
, p. 657 - 662 (2016/10/14)
In our previous work, a series of novel benzothiazepine derivatives containing pyridine moiety were successfully synthesized through chalcone 1,3-dipolar cycloaddition and determined their antiviral activity against tobacco mosaic virus (TMV). Bioassay results indicated that most of these target compounds exhibited improved curative, protection, and inactivation activity in?vivo than the commercial agent ningnanmycin. Particularly, compound 3m exhibited marked curative activity against TMV, with an EC50value of 352.2?μM, which was even better than that of ningnanmycin. The compound was identified as the most promising candidate for inhibiting plant virus and an excellent compound with antiviral activities against TMV. Structure–activity relationship experiment indicated that the 1,5-benzothiazepine moiety is crucial for potent anti-TMV activity.
Synthesis, in Vitro, and in Vivo Biological Evaluation and Molecular Docking Analysis of Novel 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one Derivatives as Anti-breast Cancer Agents
Dube, Pritam N.,Waghmare, Madhuri N.,Mokale, Santosh N.
, p. 608 - 617 (2016/03/19)
The analogs of coumarin-chalcones have been reported to exhibit antineoplastic, anti-allergic, antihepatoprotective, and estrogenic activity. Herein, we have reported 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one derivatives as a new class of compounds that exhibit selectivity for ER-α binding along with antiproliferative and cytotoxic activity on human breast cancer cell line. The active compounds which show prominent activity against estrogen receptor-alpha-positive (ER+) human breast cancer cell lines MCF-7 and Zr-75-1 are subjected to in vivo screening. The Glide XP docking was performed for designed scaffold to optimize its structural requirement for ER-α inhibition.
Synthesis and evaluation of some new substituted benzothiazepine and benzoxazepine derivatives as anticonvulsant agents
Garg, Neha,Chandra, Trilok,Archana,Jain, Amit B.,Kumar, Ashok
experimental part, p. 1529 - 1535 (2010/06/14)
A new series of 4-(4′-Hydroxyphenyl)-2-(3-substitutedphenyl)-3-(4-substitutedphenylamino methylene)-2,3-dihydro-1,5-benzothiazepines (3a-3j) and 4-(4′-Hydroxyphenyl)-2-(3-substituted phenyl)-3-(4-substitutedphenylaminomethylene)-2,3-dihydro-1,5-benzoxazep
Glucosylation of 4′-hydroxychalcones using glucosyl donor
Ingle,Kharche,Upadhyay
, p. 801 - 805 (2007/10/03)
Condensation of α-acetobromoglucose with 4′- hydroxyarylmethyleneacetophenone derivatives (chalcones) in anhydrous acetone furnishes 2,3,4,6-tetra-O-acetyl-4′-O-β-D-glucopyranosyloxychalcones. Deblocking of the latter with CH3ONa in dry methanol affords 4′-O-β-D-glucopyranosyloxychalcones. The structure of these products have been assigned on the basis of their sophisticated instrumental analysis like IR, 1H NMR, 13C NMR, FAB-MS, specific rotation, elemental analysis and chemical properties.
Intramolecular Alkylation of Phenols. Part 5. A Regiospecific Anionic Ring Closure of Phenols via Quinone Methides
Murphy, William S.,Wattanasin, Sompong
, p. 1567 - 1577 (2007/10/02)
The bis-magnesium salts of the triols (6a) and (6h) cyclise when heated in benzene with high ortho-regiospecificity to the corresponding bis-phenols (7) and (8).The triols (6k) and (6o) under the same conditions cyclise with high para-regiospecificity to the corresponding bis-phenols (7) and (8).Both (6a) and (6h) cyclise via o-quinone methides, and (6k) and (6o) via p-quinone methides.Results from the use of, inter alia, 18-crown-6, indicate that the high ortho-regiospecificity of the cyclisation of (6a) and (6h) is due to intramolecular Mg(II) bridging of the intermediate o-quinone methides.The high para-regiospecificity of cyclisation of (6k) and (6o) is due to steric hindrance towards o-cyclisation of the intermediate p-quinone methides presented by the Mg(II) cation.The unexpected facility with which (6a) and (6k) undergo ring closure is discussed.
