90892-09-4Relevant academic research and scientific papers
Biomimetic synthesis and anti-inflammatory evaluation of violacin A analogues
Wu, Wenxi,Mu, Yu,Liu, Bo,Wang, Zixuan,Guan, Peipei,Han, Li,Jiang, Mingguo,Huang, Xueshi
, (2021/04/23)
Violacin A, a chromanone derivative, isolated from a fermentation broth of Streptomyces violaceoruber, has excellent anti-inflammatory potential. Herein, a biogenetically modeled approach to synthesize violacin A and twenty-five analogues was described, which involved the preparation of aromatic polyketide precursor through Claisen condensation and its spontaneous cyclization. The inhibitory effect on nitric oxide (NO) production of all synthetic molecules was evaluated by lipopolysaccharide (LPS)-induced Raw264.7 cells. The results revealed that introduction of aliphatic amine moieties on C-7 obviously improved the anti-inflammation effect of violacin A, and also the aromatic ether instead of ketone group at side chain was favorable to increase the activity. Among them, analogue 7a and 16d were screened as the most effective anti-inflammatory candidates. Molecular mechanism research revealed that 7a and 16d acquired anti-inflammatory ability due to the inhibition of NF-κB signaling pathway.
Cobalt-Catalyzed α-Arylation of Substituted α-Bromo α-Fluoro β-Lactams with Diaryl Zinc Reagents: Generalization to Functionalized Bromo Derivatives
Br?se, Stefan,Chen, Hi-Yung,Cossy, Janine,Koch, Vanessa,Lei, Aiwen,Lorion, Mélanie M.,Nieger, Martin
supporting information, p. 13163 - 13169 (2020/09/23)
A cobalt-catalyzed cross-coupling of α-bromo α-fluoro β-lactams with diarylzinc or diallylzinc reagents is herein disclosed. The protocol proved to be general, chemoselective and operationally simple allowing the C4 functionalization of β-lactams. The substrate scope was expanded to α-bromo lactams and amides, α-bromo lactones and esters as well as N- and O-containing heterocycles.
Synthesis and in vivo anti- or pro-inflammatory activity of new bisphosphonates and vinylphosphonates
Ramírez-Marroquín, Oscar Abelardo,Jiménez-Arellanes, María Adelina,Cortés-Pacheco, Abimelek,Zambrano-Vásquez, Oscar R.,López-Torres, Adolfo
, p. 267 - 274 (2019/01/19)
Abstract: We herein report the synthesis and in vivo anti-inflammatory activity of a series of new bisphosphonate and vinylphosphonate derivatives of pyrrolidine and piperidine through a short route of synthesis. The C-alkylation of tetraethylmethylene diphosphonate with N-(bromoacetyl)pyrrolidine or N-(bromoacetyl)piperidine, respectively, yielded the corresponding α-substituted bisphosphonates in excellent yields (82–89%). Next, the Horner–Wadsworth–Emmons reaction of these bisphosphonates with aromatic aldehydes afforded final vinylphosphonates in moderate yields (26–36%). Synthesized bisphosphonates and vinylphosphonates were tested by two models of acute inflammation in male BalB/c mice, founding excellent edema inhibition by topical TPA (12-O-tetradecanoylphorbol-13-acetate) model (67.53–72.10% in comparison with indomethacin = 64.89%). However, remarkably pro-inflammatory effect by systematic carrageenan model (??9.78 to ??36.18) was observed, probably due to biotransformation. In conclusion, the new vinylphosphonates emerged as attractive topical anti-inflammatory compounds that “twist” its pharmacological activity to route of administration. Further research is needed to understand the dual effect.
First mechanosynthesis of piperlotines A, C, and derivatives through solvent-free Horner–Wadsworth–Emmons reaction
Ramírez-Marroquín, Oscar Abelardo,Manzano-Pérez, Flavio,López-Torres, Adolfo,Hernández-López, Alejandro,Cortés-Pacheco, Abimelek,Reyes-González, Miguel Angel
, p. 244 - 255 (2019/01/22)
Piperlotines are natural products characterized by an α,β-unsaturated amide moiety. These compounds found wide applications in Medicinal Chemistry like antibacterials, cytotoxic agents, anticoagulants, among others. To date, diverse methods of synthesis have been reported for piperlotines, but involving the use of catalysts, hazard reagents, anhydrous media or coupling reagents. Thus, in this work, we developed a greener method of synthesis of piperlotines A, C, and derivatives, through mechanochemical activation under solvent-free conditions. The reaction of a β-amidophosphonate, K2CO3, and an aromatic aldehyde afforded target compounds in moderate to good yields (46–77%), in an open atmosphere by grinding. It is worth to mention that this mechanochemical process was under thermodynamic control because just E isomer was isolated for every reaction. Moreover, synthesized piperlotines have been predicted by means of chemoinformatic analysis as potential therapeutic agents for the treatment of arthritis or cancer.
Imidazo ring PAR4 antagonist and medical applications thereof
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Paragraph 0740-0743, (2020/01/12)
The invention relates to an imidazo ring compound represented by formula (I) or formula (II), or a pharmaceutically acceptable salt or ester or solvate thereof. The compound disclosed by the inventioncan be used for preparing medicines for preventing or treating thromboembolic diseases.
Oseltamivir derivative as well as preparation method and application thereof
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Paragraph 0078; 0079; 0081; 0082, (2018/05/16)
The invention discloses an oseltamivir derivative, which is a brand-new oseltamivir derivative targeting a 430-cavity and modified by a carbon 1-position carboxyl group. An anti-influenza activity result of the oseltamivir derivative shows the first appli
AUTOTAXIN INHIBITOR COMPOUNDS
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Paragraph 00423, (2015/04/15)
Described herein are compounds that are autotaxin inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with autotaxin activity.
INHIBITING NEUROTRANSMITTER REUPTAKE
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Page/Page column 165, (2014/10/15)
This document relates to compounds as well as methods and materials involved in modulating neurotransmitter reuptake. For example, compounds, methods for synthesizing compounds, and methods for inhibiting neurotransmitter reuptake are provided.
α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions
Kaupang, Asmund,Bonge-Hansen, Tore
supporting information, p. 1407 - 1413 (2013/08/23)
In this work, we introduce a new class of halodiazocarbonyl compounds, α-halodiazoacetamides, which through a metal-free, ambient-temperature thermolysis perform intramolecular C-H insertions to produce α-halo-β-lactams. When carried out with α-bromodiazoacetamides bearing cyclic side chains, the thermolysis reaction affords bicyclic α-halo-β-lactams, in some cases in excellent yields, depending on the ring size and substitution pattern of the cyclic amide side chains.
Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position
Nechepurenko,Komarova,Vasil'ev,Salakhutdinov
, p. 1047 - 1053 (2013/04/23)
9-O-Acetamide analogs of berberine bromide were prepared in 20-87% yields via reaction of the isoquinoline alkaloid berberrubine with tertiary amides of bromoacetic acid. Aminolysis did not occur during reaction of methyl-2-(9-demethoxyberberine bromide-9-yl)hydroxyacetate with secondary amines. The corresponding acid or its ethyl ester was isolated.
