67483-48-1Relevant academic research and scientific papers
Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F
Kwesiga, George,Kelling, Alexandra,Kersting, Sebastian,Sperlich, Eric,Von Nickisch-Rosenegk, Markus,Schmidt, Bernd
, p. 3445 - 3453 (2020/11/30)
The prenylated isoflavones 5-deoxyprenylbiochanin A (7-hydroxy-4′-methoxy-3′-prenylisoflavone) and erysubin F (7,4′-dihydroxy-8,3′-diprenylisoflavone) were synthesized for the first time, starting from mono- or di-O-allylated chalcones, and the structure of 5-deoxy-3′-prenylbiochanin A was corroborated by single-crystal X-ray diffraction analysis. Flavanones are key intermediates in the synthesis. Their reaction with hypervalent iodine reagents affords isoflavones via a 2,3-oxidative rearrangement and the corresponding flavone isomers via 2,3-dehydrogenation. This enabled a synthesis of 7,4′-dihydroxy-8,3′-diprenylflavone, a non-natural regioisomer of erysubin F. Erysubin F (8), 7,4′-dihydroxy-8,3′-diprenylflavone (27), and 5-deoxy-3′-prenylbiochanin A (7) were tested against three bacterial strains and one fungal pathogen. All three compounds are inactive against Salmonella enterica subsp. enterica (NCTC 13349), Escherichia coli (ATCC 25922), and Candida albicans (ATCC 90028), with MIC values greater than 80.0 μM. The diprenylated natural product erysubin F (8) and its flavone isomer 7,4′-dihydroxy-8,3′-diprenylflavone (27) show in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA, ATCC 43300) at MIC values of 15.4 and 20.5 μM, respectively. In contrast, the monoprenylated 5-deoxy-3′-prenylbiochanin A (7) is inactive against this MRSA strain.
A kind of allyl-containing single carbonyl curcumin analogs in the preparation of anti-inflammation drug application
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Paragraph 0046; 0052, (2016/11/17)
The invention provides allyl-containing monocarbonyl curcumin analogs with antiinflammatory actions. In addition, the invention also provides a pharmaceutical composition of the compounds, antiinflammatory application and the like.
Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents
Liu, Zhiguo,Tang, Longguang,Zou, Peng,Zhang, Yali,Wang, Zhe,Fang, Qilu,Jiang, Lili,Chen, Gaozhi,Xu, Zheng,Zhang, Huajie,Liang, Guang
, p. 671 - 682 (2014/03/21)
Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-α and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents.
1-(PIPERIDIN-4-YL)-1H-INDOLE DERIVATIVE
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Page/Page column 64, (2010/11/28)
The present invention provides a compound represented by the formula (1) or a pharmacologically acceptable salt thereof, or a hydrate thereof (provided that a compound in which all of R4a, R4b, and R4c are hydrogen atoms is excluded.): [wherein R1 represents a hydrogen atom, R2 represents a hydrogen atom, R3 represents the formula: wherein R4a, R4b, and R4c are the same as or different from each other and each represents a hydrogen atom, a C1-6 alkyl group or a C1-6 alkoxy group, etc.]
New stable backbone linker resins for solid-phase peptide synthesis.
Gu, Wenxin,Silverman, Richard B
, p. 415 - 418 (2007/10/03)
[reaction: see text] Two new 4-methoxybenzaldehyde backbone linker resins were developed for the solid-phase synthesis of peptides. The linkers are very stable during the cleavage of common protecting groups for amines (Fmoc, Boc) and carboxylic acids (Me, All, tBu) in peptide synthesis. Cleavage from the resin with refluxing TFA is sufficiently mild for peptides containing polar and nonpolar amino acids.
Cosmetic use of benzalmalonate diorganopolysiloxanes and novel cosmetic compositions containing such compounds for the protection of skin and hair
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, (2008/06/13)
The cosmetic use is described, in particular for use as a UV filter, of benzalmalonate diorganopolysiloxanes having either formula: STR1 where R is C1 -C10 alkyl, phenyl or 3,3,3-trifluoropropyl, B is R or A, r=0-200, s=0-50, or form
New liposoluble unsaturated benzalmalonate derivatives and their use as absorbers for ultraviolet radiation in cosmetics
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, (2008/06/13)
The invention relates to an unsaturated benzalmalonate derivative of formula: STR1 in which: R1 and R2 denote a hydrogen atom, a hydroxyl, a trimethylsiloxy, a C1 -C6 straight or branched chain alkyl, C1/s
Meta-bridged styryloxy resins
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, (2008/06/13)
Polyfunctional cationically polymerizable styryloxy compounds of the formula STR1 where R1 is H or methyl; R2 is hydrocarbyl, hydrocarbyl interrupted by ether oxygen atoms, or halo substituted hydrocarbyl; R3 is H, lower alkyl, or alkoxy; G is any multivalent organic or inorganic radical free of amino or aliphatic thiol groups; and n is an integer of two or more.
