41052-88-4Relevant articles and documents
Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors
Alavi, Seyed Jamal,Seyedi, Seyed Mohammad,Saberi, Satar,Safdari, Hadi,Eshghi, Hossein,Sadeghian, Hamid
, p. 259 - 266 (2020/10/12)
In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).
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 Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway
Yang, Yan-Long,Zhou, Hui,Du, Gang,Feng, Ke-Na,Feng, Tao,Fu, Xiao-Li,Liu, Ji-Kai,Zeng, Ying
, p. 5463 - 5466 (2016/05/09)
The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted γ-butyrolactones from a shikimate origin.
Synthesis and optimization of novel allylated mono-carbonyl analogs of curcumin (MACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI) in rats
Zhu, Heping,Xu, Tingting,Qiu, Chenyu,Wu, Beibei,Zhang, Yali,Chen, Lingfeng,Xia, Qinqin,Li, Chenglong,Zhou, Bin,Liu, Zhiguo,Liang, Guang
, p. 181 - 193 (2016/06/09)
A series of novel symmetric and asymmetric allylated mono-carbonyl analogs of curcumin (MACs) were synthesized using an appropriate synthetic route and evaluated experimentally thru the LPS-induced expression of TNF-α and IL-6. Most of the obtained compounds exhibited improved water solubility as a hydrochloride salt compared to lead molecule 8f. The most active compound 7a was effective in reducing the Wet/Dry ratio in the lungs and protein concentration in bronchoalveolar lavage fluid. Meanwhile, 7a also inhibited mRNA expression of several inflammatory cytokines, including TNF-α, IL-6, IL-1β, and VCAM-1, in Beas-2B cells after Lipopolysaccharide (LPS) challenge. These results suggest that 7a could be therapeutically beneficial for use as an anti-inflammatory agent in the clinical treatment of acute lung injury (ALI).
INHIBITORS OF THE NOTCH TRANSCRIPTIONAL ACTIVATION COMPLEX AND METHODS FOR USE OF THE SAME
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, (2016/10/11)
Disclosed herein are inhibitors of the Notch transcriptional activation complex, and methods for their use in treating or preventing diseases, such as cancer. The inhibitors described herein can include compounds of Formula (I) and pharmaceutically acceptable salts thereof: Formula (I), wherein the substituents are as described.
Synthesis and biological evaluation of allylated mono-carbonyl analogues of curcumin (MACs) as anti-cancer agents for cholangiocarcinoma
Qiu, Chenyu,Hu, Yan,Wu, Ke,Yang, Ke,Wang, Nan,Ma, Yue,Zhu, Heping,Zhang, Yi,Zhou, Yunfang,Chen, Chao,Li, Shanshan,Fu, Lili,Zhang, Xiuhua,Liu, Zhiguo
, p. 5971 - 5976 (2016/12/09)
A series of new allylated mono-carbonyl curcumin analogues (MACs) were designed and synthesized. In vitro cytotoxic activities of allylated MACs 6a–h together with previously reported analogues 4a–i and 7a–e, were tested against human cholangiocarcinoma cell lines including HUCCA, QBC-939 and RBE. Of all the compounds tested, 6c exhibited potent in vitro antiproliferative activity against the three tested cancer cell lines with IC50values of 8.7, 9.3 and 8.9 μM, respectively. Cell cycle analysis showed that 6c inhibited cell proliferation due to G2/M arrest. Furthermore, mechanistic studies revealed that 6c dose-dependently increased the level of Bax and inhibited the expression of Bcl-2, to induce cancer cell apoptosis. Taken together, this work provides a novel series of anti-cancer candidates for the treatment of cholangiocarcinoma.
Symmetrical mono-carbonyl curcumin analog 6b, preparation method and applications thereof
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, (2017/01/17)
The invention relates to a micromolecular compound, which contains an allyl substituent and takes 1,4-diene-3-one as the nucleus, a preparation method and applications thereof. The provided symmetrical mono-carbonyl curcumin analog 6b has a good stability. In the cell level, the compound 6b has a very good antitumor activity, especially for human bile duct cancer, has a good development prospect, and can be used as an anticancer micromolecular lead compound in clinic.
Mono-carbonyl curcumin analogue containing piperidone structure and application
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, (2017/02/09)
The invention discloses a mono-carbonyl curcumin analogue containing a piperidone structure and application. The structure of the mono-carbonyl curcumin analogue is shown in the formula (I) or the formula (II); in the formula (I), R1 can be alkyl groups, naphthenic bases, benzyl groups, aroyl groups, substituent aroyl groups and sulfonyl groups optionally substituted by different substituent groups; in the formula (II), R2 can be piperazinyl, morpholinyl, pyrrolidyl and N, N-di-substituted alkyl optionally substituted by different substituent groups. A large amount of experimental study is performed on the technical field of mono-carbonyl curcumin analogues with substituent piperidone as a parent nucleus structure, a large amount of design, synthesis and pharmacological activity screening are performed on the mono-carbonyl curcumin analogues with substituent piperidone as the parent nucleus structure, one kind of single-carbonyl curcumin analogues with substituent piperidone as the parent nucleus structure are obtained, and the mono-carbonyl curcumin analogue containing the piperidone structure has the efficient and broad-spectrum anti-inflammatory application. Please see the formulae in the description.
Application of substituted mono carbonyl curcumin compound containing allyl in preparing antitumor drug
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, (2017/05/02)
The invention discloses application of a substituted mono carbonyl curcumin compound containing allyl in preparing antitumor drug. The mono carbonyl curcumin compound has a structure shown in a formula (I) or a pharmaceutically acceptable salt thereof, wherein A represents C, S, or O -NR1, R1 is independently selected from one or more of H, C1-C5 alkyl, phenyl benzene and benzyl group, n is 0 or 1, R is independently selected from one or more of H, hydroxyl, C1-C4, alkoxyl, pyrrolidine, morpholinyl and methyl N-piperazine. Test results show that the mono carbonyl curcumin compound has good stability and antitumor activity, and can be used as a potential antitumor drug.
A kind of allyl-containing single carbonyl curcumin analogs in the preparation of anti-inflammation drug application
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Paragraph 0046; 0050, (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.
