- Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents
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A series of novel 2-amino 3-cyano 4-aryl pyrano[2,3H]chrysin derivatives (3a-m) were efficiently synthesized by one-pot three-component reaction of aromatic aldehydes, malononitrile and chrysin and characterized by 1H NMR, 13C NMR and mass spectral data. All the newly synthesized compounds were evaluated for their in vitro antimicrobial activity (antibacterial and antifungal). Among the tested compounds, 3a, 3g, 3h, 3j and 3k showed potent antibacterial activity compared to ciprofloxacin and the compounds 3a, 3g, 3h, 3i and 3k showed excellent antifungal activity compared to itrazole. The compounds 3a, 3g, 3h and 3k exhibited potent antimicrobial activity against all the selected pathogenic bacteria and fungi and emerged as potential molecules for further development. In addition, molecular modeling studies also performed to delineate the putative binding mode of these compounds. All of these chrysin derivatives (3a-m) obeyed the Lipinski's "rule of five" and have drug-likeness. Docking scores with appreciable binding energy values also exactly correlated with the experimental antimicrobial activity. The chemscore estimated by GOLD software was found to have a good correlation with the experimental inhibitory activity. Graphical Abstract: Docking of compound 3g with protein[Figure not available: see fulltext.] A series of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives (3a-m) has been synthesized and evaluated for their antimicrobial activity along with molecular modeling studies[Figure not available: see fulltext.]
- Ramesh,Reddy, Ch. Sanjeeva,Suresh Babu,Reddy, P. Muralidhar,Srinivasa Rao,Parthasarathy
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- Extraction, Isolation and Characterization of Valuable Worked on Acacia Tortilis
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Acacia tortilis is one of the important species of genus Acacia belonging to family Leguminaceae. Though there is no more study performed on this plant but it plays important role in the countries where it found. These countries include North Africa, Arabian Peninsula and Asian countries. The various part of Acacia tortilis plant say leaves, pods, gum exudates and bark were used as antidiabetic, antidiarrhoeal, antiasthmatic and also had several other medicinal benefits. The present discussion deals with the isolation and characterization of the following compounds from the leaves of Acacia tortilis. Lupan-3-ol, 12,20-diene, Lupan-12, 20-dien 3-one, Friedelin, ?-amyrin, ?- sitosterol, Apigenin, Luteolin, Quercetin, 5,7-dihydroxy-4-p-methyl benzylisoflavone, Vitexin, 2',6'-dihydroxy chalcone-4'-O-glucoside.
- Muhaisen, Hasan M. H.
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p. 6731 - 6747
(2021/11/01)
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- In Vitro Osteogenic Differentiation and Antibacterial Potentials of Chalcone Derivatives
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Chalcone derivatives have been investigated as therapeutic agents for the anticancer, antioxidant, and anti-inflammatory fields. In this study, we have synthesized four different types of chalcone derivatives and demonstrated in vitro bioactivities. We divided these derivatives into two groups of chalcones on the basis of similar substituents on the aromatic rings, and we tested cell viability and proliferation potentials, which indicated that the methoxy substituent on the A ring could enhance cytotoxicity and antiproliferation potential depending on the chalcone concentration. We also investigated osteogenic differentiation of C2C12 cells by ALP staining, the early marker for osteogenesis, which demonstrated that the chalcones could not only induce activity of BMP-2 but also inhibit the activity of noggin, a BMP antagonist. In addition, chalcone bearing hydroxyl groups at the 2-, 4-, and 6-position on the A ring inhibited treptococcus mutans growth, a major causative agent of dental caries. Therefore, we concluded that the chalcone derivatives synthesized in this research can be good candidates for therapeutic agents promoting bone differentiation, with an expectation of inhibiting S. mutans, in dentistry.
- Choi, Daheui,Park, Jin Chan,Lee, Ha Na,Moon, Ji-Hoi,Ahn, Hyo-Won,Park, Kwangyong,Hong, Jinkee
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p. 3197 - 3204
(2018/07/25)
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- Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
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Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and showed various efficiency. Compounds D1–D30 showed no toxic effects on RAW 264.7 cells at the concentration 20 μM; among them, compounds D9, D13, and D19 exhibited best anti-inflammatory activity through decreasing IL-1β, IL-6, and TNF-α. Furthermore, their structure–activity relationships were discussed preliminarily.
- Hu, Chunling,Zhou, Zongbao,Xiang, Yuanhang,Song, Xiaoying,Wang, Hong,Tao, Kaiqi,Ye, Xiaochuan
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p. 194 - 205
(2018/04/19)
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- Bioactive Formylated Flavonoids from Eugenia rigida: Isolation, Synthesis, and X-ray Crystallography
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Two new flavonoids, rac-6-formyl-5,7-dihydroxyflavanone (1) and 2′,6′-dihydroxy-4′-methoxy-3′-methylchalcone (2), together with five known derivatives, rac-8-formyl-5,7-dihydroxyflavanone (3), 4′,6′-dihydroxy-2′-methoxy-3′-methyldihydrochalcone (4), rac-7-hydroxy-5-methoxy-6-methylflavanone (5), 3′-formyl-2′,4′,6′-trihydroxy-5′-methyldihydrochalcone (6), and 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone (7), were isolated from the leaves of Eugenia rigida. The individual (S)- and (R)-enantiomers of 1 and 3, together with the corresponding formylated flavones 8 (6-formyl-5,7-dihydroxyflavone) and 9 (8-formyl-5,7-dihydroxyflavone), as well as 2′,4′,6′-trihydroxychalcone (10), 3′-formyl-2′,4′,6′-trihydroxychalcone (11), and the corresponding 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone (7) and 2′,4′,6′-trihydroxydihydrochalcone (12), were synthesized. The structures of the isolated and synthetic compounds were established via NMR, HRESIMS, and electronic circular dichroism data. In addition, the structures of 3, 5, and 8 were confirmed by single-crystal X-ray diffraction crystallography. The isolated and synthetic flavonoids were evaluated for their antimicrobial and cytotoxic activities against a panel of microorganisms and solid tumor cell lines.
- Zaki, Mohamed A.,Nanayakkara, N. P. Dhammika,Hetta, Mona H.,Jacob, Melissa R.,Khan, Shabana I.,Mohammed, Rabab,Ibrahim, Mohamed A.,Samoylenko, Volodymyr,Coleman, Christina,Fronczek, Frank R.,Ferreira, Daneel,Muhammad, Ilias
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p. 2341 - 2349
(2016/10/04)
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- Potent CDC25B and PTP1B phosphatase inhibitors: 2′,4′,6′-trihydroxylchalcone derivatives
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In this study, we examined a series of 2′,4′,6′-trihydroxychalcone derivatives for their inhibitory activity as inhibitors of CDC25B and PTP1B. The pharmacological results showed that all of the tested compounds significantly inhibited CDC25B and PTP1B phosphatase in vitro. Among them, three compounds 2, 6, and 7 had the best inhibition activity, with inhibition rates against CDC25B were 99.56, 99.68, and 99.63 %, respectively, and with inhibition rates against PTP1B were 98.99, 99.37, and 98.08 %, respectively, which is similar to reference drugs Na3VO4 and Oleanolic acid, respectively. Cytotoxic activity assays showed compounds 2, 6, and 7 are potent against HeLa and HCT116. Moreover, compound 6 delayed the potent antitumor inhibitory activity in a colo205 xenograft model in vivo.
- Zhao, Shui-Lian,Peng, Zhou,Zhen, Xing-Hua,Jin, Hong-Guo,Han, Yan,Qu, You-Le,Guan, Li-Ping
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p. 2573 - 2579
(2015/02/19)
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- Design, synthesis and antidepressant activity evaluation 2′-hydroxy-4′,6′-diisoprenyloxychalcone derivatives
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In this study, 14 2′-hydroxy-4′,6′-diisoprenyloxychalcone compounds were synthesized and their antidepressant activities were evaluated using the forced swimming test. The pharmacological results showed that six compounds significantly reduced immobility times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among these, three compounds (4d, 4e, and 4g) exhibited better antidepressant activity, with reduced immobility time by 38.3, 34.0, and 27.4 %, respectively. For explanation of the putative mechanism of action, compounds 4e, 4g were tested in chemical induced models.
- Guan, Li-Ping,Zhao, Dong-Hai,Chang, Yue,Sun, Yu,Ding, Xiao-Li,Jiang, Jing-Fei
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p. 5218 - 5226
(2013/12/04)
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- Synthesis and studies on antidepressant activity of 2′,4′, 6′-trihydroxychalcone derivatives
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In this study, we synthesized a series of 2′,4′,6′- trihydroxychalcone derivatives and evaluated their antidepressant activities. The results of the nine compounds showed significantly reduced times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, 2-bromo-2′,4′,6′- trihydroxychalcone (3h) was found to be the most potent, and it was observed that compound 3h at dose of 10, 20, and 40 mg/kg significantly reduced the duration of immobility times in the FST and TST in mice 30 min after treatment. Springer Science+Business Media, LLC 2011.
- Sui, Xin,Quan, Ying-Chun,Chang, Yue,Zhang, Rui-Peng,Xu, Yin-Feng,Guan, Li-Ping
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p. 1290 - 1296
(2012/07/28)
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- Electron transfer-initiated Diels-Alder cycloadditions of 2′-hydroxychalcones
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An efficient approach to cyclohexenyl chalcones employing highly electron rich 2′-hydroxychalcone dienophiles via electron transfer-initiated Diels-Alder cycloaddition is described. Using the methodology, the total synthesis of nicolaiodesin C has been accomplished. Copyright
- Cong, Huan,Ledbetter, Dustin,Rowe, Gerard T.,Caradonna, John P.,Porco Jr., John A.
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supporting information; experimental part
p. 9214 - 9215
(2009/02/02)
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- INDUCTION OF PHENYLPROPANOID PATHWAY ENZYMES IN ELICITOR-TREATED CULTURES OF CEPHALOCEREUS SENILIS
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Treatment of old-man-cactus (Cephalocereus senilis) suspension cultures with chitin elicits synthesis of an aurone phytoalexin, cephalocerone.Elicitor-induced de novo synthesis of cephalocerone was demonstrated by incubating elicited cactus cultures with phenylalanine; this resulted in the labelling of five induced phenolic compounds including cephalocerone.Increased extractable activities of the phenylpropanoid pathway enzymes phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS) and chalcone isomerase (CHI) accompanied the synthesis of cephalocerone.CHS and PAL, which are both involved in the biosynthesis of cephaloce rone, showed maximum activity at 12 and 24 hr post-elicitation, respectively.CHS and CHI activities catalysing the synthesis and subsequent isomerization of 2',4',6'-trihydroxychalcone were present in the cell cultures, consistent with the formation of cephalocerone via a chalcone with no B-ring substituents. Key Word Index - Cephalocereus senilis; Cactaceae; aurone; phytoalexin; enzyme induction; suspension culture; HPLC.
- Pare, Paul W.,Mischke, Charles F.,Edwards, Robert,Dixon, Richard A.,Norman, Helen A.,Mabry, Tom J.
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p. 149 - 154
(2007/10/02)
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- Dye-sensitized Photo-oxygenation of Chalcones
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The dye-sensitized photo-oxygenation of several chalcones has been examined.Some of the chalcones give rise to degradation products while others lead to flavonol formation.A rational explanation for the observations has been proposed.The study may have a significance in the biogenesis of naturally occurring plant polyphenolics.
- Chawla, H. Mohindra,Chakrabarty, Kakoli
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p. 1511 - 1513
(2007/10/02)
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