cas 973-67-1, 5,6,7-TRIMETHOXYFLAVONE | Articles data

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Discovery and synthesis of rocaglaol derivatives inducing apoptosis in HCT116 cells via suppression of MAPK signaling pathway
Six rocaglaol derivatives were isolated from Dysoxylum gotadhora, and those compounds showed good cytotoxic activity with IC50 values ranging from 10 to 350 ng/mL against five different cancer cells. Obviously, further total synthesis of rocaglaol derivatives for medical chemistry study is of great significance. Then, twenty six rocaglaol derivatives including 25 new compounds were designed, synthesized, and evaluated for their cytotoxic activities against three human cancer cell lines: human colon cancer cells (HCT116), colorectal cancer stem cells (P6C), and human red leukocyte leukemia cells (HEL), using MTT assay. Most of derivatives showed good cytotoxic activities, with the lowest IC50 being 3.2 nM for HEL cells, which was 169 times stronger than that of the positive control (doxorubicin). Further mechanism study indicated that 11k could significantly suppress MAPK pathway in HCT116 cells, which may responsible for induction of apoptosis and cell cycle arrest.
Yang, Hao-Jie,Li, Ya-Nan,Yan, Chen,Yang, Jue,Zeng, Yan-Rong,Yi, Ping,Li, Yan-Mei,Hao, Xiao-Jiang,Yuan, Chun-Mao
(2021/03/16)

Baicalein or derivative thereof, preparation method and application of baicalein or derivative of baicalein
The invention discloses baicalein or a derivative thereof. The structure is shown in the specification, wherein R1 is hydrogen, alkyl, substituted or unsubstituted aryl; R2 is hydrogen, halogen, alkyl, alkoxy, substituted or unsubstituted amino, and subst
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Paragraph 0105; 0131-0132; 0210-0211

(2020/04/17)

Baicalein derivative as well as preparation method and application thereof (by machine translation)
The invention discloses a baicalein derivative, structure as shown in the specification : In-flight, R1 A hydrogen, alkyl, is substituted or unsubstituted aryl ;R. 2 The hydrogen, halogen, alkyl, alkoxy, may be substituted or unsubst
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Paragraph 0135; 0136; 0214; 0215

(2020/05/05)

Crystal structures of the flavonoid Oroxylin A and the regioisomers Negletein and Wogonin
The flavonoid Oroxylin A (6-methoxychrysin or 5,7-dihydroxy-6-methoxy-2- phenyl-4H-chromen-4-one, C16H12O5) and its regioisomers are of increasing interest for a variety of bioactive functions and their pharmaceutical formulation is of importance. Previous difficulties in the separation and misidentification of Oroxylin A from its regioisomers Wogonin (8-methoxychrysin or 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one) and Negletein (5,6- dihydroxy-7-methoxyflavone or 5,6-dihydroxy-7-methoxy-2-phenyl-4H-chromen- 4-one) render its full structural and powder X-ray characterization highly desirable. The low-temperature (100 K) crystal structures of Oroxylin A, Negletein and Wogonin sesquihydrate are reported for the first time. Wogonin crystallizes in two related but distinct hydrated forms. These have very similar powder diffractograms, indicating that such issues need to be addressed for its pharmaceutical formulation.
Grano, Ruel Valerio Robles De,Nisar, Madiha,Sung, Herman H.-Y.,Vashchenko, Elena V.,Vashchenko, Valerii V.,Williams, Ian D.
p. 490 - 499
(2020/05/18)

Diversity-oriented synthesis of pyrazoles derivatives from flavones and isoflavones leads to the discovery of promising reversal agents of fluconazole resistance in Candida albicans
Diversity-oriented synthesis of derivatives of natural products is an important approach for the discovery of novel drugs. In this paper, a series of novel 3,4-diaryl-1H-pyrazoles and 3,5-diaryl-1H-pyrazoles derivatives were synthesized through the one-po
Cui, Chang-Yi,Liu, Jun,Zheng, Hong-Bo,Jin, Xue-Yang,Zhao, Xiao-Yu,Chang, Wen-Qiang,Sun, Bin,Lou, Hong-Xiang
supporting information
p. 1545 - 1549
(2018/04/02)

Activities of Wogonin Analogs and Other Flavones against Flavobacterium columnare
In our on-going pursuit to discover natural products and natural product-based compounds to control the bacterial species Flavobacterium columnare, which causes columnaris disease in channel catfish (Ictalurus punctatus), we synthesized flavone and chalcone analogs, and evaluated these compounds, along with flavonoids from natural sources, for their antibacterial activities against two isolates of F. columnare (ALM-00-173 and BioMed) using a rapid bioassay. The flavonoids chrysin (1a), 5,7-dihydroxy-4′-methoxyflavone (11), isorhamnetin (26), luteolin (27), and biochanin A (29), and chalcone derivative 8b showed strong antibacterial activities against F. columnare ALM-00-173 based on minimum inhibition concentration (MIC) results. Flavonoids 1a, 8, 11, 13 (5,4′-dihydroxy-7-methoxyflavone), 26, and 29 exhibited strong antibacterial activities against F. columnare BioMed based upon MIC results. The 24-h 50% inhibition concentration (IC50) results revealed that 27 and 29 were the most active compounds against F. columnare ALM-00-173 (IC50 of 7.5 and 8.5 mg/l, resp.), while 26 and 29 were the most toxic compound against F. columnare BioMed (IC50 of 9.2 and 3.5 mg/l, resp.). These IC50 results were lower than those obtained for wogonin against F. columnare ALM-00-173 and F. columnare BioMed (28.4 and 5.4 mg/l, resp.). However, based on MIC results, none of the compounds evaluated in this study were as active as wogonin (MIC 0.3 mg/l for each F. columnare isolate). Further modification of the wogonin structure to enhance antibacterial is of interest.
Tan, Cheng-Xia,Schrader, Kevin K.,Khan, Ikhlas A.,Rimando, Agnes M.
p. 259 - 272
(2015/10/19)

COMPOSITION AND METHOD FOR TREATING OR PREVENTING INFLUENZA VIRUS INFECTION
The present invention provides a pharmaceutical composition and method for treating or preventing influenza virus infection in a subject comprising administering the subject with a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of compounds provided in this invention. In addition, the prevent invention provides new compounds for treating or preventing influenza virus infection.
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(2015/12/23)

Synthesis and evaluation of selenoflavones that have potential neuroprotective effects
We synthesized selenoflavones and evaluated their physicochemical properties and antioxidant effects. When oxygen was substituted with selenium, the compounds exhibited improved polarity and lipophilicity, implying that this change could lead to better BBB penetration. Selenoflavones revealed more potent antioxidant activity in our in-vitro assay. This suggests that selenoflavones would be more druggable than flavones and have a better potential as a neuroprotective agent.
Choi, Yong-Sung,Kim, Yoon-Jung,Lee, Ju Yeun,Lee, Jinu,Jeong, Jin-Hyun
p. 2794 - 2805
(2015/03/04)

Synthesis and anti-influenza activities of novel baicalein analogs
A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC50) at around 4.0-4.5 μM, and a selective index (SI=50% cytotoxic concentration (CC50)/EC 50)>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.
Chung, Shu-Ting,Chien, Pei-Yu,Huang, Wen-Hsin,Yao, Chen-Wen,Lee, An-Rong
p. 415 - 421
(2014/05/20)

4′-Bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages
The regulations of the NO and PGE2 productions are research topics of interest in the field of anti-inflammatory drug development. In the present study, 5,6,7-trimethoxy- and 5,6,7-trihydroxyflavones 3a-3g were synthesized from cinnamic acid derivatives. In particular, 4′-bromo-5,6,7- trimethoxyflavone (3b) most potently inhibited the productions of NO and PGE2 in LPS-treated RAW 264.7 cells (IC50 = 14.22 ± 1.25 and 10.98 ± 6.25 μM, respectively), and these inhibitory effects were more potent than those of oroxylin A or baicalein. Consistent with these findings, 3b concentration-dependently reduced the LPS-induced expressions of iNOS and COX-2 at the protein and mRNA levels. In addition, the release of TNF-α, IL-6, and IL-1β and the mRNA expressions of these cytokines were reduced by 3b in a concentration-dependent manner. Furthermore, 3b attenuated the LPS-induced transcriptional activities of NF-κB and this was accompanied by parallel reductions in the degradation and phosphorylation of IκB-α, and consequently by a decrease in the nuclear translocation of the p65 subunit of NF-κB. Taken together, these results suggest that suppressions of the expressions of iNOS, COX-2, TNF-α, IL-6, and IL-1β via NF-κB inactivation are responsible for the anti-inflammatory effects of 3b.
Kim, Dong Han,Yun, Chang Hyeon,Kim, Min Hwan,Naveen Kumar, Ch.,Yun, Bo Hee,Shin, Ji-Sun,An, Hyo Jin,Lee, Young Hun,Yun, Yong Don,Rim, Hong-Kun,Yoo, Min-Sang,Lee, Kyung-Tae,Lee, Yong Sup
p. 700 - 705
(2012/03/26)

Oroxylin A analogs exhibited strong inhibitory activities against iNOS-mediated nitric oxide (NO) production
A number of oroxylin A analogs were prepared and evaluated for their inhibitory activities against iNOS-mediated nitric oxide (NO) production from LPS-stimulated BV2 cells. The analogs were synthesized from purchased 2′-hydroxy-4,5,6-trimethoxyacetophenone and aldehydes in 3 steps. Among the tested compounds, several analogs (3b, 3c, 3d, 3f) exhibited strong inhibitory activities. Especially, the analog with 4-nitrophenyl group (3b) showed stronger inhibitory activity (IC50 = 4.73 μM) than that of wogonin (IC50 = 7.80 μM).
Pham, Tuan-Ahn. N.,Che, Haiyan,Phan, Phuong-Thuy T.,Lee, Jae-Won,Kim, Sung-Soo,Park, Haeil
p. 2534 - 2535
(2012/05/05)

Synthesis of ring A-modified baicalein derivatives
Baicalein, an important active constituent of the traditional Chinese herb Scutellaria baicalensis, exhibited antitumor activity and inhibitory activity against P-gp 170. The syntheses of 25 baicalein derivatives, 2-26 (Table), are described here (Scheme
Wang, Jun-Fei,Ding, Ning,Zhang, Wei,Wang, Peng,Li, Ying-Xia
experimental part
p. 2221 - 2230
(2012/01/14)

Divergent approach to flavones and aurones via dihaloacrylic acids. unexpected dependence on the halogen atom
The reaction of phenols with 7a led to the synthesis of aurones, while the reaction of phenols with 7b led to the synthesis of flavones.
Kraus, George A.,Gupta, Vinayak
supporting information; experimental part
p. 5278 - 5280
(2011/02/21)

Total synthesis of baicalein
In this paper, a simple and novel synthesis of baicalein is described. This transformation features the novel synthesis of helilandin B and a different way to demethylate. The overall yield of 59% is acceptable.
Chen, Duo-Zhi,Yang, Jian,Yang, Bo,Wu, Yuan-Shuang,Wu, Ting
experimental part
p. 124 - 128
(2010/08/05)

Obtaining new flavanones exhibiting antifungal activities by methyltrioxorhenium-catalyzed epoxidation-methanolysis of flavones
New 3-hydroxy-2-methoxyflavanones have been obtained through epoxidation-methanolysis of the corresponding flavone with urea-hydrogen peroxide (UHP)/methyltrioxorhenium (CH3ReO3, MTO) catalytic system in methanol as nucleophilic solv
Bernini, Roberta,Mincione, Enrico,Provenzano, Gianfranco,Fabrizi, Giancarlo,Tempesta, Sabrina,Pasqualetti, Marcella
p. 7561 - 7566
(2008/12/20)

α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors
The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4- trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyl- containing flavonoid analogs were investigat
Gao, Hong,Kawabata, Jun
p. 1661 - 1671
(2007/10/03)

COMPOUNDS AND METHODS TO INCREASE ANTI-P-GLYCOPROTEIN ACTIVITY OF BAICALEIN BY ALKYLATION ON THE A RING
The present invention is directed to analogs of baicalein according to formula (I): where R5 is H, (CI-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl group, an acyl group, a C1-C20 alkyl or ether group, a phosphate, diphosphate, triphosphate or phosphodiester group; R6 and R7 are each independently H, (C1-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl or together form a -OCR1R20- group wherein each of R1 and R2 is independently H, a C1-C3 alkyl group or an optionally substituted phenyl or benzyl group; and R8 is H, OH, an O-acyl group, a C1,-C4 alkyl or alkoxy group, F, Cl, Br or I, or a pharmaceutically acceptable salt thereof, which exhibit anti-P-glycoprotein activity and methods of enhancing the bioavailability of active compounds, especially orally administered compounds, by inhibition of P-glycoprotein 170 (P-gp 170) and/or CYP450 enzyme, especially CYP450 3A4 enzyme. Pharmaceutical compositions based upon these novel derivatives according to the present invention are also described herein.
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Page/Page column 29

(2010/02/13)

Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin a as antibacterial agents
A series of Oroxylin A derivatives, prepared by alkylation and condensation, were fully characterized by spectroscopic methods. All the derivatives were screened for antibacterial activity against a panel of susceptible and resistant Gram-positive and Gram-negative organisms. It was observed that acylation of 7-OH group in Oroxylin A significantly enhanced the activity as compared to their parent compound (Oroxylin A).
Suresh Babu,Hari Babu,Srinivas,Sastry,Hara Kishore,Murty,Madhusudana Rao
p. 3953 - 3956
(2007/10/03)

Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring
The aqueous extract of Scutellariae baicalensis Georgi has inhibitory activity against P-gp 170, a multiple drug resistant gene product. Baicalein, one of the major flavones, was found to be responsible for this activity. The hydroxyl groups of the A ring
Lee, Yashang,Yeo, Hosup,Liu, Shwu-Huey,Jiang, Zaoli,Savizky, Ruben M.,Austin, David J.,Cheng, Yung-Chi
p. 5555 - 5566
(2007/10/03)

Synthesis and anticancer activities of 5,6,7-trimethylbaicalein derivatives
The aim of this study was to develop potential anticancer agents based on a naturally occurring baicalein, a flavonoid from Scatellariae radix. Cinnamic acid derivatives were converted to corresponding chlorides and then condensed with 3,4,5-trimethoxyphe
Liao, Hua-Lin,Hu, Ming-Kuan
p. 1162 - 1165
(2007/10/03)

Methods of synthesizing flavonoids and chalcones
Simple and efficient total syntheses of flavonoids including baicalein, oroxylin A and wogonin are described herein. Simultaneous syntheses of oroxylin A and wogonin are also described.
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Page 2-3

(2010/02/09)

Novel synthesis of flavonoids of Scutellaria baicalensis Georgi.
A concise and efficient total synthesis of the flavonoids baicalein, oroxylin A and wogonin was described. Intramolecular oxidative cyclization followed by demethylation of chalcone 1, readily prepared from trimethoxyphenol, afforded, depending upon the controlled conditions, baicalein or oroxylin A in excellent yields. Demethylation of 1 yielded 3, which, by oxidation with I(2)/dimethyl sulfoxide (DMSO), was readily converted to oroxylin A and wogonin after column chromatography.
Huang, Wen-Hsin,Chien, Pei-Yu,Yang, Ching-Huey,Lee, An-Rong
p. 339 - 340
(2007/10/03)

Synthesis of some commonly occurring 2-phenyl-4H-1-benzopyran-4-ones: Revised structures for three natural products
5-Hydroxy-6,7-dimethoxyflavone, 5-hydroxy-7,8-dimethoxyflavone, 5-hydroxy-3,7-dimethoxyflavone, 3-hydroxy-5,7-dimethoxyflavone, 5-hydroxy-7,8-dimethoxyisoflavone and 5,7-dihydroxy-3-methoxyflavone and their derivatives have been synthesised to confirm the
Parmar, Virinder S.,Gupta, Sandhya,Sinha, Rita,Sharma, Sunil K.
p. 244 - 256
(2007/10/02)

Synthesis of Highly Functionalized Flavones and Chromones Using Cycloacylation Reactions and C-3 Functionalization. A Total Synthesis of Hormothamnione
The cycloacylations of hydroxy- and methoxy-substituted phenols with aryl- and alkylpropiolic acids using Eaton's reagent (10percent phosphorus pentoxide in methanesulfonic acid) gives highly substituted flavones and chromones in up to 63 percent yield.Styrylchromones were prepared from 2-methylchromones by condensation reactions of the 2-methyl group with various substituted benzaldehydes in sodium ethoxide and ethanol in almost quantitative yield.Methylation or hydroxylation at C-3 of these highly substituted flavones and styrylchromones was accomplished in a highly regioselective manner employing lithium diisopropylamide followed by quenching with an electrophile.Quenching of the initial anion with methyl triflate gave 3-methyl products while quenching of the initial anion with trimethylborate followed by oxidation gave 3-hydroxy products.A total synthesis of the naturally occurring styrylchromone hormothamnione, containing a 3-methyl substituent, is reported by use of these synthetic techniques.
McGarry, Lynda W.,Detty, Michael R.
p. 4349 - 4356
(2007/10/02)

5,6,7-TRISUBSTITUTED FLAVONES FROM GOMPHRENA MARTIANA
Two 5,6,7-trisubstituted flavones have been isolated from Gomphrena martiana and indentified as 5,6-dimethoxy-7-hydroxyflavone and 5,6-dihydroxy-6-methoxyflavone.Key Word Index -Gomphrena martiana; Amaranthaceae; flavonoids; 5,6-dimethoxy-7-hydroxyflavone; 5,7-dihydroxy-6-methoxyflavone.
Buschi, C. A.,Pomilio, A. B.,Gros, E. G.
p. 1178 - 1179
(2007/10/02)