Design, synthesis, biological evaluation and molecular docking studies of novel 3-aryl-4-anilino-2 H -chromen-2-one derivatives targeting ERα as anti-breast cancer agents

Luo, Guoshun; Chen, Mingqi; Lyu, Weiting; Zhao, Ruheng; Xu, Qian; Qin, You

doi:10.1016/j.bmcl.2017.04.029

Cited by 34 publications

(14 citation statements)

References 31 publications

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“…Because of the shift of electronic density on carbon atoms as a result of correlation with electronegative oxygen the signals of C 6 and C 4 atoms passed into a low pole area of spectrum and were at 155.18 and 175.43 ppm respectively. Equivalent couple of atoms of pyridine fragment С 19,23 with low shift of the electronic density on carbon nucleus was found at 122.02 ppm. Whereas other couple of pyridine carbons С 22, 22 with low screening of carbon nucleus was observed in lowest pole area at 150.26 ppm.…”

Section: Resultsmentioning

confidence: 95%

“…210-211°С. 1 Н NMR spectrum, δ, ppm: 2.41 s (3Н, Н 17 ), 7.61-7.88 m (6Н, Н 7,8,10,12,19,23 РМК «Ұлттық биотехнология орталығы», Нұр-Сұлтан, Қазақстан…”

Section: N'-((6-methyl-4-oxo-4н-chromen-3-il)methylene) Isonicotinohyunclassified

“…belonging to group of antioxidant substances [1]. By reason of low toxicity for mammals and essential solubility, a chromone fragment is one of the exclusive structural blocks to develop the pharmacological important substances [9][10][11][12][13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Structure and Anti-Radical Activity of 6-Methyl-4-Oxo-4н-Chromen-3-Acylhydrazones

Нуркенов¹,

Ibraev²,

Сейлханов³

et al. 2019

JSC «D.V. SOKOLSKY INSTITUTE OF FUEL, CATALYSIS AND ELECTROCHEM

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News of the Academy of sciences of the Republic of Kazakhstan 2 NAS RK is pleased to announce that News of NAS RK. Series of chemistry and technologies scientific journal has been accepted for indexing in the Emerging Sources Citation Index, a new edition of Web of Science. Content in this index is under consideration by Clarivate Analytics to be accepted in the Science Citation Index Expanded, the Social Sciences Citation Index, and the Arts & Humanities Citation Index. The quality and depth of content Web of Science offers to researchers, authors, publishers, and institutions sets it apart from other research databases. The inclusion of News of NAS RK. Series of chemistry and technologies in the Emerging Sources Citation Index demonstrates our dedication to providing the most relevant and influential content of chemical sciences to our community. Қазақстан Республикасы Ұлттық ғылым академиясы "ҚР ҰҒА Хабарлары. Химия жəне технология сериясы" ғылыми журналының Web of Science-тің жаңаланған нұсқасы Emerging Sources Citation Index-те индекстелуге қабылданғанын хабарлайды. Бұл индекстелу барысында Clarivate Analytics компаниясы журналды одан əрі the Science Citation Index Expanded, the Social Sciences Citation Index жəне the Arts & Humanities Citation Index-ке қабылдау мəселесін қарастыруда. Webof Science зерттеушілер, авторлар, баспашылар мен мекемелерге контент тереңдігі мен сапасын ұсынады. ҚР ҰҒА Хабарлары. Химия жəне технология сериясы Emerging Sources Citation Index-ке енуі біздің қоғамдастық үшін ең өзекті жəне беделді химиялық ғылымдар бойынша контентке адалдығымызды білдіреді. НАН РК сообщает, что научный журнал «Известия НАН РК. Серия химии и технологий» был принят для индексирования в Emerging Sources Citation Index, обновленной версии Web of Science. Содержание в этом индексировании находится в стадии рассмотрения компанией Clarivate Analytics для дальнейшего принятия журнала в the Science Citation Index Expanded, the Social Sciences Citation Index и the Arts & Humanities Citation Index. Web of Science предлагает качество и глубину контента для исследователей, авторов, издателей и учреждений. Включение Известия НАН РК в Emerging Sources Citation Index демонстрирует нашу приверженность к наиболее актуальному и влиятельному контенту по химическим наукам для нашего сообщества.

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Section: Resultsmentioning

confidence: 95%

Section: N'-((6-methyl-4-oxo-4н-chromen-3-il)methylene) Isonicotinohyunclassified

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Synthesis, Structure and Anti-Radical Activity of 6-Methyl-4-Oxo-4н-Chromen-3-Acylhydrazones

Нуркенов¹,

Ibraev²,

Сейлханов³

et al. 2019

JSC «D.V. SOKOLSKY INSTITUTE OF FUEL, CATALYSIS AND ELECTROCHEM

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“…Nearly 105 ligands reported as antagonists of ERa such as benzofurans 22, diphenyl amine analogs 23, sulfoximine-based acyclic triaryl olefins 24, isoxazole derivatives 25 thiazolidinone derivatives 26, tamoxifen mimics 27, pyrazolo[1,5-a]pyrimidine conjugates 28 chromen-2-one derivatives 29 etc. Many of those compounds are serving as anticancer agents 30 antifungal agents 31 and anti-inflammatory agents 32 etc.…”

Section: Methodsmentioning

confidence: 99%

Virtual screening of novel compounds as potential ERα inhibitors

2019

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Majority of breast cancers diagnosed today are estrogen receptor (ER)-positive, however, progesterone receptor-positive (PR-positive) is also responsible for breast cancer. Tumors that are ER/PR-positive are much more likely to respond to hormone therapy than tumors that are ER/PR-negative. Nearly 105 ERa inhibitors from literature when docked resulted in 31 compounds (pyrazolo[1,5-a]pyrimidine analogs and chromen-2-one derivatives) with better binding affinities. The maximum score obtained was -175.282 kcal/mol for compound, [2-(4- Fluoro-phenylamino)-pyridin-3-yl]-{4-[2-phenyl-7- (3, 4, 5-trimethoxy-phenyl)-pyrazolo[1,5-a]pyrimidine-5-carbonyl]-piperazin-1-yl}-methanone. The major H-bond interactions are observed with Thr347. In pursuit to identify novel ERa inhibitory ligands, virtual screening was carried out by docking pyrazole, bipyrazole, thiazole, thiadiazole etc scaffold analogs from literature.34 bipyrazoles from literature revealed Compound 2, ethyl 5-amino-1-(5-amino-3-anilino-4-ethoxycarbonyl-pyrazol-1-yl)-3-anilino-pyrazole-4-carboxylate, with -175.9 kcal/mol binding affinity with the receptor, where a favourable H-bond was formed with Thr347.On the other hand, screening 2035 FDA approved drugs from Drug Bank database resulted in 11 drugs which showed better binding affinities than ERa bound tamoxifen. Consensus scoring using 5 scoring schemes such as Mol Dock score, mcule, SwissDock, Pose&Rank and DSX respectively resulted in better rank-sumsfor Lomitapide, Itraconazole, Cobicistat, Azilsartanmedoxomil, and Zafirlukast.

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“…Moreover, literature survey indicated that thiazolylcoumarin hybrids (Abdul Rahman et al, 2016[ 1 ]; Vaarla et al, 2015[ 75 ]; Sreekanth et al, 2014[ 67 ]; Srimanth et al, 2002[ 68 ]) and other aryl(heteroaryl)coumarin hybrids (Zhang et al, 2017[ 83 ]; Pangal et al, 2017[ 50 ]; Luo et al, 2017[ 40 ]; Garazd et al, 2017[ 20 ]; Holiyachi et al, 2016[ 28 ]; Goel et al, 2015[ 22 ]; Zhang et al, 2014[ 84 ]; Kamal et al, 2009[ 33 ]; Ganina et al, 2008[ 19 ]) have promising antitumor activity.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis and antitumor evaluation of a new series of thiazolylcoumarin derivatives

Gabr

El‐Gohary

El‐Bendary

et al. 2017

EXCLI Journal; 16:Doc1114; ISSN 1611-2156

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Design, synthesis, biological evaluation and molecular docking studies of novel 3-aryl-4-anilino-2 H -chromen-2-one derivatives targeting ERα as anti-breast cancer agents

Cited by 34 publications

References 31 publications

Synthesis, Structure and Anti-Radical Activity of 6-Methyl-4-Oxo-4н-Chromen-3-Acylhydrazones

Synthesis, Structure and Anti-Radical Activity of 6-Methyl-4-Oxo-4н-Chromen-3-Acylhydrazones

Virtual screening of novel compounds as potential ERα inhibitors

Microwave-assisted synthesis and antitumor evaluation of a new series of thiazolylcoumarin derivatives

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