Reaction of 2-cyano[(4-oxo-4H-chromen-3-yl)methylidene]acetohydrazide with phosphorus reagents: Synthesis and evaluation of anticancer activities of some novel 1,2-azaphospholes, 1,2,3-diazaphospholidine, and 1,3,2-diaza-phosphinanes bearing a chromone ring

被引：19

作者：

Ali, Tarik E. ^{[1
]}

Ali, Mamdouh M. ^{[2
]}

Abdel-Kariem, Somaia M. ^{[1
]}

Ahmed, Marwa M. ^{[1
]}

机构：

[1] Ain Shams Univ, Dept Chem, Fac Educ, Cairo, Egypt

[2] Natl Res Ctr, Div Genet Engn & Biotechnol, Dept Biochem, Giza, Egypt

来源：

SYNTHETIC COMMUNICATIONS | 2017年 / 47卷 / 16期

关键词：

1; 2; 3-Diazaphospholidine; 2-azaphosphole; 3; 2-diazaphosphinane; anticancer; chromone; hydrazine; VEGF inhibition; ENDOTHELIAL GROWTH-FACTOR; STRUCTURAL INVESTIGATIONS; BIOLOGICAL EVALUATION; CONVENIENT SYNTHESIS; REACTION-PRODUCTS; DERIVATIVES; ANGIOGENESIS; HETEROCYCLES; ANTIOXIDANT; EXPRESSION;

D O I：

10.1080/00397911.2017.1332224

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 1,2-azaphospholes, 1,2,3-diazaphospholidine, 1,3,2-diaza-phosphinanes bearing a chromone ring as well as dialkyl pyrazolopyrimidine phosphonates have been synthesized from treatment of multifunctional 2-cyano[(4-oxo-4H-chromen-3-yl)methylidene]acetohydrazide (2), some phosphorus reagents such as phosphonic acid and its esters, and phosphorus sulfides as well as phosphorus halides in dry dioxane. The isolated products were evaluated for their anticancer activities and on the expression of vascular endothelial growth factor (VEGF) inhibition. Among the isolated products, compounds 3 and 10 exhibited higher effect against breast cancer cells than the reference drug and on the expression of VEGF inhibition. [GRAPHICS]

引用

页码：1458 / 1470

页数：13

共 17 条

[1] Reaction of 2-cyano-3-(4-oxo-4H-chromen-3-yl)prop-2-enamide with some phosphorus reagents: synthesis of some novel diethyl phosphonates, 1,2,3-diazaphosphinanes, 1,2,3-thiazaphosphinine and 1,2-azaphospholes bearing a chromone ring
Ali, Tarik E.
Hassan, Mohamed M.
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (01) : 173 - 189
[2] Reaction of 2-cyano-3-(4-oxo-4H-chromen-3-yl)prop-2-enamide with some phosphorus reagents: synthesis of some novel diethyl phosphonates, 1,2,3-diazaphosphinanes, 1,2,3-thiazaphosphinine and 1,2-azaphospholes bearing a chromone ring
Tarik E. Ali
Mohamed M. Hassan
Research on Chemical Intermediates, 2018, 44 : 173 - 189
[3] Reaction of 2-hydroxy-N′-1(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide with some phosphorus reagents: Synthesis and evaluation of anticancer activities of some novel α-hydrazinophosphonic acid, 1,4,5,2-oxadiazaphosphinines and 1,3,2-benzoxazaphosphinines bearing a chromone ring.
Ali, Tarik E.
Ali, Mamdouh M.
Abdel-kariem, Somaia M.
Ahmed, Marwa M.
20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016,
[4] Reaction of 2-hydroxy-N′-[(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide with some phosphorus reagents. Synthesis and evaluation of anticancer activity of novel α-hydrazinophosphonic acid, 1,4,5,2λ5-oxadiazaphosphinines, and 1,3,2λ5-benzoxazaphosphinines bearing a chromone ring
Ali, T. E.
Ali, M. M.
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[5] EFFICIENT SYNTHESIS AND ANTICANCER ACTIVITIES OF SOME NOVEL FUNCTIONALIZED (4-OXO-4H-CHROMEN-3-YL)2-SELENOXO-1,2-DIHYDROPYRIMIDINES
Ali, Tarik E.
Assiri, Mohammed A.
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Ali, Abeer E. M.
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HETEROCYCLES, 2020, 100 (11) : 1831 - 1844
[6] SYNTHESIS AND CYTOTOXICITY PROPERTIES OF SOME NOVEL FUNCTIONALIZED 2-{2-[(4-OXO-4H-CHROMEN-3-YL)-METHYLENE]-HYDRAZINYL}-1,3-SELENAZOLES
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[7] Ultrasound-assisted Synthesis of Novel 4-[3-acetyl-2-(N-alkyl(aryl)acetamido)-1,3,4-thiadiazol-5-yl]-3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazoles: Anticancer Activities, Apoptotic, Cell Cycle, Molecular Docking, and ADMET Studies
Alsolimani, Ayat K.
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[8] Synthesis of Chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazines and -diazepines by the Reaction of Substituted 2-(3-Acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1, n-Diamines
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SYNLETT, 2018, 29 (08) : 1107 - 1111
[9] m Reaction of 2-imino-2H-chromene-3-carboxamide with phosphorus sulfides: Synthesis of novel 2-sulfido-2,3-dihydro-4H-chromeno[2,3-d][1,3,2]diaza-phosphinines
Hassanin, Noha M.
Ali, Tarik E.
El-Shaaer, Hafez M.
Hassan, Mohamed M.
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[10] Synthesis and Pharmacological Activities of Some New 2-[1-Heptyl-3-(4-methoxybenzyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]acetohydrazide Derivatives
Bekircan, Olcay
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