354782-83-5Relevant academic research and scientific papers
Flavonoid compound as well as preparation method and application thereof
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Paragraph 0103-0105; 0115-0117, (2021/10/20)
The invention discloses a flavonoid compound as well as a preparation method and application thereof, wherein the flavonoid compound comprises flavonoid compound FLM_M_1-24. Flavone derivatives FLM_M_25-40 and isoflavone derivatives FLM_M_M_41-48. The flavonoid compound can be used for preparing a modulator with an adjusting effect on Huh7-Nogo expression of B cells of human liver cancer cell lines, and specifically, the flavonoids compound has good inhibitory activity on Huh7-Nogo expression of human liver cancer cell line B cells.
Synthesis of aminoalkoxy substituted 4,5-diphenylisoxazole derivatives as potential anti-osteoporotic agents
Chen, Yeh-Long,Tseng, Chih-Hua,Lo, You-Chih,Lin, Ru-Wei,Chen, Chain-Fu,Wang, Gwo-Jaw,Ho, Mei-Ling,Tzeng, Cherng-Chyi
, p. 748 - 755 (2013/09/23)
Certain 4,5-diarylisoxazole derivatives have been found to possess broad biological effects, including antiinflammatory and anticancer activities. Recently, we have reported preparation of certain isoflavone derivatives and investigated for their anti-osteoporotic and antiproliferative activities in a detailed SAR study. The present report describes the conversion of isoflavones into novel 4,5-diphenylisoxazole derivatives by the treatment with NH 2OH. Alkylation followed by amination of these 4,5-diphenylisoxazoles gave the desired aminoalkoxy substituted 4,5-diphenylisoxazole derivatives. These compounds were evaluated in vitro for the osteogenic differentiation and quantification of mineralization. Although 5-isopropoxy-2-[4-(4-methoxyphenyl) isoxazol-5-yl]phenol (3) exhibited approximately 2.8-fold more activity than the positive Ipriflavone in the promotion of osteoblast activity (277% mineralization), the low cell viability (6%) and high cytotoxicity (68%) prompted us to further pursue more suitable candidates. A series of aminoalkyl side chains were introduced with aims to decrease cytotoxicity. Among them, 5-{4-isopropoxy-2-[4-(pyrrolidin-1-yl)butoxy]phenyl}-4-(4-methoxyphenyl) isoxazole (7a) exhibited approximately 2-fold more activity than the positive Ipriflavone in the promotion of osteoblast activity (194% mineralization) with comparable cell viability (71% v.s. 77%). Compound 7a was non cytotoxic against hADSCs and therefore, was selected as a lead for further structural optimization.
Synthetic analogs of daidzein, having more potent osteoblast stimulating effect
Yadav, Dinesh K.,Gautam, Abnish K.,Kureel, Jyoti,Srivastava, Kamini,Sahai, Mahendra,Singh, Divya,Chattopadhyay, Naibedya,Maurya, Rakesh
supporting information; experimental part, p. 677 - 681 (2011/03/18)
A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein.
ISOXAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
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Page/Page column 2-3, (2009/09/07)
An isoxazole derivative is provided. The isoxazole derivative has following formula: wherein R1, R2, R3, R4 and R5, independently, include hydrogen, hydroxy or C1-C12 alkoxy opti
Thallium(III) p-tosylate mediated oxidative 2,3-aryl rearrangement: A new useful route to ipriflavone and its analogs
Muthukrishnan,Singh, Om V.
experimental part, p. 3875 - 3883 (2009/04/11)
A new route for the synthesis of ipriflavone, an antiosteoporotic agent, is described that has four steps and 60% yields starting from resacetophenone (2). The key step of the present methodology is thallium(III) p-tosylate mediated oxidative 2,3-aryl rearrangement of flavanone to generate the isoflavone ring system of ipriflavone in a highly efficient manner. Copyright Taylor & Francis Group, LLC.
