2555-38-6Relevant academic research and scientific papers
Stereoselective synthesis of carbohydrate fused pyrano[3,2-c]pyranones as anticancer agents
Kumari, Priti,Gupta, Sonal,Narayana, Chintam,Ahmad, Shakeel,Vishnoi, Nidhi,Singh, Shailja,Sagar, Ram
supporting information, p. 13985 - 13997 (2018/08/21)
Pyrano[3,2-c]pyranone is an important structural motif present in many natural products exhibiting diverse biological activities. Two series of carbohydrate fused pyrano[3,2-c]pyranone derivatives (n = 20) were efficiently synthesized starting from 2-C-formyl galactal and 2-C-formyl glucal, reacting with various 4-hydroxycoumarins in a very short reaction time (10 min) under microwave assisted conditions. The anticancer activity of these synthesized pyrano[3,2-c]pyranones was determined in detail through cellular assays against MCF-7 (breast), MDA-MB-231 (breast) and HepG2 (liver) cancer cell lines. The newly synthesized pyrano[3,2-c]pyranones were screened for their cell-viability and anti-proliferative activity against MCF-7, MDA-MB-231 and HepG2 cell lines. Compounds 12, 13 and 14 exhibited high growth inhibitory potencies selectively against MCF-7 cells with half-maximal inhibitory concentration (IC50) values of 19.9, 14.5 and 10.9 μM respectively. Compounds 12, 13, 14, 15 and 19 inhibited the growth of MDA-MB-231 cells (breast) by 43, 44, 37, 31 and 45% respectively. However, no inhibitory effect was observed for these compounds in the human liver cancer cell line (HepG2) and normal cell lines (HEK293, human embryonic kidney cells). Mechanistic studies showed that these compounds alter the cell morphology and cause G2/M arrest in MCF-7. Further studies showed that compounds 12, 13 and 14 significantly inhibited cell migration which was accompanied by altered microtubule distribution. An enhanced accumulation of these compounds in cells was observed as compared to the 4-hydroxycoumarins precursor in the intracellular uptake assay. These findings confirm that carbohydrate fused pyrano[3,2-c]pyranones are better candidates for anticancer activity.
Natural product Hirtellanine B and its derivatives in the preparation process for the preparation of medicine for treating tumor with the application of the
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Paragraph 0051; 0137, (2016/10/10)
The present invention provides a preparation method of a natural product Hirtellanine B, wherein 2,4,6-trihydroxyacetophenone is adopted as a raw material, and steps of compound a preparation, compound b preparation, compound c preparation, compound d preparation, compound e preparation, compound f preparation, compound g preparation, and the like are performed to prepare the natural product Hirtellanine B. According to the present invention, biological activity screening is performed on Hirtellanine B and 14 Hirtellanine B derivatives, and results show that the natural product Hirtellanine B can inhibit proliferations of Jurkat cells, Raji cells and K562 cells, and the compounds provide a certain inhibition activity for tumor cells. The method has characteristics of easily available raw material, high reaction yield and reasonable operation, and is suitable for industrial production. The Hirtellanine B and the derivatives thereof can be used for preparing tumor treatment drugs, and have great clinical values. The natural product Hirtellanine B preparation method reaction formulas are as the follows.
4 - aromatic amine - coumarin derivatives and its preparation method and medical use (by machine translation)
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Paragraph 0036; 0053; 0054; 0055; 0107; 0108; 0109, (2016/11/21)
The invention relates to the field of pharmaceutical chemistry, in particular relates to a series of 4?Aromatic amine?Coumarin derivatives, method for their preparation and use in medicine, in particular for the treatment of tumor, such as breast cancer, and the like. The present invention relates to compounds of the general structure is as follows, each group in the formula is defined in the specification. (by machine translation)
Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
Rao, Maddali L.N.,Kumar, Abhijeet
, p. 6995 - 7005 (2015/03/14)
Cross-coupling reactions of differently substituted 4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2-4 h conditions. The utility of the methodology was explored in the synthesis of a few natural occurring neoflavones (3.27-3.30). In addition, the 4-arylcoumarin 3.1 product is a useful precursor for the preparation of (R)-tolterodine.
Synthesis and cytotoxic activity of non-naturally substituted 4-oxycoumarin derivatives
Serra, Silvia,Delogu, Giovanna,Casu, Laura,Vazquez-Rodriguez, Saleta,Santana, Lourdes,Uriarte, Eugenio,Chicca, Andrea,Gertsch, Juerg
, p. 5791 - 5794,4 (2020/07/31)
Coumarins are a large family of natural and synthetic compounds exerting different pharmacological effects, including cytotoxic, anti-inflammatory or antimicrobial. In the present communication we report the synthesis of a series of 12 diversely substituted 4-oxycoumarin derivatives including methoxy substituted 4-hydroxycoumarins, methyl, methoxy or unsubstituted 3-aryl-4-hydroxycoumarins and 4-benzyloxycoumarins and their anti-proliferative effects on breast adenocarcinoma cells (MCF-7), human promyelocytic leukemia cells (HL-60), human histiocytic lymphoma cells (U937) and mouse neuroblastoma cells (Neuro2a). The most potent bioactive molecule was the 4-hydroxy-5,7- dimethoxycoumarin (compound 1) which showed similar potency (IC50 0.2-2 μM) in all cancer cell lines tested. This non-natural product reveals a simple bioactive scaffold which may be exploited in further studies.
The rhodium carbenoid route to 3-aryl-4-hydroxycoumarins: Synthesis of derrusnin
Goldoni, Luca,Cravotto, Giancarlo,Penoni, Andrea,Tollari, Stefano,Palmisano, Giovanni
, p. 927 - 930 (2007/10/03)
3-Aryl-4-hydroxycoumarins have been obtained in satisfactory yields and selectivity through a Rh(II)-mediated arylation of diazocoumarin. The utility of this approach is demonstrated by synthesis of the natural product derrusnin.
Application of Aryllead(IV) Derivatives to the Preparation of 3-Aryl-4-hydroxy-1-benzopyran-2-ones
Barton, Derek H. R.,Donnelly, Dervilla M. X.,Finet, Jean-Pierre,Guiry, Patrick J.
, p. 1365 - 1376 (2007/10/02)
Aryllead triacetates are chemoselective and regioselective reagents for the preparation of 3-aryl-4-hydroxy-1-benzopyran-2-ones in good to excellent yields by C-3 arylation of the preformed 4-hydroxy-1-benzopyran-2-one ring.This approach was applied to th
