- An efficient transformation of furano-hydroxychalcones to furanoflavones via base mediated intramolecular tandem O-arylation and C-O bond cleavage: A new approach for the synthesis of furanoflavones
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A new and efficient potassium carbonate mediated intramolecular tandem O-arylation followed by C-O bond cleavage of furano-hydroxychalcones is described. The treatment of furano-hydroxychalcones pongamol (1a) and ovalitenone (2a) with potassium carbonate
- Sharma, Rajni,Vishwakarma, Ram A.,Bharate, Sandip B.
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- Furanoflavones pongapin and lanceolatin B blocks the cell cycle and induce senescence in CYP1A1-overexpressing breast cancer cells
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Expression of cytochrome P450-1A1 (CYP1A1) is suppressed under physiologic conditions but is induced (a) by polycyclic aromatic hydrocarbons (PAHs) which can be metabolized by CYP1A1 to carcinogens, and (b) in majority of breast cancers. Hence, phytochemicals or dietary flavonoids, if identified as CYP1A1 inhibitors, may help in preventing PAH-mediated carcinogenesis and breast cancer. Herein, we have investigated the cancer chemopreventive potential of a flavonoid-rich Indian medicinal plant, Pongamia pinnata (L.) Pierre. Methanolic extract of its seeds inhibits CYP1A1 in CYP1A1-overexpressing normal human HEK293 cells, with IC50 of 0.6 μg/mL. Its secondary metabolites, the furanoflavonoids pongapin/lanceolatin B, inhibit CYP1A1 with IC50 of 20 nM. Although the furanochalcone pongamol inhibits CYP1A1 with IC50 of only 4.4 μM, a semisynthetic pyrazole-derivative P5b, has ~10-fold improved potency (IC50, 0.49 μM). Pongapin/lanceolatin B and the methanolic extract of P. pinnata seeds protect CYP1A1-overexpressing HEK293 cells from B[a]P-mediated toxicity. Remarkably, they also block the cell cycle of CYP1A1-overexpressing MCF-7 breast cancer cells, at the G0-G1 phase, repress cyclin D1 levels and induce cellular-senescence. Molecular modeling studies demonstrate the interaction pattern of pongapin/lanceolatin B with CYP1A1. The results strongly indicate the potential of methanolic seed-extract and pongapin/lanceolatin B for further development as cancer chemopreventive agents.
- Sharma, Rajni,Williams, Ibidapo S.,Gatchie, Linda,Sonawane, Vinay R.,Chaudhuri, Bhabatosh,Bharate, Sandip B.
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p. 6076 - 6086
(2018/11/23)
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- Synthesis of benzofuran scaffold-based potential PTP-1B inhibitors
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Protein tyrosine phosphatase 1B (PTP-1B) is an enzyme that plays a critical role in down-regulating insulin signaling through dephosphorylation of the insulin receptor. Studies have shown that PTP-1B knockout mice showed increased insulin sensitivity in m
- Dixit, Manish,Tripathi, Brajendra K.,Tamrakar, Akhilesh K.,Srivastava, Arvind K.,Kumar, Brijesh,Goel, Atul
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p. 727 - 734
(2007/10/03)
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- Amberlyst 15-catalyzed efficient synthesis of 5-acetyl-4-hydroxy-coumarone and 5-acetyl-6-hydroxy-coumarone: Crucial precursors for several naturally occurring furanoflavones
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A novel approach to the total synthesis of naturally occurring furanoflavones and furanochalcones is described. Angular and linear furanoflavones and furanochalcones have been prepared in just four steps, using economical reagents and simple reaction cond
- Goel, Atul,Dixit, Manish
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p. 1990 - 1994
(2007/10/03)
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- Three dibenzoylmethane derivatives from Lonchocarpus species
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Three new dibenzoylmethane derivatives were isolated from petrol extracts of the roots of Lonchocarpus latifolius and L. muehlbergianus. Molecular structures were determined from spectroscopic data, especially NMR techniques. An alkyl group bonded to the central carbon (C-8) of a natural dibenzoylmethane, had not been found before. Spectral data analysis suggested a preponderance of the respective diketotautomers.
- Magalhaes, Aderbal F.,Tozzi, Ana Maria A.,Magalhaes, Eva G.,Blanco, Ivani S.,Nogueira, Marisa A.
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p. 1029 - 1033
(2007/10/03)
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- A NEW ROUTE FOR THE SYNTHESIS OF FURANOFLAVONE AND FURANOCHALCONE NATURAL PRODUCTS
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An efficient synthesis of furanoflavones and furanochalcones has been carried out starting from a dihydrobenzofuran derivative.Key Words: Total synthesis, lanceolatin B, pongaglabrone, isopongaglabol, isopongaglabol methyl ether, pongol, pongamol, ovalite
- Lee, Yong Rok,Morehead, Andrew T.
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p. 4909 - 4922
(2007/10/02)
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- Dipolar Cycloaddition of Rhodium Carbenoids with Vinyl Esters. Total Synthesis of Pongamol and Lanceolatin B.
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A new method for dipolar cycloaddition of diazocyclohexane-1,3-diones, leading to benzofuran derivatives, has been applied to the total synthesis of natural products from Tephrosia and Pongamia.
- Pirrung, Michael C.,Lee, Yong Rok
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p. 6231 - 6234
(2007/10/02)
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