- Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents
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A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.
- Zhong, Hui,Zhou, Jia,An, Xiao-Hong,Hua, Ying-Rong,Lai, Yi-Fan,Zhang, Rui,Ahmad, Owais,Zhang, Ye,Shang, Jing
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p. 523 - 533
(2019/04/01)
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- Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers
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A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.
- Romero, Kevin J.,Galliher, Matthew S.,Raycroft, Mark A. R.,Chauvin, Jean-Philippe R.,Bosque, Irene,Pratt, Derek A.,Stephenson, Corey R. J.
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supporting information
p. 17125 - 17129
(2018/12/04)
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- The polyfunctional polymerizable compound
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PROBLEM TO BE SOLVED: To provide a polymerizable compound that exhibits excellent dissolvability with other liquid crystal compounds when it constitutes a polymerizable liquid crystal composition and that exhibits excellent heat resistance and mechanical strength when the polymerizable liquid crystal composition is cured. SOLUTION: The compound represented by general formula (I) is useful as a constituting member of a polymerizable composition as it has excellent dissolvability with other liquid crystal compounds. The polymerizable liquid crystal composition comprising the polymerizable compound has a wide liquid crystal phase temperature range. The optical anisotropic body obtained by using the polymerizable composition exhibits high heat resistance and is useful for applications such as a polarizing plate, a retardation plate and the like. COPYRIGHT: (C)2010,JPOandINPIT
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Paragraph 0070; 0071
(2019/09/07)
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- Flavone-based novel antidiabetic and antidyslipidemic agents
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The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 70b, 90a, and 90b of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations. Published 2012 by the American Chemical Society.
- Verma, Alok K.,Singh, Himanshu,Satyanarayana, Mavurapu,Srivastava, Swayam P.,Tiwari, Priti,Singh, Amar B.,Dwivedi, Anil K.,Singh, Shio K.,Srivastava, Mukesh,Nath, Chandishwar,Raghubir, Ram,Srivastava, Arvind K.,Pratap, Ram
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p. 4551 - 4567
(2012/07/30)
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- OXY SUBSTITUTED FLAVONES AS ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC AGENTS
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The present invention provides novel substituted flavone derivatives which exhibit anti- hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type ii diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.
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Page/Page column 16
(2010/11/08)
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- Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter hydrocarbonoclasticus, an Oil-Degrading Bacteria
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A modular synthesis was developed to access petrobactin, a catechol-containing siderophore isolated from Marinobacter hydrocarbonoclasticus. A range of petrobactin homologues with differing dihydroxybenzamide motifs and in one case an increased number of
- Gardner, Richard Andrew,Kinkade, Rebecca,Wang, Chaojie,Phanstiel IV, Otto
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p. 3530 - 3537
(2007/10/03)
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- Novel flavonoids
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Novel flavonoids of formula (I) 1where A and E form together a C—C or C=C bond; R1, R2, R3, and R4 are H, OH, O(CH2)n— aromatic group, n=0-8; O(CH2)n N(CH3)q with n=0-8, q=0-3; O(CH2)n OH with n=1-8; O(CH2)n-halide with n=1-8; O(CH2)n COOH with n=0-8; O(CH2)n COOR′ with n=0-8 and R′ is C1-C8 alkyl or an aromatic group; O(CH2)n CONH R″ with n=0-8 and R″ is C1-C8 alkyl or an aromatic group, and sugars in mono-, di- or trimeric form or analogues thereof, with the proviso that R1 is not H, at least two of R2, R3 and R4 are H, and at most one of R1, R2, R3 and R4 is OH, are useful for the treatment of drug-induced toxicity, doxorubicin-induced cardiotoxicity, free radical mediated diseases, lung diseases, cancer, diabetes mellitus, cardiovascular disease, or arteriosclerosis.
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- New aromatic inhibitors of EPSP synthase incorporating hydroxymalonates as novel 3-phosphate replacements
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A new, aromatic analogue of the EPSP synthase enzyme reaction intermediate 1 has been identified, which contains a 3-hydroxymalonate moiety in place of the usual 3-phosphate group. This simplified inhibitor was readily prepared in five steps from ethyl 3,4-dihydroxybenzoate. The resulting tetrahedral intermediate mimic 9 is an effective, competitive inhibitor versus S3P with an apparent K(i) of 0.57 ± 0.06 μM. This result demonstrates that 3-hydroxymalonates exhibit potencies comparable to aromatic inhibitors containing the previously identified 3-malonate ether replacements and can thus function as suitable 3-phosphate mimics in this system. These new compounds provide another example in which a simple benzene ring can be used effectively in place of the more complex shikimate ring in the design of EPSP synthase inhibitors. Furthermore, the greater potency of 9 versus the glycolate derivative 10 and the 5-deoxy analog 11, again confirms the requirement for multiple anionic charges at the dihydroxybenzoate 5-position in order to attain effective inhibition of this enzyme.
- Shah, Ajit,Font, Jose L.,Miller, Michael J.,Ream, Joel E.,Walker, Mark C.,Sikorski, James A.
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p. 323 - 334
(2007/10/03)
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