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Damodar, Kongara,Lee, Jeong Tae,Kim, Jin-Kyung,Jun, Jong-Gab Elsevier 2018 Bioorganic & medicinal chemistry letters Vol.28 No.11
<P><B>Abstract</B></P> <P>Syntheses of natural homoisoflavonoids, (±)-portulacanones A–C (<B>4</B>, <B>8</B> and <B>9</B>), portulacanone D (<B>6</B>), isolated from <I>Portulaca oleracea</I> L. (POL) and their derivatives (<B>3</B>, <B>5</B> and <B>7</B>) have been achieved for the first time along with the synthesis of known derivatives (<B>1</B> and <B>2</B>) and their <I>in vitro</I> inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages was evaluated as an indicator of anti-inflammatory activity. All the compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without obvious cytotoxicity. Compounds <B>3</B> (97.2% at 10 μM; IC<SUB>50</SUB> = 1.26 µM) followed by <B>6</B> (portulacanone D) (92.5% at 10 μM; IC<SUB>50</SUB> = 2.09 µM), <B>1</B> (91.4% at 10 μM; IC<SUB>50</SUB> = 1.75 µM) and <B>7</B> (83.0% at 10 μM; IC<SUB>50</SUB> = 2.91 µM) were the most potent from the series. This finding was further correlated with the suppressed expression of iNOS induced by LPS. Our promising preliminary results may provide the basis for the assessment of compound <B>3</B> as a lead structure for a NO production-targeted anti-inflammatory drug development and also could support the usefulness of POL as a folklore medicinal plant in the treatment of inflammatory diseases.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates
Kongara Damodar,전종갑 대한화학회 2014 Bulletin of the Korean Chemical Society Vol.35 No.12
Simple and practical synthesis of natural benzofuran derivative eupomatenoid-6 via Horner-Emmons type condensation as the key step is described. The umpolung property of aldehyde derivative, α-aminophosphonate was efficiently employed in this reaction. α-Aminophosphonate of anisaldehyde subjected to Horner-Emmons type condensation with 5-bromo-2-methoxybenzaldehyde to yield the deoxybenzoin, which was further methylated and then underwent tandem demethylation-cyclodehydration to afford the benzofuran scaffold in excellent yield. Finally Suzuki coupling with propenyl boronic acid afforded eupomatenoid-6 with an overall yield of 56.8%.
Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates
Damodar, Kongara,Jun, Jong-Gab Korean Chemical Society 2014 Bulletin of the Korean Chemical Society Vol.35 No.12
Simple and practical synthesis of natural benzofuran derivative eupomatenoid-6 via Horner-Emmons type condensation as the key step is described. The umpolung property of aldehyde derivative, ${\alpha}$-aminophosphonate was efficiently employed in this reaction. ${\alpha}$-Aminophosphonate of anisaldehyde subjected to Horner-Emmons type condensation with 5-bromo-2-methoxybenzaldehyde to yield the deoxybenzoin, which was further methylated and then underwent tandem demethylation-cyclodehydration to afford the benzofuran scaffold in excellent yield. Finally Suzuki coupling with propenyl boronic acid afforded eupomatenoid-6 with an overall yield of 56.8%.
An Expeditious Stereoselective Synthesis of (−)-Pinidinone from Ethyl Acetoacetate
Kongara Damodar,전종갑 대한화학회 2016 Bulletin of the Korean Chemical Society Vol.37 No.4
An expeditious stereoselective synthesis of a naturally occurring 2,6-disubstituted piperidine alkaloid, (−)-pinidinone, has been accomplished with an overall yield of 31% in total eight steps. The synthesis involves ethyl acetoacetate as the starting material and the stereoselective α-aminoallylation of aldehyde with (S)-tert-butanesulfinamide, allyl bromide, and indium and Grubbs’ olefin cross-metathesis as the pivotal steps.
Unified syntheses of gramniphenols F and G, cicerfuran, morunigrol C and its derivative
Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab Elsevier 2016 Tetrahedron letters: the international organ for t Vol.57 No.10
<P><B>Abstract</B></P> <P>The first syntheses of natural benzofurans, gramniphenols F and G, morunigrol C and its 3′,5′-di-<I>O</I>-methyl analogue along with the synthesis of cicerfuran are achieved by a unified synthetic sequence using 7-hydroxycoumarin, 5-bromoresorcinol, 2,4-dihydroxybenzaldehyde, and sesamol as building blocks. Ramirez <I>gem</I>-dibromoolefination, Miyaura borylation, Suzuki coupling have been successfully exploited in the synthesis. Additionally, their <I>anti</I>-inflammatory effects were also investigated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. The compounds exhibited significant inhibition of iNOS mediated nitric oxide (NO) production with no cytotoxicity at 10μM concentration and IC<SUB>50</SUB> values are found in the range from 9.1 to 25.2μM.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Synthesis, Anti-inflammatory, and Arginase Inhibitory Activity of Piceatannol and Its Analogs
문인수,Kongara Damodar,김진경,유승우,전종갑 대한화학회 2017 Bulletin of the Korean Chemical Society Vol.38 No.3
The present study describes the synthesis of piceatannol (2) and its analogs (3–8) using Wittig-Horner reaction, Colvin rearrangement, and Sonogashira reaction as key steps and also evaluation of their inhibitory potency on the production of inflammatory mediator nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. Three compounds 7 (90.1%), 8 (60.8%), and 6 (55.2%) were found to potently inhibit NO production induced by LPS without affecting the viability of RAW-264.7 cells. In addition, their Arginase I and II inhibition activity was also evaluated. In this study, three compounds, i.e., compounds 2–4 were showed good inhibition activity to both arginase I and II. Of the synthesized compounds, compound 2 exhibited maximum inhibitory activity of 28% (arginase I) and 26% (arginase II) at 10 μM concentration followed by compounds 3 and 4 of 20 and 22% to arginase I, 22 and 23% to arginase II, respectively.
장하영,Kongara Damodar,김진경,전종갑 대한화학회 2017 Bulletin of the Korean Chemical Society Vol.38 No.12
An efficient first synthesis of 2,5-diaryloxazoles 1–5 was accomplished from commercially inexpensive precursors and in overall yields of 38–48%. The synthesis proceeds via α-aminoketones and cyclodehydration (Robinson–Gabriel reaction) as key step. Next, these oxazoles were examined for their inhibitory effect against nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells and were found to display concentration-dependent inhibition of NO production without cytotoxicity. Of note, compound 3 (70.7%; IC50 = 2.33 μM) was identified as a potent inhibitor in view of its comparable inhibitory effect with the positive control, NG-monomethyl-L-arginine acetate (L-NMMA) (79.3%; IC50 = 4.51 μM) followed by compounds 5 (68.3%; IC50 = 2.30 μM) and 2 (53.9%; IC50 = 6.31 μM). As a whole, compound 3 may hold great promise for further development of NO production targeted anti-inflammatory agent.
Woo, Hyeong Ryeol,Damodar, Kongara,Lee, Yeontaek,Lim, Soon-sung,Jeon, Sung Ho,Lee, Jeong Tae Korean Chemical Society 2020 대한화학회지 Vol.64 No.2
A novel pharmacophore with epinastine (1) and NSAID moieties (2-5) was designed by molecular hybridization approach. The hybrid compounds 6-9 were synthesized by EDCI/HOBt or HATU-mediated coupling of 1 with salicylic acid (2), mefenamic acid (3), indomethacin (4) and naproxen (5), respectively, and were assessed for their inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages in vitro. The Hybrids were found to exhibit significant NO production inhibitory effects with half-maximal inhibitory concentration (IC<sub>50</sub>) values ranging in between 15.96 ± 1.32 and 36.68 ± 2.53 μM and were non-cytotoxic to macrophages. Comparing the inhibition concentration (IC<sub>50</sub>), cytotoxicity concentration (CC<sub>50</sub>) and in vitro efficacy index (iEI), 6 (IC<sub>50</sub> = 17.97 ± 1.92 μM; iEI = 11.13) and 9 (IC<sub>50</sub> = 15.96 ± 1.32 μM; iEI = 12.53) were better suited than other hybrids as well as their parent compound. Our findings signify that hybrids 6 and 9 may serve as platforms for continued investigations for the development of more efficient anti-inflammatory agents.
Substituents modification of <i>meso</i>-aryl BODIPYs for tuning photophysical properties
Ko, Sangwon,Kim, Cheul Yong,Damodar, Kongara,Lim, Hyun Min,Kim, Jin Ho,Lee, Chang-Hee,Lee, Jeong Tae Elsevier 2018 Tetrahedron Vol.74 No.2
<P><B>Abstract</B></P> <P>We successfully synthesized eight <I>meso</I>-aryl BODIPYs with 2,6-diethyl- or 1,2,6,7-tetraethyl substituents and characterized their photophysical properties. The steric hindrance resulting from the phenolic group in the <I>meso</I>-aryl moiety and the ethyl groups on the BODIPY core affected the synthesis of dipyrromethanes as an intermediate as well as the UV–Vis absorption and fluorescence emission of the BODIPYs due to the constrained rotation of the aryl ring. The potential use of the <I>meso</I>-hydroxyphenyl BODIPY as a pH sensor was also shown by the pH-dependent fluorescence emissions.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>