Transition-metal-free, atom-economical cascade synthesis of novel 2-sulfonated-benzo[<i>f</i>][1,7]naphthyridines and their cytotoxic activities

Arepalli, Sateesh Kumar,Choi, Yunseon,Lee, Kiho,Kang, Jong-Soon,Jung, Jae-Kyung,Lee, Heesoon Elsevier 2018 Tetrahedron Vol.74 No.14

<P><B>Abstract</B></P> <P>An efficient, transition-metal-free cascade synthetic method has been developed for new 2-aryl/heteroaryl sulfonated benzo[<I>f</I>][1,7]naphthyridines. It is <I>tert</I>-butyl hydroperoxide (TBHP) mediated highly regioselective sulfonylation‒cyclization‒aromatization process between <I>N</I>-(3-aryl/heteroarylprop-2-yn-1-yl)quinolin-3-amines and aryl/heteroaryl sulfonylhydrazides. This synthetic protocol offers one-step strategy for CS and CC bond formations with a broad range of functional group tolerance. It is a simple, mild, and atom-economical route for the synthesis of various valuable functionalized 1, 2-aryl/heteroaryl sulfonated benzo[<I>f</I>][1,7]naphthyridines in moderate yields. Since the core motif of 2-sulfonated benzo[<I>f</I>][1,7]naphthyridines are biologically and pharmaceutically important (TLR activity 7, 8 modulators). Additionally, the synthesized derivatives were evaluated for their <I>in vitro</I> cytotoxic activities against six human cancer cell lines including lung (NCIH23), colon (HCT15), gastric (NUCG-3), renal (ACHN), prostate (PC-3), and breast (MDA-MB-231) cell lines. These compounds displayed significant cytotoxic activities against all tested human cancer cell lines.</P> <P><B>Highlights</B></P> <P> <UL> <LI> This synthetic method is simple, mild, efficient, and atom-economic. </LI> <LI> It is a highly regioselective, transition-metal-free and cascade synthesis. </LI> <LI> It is a one-pot sulfonyl radical addition – cyclization – aromatization process. </LI> <LI> One-step strategy for CC & CS bond formations. </LI> <LI> First report on the synthesis of novel 2-aryl/heteroaryl sulfonated benzo[<I>f</I>][1,7]naphthyridines. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

작은 기체 분리를 위한 3옹스트롱 크기 무기질 분리막 개발 연구

Arepalli Devipriyanka,김동우,김민지,조철희 한국막학회 2022 한국막학회 총회 및 학술발표회 Vol.2022 No.11

Novel NF-κB inhibitors: a patent review (2011 - 2014)

Arepalli, Sateesh Kumar,Choi, Minho,Jung, Jae-Kyung,Lee, Heesoon Informa UK, Ltd. 2015 Expert opinion on therapeutic patents Vol.25 No.3

<P>Importance of the field: The NF-kappa B family of transcription factors has a vital role in coordinating the expression of a wide variety of genes that control immune responses. The dysfunction of NF-kappa B has been associated with diseases ranging from inflammation to cancer. Areas covered: In this review, authors provided information on the role of NF-kappa B in human health and on recently developed inhibitors from patents granted in 2011 - 2014. The reader will gain an understanding of the mechanisms of NF-kappa B function as well as the structures and biological activities of recently developed NF-kappa B inhibitors. Expert opinion: Constitutive NF-kappa B activation is likely involved in the pathogenesis of several diseases. Researchers need to consider the specific mechanism of each invented NF-kappa B inhibitor, as well as the properties of the cellular, in vitro and in vivo assays and targeted diseases. For new drug development, they need various biological tests to assess the potential side effects and optimization of the biological activity.</P>

Effect of H₂S Concentration and Sulfurization Temperature on the Properties of Cu₂ZnSnS₄ Thin Films

Arepalli, Vinaya Kumar,Kim, Eui-Tae Materials Research Society of Korea 2015 한국재료학회지 Vol.25 No.12

This study reports the effects of $H_2S$ gas concentration on the properties of $Cu_2ZnSnS_4(CZTS)$ thin films. Specifically, sulfurization process with low $H_2S$ concentrations of 0.05% and 0.1%, along with 5% $H_2S$ gas, was studied. CZTS films were directly synthesized on Mo/Si substrates by chemical bath deposition method using copper sulfate, zinc sulfate heptahydrate, tin chloride dihydrate, and sodium thiosulfate pentahydrate. Smooth CZTS films were grown on substrates at optimized chemical bath deposition condition. The CZTS films sulfurized at low $H_2S$ concentrations of 0.05 % and 0.1% showed very rough and porous film morphology, whereas the film sulfurized at 5% $H_2S$ yielded a very smooth and dense film morphology. The CZTS films were fully crystallized in kesterite crystal form when they were sulfurized at $500^{\circ}C$ for 1 h. The kesterite CZTS film showed a reasonably good room-temperature photoluminescence spectrum that peaked in a range of 1.4 eV to 1.5 eV, consistent with the optimal bandgap for CZTS solar cell applications.

Development of 13<i>H</i>-benzo[<i>f</i>]chromeno[4,3-<i>b</i>][1,7]naphthyridines and their salts as potent cytotoxic agents and topoisomerase I/IIα inhibitors

Arepalli, Sateesh Kumar,Lee, Chaerim,Sim, Seongrak,Lee, Kiho,Jo, Hyunji,Jun, Kyu-Yeon,Kwon, Youngjoo,Kang, Jong-Soon,Jung, Jae-Kyung,Lee, Heesoon Elsevier 2018 Bioorganic & medicinal chemistry Vol.26 No.18

<P><B>Abstract</B></P> <P>A novel series of 35 angularly fused pentacyclic 13<I>H</I>-benzo[<I>f</I>]chromeno[4,3-<I>b</I>][1,7]naphthyridines and 13<I>H</I>-benzo[<I>f</I>]chromeno[4,3-<I>b</I>][1,7]naphthyridin-5-ium chlorides were designed and synthesized. Their cytotoxic activities were investigated against six human cancer cell lines (NCIH23, HCT15, NUGC-3, ACHN, PC-3, and MDA-MB-231). Among all screened compounds; <B>28</B>, <B>30</B>, <B>34</B>, <B>35</B>, <B>46</B>, <B>48</B>, <B>52</B>, and <B>53</B> compounds exhibited potent cytotoxic activities against all tested human cancer cell lines. Further, these potent lead cytotoxic agents were evaluated against human Topoisomerase I and IIα inhibition. Among them, the compound <B>48</B> exhibited dual Topoisomerase I and IIα inhibition especially at 20 μM concentrations the compound <B>48</B> exhibited 1.25 times more potent Topoisomerase IIα inhibitory activity (38.3%) than the reference drug etoposide (30.6%). The compound <B>52</B> also exhibited excellent (88.4%) topoisomerase I inhibition than the reference drug camptothecin (66.7%) at 100 μM concentrations. Molecular docking studies of the compounds <B>48</B> and <B>52</B> with topo I discovered that they both intercalated into the DNA single-strand cleavage site where the compound <B>48</B> have van der Waals interactions with residues Arg364, Pro431, and Asn722 whilst the compound <B>52</B> have with Arg364, Thr718, and Asn722 residues. Both the compounds <B>48</B> and <B>52</B> have π–π stacking interactions with the stacked DNA bases. The docking studies of the compound <B>48</B> with topo IIα explored that it was bound to the topo IIα DNA cleavage site where etoposide was situated. The benzo[<I>f</I>]chromeno[4,3-<I>b</I>][1,7]naphthyridine ring of the compound <B>48</B> was stacked between the DNA bases of the cleavage site with π–π stacking interactions and there were no hydrogen bond interactions with topo IIα.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Novel thirty-five angularly fused heterocycles were designed, synthesized and evaluated. </LI> <LI> Eight compounds displayed significant cytotoxic activities against all tested human cancer cell lines. </LI> <LI> The compound <B>48</B> exhibited dual human Topoisomerase I and IIα inhibition. </LI> <LI> The compound <B>52</B> exhibited 1.32 times more potent topo I inhibition than camptothecin. </LI> <LI> Molecular docking explored the binding sites of the compounds <B>48</B> and <B>52</B> with Topo I and IIα. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Hydroxy-Sodalite (H-SOD) Composite Membrane for Water Vapor Separation at Around 200℃

Arepalli Devipriyanka,조철희 한국에너지학회 2018 한국에너지공학회 학술발표회 Vol.2018 No.04

Synthesis of <i>N</i>-arylindazole-3-carboxamide and <i>N</i>-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis

Arepalli, Sateesh Kumar,Lee, Chaerim,Jung, Jae-Kyung,Kim, Youngsoo,Lee, Kiho,Lee, Heesoon Elsevier 2019 Bioorganic & medicinal chemistry letters Vol.29 No.18

<P><B>Abstract</B></P> <P>We have designed and synthesized twenty-six <I>N</I>-arylindazole-3-carboxamide (<B>3a-p</B>) and <I>N</I>-benzoylindazole (<B>6a-j</B>) derivatives to discover with excellent inhibition activities of α-MSH-stimulated melanogenesis. In the bio evaluation studies of these compounds, we discovered eighteen compounds, out of twenty-six exhibited more potent inhibition than the positive control arbutin. From the SAR studies, we identified <B>3k</B> and <B>6g</B> as lead compounds which displayed almost 5 and 9 times more potent inhibition of α-MSH-stimulated melanogenesis respectively than the reference arbutin. It is also evident the presence of electron withdrawing group at para position (R<SUP>3</SUP>) for the compounds (<B>3a-p</B>) and presence of +M group at ortho position (R<SUP>5</SUP>) for the compounds (<B>6a-j</B>) were crucial for their excellent inhibition activities of α-MSH-stimulated melanogenesis.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Twenty-six indazole analogs were designed, synthesized and evaluated as α-MSH inhibitors. </LI> <LI> Eighteen compounds exhibited more potent inhibition than reference arbutin. </LI> <LI> The compound (<B>3k</B>) displayed 5 times more α-MSH inhibition than arbutin. </LI> <LI> The compound (<B>6g</B>) displayed 9 times more α-MSH inhibition than arbutin. </LI> <LI> Structure-activity relationship was developed. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Design, synthesis and biological evaluation of 1,3-diphenylbenzo[<i>f</i>][1,7]naphthyrdines

Arepalli, Sateesh Kumar,Park, Byeongwoo,Lee, Kiho,Jo, Hyunji,Jun, Kyu-Yeon,Kwon, Youngjoo,Kang, Jong-Soon,Jung, Jae-Kyung,Lee, Heesoon Pergamon 2017 Bioorganic & medicinal chemistry Vol.25 No.20

<P><B>Abstract</B></P> <P>A novel series of twenty 1,3-diphenylbenzo[<I>f</I>][1,7]benzonaphthyrdine derivatives were designed and synthesized through intermolecular imino Diels-Alder reaction. Their <I>in vitro</I> cytotoxic activities were evaluated against six human cancer cell lines (NCIH23, HCT15, NUGC-3, ACHN, PC-3, and MDA-MB-231). Majority of synthesized compounds exhibited significant cytotoxic activities against all tested human cancer cell lines. Among them <B>4l</B>, <B>4m</B>, and <B>4o</B> derivatives exhibited most promising cytotoxic activities. Furthermore these compounds were evaluated against human Topoisomerase IIα inhibition. Interestingly, the compound <B>4l</B> exhibited 1.3 and 1.2 times more potent human Topoisomerase IIα inhibition than the reference drug etoposide in both 100µM and 20µM concentrations respectively. Molecular docking studies for the compound <B>4</B>l have also been executed by Sybyl X-2.1 in which it reveals the binding site of the compound <B>4l</B> with topo IIα DNA cleavage site where etoposide was situated. The benzo[<I>f</I>][1,7]naphthyridine ring was stacked between the DNA bases of the cleavage site.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Novel benzo[<I>f</I>][1,7]naphthyrdines were designed and synthesized. </LI> <LI> One-pot, atom-economy, regio-selective and multi-component reaction. </LI> <LI> Half of the compounds exhibited significant <I>in vitro</I> cytotoxic activities. </LI> <LI> The compound <B>4l</B> displayed excellent human Topo IIα inhibition than the etoposide. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Influence of working pressure on the structural, optical, and electrical properties of RF-sputtered SnS thin films

Arepalli, Vinaya Kumar,Shin, Yeonbae,Kim, Jeha Elsevier 2018 Superlattices and microstructures Vol.122 No.-

<P><B>Abstract</B></P> <P>We report the one-step deposition of the SnS thin films by RF-sputtering at 300 °C using a single SnS target. The influence of working pressure on the structural, optical, and electrical properties of deposited SnS films were characterized by scanning electron microscopy, electron dispersive spectroscopy, atomic force microscopy, X-diffraction, micro-Raman spectroscopy, UV–Visible spectroscopy, and Hall measurement analysis. As pressure increased, the SnS film thickness was typically reduced with increased grain size and surface roughness. All the films showed the [Sn/S] ratio close to stoichiometric SnS except the samples grown at 40 mTorr and 50 mTorr had the more atomic sulfur deficiency. XRD revealed the orthorhombic crystal phase of SnS with (111) preferred orientation. The micro Raman study confirmed the orthorhombic crystal structure of SnS without any secondary phase except the samples grown at 40 mTorr and 50 mTorr exhibited the minor impurity phase of Sn<SUB>2</SUB>S<SUB>3</SUB>. The direct energy band gap was decreased with the increase of working pressure and was varied in the range of 1.20–1.31 eV. The optical absorption coefficient was increased with pressure, and the samples grown at 50 mTorr showed the highest absorption coefficient of 1.1 × <SUP> 10 5 </SUP> cm<SUP>−1</SUP>. The electrical properties confirmed that the SnS films exhibited the p-type conductivity with reduced resistivity and increased hole mobility with increased pressures. The SnS deposited at 30 mTorr showed highest hole concentration of 6.95 × <SUP> 10 15 </SUP> cm<SUP>−3</SUP>. Based on these growth properties the SnS thin films deposited at 30 mTorr was concluded as a promising absorber material for the solar cell applications.</P> <P><B>Highlights</B></P> <P> <UL> <LI> At 300 °C, the SnS exhibited the orthorhombic crystal structure with (111) preferred plane at all working pressures. </LI> <LI> The reduction in film thickness and an increase in the grain size was observed with increase of pressure from 6–50 mTorr. </LI> <LI> The optical energy band gap was decreased with pressure and was in the range of 1.20–1.31 eV. </LI> <LI> All the SnS thin films showed the p-type conductivity with the hole concentration of 10<SUP>15</SUP> cm<SUP>−3</SUP>. </LI> <LI> The SnS at 30 mTorr was concluded as an efficient absorber material for the solar cell applications. </LI> </UL> </P>

Synthesis of defect-free improved microstructure of H-SOD zeolite membranes for the separation of H2O/H2 mixtures at elevated temperatures

Arepalli Devipriyanka,Churl-Hee Cho 한국막학회 2022 한국막학회 총회 및 학술발표회 Vol.2022 No.04