Antidyslipidemic and antioxidative activities of 8-hydroxyquinoline derived novel keto-enamine Schiffs bases.

Abstract:

:8-Hydroxyquinoline when subjected to Duff reaction resulted in the formation of unexpected 7-methylaminomethylene-8-oxo-7, 8-dihydroquinoline-5-carbaldehyde 2, which existed in the keto-enamine form, in which the aromaticity of the relevant ring was disrupted, which upon subsequent treatment with various primary amines resulted in its nucleophilic substitution of aliphatic methyl amine. These interesting novel derivatives were evaluated in vitro for their antioxidant and in vivo for their antidyslipidemic and post-heparin lipolytic activities. Compound 6 was found to be most active antidyslipidemic and antioxidative agent in this series, respectively, and thus represent a new class of promising lead.

journal_name

Eur J Med Chem

authors

Sashidhara KV,Kumar A,Bhatia G,Khan MM,Khanna AK,Saxena JK

doi

10.1016/j.ejmech.2008.08.004

subject

Has Abstract

pub_date

2009-04-01 00:00:00

pages

1813-8

issue

4

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(08)00363-2

journal_volume

44

pub_type

杂志文章
  • Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study.

    abstract::Inspired by the traditional Chinese herbal pair of Polygala tenuifolia-Acori Tatarinowii for treating epilepsy, 33 novel substituted cinnamic α-asaronol esters and analogues were designed by Combination of Traditional Chinese Medicine Molecular Chemistry (CTCMMC) strategy, synthesized and tested systematically not onl...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111650

    authors: Bai Y,He X,Bai Y,Sun Y,Zhao Z,Chen X,Li B,Xie J,Li Y,Jia P,Meng X,Zhao Y,Ding Y,Xiao C,Wang S,Yu J,Liao S,Zhang Y,Zhu Z,Zhang Q,Zhao Y,Qin F,Zhang Y,Wei X,Zeng M,Liang J,Cuan Y,Shan G,Fan TP,Wu B

    更新日期:2019-12-01 00:00:00

  • Discovery of 3-phenylquinolinylchalcone derivatives as potent and selective anticancer agents against breast cancers.

    abstract::A number of 3-phenylquinolinylchalcone derivatives were synthesized and evaluated in vitro for their antiproliferative activities against three breast cancer cell lines (MCF-7, MDA-MB-231, and SKBR-3), and a non-cancer normal epithelial cell line (H184B5F5/M10). Among them, (E)-3-[3-(4-methoxyphenyl)quinolin-2-yl]-1-(...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.04.054

    authors: Tseng CH,Tzeng CC,Hsu CY,Cheng CM,Yang CN,Chen YL

    更新日期:2015-06-05 00:00:00

  • Steroidal N-Sulfonylimidates: Synthesis and biological evaluation in breast cancer cells.

    abstract::Unique derivatives of androstene and estrane series containing N-sulfonylimidate pendants were prepared from 17α-ethynyl steroids via Cu-catalyzed azide-alkyne cycloaddition to tosyl azide in the presence of alcohols. The synthesized compounds were screened for cytotoxicity against human breast cancer cell lines and E...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.06.048

    authors: Volkova YA,Kozlov AS,Kolokolova MK,Uvarov DY,Gorbatov SA,Andreeva OE,Scherbakov AM,Zavarzin IV

    更新日期:2019-10-01 00:00:00

  • Design, synthesis, and X-ray studies of potent HIV-1 protease inhibitors incorporating aminothiochromane and aminotetrahydronaphthalene carboxamide derivatives as the P2 ligands.

    abstract::We describe the design, synthesis, and biological evaluation of a series of novel HIV-1 protease inhibitors with carboxamide derivatives as the P2 ligands. We have specifically designed aminothiochromane and aminotetrahydronaphthalene-based carboxamide ligands to promote hydrogen bonding and van der Waals interactions...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.09.046

    authors: Ghosh AK,Jadhav RD,Simpson H,Kovela S,Osswald H,Agniswamy J,Wang YF,Hattori SI,Weber IT,Mitsuya H

    更新日期:2018-12-05 00:00:00

  • Structure activity relationships of quinoline-containing c-Met inhibitors.

    abstract::A series of quinoline-containing c-Met inhibitors were prepared and studied. Chemistry was developed to introduce a pyridyl moiety onto the 2-aryl ring present in a lead molecule which mitigated the potential for quinone formation relative to the original compound. The study also assessed the importance of an acylthio...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.08.011

    authors: Kung PP,Funk L,Meng J,Alton G,Padrique E,Mroczkowski B

    更新日期:2008-06-01 00:00:00

  • Polymeric bile acid sequestrants: Review of design, in vitro binding activities, and hypocholesterolemic effects.

    abstract::Polymeric bile acid sequestrants (BAS) have recently attracted much attention as lipid-lowering agents. These non-absorbable materials specifically bind bile acids (BAs) in the intestine, preventing bile acid (BA) reabsorption into the blood through enterohepatic circulation. Therefore, it is important to understand t...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.12.015

    authors: Heřmánková E,Žák A,Poláková L,Hobzová R,Hromádka R,Širc J

    更新日期:2018-01-20 00:00:00

  • Antimycobacterial activity of natural products and synthetic agents: pyrrolodiquinolines and vermelhotin as anti-tubercular leads against clinical multidrug resistant isolates of Mycobacterium tuberculosis.

    abstract::Various classes of natural products and synthetic compounds were tested against reference strains and clinical multidrug resistant isolates of Mycobacterium tuberculosis. Vermelhotin (19), a natural tetramic acid from fungi, was the most active toward clinical MDR TB isolates (MIC 1.5-12.5 μg/mL). Synthetic compounds ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.10.026

    authors: Ganihigama DU,Sureram S,Sangher S,Hongmanee P,Aree T,Mahidol C,Ruchirawat S,Kittakoop P

    更新日期:2015-01-07 00:00:00

  • Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5α-reductase inhibitors.

    abstract::A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5α-reductase was studied. They were prepared from the reaction of EGCG with tert-butyldimethylsilyl chloride followed by reductive cleavage of the ester bond. The resultant (-)-epigallocatechins penta-O-tert-butyldimethylsi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.10.011

    authors: Lin SF,Lin YH,Lin M,Kao YF,Wang RW,Teng LW,Chuang SH,Chang JM,Yuan TT,Fu KC,Huang KP,Lee YS,Chiang CC,Yang SC,Lai CL,Liao CB,Chen P,Lin YS,Lai KT,Huang HJ,Yang JY,Liu CW,Wei WY,Chen CK,Hiipakka RA,Liao S

    更新日期:2010-12-01 00:00:00

  • Development of 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives as novel enoyl-acyl carrier protein reductase (InhA) inhibitors for the treatment of tuberculosis.

    abstract::InhA, the enoyl acyl carrier protein reductase of Mycobacterium tuberculosis (MTB) is an attractive target for developing novel anti-tubercular agents. Twenty eight 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives were synthesized and evaluated for their in vitro MTB InhA inhibition. Compounds were further evaluated ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.09.028

    authors: Pedgaonkar GS,Sridevi JP,Jeankumar VU,Saxena S,Devi PB,Renuka J,Yogeeswari P,Sriram D

    更新日期:2014-10-30 00:00:00

  • Synthesis and evaluation of novel rutaecarpine derivatives and related alkaloids derivatives as selective acetylcholinesterase inhibitors.

    abstract::A series of novel rutaecarpine derivatives and related alkaloid derivatives 3-aminoalkanamido-substituted rutaecarpine 4a-f and 7,8-dehydrorutaecarpine 5a-c, and 6-aminoalkanamido-substituted 3-[2-(3-Indolyl)ethyl]-4(3a)-quinazolinones 8a-c, were synthesized and subjected to pharmacological evaluation as acetylcholine...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.044

    authors: Wang B,Mai YC,Li Y,Hou JQ,Huang SL,Ou TM,Tan JH,An LK,Li D,Gu LQ,Huang ZS

    更新日期:2010-04-01 00:00:00

  • A new class of analgesic agents toward prostacyclin receptor inhibition: synthesis, biological studies and QSAR analysis of 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazolines.

    abstract::By studying the structural similarity of analgesic imidazolines and 2-phenylnitronyl nitroxides, 20 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazolines (2a-t) were newly synthesized as selective antagonists of prostacyclin receptor (IP receptor). In the in vivo tail-flick assay, 2a-t (dose, 0.13 mmol/kg) r...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.07.007

    authors: Zhao M,Li Z,Peng L,Tang YR,Wang C,Zhang Z,Peng S

    更新日期:2008-05-01 00:00:00

  • Synthesis and pharmacological evaluation of new N-phenylpiperazine derivatives designed as homologues of the antipsychotic lead compound LASSBio-579.

    abstract::In an attempt to increase the affinity of our antipsychotic lead compound LASSBio-579 (1-((1-(4-chlorophenyl)-1H-pyrazol-4-yl)methyl)-4-phenylpiperazine; (2)) for the 5-HT(2A) receptor, we synthesized five new N-phenylpiperazine derivatives using a linear synthetic route and the homologation strategy. The binding prof...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.05.027

    authors: Pompeu TE,Alves FR,Figueiredo CD,Antonio CB,Herzfeldt V,Moura BC,Rates SM,Barreiro EJ,Fraga CA,Noël F

    更新日期:2013-08-01 00:00:00

  • Repurposed drug candidates for antituberculosis therapy.

    abstract::Antibiotics have been a key part of clinical treatments for more than 70 years. Long-term use of antimicrobial treatments has led to the development of severe bacterial resistance, which has become increasingly serious due to antibiotic abuse, resulting in the treatment of bacterial infections becoming challenging. Th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112175

    authors: An Q,Li C,Chen Y,Deng Y,Yang T,Luo Y

    更新日期:2020-04-15 00:00:00

  • PASS-assisted design, synthesis and antioxidant evaluation of new butylated hydroxytoluene derivatives.

    abstract::New multipotent antioxidants (MPAOs), namely 1,3,4-thiadiazoles and 1,2,4-triazoles bearing the well-known free radical scavenger butylated hydroxytoluene (BHT), were designed and synthesized using an acid-(base-) catalyzed intramolecular dehydrative cyclization reaction of the corresponding 1-acylthiosemicarbazides. ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.10.001

    authors: Ariffin A,Rahman NA,Yehye WA,Alhadi AA,Kadir FA

    更新日期:2014-11-24 00:00:00

  • New transition metal ion complexes with benzimidazole-5-carboxylic acid hydrazides with antitumor activity.

    abstract::Metal complexes of 2-methyl-1H-benzimidazole-5-carboxylic acid hydrazide (4a; L(1)) and its Schiff base 2-methyl-N-(propan-2-ylidene)-1H-benzimidazole-5-carbohydrazide (5a; L(2)) with transition metal ions e.g., copper, silver, nickel, iron and manganese were prepared. The complexes formed were 1:1 or 1:2 M:L complexe...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.07.013

    authors: Galal SA,Hegab KH,Kassab AS,Rodriguez ML,Kerwin SM,el-Khamry AM,el-Diwani HI

    更新日期:2009-04-01 00:00:00

  • Discovery of pentacyclic triterpene 3β-ester derivatives as a new class of cholesterol ester transfer protein inhibitors.

    abstract::A series of pentacyclic triterpene 3β-ester derivatives were designed, synthesized and evaluated as a new class of cholesteryl ester transfer protein (CETP) inhibitors for the treatment of dyslipidemia. In vitro screening assay showed that 5 out of 30 compounds displayed moderate inhibiting human CETP activity with IC...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.08.012

    authors: Chen D,Huang X,Zhou H,Luo H,Wang P,Chang Y,He X,Ni S,Shen Q,Cao G,Sun H,Wen X,Liu J

    更新日期:2017-10-20 00:00:00

  • Design, synthesis and anticholinesterase activity of novel benzylidenechroman-4-ones bearing cyclic amine side chain.

    abstract::A series of 3-(4-(aminoalkoxy)benzylidene)-chroman-4-ones 7a-r were designed and synthesized as analogs of homoisoflavonoids which are well known natural products with diverse pharmacological properties related to Alzheimer's disease. The in vitro anti-cholinesterase activity of designed compounds 7a-r against AChE an...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.04.055

    authors: Pourshojaei Y,Gouranourimi A,Hekmat S,Asadipour A,Rahmani-Nezhad S,Moradi A,Nadri H,Moghadam FH,Emami S,Foroumadi A,Shafiee A

    更新日期:2015-06-05 00:00:00

  • Antiproliferative effect of novel platinum(II) and palladium(II) complexes on hepatic tumor stem cells in vitro.

    abstract::Novel platinum and palladium complexes with (2-isopropoxyphenyl)dicyclohexylarsine and (2-methoxyphenyl)dicyclohexylarsine ligands were synthesized and tested on different tumor cells. Adducts with general formula MX(2)L(2) (M = Pt(II), Pd(II); X = Cl or I; L = organoarsenic ligand) were fully characterized. According...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.12.001

    authors: Miklášová N,Fischer-Fodor E,Lönnecke P,Tomuleasa CI,Virag P,Schrepler MP,Mikláš R,Dumitrescu LS,Hey-Hawkins E

    更新日期:2012-03-01 00:00:00

  • Synthesis and in vitro antitumour activity evaluation of 1-aryl-1H,3H-thiazolo[4,3-b]quinazolines.

    abstract::A series of 1H,3H-thiazolo[4,3-b]quinazolines (2a-i) were synthesized and evaluated for their in vitro antitumour activity against ca. 60 human tumour cell lines. They exhibited moderate (2c, 2d, 2f and 2g) to strong (2a, 2b, 2e, 2h and 2i) cell-growth inhibition at a concentration of 10(-4) M, but weak activity at lo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)01195-8

    authors: Grasso S,Micale N,Monforte AM,Monforte P,Polimeni S,Zappalà M

    更新日期:2000-12-01 00:00:00

  • The discovery of new potent non-peptide Angiotensin II AT1 receptor blockers: a concise synthesis, molecular docking studies and biological evaluation of N-substituted 5-butylimidazole derivatives.

    abstract::A convenient and facile synthesis, in silico docking studies and in vitro biological evaluation of N-substituted 5-butylimidazole derivatives as potent Angiotensin II (ANG II) receptor type 1 (AT1) blockers (ARBs) has been reported in the current study. Our efforts have been directed towards the development of an effi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.07.040

    authors: Agelis G,Resvani A,Durdagi S,Spyridaki K,Tůmová T,Slaninová J,Giannopoulos P,Vlahakos D,Liapakis G,Mavromoustakos T,Matsoukas J

    更新日期:2012-09-01 00:00:00

  • Promising applications of steroid сonjugates for cancer research and treatment.

    abstract::The conjugation of biologically active molecules is a powerful tool for drug discovery used to target a variety of multifunctional diseases including cancer. Conjugated drugs can provide combination therapies in a single multi-functional agent and, by doing so, be more specific and powerful than conventional classic t...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.113089

    authors: А Zolottsev V,Latysheva АS,Pokrovsky VS,Khan II,Misharin AY

    更新日期:2021-01-15 00:00:00

  • Design, synthesis and biological activities of novel oxazolo[4,5-g]quinazolin-2(1H)-one derivatives as EGFR inhibitors.

    abstract::A series of oxazolo[4,5-g]quinazolin-2(1H)-one derivatives employing Erlotinib as lead compound were synthesized and evaluated for their EGFR inhibition activity. These compounds having variation at the 1 and 8-position, included ether and esters hydrophilic side-chain and aromatic head fragment, respectively. All the...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.07.008

    authors: Yin S,Zhou L,Lin J,Xue L,Zhang C

    更新日期:2015-08-28 00:00:00

  • Additivity or cooperativity: which model can predict the influence of simultaneous incorporation of two or more functionalities in a ligand molecule?

    abstract::Predicting how binding affinity responds to ligand structural modifications in structure-activity relationship studies (SAR) is a major challenge in medicinal chemistry. This is particularly true when two or more of these modifications are carried out simultaneously. In this study, we present binding affinity data fro...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.11.056

    authors: Nasief NN,Hangauer D

    更新日期:2015-01-27 00:00:00

  • Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.

    abstract::The oxidation of bioorganic materials by air and, particularly, the oxidative stress involved in the cell loss and other pathologies associated with neurodegenerative diseases (NDs) are of enormous social and economic importance. NDs generally involve free radical reactions, beginning with the formation of an initiati...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.03.061

    authors: Losada-Barreiro S,Bravo-Díaz C

    更新日期:2017-06-16 00:00:00

  • Synthesis and biological screening of 2'-aryl/benzyl-2-aryl-4-methyl-4',5-bithiazolyls as possible anti-tubercular and antimicrobial agents.

    abstract::A series of 2'-aryl/benzyl-2-aryl-4-methyl-4',5-bithiazolyl derivatives, 25-64 were synthesized and evaluated for inhibitory activity against Mycobacterium smegmatis MC(2) 155 strain and antimicrobial activities against four pathogenic bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Proteus vul...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.03.016

    authors: Abhale YK,Sasane AV,Chavan AP,Deshmukh KK,Kotapalli SS,Ummanni R,Sayyad SF,Mhaske PC

    更新日期:2015-04-13 00:00:00

  • Synthesis and biological evaluation of novel structural hybrids of benzofuroxan derivatives and fluoroquinolones.

    abstract::A series of novel hybrids based on benzofuroxan derivatives and fluoroquinolones (4a-d-6a-d) have been synthesized. Unexpectedly, the reactions have resulted in salt products formation during the hydrolysis of benzofuroxans by water molecules being present in the solvent instead of usual substitution products. All the...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.03.086

    authors: Chugunova E,Akylbekov N,Bulatova A,Gavrilov N,Voloshina A,Kulik N,Zobov V,Dobrynin A,Syakaev V,Burilov A

    更新日期:2016-06-30 00:00:00

  • Rigid aromatic linking moiety in cationic lipids for enhanced gene transfection efficiency.

    abstract::Although numerous cationic lipids have been developed as non-viral gene vectors, the structure-activity relationship (SAR) of these materials remains unclear and needs further investigation. In this work, a series of lysine-derived cationic lipids containing linkages with different rigidity were designed and synthesiz...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.05.038

    authors: Wang B,Zhao RM,Zhang J,Liu YH,Huang Z,Yu QY,Yu XQ

    更新日期:2017-08-18 00:00:00

  • Further optimization of plakortin pharmacophore: structurally simple 4-oxymethyl-1,2-dioxanes with promising antimalarial activity.

    abstract::For the optimization of the plakortin pharmacophore, we recently proposed a straightforward synthesis of 4-carbomethoxy-3-methoxy-1,2-dioxanes as potential antimalarial drug candidates. Herein we report the chemoselective reduction of the 4-carbomethoxy group which has allowed us to prepare in good yields twenty-four ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.10.050

    authors: Persico M,Parapini S,Chianese G,Fattorusso C,Lombardo M,Petrizza L,Quintavalla A,Rondinelli F,Basilico N,Taramelli D,Trombini C,Fattorusso E,Taglialatela-Scafati O

    更新日期:2013-01-01 00:00:00

  • Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase.

    abstract::A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superio...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.11.023

    authors: Marcu A,Schurigt U,Müller K,Moll H,Krauth-Siegel RL,Prinz H

    更新日期:2016-01-27 00:00:00

  • An orally available inverse agonist of estrogen-related receptor gamma showed expanded efficacy for the radioiodine therapy of poorly differentiated thyroid cancer.

    abstract::Estrogen-related receptor gamma (ERRγ) is the NR3B subgroup of associated transcription factors. In this report, a new generation of a potent and selective ERRγ inverse agonist (25) with good biocompatibility was proposed. We also explored the potential of the newly developed compound 25 in the PDTC model to expand th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112501

    authors: Kim J,Hwang H,Yoon H,Lee JE,Oh JM,An H,Ji HD,Lee S,Cha E,Ma MJ,Kim DS,Lee SJ,Kadayat TM,Song J,Lee SW,Jeon JH,Park KG,Lee IK,Jeon YH,Chin J,Cho SJ

    更新日期:2020-11-01 00:00:00