当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Discovery of novel triazolo[4,3-b]pyridazin-3-yl-quinoline derivatives as PIM inhibitors.

Discovery of novel triazolo[4,3-b]pyridazin-3-yl-quinoline derivatives as PIM inhibitors.

Abstract：

:PIM kinase family (PIM-1, PIM-2 and PIM-3) is an appealing target for the discovery and development of selective inhibitors, useful in various disease conditions in which these proteins are highly expressed, such as cancer. The significant effort put, in the recent years, towards the development of small molecules exhibiting inhibitory activity against this protein family has ended up with several molecules entering clinical trials. As part of our ongoing exploration for potential drug candidates that exhibit affinity towards this protein family, we have generated a novel chemical series of triazolo[4,3-b]pyridazine based tricycles by applying a scaffold hopping strategy over our previously reported potent pan-PIM inhibitor ETP-47453 (compound 2). The structure-activity relationship studies presented herein demonstrate a rather selective PIM-1/PIM-3 biochemical profile for this novel series of tricycles, although pan-PIM and PIM-1 inhibitors have also been identified. Selected examples show significant inhibition of the phosphorylation of BAD protein in a cell-based assay. Moreover, optimized and highly selective compounds, such as 42, did not show significant hERG inhibition at 20 μM concentration, and proved its antiproliferative activity and utility in combination with particular antitumoral agents in several tumor cell lines.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Martínez-González S,Rodríguez-Arístegui S,Gómez de la Oliva CA,Hernández AI,González Cantalapiedra E,Varela C,García AB,Rabal O,Oyarzabal J,Bischoff JR,Klett J,Albarrán MI,Cebriá A,Ajenjo N,García-Serelde B,Gómez-Casero E,

doi

10.1016/j.ejmech.2019.02.022

subject

Has Abstract

pub_date

2019-04-15 00:00:00

pages

87-109

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(19)30136-9

journal_volume

168

pub_type

杂志文章

相关文献

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • Design, synthesis and biological evaluation of quinazoline-phosphoramidate mustard conjugates as anticancer drugs.

    abstract：:A series of novel compounds with phosphoramide mustard functionality incorporated into the quinazoline scaffold of EGFR/HER2 inhibitors were designed and synthesized as multi-target-directed ligands against tumor cells. In vitro assays showed that tumor cell lines with high HER2 level were more sensitive to the compou...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.12.055

    authors： Lin S,Li Y,Zheng Y,Luo L,Sun Q,Ge Z,Cheng T,Li R

    更新日期：2017-02-15 00:00:00

  • Design, synthesis, and structure-activity relationship study of glycyrrhetinic acid derivatives as potent and selective inhibitors against human carboxylesterase 2.

    abstract：:Human carboxylesterase 2 (hCE2), one of the major carboxylesterases in the human intestine and various tumour tissues, plays important roles in the oral bioavailability and treatment outcomes of ester- or amide-containing drugs or prodrugs, such as anticancer agents CPT-11 (irinotecan) and LY2334737 (gemcitabine). In ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.02.020

    authors： Zou LW,Li YG,Wang P,Zhou K,Hou J,Jin Q,Hao DC,Ge GB,Yang L

    更新日期：2016-04-13 00:00:00

  • Novel pyrazolopyridine derivatives as potential angiogenesis inhibitors: Synthesis, biological evaluation and transcriptome-based mechanistic analysis.

    abstract：:Modified purine derivatives exemplified by pyrazolopyrimidines have emerged as highly selective inhibitors of several angiogenic receptor tyrosine kinases. Herein, we designed and synthesized a new series of substituted pyrazolopyridines and explored their ability to influence crucial pro-angiogenic attributes of endo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.05.035

    authors： Michailidou M,Giannouli V,Kotsikoris V,Papadodima O,Kontogianni G,Kostakis IK,Lougiakis N,Chatziioannou A,Kolisis FN,Marakos P,Pouli N,Loutrari H

    更新日期：2016-10-04 00:00:00

  • Design and characterization of α-lipoic acyl shikonin ester twin drugs as tubulin and PDK1 dual inhibitors.

    abstract：:Shikonin exhibits powerful anticancer activities for various cancer cells, but its poor solubility and strong toxicity hinder its development as clinical anticancer agent. We previously confirmed that shikonin and its derivatives can disturb mitosis through targeting tubulin. In this study, α-lipoic acid, the naturall...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.12.019

    authors： Lin HY,Han HW,Sun WX,Yang YS,Tang CY,Lu GH,Qi JL,Wang XM,Yang YH

    更新日期：2018-01-20 00:00:00

  • Angiotensin II--AT1 receptor antagonists: design, synthesis and evaluation of substituted carboxamido benzimidazole derivatives.

    abstract：:A series of 5-(alkyl and aryl)carboxamido benzimidazole derivatives had been designed, synthesized and evaluated for in vitro angiotensin II--AT1 receptor antagonism and in vivo antihypertensive activities. The pharmacological activities were inversely related to the size of alkyl and aryl substituents. It can be sugg...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2007.11.008

    authors： Shah DI,Sharma M,Bansal Y,Bansal G,Singh M

    更新日期：2008-09-01 00:00:00

  • Synthesis and in vitro and in vivo biological evaluation of novel derivatives of flexicaulin A as antiproliferative agents.

    abstract：:As our research focuses on anticancer drugs, a series of novel derivatives of flexicaulin A (FA), an ent-kaurene diterpene, condensed with an aromatic ring were synthesized, and their antiproliferative activities against four human cancer cell lines (TE-1, EC109, MCF-7, and MGC-803) were evaluated. The activities of m...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112789

    authors： Huo JF,Hu TX,Dong YL,Zhao JZ,Liu XJ,Li LL,Zhang XY,Li YF,Liu HM,Ke Y,Wang C

    更新日期：2020-12-15 00:00:00

  • Flavonoids from Chinese bayberry leaves induced apoptosis and G1 cell cycle arrest via Erk pathway in ovarian cancer cells.

    abstract：:Ovarian cancer is one of the leading causes of death related to the female reproductive system in western countries. Adverse side effects and resistance to platinum based chemotherapy have become the major obstacles for ovarian cancer treatment. Natural products have gained great attention in cancer treatment in recen...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.01.084

    authors： Zhang Y,Chen S,Wei C,Rankin GO,Ye X,Chen YC

    更新日期：2018-03-10 00:00:00

  • A "natural" approach: synthesis and cytoxicity of monodesmosidic glycyrrhetinic acid glycosides.

    abstract：:Several pentacyclic triterpenoic acids have shown noteworthy antitumor activity, among them betulinic acid as well as oleanolic acid and derivatives thereof. Glycyrrhetinic acid (GA) exhibits some cytotoxic activity albeit this compound is not as active as betulinic acid, but GA came in the focus of scientific interes...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.11.024

    authors： Schwarz S,Siewert B,Xavier NM,Jesus AR,Rauter AP,Csuk R

    更新日期：2014-01-24 00:00:00

  • Anthracene-9, 10-dione derivatives induced apoptosis in human cervical cancer cell line (CaSki) by interfering with HPV E6 expression.

    abstract：:A new series of anthracene-9, 10-dione derivatives have been synthesized to increase cytotoxic activity against human papillomavirus (HPV) positive cancer cell line, CaSki. The highest cytotoxicity was achieved by 4-(benzylamino)-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl 4-ethylbenzenesulfonate (5) with the inhib...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.02.006

    authors： Sangthong S,Sangphech N,Palaga T,Ngamrojanavanich N,Puthong S,Vilaivan T,Muangsin N

    更新日期：2014-04-22 00:00:00

  • Structure-based drug design: Synthesis and biological evaluation of quinazolin-4-amine derivatives as selective Aurora A kinase inhibitors.

    abstract：:Aurora kinases play critical roles in the regulation of the cell cycle and mitotic spindle assembly. Aurora A kinase, a member of the Aurora protein family, is frequently highly expressed in tumors, and selective Aurora A inhibition serves as a significant component of anticancer therapy. However, designing highly sel...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.08.053

    authors： Long L,Wang YH,Zhuo JX,Tu ZC,Wu R,Yan M,Liu Q,Lu G

    更新日期：2018-09-05 00:00:00

  • In situ and in silico evaluation of amine- and folate-terminated dendrimers as nanocarriers of anesthetics.

    abstract：:The search for new nano-systems for targeted biomedical applications and controlled drug release has attracted significant attention in polymer chemistry, pharmaceutics, and biomaterial science. Controlled drug delivery has many advantages over conventional drug administration, such as reduction of side effects, maint...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.11.040

    authors： Carrasco-Sánchez V,Vergara-Jaque A,Zuñiga M,Comer J,John A,Nachtigall FM,Valdes O,Duran-Lara EF,Sandoval C,Santos LS

    更新日期：2014-02-12 00:00:00

  • Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol and its enantiomers. Part 1.

    abstract：:The synthesis of (2RS)-1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol ((RS)-9) and its enantiomers has been described and tested for electrocardiographic, antiarrhythmic, hypotensive and spasmolytic activities as well as for alpha(1)-, alpha(2)- and beta(1)-adrenoceptors' binding affinities. All ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2008.05.019

    authors： Groszek G,Bednarski M,Dybała M,Filipek B

    更新日期：2009-02-01 00:00:00

  • Synthesis and antimicrobial activities of a new series of 4-S-[4(1)-amino-5(1)-oxo-6(1)-substituted benzyl-4(1),5(1)-dihydro-1(1),2(1),4(1)-triazin-3-yl]mercaptoacetyl-3-arylsydnones.

    abstract：:The synthesis of some 4-S-(4(1)-amino-5(1)-oxo-6(1)-substituted benzyl-4(1),5(1)-dihydro-1(1),2(1),4(1)-triazin-3-yl)mercaptoacetyl-3-arylsydnones by the reaction of 3-aryl-4-bromoacetylsydnones with 6-substituted-4-amino-3-mercapto-1,2,4-triazin-5-ones is described. The IR, (1)H NMR, mass spectra and elemental analys...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2008.02.003

    authors： Hegde JC,Girisha KS,Adhikari A,Kalluraya B

    更新日期：2008-12-01 00:00:00

  • Discovery of 5-bromo-4-phenoxy-N-phenylpyrimidin-2-amine derivatives as novel ULK1 inhibitors that block autophagy and induce apoptosis in non-small cell lung cancer.

    abstract：:UNC51-like kinase1 (ULK1) recruits its binding partners and initiates the autophagy process in cancer. ULK1 is significantly overexpressed in Non-small cell lung cancer (NSCLC) and negatively correlated with clinical prognosis in NSCLC patients. Based upon the binding features of ULK1, we explored the pharmacophore mo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112782

    authors： Sun D,Yang Z,Zhen Y,Yang Y,Chen Y,Yuan Y,Zhang L,Zeng X,Chen L

    更新日期：2020-12-15 00:00:00

  • Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare.

    abstract：:In our continued efforts to improve the potential utility of the α-methylene-γ-lactone scaffold, 62 new and 59 known natural α-methylenelactam analogues including α-methylene-γ-lactams, α-arylidene-γ and δ-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the α-methylenelactone s...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.02.050

    authors： Delong W,Lanying W,Yongling W,Shuang S,Juntao F,Xing Z

    更新日期：2017-04-21 00:00:00

  • Cannabinoid agonists showing BuChE inhibition as potential therapeutic agents for Alzheimer's disease.

    abstract：:Designing drugs with a specific multi-target profile is a promising approach against multifactorial illnesses as Alzheimer's disease. In this work, new indazole ethers that possess dual activity as both cannabinoid agonists CB2 and inhibitors of BuChE have been designed by computational methods. On the basis of this k...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.11.026

    authors： González-Naranjo P,Pérez-Macias N,Campillo NE,Pérez C,Arán VJ,Girón R,Sánchez-Robles E,Martín MI,Gómez-Cañas M,García-Arencibia M,Fernández-Ruiz J,Páez JA

    更新日期：2014-02-12 00:00:00

  • Molecular design, synthesis and biological research of novel pyridyl acridones as potent DNA-binding and apoptosis-inducing agents.

    abstract：:A series of novel pyridyl acridone derivatives comprised of a pseudo-five-cyclic system to extend the π-conjugated acridone chromophore, were designed and synthesized as potent DNA binding antitumor compounds. Most synthesized compounds displayed good activity against human leukemia K562 cells in MTT tests, with compo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.02.003

    authors： Zhang B,Chen K,Wang N,Gao C,Sun Q,Li L,Chen Y,Tan C,Liu H,Jiang Y

    更新日期：2015-03-26 00:00:00

  • The structural requirements of histone deacetylase inhibitors: C4-modified SAHA analogs display dual HDAC6/HDAC8 selectivity.

    abstract：:Histone deacetylase (HDAC) enzymes govern the post-translational acetylation state of lysine residues on protein substrates, leading to regulatory changes in cell function. Due to their role in cancers, HDAC proteins have emerged as promising targets for cancer treatment. Four HDAC inhibitors have been approved as ant...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.10.076

    authors： Negmeldin AT,Knoff JR,Pflum MKH

    更新日期：2018-01-01 00:00:00

  • Known drug space as a metric in exploring the boundaries of drug-like chemical space.

    abstract：:In this work, marketed drug compounds (or known drug space) were used as a metric to test the principles of eliminating parent structures of the nitrenium ion (aryl-amine/nitro compounds) as well as sulphur and halogen containing molecules from screening compound collections. Molecules containing such moieties and/or ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2009.08.014

    authors： Mirza A,Desai R,Reynisson J

    更新日期：2009-12-01 00:00:00

  • Synthesis of new isoxazoline-based acidic amino acids and investigation of their affinity and selectivity profile at ionotropic glutamate receptors.

    abstract：:The synthesis of four new isoxazoline-based amino acids being analogues of previously described glutamate receptor ligands is reported and their affinity for ionotropic glutamate receptors is analyzed in comparison with that of selected model compounds. Molecular modelling investigations have been carried out to ratio...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2010.12.020

    authors： Pinto A,Conti P,Grazioso G,Tamborini L,Madsen U,Nielsen B,De Micheli C

    更新日期：2011-02-01 00:00:00

  • Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway.

    abstract：:Ferrocene compounds are a class of biologically active compounds that has antitumour and antifungal properties. This study investigated the induction of apoptosis in human fibrosarcoma cells (HT1080) after treatment with a series of 6-ferrocenyl-3-subsituted7H-1,2,4-triazolo[3,4-b]- 1,3,4-thiadiazine (FTFs). We found ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.08.007

    authors： Miao R,Wei J,Lv M,Cai Y,Du Y,Hui X,Wang Q

    更新日期：2011-10-01 00:00:00

  • Identification of crizotinib derivatives as potent SHIP2 inhibitors for the treatment of Alzheimer's disease.

    abstract：:SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2) is a lipid phosphatase that produce phosphatidylinositol 3,4-bisphosphate (PI(3,4)P2) from phosphatidylinositol 3,4,5-triphosphate (PI(3,4,5)P3), and is involved in many diseases such as neurodegenerative diseases. A recent report demonstrating that SHIP2 inhibit...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.07.071

    authors： Lim JW,Kim SK,Choi SY,Kim DH,Gadhe CG,Lee HN,Kim HJ,Kim J,Cho SJ,Hwang H,Seong J,Jeong KS,Lee JY,Lim SM,Lee JW,Pae AN

    更新日期：2018-09-05 00:00:00

  • Discovery of pyrazole as C-terminus of selective BACE1 inhibitors.

    abstract：:We recently discovered and reported dual inhibitor 5 of AChE and BACE1 with N-benzylpiperidine ethyl as C-terminus. Compound 5 showed potent inhibitory activities for BACE1, and could reduce endogenous Aβ1-40 production in APP transgenic mice. In present work, we rapidly identified substituted triazole as the C-termin...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.06.027

    authors： Zou Y,Xu L,Chen W,Zhu Y,Chen T,Fu Y,Li L,Ma L,Xiong B,Wang X,Li J,He J,Zhang H,Xu Y,Li J,Shen J

    更新日期：2013-10-01 00:00:00

  • Synthesis and cytotoxicity of novel ursolic acid derivatives containing an acyl piperazine moiety.

    abstract：:This study designed and synthesized a series of novel ursolic acid derivatives in an attempt to develop potent antitumor agents. Their structures were confirmed using MS, IR, (1)H NMR and (13)C NMR. The inhibitory activities of the title compounds against the MGC-803 (gastric cancer cell) and Bcap-37 (breast cancer ce...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2012.08.048

    authors： Liu MC,Yang SJ,Jin LH,Hu DY,Xue W,Song BA,Yang S

    更新日期：2012-12-01 00:00:00

  • Synthesis of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as potential antitumor and antifungal agents.

    abstract：:A new series of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines 6a-g and 7a-g were obtained with high regioselectivity from the reaction of triamino- or tetraaminopyrimidines 4 and 5 with α,β-unsaturated carbonyl compounds 3a-g based on 2,4-dichlorothiazol-5-carbaldehyde 1. Twelve of the synthesized...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.01.053

    authors： Ramírez J,Svetaz L,Quiroga J,Abonia R,Raimondi M,Zacchino S,Insuasty B

    更新日期：2015-03-06 00:00:00

  • Para-sulfonatocalix[n]arene-based biomaterials: Recent progress in pharmaceutical and biological applications.

    abstract：:The history, properties, and characteristics of para-sulfonato-calixarenes are described. On the one hand, the inherent antibacterial and antifungal properties against microorganisms, and on the other hand non-toxicity of these supramolecules toward human organs are analyzed. The resulting biocompatibility of para-sul...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2020.112121

    authors： Bahojb Noruzi E,Molaparast M,Zarei M,Shaabani B,Kariminezhad Z,Ebadi B,Shafiei-Irannejad V,Rahimi M,Pietrasik J

    更新日期：2020-03-15 00:00:00

  • Synthesis and characterization of binary and ternary complexes of diclofenac with a methyl-beta-CD and monoethanolamine and in vitro transdermal evaluation.

    abstract：:Here, we describe the chemical characterization of the inclusion complex between diclofenac (DCF) and methyl-beta-cyclodextrin (M-beta-CD) in the presence or absence of monoethanolamine (MEA). Several techniques were used to analyze the complex both in solution and in the solid state. Solubility of DCF was increased b...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2010.05.068

    authors： Mora MJ,Longhi MR,Granero GE

    更新日期：2010-09-01 00:00:00

  • 10-Boronic acid substituted camptothecin as prodrug of SN-38.

    abstract：:Malignant tumor cells have been found to have high levels of reactive oxygen species such as hydrogen peroxide (H2O2), supporting the hypothesis that a prodrug could be activated by intracellular H2O2 and lead to a potential antitumor therapy. In this study, the 7-ethyl-10-boronic acid camptothecin (B1) was synthesize...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.03.063

    authors： Wang L,Xie S,Ma L,Chen Y,Lu W

    更新日期：2016-06-30 00:00:00

  • Synthesis and evaluation of xanthine oxidase inhibitory and antioxidant activities of 2-arylbenzo[b]furan derivatives based on salvianolic acid C.

    abstract：:Xanthine oxidase (XO) is the key enzyme in humans which is related to a variety of diseases such as gout, hyperuricemia and cardiovascular diseases. In this work, a series of 2-arylbenzo[b]furan derivatives were synthesized based on salvianolic acid C, and they were evaluated for xanthine oxidase inhibitory and antiox...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.08.019

    authors： Tang HJ,Zhang XW,Yang L,Li W,Li JH,Wang JX,Chen J

    更新日期：2016-11-29 00:00:00

  • Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives.

    abstract：:A series of 2-substituted amino-3-chloro-1,4-naphthoquinone derivatives (3-12) were synthesized as anticancer agents and tested against four cancer cell lines including HepG2, HuCCA-1, A549 and MOLT-3. The most potent cytotoxic activity against the HepG2, HuCCA-1 and A549 cell lines was found to be m-acetylphenylamino...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.07.024

    authors： Prachayasittikul V,Pingaew R,Worachartcheewan A,Nantasenamat C,Prachayasittikul S,Ruchirawat S,Prachayasittikul V

    更新日期：2014-09-12 00:00:00