Staff – Medicinal Chemistry

Dr. Poonsakdi Ploypradith

Category Staff - Medicinal Chemistry
26 Jan 2023
1,632
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Name : Dr. Poonsakdi Ploypradith (Expert Scientist)
Office Address : Room : R517 / R403B
Laboratory of Medicinal Chemistry
54 Kamphaeng Phet 6 Talat Bang Khen, Lak Si, Bangkok 10210, Thailand
Tel : +66 2553 8555 (ext. 3069, 3044)
Email : [email protected]

Research Interests
Synthetic methodology: stereoselective cyclization
Total synthesis of natural products
Medicinal chemistry of selected bioactive natural/synthetic compounds

Education
1997 – 1999 Ph.D. Organic Chemistry, The Johns Hopkins University, U.S.A.
1994 – 1996 M.A. Organic Chemistry, The Johns Hopkins University, U.S.A.
1990 – 1994 B.A. Chemistry, The Johns Hopkins University, U.S.A.

Work Experiences
2022 – present Expert Scientist, Chulabhorn Research Institute, Thailand
2015 – 2022 Research Scientist II, Chulabhorn Research Institute, Thailand
2009 – 2015 Research Scientist I, Chulabhorn Research Institute, Thailand
2000 – 2009 Research Scientist, Chulabhorn Research Institute, Thailand
2007 – present Lecturer, Program in Chemical Sciences, Chulabhorn Graduate Institute, Thailand

Awards
2017 Lectureship Award to Taiwan (Asian Core Program)
2017 Lectureship Award to Korea (Asian Core Program)
2011 Lectureship Award to Hong Kong (Asian Core Program)
2011 Lectureship Award to Malaysia (Asian Core Program)
2009 Lectureship Award to Taiwan (Asian Core Program)
2009 Lectureship Award to Singapore (Asian Core Program)
2008 Lectureship Award to Korea (Asian Core Program)
2008 Lectureship Award to China (Asian Core Program)
1995 The Ernest M Marks Award for Excellence in Research and Instructrion, John Hopkins University
1994 Phi Beta Kappa National Honor Society, Johns Hopkins University, U.S.A.
1993 Golden Key National Honor Society, Johns Hopkins University, U.S.A.
1993 Alpha Epsilon Delta Premedical Honor Society, Johns Hopkins University, U.S.A.
1989 – 1994 King’s Scholarship

Publications
Selected Publications

  1. Akkarasereenon, K.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. Functionalized Chromans from ortho-Quinone Methides and Arylallenes. J. Org. Chem. Accepted.
  2. Songthammawat, P.; Phumjan, T.; Ruchirawat, S.; Ploypradith, P. 4b-Aryltetrahydroindeno[1,2-a]indenes from Acid-Catalyzed Transannular Cyclization of Benzannulated Cyclooctene Alcohols. Synlett 2022, 33, 1312–1316.
  3. Tangdenpaisal, K.; Songthammawat, P.; Ruchirawat, S.; Ploypradith, P. Total Synthesis of Palodesangrens A and C. J. Org. Chem. 2022, 87, 386–398.
  4. Klumthong, K.; Chalermsub, P.; Sopha, P.; Ruchirawat, S.; Ploypradith, P. An Expeditious Modular Hybrid Strategy for the Diversity-Oriented Synthesis of Lamellarins/Azalamellarins with Anticancer Cytotoxicity. J. Org. Chem. 2021, 86, 14883–14902.
  5. Phumjan, T.; Songthammawat, P.; Jongcharoenkamol, J.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. Substituted 9-Anthraldehydes from Dibenzocycloheptanol Epoxides via Acid-Catalyzed Epoxide Opening/Semipinacol Rearrangement. J. Org. Chem. 2021, 86, 13322–13349.
  6. Akkarasereenon, K.; Tangdenpaisal, K.; Ruchirawat, S.; Ploypradith, P. Chemoselective Acid-Catalyzed [4+2]-Cycloaddition Reactions of ortho-Quinone Methides and Styrenes/Stilbenes/Cinnamates. Org. Biomol. Chem. 2020, 18, 8854–8866.
  7. Tangdenpaisal, K.; Songthammawat, P.; Akkarasereenon, K.; Chuayboonsong, K.; Ruchirawat, S.; Ploypradith, P. Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core. J. Org. Chem. 2019, 84, 13410–13429.
  8. Lekky, A.; Ruengsatra, T.; Ruchirawat, S.; Ploypradith, P. Stereoselective Convergent Synthesis of Tetrahydro-5H-benzo[c]fluorene via Nine-Membered Ring-Closing Metathesis and Transannular Acid-Mediated Cyclization/Nucleophilic Addition. J. Org. Chem. 2019, 84, 5277–5291.
  9. Jongcharoenkamol, J.; Chuathong, P; Amako, Y.; Kono, M.; Poonswat, K.; Ruchirawat, S; Ploypradith, P. Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of (Z)- and (E)-(2-Stibenyl)methanols and its Application for the Synthesis of Paucifloral F Derivatives. J. Org. Chem. 2018, 83, 13184–13210.
  10. Songthammawat, P.; Wangngae, S.; Matsumoto, K.; Duangkamol, C.; Ruchirawat, S.; Ploypradith, P. Bio-Inspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH4-Mediated Isomerization, and Acid-Mediated Cyclization. J. Org. Chem. 2018, 83, 5225–5241.
  11. Tangdenpaisal, K.; Chuayboonsong, K.; Ruchirawat, S.; Ploypradith, P. A Divergent Strategy for the Diastereoselective Synthesis of the Tricyclic 6,7-diaryl-tetrahydro-6H-benzo[c]chromene Core via Pt(IV)-catalyzed Cycloaddition of ortho-Quinone Methides and Olefin Ring-closing Metathesis. J. Org. Chem. 2017, 82, 2672–2688.
  12. Theppawong, A.; Ploypradith, P.; Chuawong, P.; Ruchirawat, S.; Chittchang, M. Facile and Divergent Synthesis of Lamellarins and Lactam-Containing Derivatives with Improved Drug-likeness and Biological Activities. Chem. Asian J. 2015, 10, 2631–2650.
  13. Tangdenpaisal, K.; Chuayboonsong, K.; Sukjarean, P.; Katesampao, V.; Noiphrom, N.; Ruchirawat, S.; Ploypradith, P. Synthesis of C4-C5 Cycloalkyl-Fused and C6-Modified Chromans via ortho-Quinone Methides. Chem. Asian J. 2015, 10, 1050–1064.
  14. Tangdenpaisal, K.; Worayuthakarn, R.; Karnkla, S.; Ploypradith, P.; Intachote, P.; Sengsai, S.; Saimanee, B.; Ruchirawat, S.; Chittchang, M. Designing New Analogs for Streamlining the Structure of Cytotoxic Lamellarin Natural Products. Chem. Asian J. 2015, 10, 925–937.
  15. Sarnpitak, P.; Trongchit, K.; Kostenko, Y.; Sathalalai, S.; Gleeson, M. P.; Ruchirawat, S.; Ploypradith, P. Synthesis of Substituted 2-Arylindanes from E-(2-Stilbenyl)methanols via Lewis Acid-Mediated Cyclization and Nucleophililc Transfer from Trialkylsilyl Reagents.  J. Org. Chem. 2013, 78, 8281–8296.
  16. Tangdenpaisal, K.; Phakhodee, W.; Ruchirawat, S.; Ploypradith, P. Facile Synthesis of Diarylmethanes via Quinone Methides.  Tetrahedron 2013, 69, 933–941.
  17. Radomkit, S.; Sarnpitak, P.; Tummatorn, J.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. Pt(IV)- and Au(III)-Catalyzed Generation of o-Quinone Methides and [4+2]-Cycloaddition Reactions. Tetrahedron 2011, 67, 3904–3914.
  18. Tummatorn, J.; Ruchirawat, S.; Ploypradith, P. A Convergent General Strategy for the Functionalized 2-Aryl Cycloalkyl-fused Chromans: Intramolecular Hetero Diels—Alder (HDA) Reactions of ortho-Quinone Methides (o-QMs).  Chem. Eur. J. 2010, 16, 1445–1448.
  19. Batsomboon, P.; Phakhodee, W.; Ruchirawat, S.; Ploypradith, P. Generation of ortho-Quinone Methides by p-TsOH on Silica and Their Hetero-Diels—Alder Reactions with Styrenes.  J. Org. Chem. 2009, 74, 4009–4012.
  20. Tangdenpaisal, K.; Sualek, S.; Ruchirawat, S.; Ploypradith, P. Factors Affecting Orthogonality in the Deprotection of 2,4-Di-Protected Aromatic Ethers Employing Solid-Supported Acids.  Tetrahedron 2009, 65, 4316–4325.
  21. Chittchang, M.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. Cytotoxicities and Structure-Activity Relationships of Natural and Unnatural Lamellarins towards Cancer Cell Lines.  ChemMedChem 2009, 4, 457–465.
  22. Ploypradith, P.; Cheryklin, P.; Niyomtham, N.; Bertoni, D. R.; Ruchirawat, S. Solid-Supported Acids as Mild and Versatile Reagents for the Deprotection of Aromatic Ethers.  Org. Lett. 2007, 9, 2637–2640.
  23. Ploypradith, P.; Petchmanee, T.; Sahakitpichan, P.; Litvinas, N. D.; Ruchirawat, S. Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings.  J. Org. Chem. 2006, 71, 9440–9448.
  24. Petchmanee, T.; Ploypradith, P.; Ruchirawat, S. Solid-Supported Acids for Debenzylation of Aryl Benzyl Ethers.  J. Org. Chem. 2006, 71, 2892–2895.
  25. Ploypradith, P.; Kagan, R. K.; Ruchirawat, S. Utility of Polymer-Supported Reagents in the Total Synthesis of Lamellarins.  J. Org. Chem. 2005, 70, 5119–5125.
  26. Ploypradith, P.; Mahidol, C.; Sahakitpichan, P.; Wongbundit, S.; Ruchirawat, S. A Highly Efficient Synthesis of Lamellarins K and L by the Michael Addition/Ring-Closure Reaction of Benzyldihydroisoquinoline Derivatives with Ethoxycarbonyl-beta-nitrostyrenes.  Angew. Chem. Int. Ed. 2004, 43, 866–868.
  27. Ploypradith, P.; Jinagleung, W.; Pavaro, C.; Ruchirawat, S. Further Development in the Synthesis of Lamellarin Alkaloids via Metal-halogen Exchange.  Tetrahedron Lett. 2003, 44, 1363–1366.

Other Publications

  1. Ngamnithiporn, A.; Cheuntragool, P.; Ploypradith, P.; Ruchirawat, S. Syntheses of 3-Aryl Tetrahydroisoquinolines via an Intermolecular [4 + 2] Cycloaddition of Sultines with Imines. Org. Lett. 2022, 24, 4192–4196.
  2. Pailee, P.; Ploypradith, P.; Mahidol, C.; Ruchirawat, S.; Prachyawarakorn, V. Dulcisenes C-E, Polyoxygenated Cyclohexenes, from Ulvaria dulcis Dunal and their Cytotoxic Activity. Phytochemistry 2022, 202, 114398.
  3. Sopha, P.; Phutubtim, N.; Chantrathonkul, B.; Ploypradith, P.; Ruchirawat, S.; Chittchang, M. Roles of Autophagy in Relation to Mitochondrial Stress Responses of HeLa Cells to Lamellarin Cytotoxicity. Toxicology 2021, 462, 152963.
  4. Akkarasamiyo, S.; Ruchirawat, S.; Ploypradith, P.; Samec, J. S. M. Transition-Metal-Catalyzed Suzuki-Miyaura-Type Cross-Coupling Reactions of p-Activated Alcohols. Synthesis 2020, 52, 645–659.
  5. Pailee, P.; Prawat, H.; Ploypradith, P.; Mahidol, C.; Ruchirawat, S.; Prachyawarakorn, W. Atalantiaphyllines A-G, Prenylated Acridones from Atalantia monophyla DC. and their Aromatase Inhibition and Cytotoxic Activities. Phytochemistry 2020, 180, 112525.
  6. Toewiwat, N.; Whangsuk, W.; Ploypradith, P.; Mongkolsuk, S.; Loprasert, S. Cefoperazone Induces Esterase B Expression by EstR and Esterase B Enhances Cefoperazone Activity at the Periplasm. Int. J. Med. Microbiol. 2020, 310, 151396.
  7. Eurtivong, C.; Choowongkomon, K.; Ploypradith, P.; Ruchirawat, S. Molecular Docking Study of Lamellarin Analogues and Identification of Potential Inhibitors of HIV-1 Integrase Strand Transfer Complex by Virtual Screening. Heliyon 2019, 5, e02811.
  8. Ieawsuwan, W.; Pingaew, R.; Kunkaewom, S.; Ploypradith, P.; Ruchirawat, S. Scandium(III)-Triflate-Catalyzed Pinacol-Pinacolone Rearrangement and Cyclization of 1,2-Diaryl-1,2-Ethanediol: A Versatile Synthesis of 1-Aryl-2,3-Dihydro-1H-Benzazepines. Asian J. Org. Chem. 2019, 8, 1441–1447.
  9. Sungkeeree, P.; Toewiwat, N.; Whangsuk, W.; Ploypradith, P.; Mongkolsuk, S.; Loprasert, S. The Esterase B from Sphingobium sp. SM42 Has the New Dearenethiolase Activity against Cephalosporin Antibiotics. Biochem. Biophys. Res. Commun. 2018, 506, 231–236.
  10. Kitisripanya, T.; Inyai, C.; Krittanai, S.; Likhitwitayawuid, K.; Sritularak, B.; Ploypradith, P.; Tanaka, H.; Morimoto, S.; Putalun, W. Monoclonal Antibody-based Immunoassay for Determination of Oxyresveratrol from Artocarpus lacucha Buch.-Ham. J. Nat. Med. 2017, 71, 523–530.
  11. Tadtong, S.; Chatsumpun, N.; Sritularak, B.; Jongbunprasert, V.; Ploypradith, P.; Likhitwitayawuid, K. Effects of Oxyresveratrol and its Derivatives on Cultured P19-derived Neurons. Trop. J. Pharm. Res. 2016, 15, 2619–2628.
  12. Yasamut, K.; Jongcharoenkamol, J.; Ruchirawat, S.; Ploypradith, P. A Modified Cu(0)-Cu(I)-mediated Caryl-Caryl Ullmann Coupling for the Synthesis of Biaryls. Tetrahedron 2016, 72, 5994–6000.
  13. Chatsumpun, N.; Chuanasa, T.; Sritularak, B.; Lipipun, V.; Jongbunprasert, V.; Ruchirawat, S.; Ploypradith, P.; Likhitwitayawuid, K. Oxyresveratrol: Structural Modification and Evaluation of Biological Activities. Molecules 2016, 21, 489.
  14. Tangdenpaisal, K.; Ruchirawat, S.; Ploypradith, P. Synthesis of the Thyroid Hormone Analog GC-1 via Bi(OTf)3-Catalyzed Benzylation.  Tetrahedron 2014, 70, 6789–6795.
  15. Disadee, W.; Ploypradith, P.; Aree, T.; Ruchirawat, S. A Novel Approach for the Synthesis of Lophocladines A, B and C1 Analogues.  Tetrahedron Lett. 2011, 52, 6142–6144.
  16. Thipnate, P.; Chittchang, M.; Thasana, N.; Saparpakorn, P.; Ploypradith, P.; Hannongbua, S. Exploring the Molecular Basis for Selective Cytotoxicity of Lamellarins against Human Hormone-Dependent T47D and Hormone-Independent MDA-MB-231 Breast Cancer Cells. Monatsh. Chem. 2011, 142, 97–109.
  17. Pungkham, H.; Swatdipakdi, N.; Theerasilp, M.; Chittchang, M.; Karnkla, S.; Ploypradith, P.; Nasongkla, N. PEG-b-PCL and PEG-b-PLA Polymeric Micelles as Nanocarriers for Lamellarin N Delivery. IEEE 2011, 3245–3248.
  18. Chittchang, C.; Gleeson, M. P.; Ploypradith, P.; Ruchirawat, S. Assessing the Drug-Likeness of Lamellarins, a Marine Derived Natural Product Class with Diverse Oncological Activities.  Eur. J. Med. Chem. 2010, 45, 2165–2172.
  19. Phakhodee, W.; Ploypradith, P.; Sahakitpichan, P.; Ruchirawat, S. A New Synthetic Approach towards Isoquinobenzazepinone and Isoindolinobenzazepinone Using Acid-Mediated Cyclisation and Heck Reaction.  Tetrahedron 2009, 65, 351–356.
  20. Baunbæk, D.; Trinkler, N.; Ferandin, Y.; Lozach, O.; Ploypradith, P.; Ruchirawat, S.; Ishibashi, F.; Iwao, M.; Meijer, L. Anticancer Alkaloid Lamellarins Inhibit Protein Kinases.  Mar. Drugs 2008, 6, 514–527.
  21. Worayuthakarn, R.; Boonya-udtayan, S.; Arom-oon, E.; Ploypradith, P.; Ruchirawat, S.; Thasana, N. Synthesis of Unsymmetrical Benzil Licoagrodione.  J. Org. Chem. 2008, 73, 7432–7435.
  22. Likhitwitayawuid, K.; Sornsute, A.; Sritularak, B.; Ploypradith, P. Chemical Transformations of Oxyresveratrol (trans-2,4,3’,5’-tetrahydroxystilbene) into a Potent Tyrosinase Inhibitor and a Strong Cytotoxic Agent.  Bioorg. Med. Chem. Lett. 2006, 16, 5650–5653.
  23. Ploypradith, P. Development of Artemisinin and Its Structurally Simplified Trioxane Derivatives as Antimalarial Drugs.  Invited Review, Acta Tropica 2004, 89, 329–342.
  24. Bachi, M. D.; Korshin, E. E.; Hoos, R.; Szpilman, A. M.; Ploypradith, P.; Xie, S.; Shapiro, T. A.; Posner, G. H. A Short Synthesis and Biological Evaluation of Potent and Nontoxic Antimalarial Bridged Bicyclic b-Sulfonyl-endoperoxides.  J. Med. Chem. 2003, 46, 2516–2533.
  25. Takai, S.; Ploypradith, P.; Hamajima, A.; Kira, K.; Isobe, M. Sodium Hypophosphite Decomplexation of Acetylenebiscobalthexacarbonyls to cis-Olefins. Synlett 2002, 588–592.
  26. Posner, G. H.; Jeon, H. B.; Ploypradith, P.; Paik, I.-H.; Borstnik, K.; Xie, S.; Shapiro, T. A. Orally Active, Water-Soluble Antimalarial 3-Aryltrioxanes: Short Synthesis and Preclinical Efficacy Testing in Rodents.  J. Med. Chem. 2002, 45, 3824–3828.
  27. Posner, G. H.; Ploypradith, P.; Parker, M. H.; O’Dowd, H.; Woo, S. H.; Northrop, J. K.; Krasavin, M.; Dolan, P.; Kensler, T. W.; Xie, S.; Shapiro, T. A. Antimalarial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers.  J. Med. Chem. 1999, 42, 4275–4280.
  28. O’Dowd, H.; Ploypradith, P.; Xie, S.; Shapiro, T. A.; Posner, G. H. Antimalarial Artemisinin Analogs.  Synthesis via Chemoselective C-C Bond Formation and Preliminary Biological Evaluation.  Tetrahedron 1999, 55, 3625–3636.
  29. Posner, G. H.; Parker, M. H.; Northrop, J. N.; Elias, J. S.; Ploypradith, P.; Xie, S.; Shapiro, T. A. Orally Active, Hydrolytically Stable, Semisynthetic, Antimalarial Trioxanes in the Artemisinin Family.  J. Med. Chem. 1999, 42, 300–304.
  30. Woo, S. H.; Parker, M. H.; Ploypradith, P.; Northrop, J. K.; Posner, G. H. Direct Conversion of Pyranose Anomeric OH®F®R in the Artemisinin Family of Antimalarial Trioxanes.  Tetrahedron Lett. 1998, 39, 1533–1536.
  31. Posner, G. H.; O’Dowd, H.; Ploypradith, P.; Cumming, J. N.; Xie, S.; Shapiro, T. A. Antimalarial Cyclic Peroxy Ketals. J. Med. Chem. 1998, 41, 2164–2167.
  32. Posner, G. H.; Cumming, J. N.; Woo, S. H.; Ploypradith, P.; Xie, S.; Shapiro, T. A. Orally Active Antimalarial 3-Substituted Trioxanes: New Synthetic Methodology and Biological Evaluation. J. Med. Chem. 1998, 41, 940–951.
  33. Bachi, M. D.; Korshin, E.; Ploypradith, P.; Cumming, J. N.; Xie, S.; Shapiro, T. A.; Posner, G. H. Synthesis and In Vitro Antimalarial Activity of Sulfone Endoperoxides.  Bioorg. Med. Chem. Lett. 1998, 8, 903–908.
  34. Posner, G. H.; O’Dowd, H.; Caffero, T.; Cumming, J. N.; Ploypradith, P.; Xie, S.; Shapiro, T. A. Antimalarial Sulfone Trioxanes.  Tetrahedron Lett. 1998, 39, 2273–2276.
  35. Posner, G. H.; Ploypradith, P.; Hapangama, W.; Wang, D.; Cumming, J. N.; Dolan, P.; Kensler, T. W.; Klinedinst, D.; Shapiro, T. A.; Zheng, Q. Y.; Murray, C. K.; Pilkington, L. G.; Jayasinghe, L. R.; Bray, J. F.; Daughenbaugh, R. Trioxane Dimer Have Potent Antimalarial, Antiproliferative, and Antitumor Activities in vitro. Bioorg. Med. Chem. 1997, 5, 1257–1265.
  36. Posner, G. H.; Cumming, J. N.; Ploypradith, P.; Oh, C. H. Evidence for Fe(IV)=O in the Molecular Mechanism of Action of the Trioxane Antimalarial Artemisinin.  J. Am. Chem. Soc. 1995, 117, 5885–5886.

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