Staff – Medicinal Chemistry

Assoc. Prof. Dr. Charnsak Thongsornkleeb

Category Staff - Medicinal Chemistry
26 Jan 2023
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Name : Assoc. Prof. Dr. Charnsak Thongsornkleeb (Research Scientist II)
Office Address : Room : R412 / R619
Laboratory of Medicinal Chemistry
54 Kamphaeng Phet 6 Talat Bang Khen, Lak Si, Bangkok 10210, Thailand
Tel : +66 2553 8555 (ext. 3089, 3041)
Email : [email protected]

Research Interests
Synthetic methodology
Synthesis of heterocycles
Radical chemistry

Education
2000 – 2006 Ph.D Organic Chemistry, Massachusetts Institute of Technology, U.S.A.
1997 – 2000 B.S. Chemistry, University of Connecticut, U.S.A.

Work Experiences
2019 – present Research Scientist II, Chulabhorn Research Institute, Thailand
2015 – 2019 Research Scientist I, Chulabhorn Research Institute, Thailand
2008 – 2015 Research Scientist, Chulabhorn Research Institute, Thailand

Awards
1996 – 2005 Development and Promotion of Science and Technology Talents Project Scholarship
2018 Asian CORE Program (ACP) Lectureship Award from People Republic of China (PRC)
2017 Asian CORE Program (ACP) Lectureship Award from Japan
2015 Newton Professional Development Training for Mid-Career Researchers
2012 Asian CORE Program (ACP) Lectureship Award from the Republic of China (Taiwan)
2006 – 2008 Postdoctoral Fellow from the City University of New York, USA
1999 – 2000 The Catherine DeStefano Rossi Memorial Scholar, University of Connecticut, USA
1998 – 1999 Dean’s List Scholar, College of Liberal Arts and Sciences, University of Connecticut, USA

Publications
Selected Publications

  1. Chaisan, N.; Ruengsangtongkul, S.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Dihalooxygenation of Alkynes and Alkynols: Preparation of 2,2-Dihaloketones and gem-Dihalolactols. Synlett 2022, 33, 1426–1430.
  2. Ruengsangtongkul, S.; Kuribara, T.; Chaisan, N.; Tummatorn, J.; Thongsornkleeb,C.; Ruchirawat, S. Ceric Ammonium Nitrate‐Promoted Oxidative Coupling of Terminal Alkynes and 1,3‐Ketoesters: A Synthesis of Unsymmetrical 1,1,2‐Triacylalkenes. Synlett 2022, 33, 1329–1334.
  3. Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. A Compilation of Synthetic Strategies to Access the Most Utilized Indoloquinoline Motifs. Chem. Asian J. 2022, 17, e202200040.
  4. Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Utilization of ortho-alkynylarylcarbonyl derivatives for creating structurally diverse chemical compounds. Org. Biomol. Chem. 2021, 19, 5982–5998.
  5. Punjajom, K.; Tummatorn, J.; Ruchirawat, S.; Thongsornkleeb, C. PdCl2‐Catalyzed Oxidative Cyclization of N‐(2’‐Alkynylaryl)‐1,3‐ketoamides: Synthesis of 3,4‐Diacyl‐2‐Quinolones. Asian J. Org. Chem. 2021, 10, 906–917.
  6. Chaisan, N.; Ruengsangtongkul, S.; Tummatorn, J.; Ruchirawat, S.; Chainok, K.; Thongsornkleeb, C. Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[d][1,3]oxazines and Their Application in the Synthesis of 4H-Furo[3,2-b]indoles. J. Org. Chem. 2021, 86, 4671–4698.
  7. Norseeda, K.; Chaisan, N.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters. J. Org. Chem. 2019, 84, 16222–16236.
  8. Tummatorn, J.; Punjajom, K.; Rodphon, W.; Ruengsangtongkul, S.; Chaisan, N.; Lumyong, K.; Thongsornkleeb, C.; Nimnual, P.; Ruchirawat, S. Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3. Org. Lett. 2019, 21, 4694–4697.
  9. Ruengsangtongkul, S.; Chaisan, N.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters. Org. Lett. 2019, 21, 2514–2517.
  10. Chaisan, N.; Kaewsri, W.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles. Tetrahedron Lett. 2018, 59, 675–680.
  11. Kaewsri, W.; Norseeda, K.; Ruengsangtongkul, S.; Chaisan, N.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Synthesis of 2-cyclohexenone-2-carboxylate and 4-chloro-2-cyclohexenone-2-carboxylate derivatives via cyclization of alkyne-tethered 1,3-ketoesters. Asian J. Org. Chem. 2018, 7, 203–211.
  12. Kaewsri, W.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Isomerizable (E/Z)-alkynyl-O-methyl oximes employing TMSCl–NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles. RSC Adv. 2016, 6, 48666–48675.
  13. Aroonkit, P.; Thongsornkleeb, C.; Tummatorn, J.; Krajangsri, S.; Mungthin, M.; Ruchirawat, S. Synthesis of isocryptolepine analogues and their structure–activity relationship studies as antiplasmodial and antiproliferative agents. Eur. J. Med. Chem. 2015, 94, 56–62.
  14. Maibunkaew, T.; Thongsornkleeb, C.; Tummatorn, J.; Bunrit, A.; Ruchirawat, S. Practical and Metal-Free Electrophilic Aromatic Halogenation by Interhalogen Compounds Generated In Situ from N-Halosuccinimide and Catalytic TMSCl. Synlett 2014, 25, 1769–1775.
  15. Thongsornkleeb, C.; Rabten, W.; Bunrit, A.; Tummatorn, J.; Ruchirawat, S. Facile access to 2,5-disubstituted-4-chloromethyl-3-iodofuran derivatives via ICl-mediated cyclization of 1-alkyl-2-alkynylallylic alcohols. Tetrahedron Lett. 2012, 53, 6615–6619.
  16. Bunrit, A.; Ruchirawat, S.; Thongsornkleeb, C. A simple microwave-assisted preparation of 2-bromo-1-alkenes from 1-alkynes using the LiBr–TMSCl–TEAB reagent system. Tetrahedron Lett. 2011, 52, 3124–3127.

Other Publications

  1. Palavong, N.; Jantrapirom, J.; Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S. Acid-dependent Divergent Conversion of ortho-Arylcyclopropanecarbonyl Carboxaldehydes for the Synthesis of Furanodibenzocycloheptenes and Dibenzocycloheptenes. Asian J. Org. Chem. 2022, e202200507 (manuscript accepted)
  2. Rodphon, W.; Jaithum, K.; Linkhum, S.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Synthesis of Naphtho[2,3-d]oxazoles via Ag(I) Acid-Mediated Oxazole-Benzannulation of ortho-Alkynylamidoarylketones. J. Org. Chem. 2022 (ASAP) (DOI: 10.1021/acs.joc.2c00940).
  3. Khorphueng, P.; Tummatorn, J.; Patumanon, W.; Thongsornkleeb, C.; Chonradeenitchakul, S.; Ruchirawat, S. Photoinduced C–C bond cleavage for the synthesis of 2,4-disubstituted-1-naphthols from indenone derivatives and sulfoxonium ylide. Org. Biomol. Chem. 2022, 20, 5520–5524.
  4. Laohapaisan, P.; Lumyong, K.; Tummatorn, J.; Thongsornkleeb, C.; Chatwichien, J.; Supantanapong, N.; Ruchirawat, S. Ag(I)-Catalyzed/Acid-Mediated Cascade Cyclization of ortho-Alkynylaryl-1,3-dicarbonyls to Access Arylnaphthalenelactones and Furanonaphthol Libraries via Aryl-Disengagement. Chem. Asian J. 2021, 17, e202101212.
  5. Rodphon, W.; Laohapaisan, P.; Supantanapong, N.; Reamtong, O.; Ngiwsara, L.; Lirdprapamongkol, K.; Thongsornkleeb, C.; Khunnawutmanotham, N.; Tummatorn, J.; Svasti, J.; Ruchirawat, S. Synthesis of Isocryptolepine-Triazole Adducts and Evaluation of Their Cytotoxic Activity. ChemMedChem 2021, 16, 3750–3762.
  6. Reamtong, O.; Lapmanee, S.; Tummatorn, J.; Palavong, N.; Thongsornkleeb, C.; Ruchirawat, S. Synthesis of Benzoazepine Derivatives via Azide Rearrangement and Evaluation of Their Antianxiety Activities. ACS Med. Chem. Lett. 2021, 12, 1449–1458.
  7. Jaithum, K.; Tummatorn, J.; Boekfa, B.; Thongsornkleeb, C.; Chainok, K.; Ruchirawat, S. Diastereoselective Synthesis of Spirocyclic Ether from ortho-Carbonylarylacetylenols via Silver-Catalyzed Cyclization under Acidic Conditions. Adv. Synth. Catal. 2021, 363, 3812–3834.
  8. Rodphon, W.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Synthesis of 4‐Acylchromene via Highly Chemoselective Iodine‐Catalyzed Cyclization of Alkynylarylether Dimethylacetals. Chem. Asian J. 2020, 15, 3475–3486.
  9. Laohapaisan, P.; Chuangsoongnern, P.; Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S. Divergent Synthesis of 3-Hydroxyfluorene and 4-Azafluorene Derivatives from ortho-Alkynylarylketones. J. Org. Chem. 2019, 84, 14451–14460.
  10. Nimnual, P.; Tummatorn, J.; Boekfa, B.; Thongsornkleeb, C.; Ruchirawat, S.; Piyachat, P.; Punjajom, K. Construction of 5-Aminotetrazoles via in Situ Generation of Carbodiimidium Ions from Ketones Promoted by TMSN3/TfOH. J. Org. Chem. 2019, 84, 5603–5613.
  11. Supantanapong, N.; Chuangsoongnern, P.; Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S. One-pot sequential synthesis of 3-carbonyl-4-arylbenzo[f]indole and 3-carbonyl-4-arylnaphthofuran fluorophores. Org. Chem. Front. 2019, 6, 1340–1355.
  12. Akkachairin, B.; Tummatorn, J.; Khamsuwan, N.; Thongsornkleeb, C.; Ruchirawat, S. Domino N2-Extrusion-Cyclization of Alkynylarylketone Derivatives for the Synthesis of Indoloquinolines and Carbocycle-Fused Quinolines. J. Org. Chem. 2018, 83, 11254–11268.
  13. Nimnual, P.; Norseeda, K.; Akkachairin, B.; Tummatorn, J.; Laohapaisan, P.; Supantanapong, N.; Chuangsoongnern, P.; Thongsornkleeb, C.; Sittihan, S.; Ruchirawat, S.; Rodphon, W. Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A. Asian J. Org. Chem. 2018, 7, 932–945.
  14. Chuangsoongnern, P.; Surinrach, C.; Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S. Iodine-Mediated Cyclization of ortho-Alkynylaryl Ketones for the Synthesis of Indenone Derivatives. Eur. J. Org. Chem. 2017, 2017, 5102–5109.
  15. Akkachairin, B.; Tummatorn, J.; Supantanapong, N.; Nimnual, P.; Thongsornkleeb, C.; Ruchirawat, S. Silver-Catalyzed Cyclization of ortho-Carbonylarylacetylenols for the Synthesis of Dihydronaphthofurans. J. Org. Chem. 2017, 82, 3727–3740.
  16. Jantaree, P.; Lirdprapamongkol, K.; Kaewsri, W.; Thongsornkleeb, C.; Choowongkomon, K.; Atjanasuppat, K.; Ruchirawat, S.; Svasti, J. Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway. J. Agric. Food Chem. 2017, 65, 2299–2306.
  17. Norseeda, K.; Tummatorn, J.; Krajangsri, S.; Thongsornkleeb, C.; Ruchirawat, S. Synthesis of 6-Alkyl-6H-benzo[c]chromene Derivatives by Cyclization/Selective Ether Cleavage in One Pot: Total Synthesis of Cannabinol. Asian J. Org. Chem. 2016, 5, 792–800.
  18. Nimnual, P.; Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S. Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles and Benzisoxazoles. J. Org. Chem. 2015, 80, 8657–8667.
  19. Tummatorn, J.; Poonsilp, P.; Nimnual, P.; Janprasit, J.; Thongsornkleeb, C.; Ruchirawat, S. Regioselective Synthesis of 3‑Bromoquinoline Derivatives and Diastereoselective Synthesis of Tetrahydroquinolines via Acid-Promoted Rearrangement of Arylmethyl Azides. J. Org. Chem. 2015, 80, 4516–4525.
  20. Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S.; Thongaram, P.; Kaewmee, B. Convenient and Direct Azidation of sec-Benzyl Alcohols by Trimethylsilyl Azide with Bismuth(III) Triflate Catalyst. Synthesis 2015, 47, 323–329.
  21. Tummatorn, J.; Krajangsri, S.; Norseeda, K.; Thongsornkleeb, C.; Ruchirawat, S. A new synthetic approach to 6-unsubstituted phenanthridine and phenanthridine-like compounds under mild and metal-free conditions. Org. Biomol. Chem. 2014, 12, 5077–5081.
  22. Tummatorn, J.; Gleeson, M. P.; Krajangsri, S.; Thongsornkleeb, C.; Ruchirawat, S. ZrCl4-promoted facile synthesis of indole derivatives. RSC Adv. 2014, 4, 20048–20052.
  23. Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S.; Gettongsong, T. Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process. Org. Biomol. Chem. 2013, 11, 1463–1467.
  24. Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S. Acid-promoted rearrangement of arylmethyl azides: applications toward the synthesis of N-arylmethyl arenes and polycyclic heteroaromatic compounds. Tetrahedron 2012, 68, 4732–4739.
  25. Fearnley, S. P.; Thongsornkleeb, C. Oxazolone Cycloadducts as Heterocyclic Scaffolds for Alkaloid Construction: Synthesis of (±)-2-epi-Pumiliotoxin C. J. Org. Chem. 2010, 75, 933–936.
  26. Thongsornkleeb, C.; Danheiser, R. L. A Practical Method for the Synthesis of 2-Alkynylpropenals.  J. Org. Chem. 2005, 70, 2364–2367.
  27. Bailey, W. F.; England, M. D.; Mealy, M. J.; Thongsornkleeb, C.; Teng, L.  Facile O-Deallylation of Allyl Ethers via SN2′ Reaction with tert-Butyllithium.  Org. Lett. 2000, 2, 489–491.

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