Staff – Medicinal Chemistry

Assoc. Prof. Dr. Nopporn Thasana

Category Staff - Medicinal Chemistry
26 Jan 2023
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Name : Assoc. Prof. Dr. Nopporn Thasana (Research Scientist II)
Office Address : Room : R412 / R403B / R404
Laboratory of Medicinal Chemistry
54 Kamphaeng Phet 6 Talat Bang Khen, Lak Si, Bangkok 10210, Thailand
Tel : +66 2553 8555 (ext. 3041, 3044)
Email : [email protected]

Research Interests
Synthetic Methodology of Heterocycles Derived from Oxazolone Derivatives
Total Synthesis of Natural Products
Natural Products Chemistry of Ferns and Lycophytes
NMR-based Metabolomics of Ferns and Lycophytes

Education
1999 – 2003 Ph.D. Organic Chemistry, Mahidol University, Thailand
1993 – 1996 M.Sc. Organic Chemistry, Mahidol University, Thailand
1989 – 1992 B.Sc. Chemistry, Ramkhamhaeng University, Bangkok

Work Experiences
2018 – present Associate Professor, Chemical Sciences Program, Chulabhorn Graduate Institute, Chulabhorn Royal Academy
2018 – present Chemical Sciences Program Committee, Chulabhorn Graduate Institute, Chulabhorn Royal Academy
2015 – present Research Scientist II, Laboratory of Medicinal Chemistry, Chulabhorn Research Institute
2013 – 2019 Lab Manager, Chemical Biology Program, Chulabhorn Graduate Institute
2010 – 2015 Research Scientist I, Laboratory of Medicinal Chemistry, Chulabhorn Research Institute
2007 – 2018 Lecturer, Chemical Biology Program, Chulabhorn Graduate Institute
2007 – 2018 Chemical Biology Program Committee, Chulabhorn Graduate Institute
1997 – 2010 Research Scientist, Laboratory of Medicinal Chemistry, Chulabhorn Research Institute

Awards
2019 “Chirantan Rasayan Sanstha” Gold Medal Award in the International Symposium Advance Renewable & Functional Materials (Rasayan 4) at Gope Palace, Midnapore. West Bengal, India
2018 Asian Core Program Lectureship Award (Visit to Japan and Korea): The 13th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-13)
2017 Asian Core Program Lectureship Award (Visit to China): The 12th International Conference on Cutting-Edge Organic Chemistry in Asia/The 3rd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-12/ARNCEOCA-3)
2015 Asian Core Program Lectureship Award (Visit to Singapore): The 10th International Conference on Cutting-Edge Organic Chemistry in Asia/The 1st Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-10/ARNCEOCA-1)
2015 The Thailand Research Fund on the Royal Golden Jubilee Scholarship (RGJ17) (PHD/0127/2557; Baht 1,112,000)
2013 The Thailand Research Fund on the Royal Golden Jubilee Scholarship (RGJ16) (PHD/0221/2556; Baht 1,375,000)
2011 Asian Core Program Lectureship Award (Visit to Korea and Taiwan): The 6th International Conference on Cutting-Edge Organic Chemistry in Asia/The 2nd New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-6/NICCEOCA-2)
2010 The Thailand Research Fund on the Royal Golden Jubilee Scholarship (RGJ12) (RGJ52K0028; Baht 1,488,336)
2009 Japan Society for the Promotion of Science-Asian Core Program (JSPS-ACP) on Cutting-Edge Organic Chemistry in Asia: Visiting Scholar at Graduate School of Bio-agriculture, Nagoya University, Japan (JSPS-ACP; Yen 600,000) Host: Professor Toshio Nishikawa
2007 Science and Technology Research Grants; 13th Thailand Toray Science Foundation: (TTSF; Investigator; Baht 238,000)
2003 Japan Society for the Promotion of Science (JSPS)-National Research Council of Thailand (NRCT) Core University Program: Visiting Scholar at Graduate School of Bio-agriculture, Nagoya University, Japan (JSPS-NRCT; Yen 600,000) Host: Professor Minoru Isobe
2001 The Postgraduate Education and Research Program in Chemistry (PERCH), Mahidol University
1999 The Thailand Research Fund on the Royal Golden Jubilee Scholarship (TRF/RGJ. 3.O.MU/41/G.1; Baht 1,195,000): Visiting Student at Bristol University, UK Host: Professor Timothy Gallagher

Publications
Selected Publications

  1. Demehin, A. A.; Thamnarak, W.; Lamtha, T.; Chatwichien, J.; Eurtivong, C.; Choowongkomon, K.; Chainok, K.; Ruchirawat, S.; Thasana, N. Siamenflavones A-C, Three New Biflavonoids from Selaginella siamensis Hieron. and Biflavonoids from Spike Mosses as EGFR Inhibitor. Phytochemistry 2022, 113374, doi.org/10.1016/j.phytochem.2022.113374.
  2. Worayuthakrn, R.; Suddee, N.; Nealmongkol, P.; Ruchirawat, S.; Thasana, N. Copper-mediated C-O/C-N Bond Formation: A Facile Synthesis of 3-Amidocoumarin, 3-Amidoazacoumarin and N-Aeroylindole Derivatives. Synlett 2022, 33, 1431–1437, doi: 10.1055/a-1784–1973.
  3. Thamnarak, W.; Eurtivong, C.; Pollawatn, R.; Ruchirawat, S.; Thasana, N. Two New Norlignans, Siamensinols A and B, from Selaginella siamensis Hieron. and Their Biological Activities. Nat. Prod. Res. 2021, 1–10, doi 10.1080/14786419.2021.2022664.
  4. Anukanon, S.; Pongpamorn, P.; Tiyabhorn, W.; Chatwichien, J.; Niwetmarin, W.; Sessions, R. B.; Ruchirawat, S.; Thasana, N. In silico-guided Rational Drug Design and Semi-synthesis of C(2) Functionalized Huperzine A Derivatives as Acetylcholinesterase Inhibitor. ACS Omega 2021, 6, 19924–19939, doi.org/10.1021/acsomega.1c02875.
  5. Worayuthakarn, R.; Deesiri, S.; Chainok, K.; Wannarit, N.; Ruchirawat, S.; Thasana, N. Highly Regioselective Tandem Reaction of Ene-Yne-Oxazolones Induced by H-Phosphonates: Construction of Phosphinylindane Derivatives. J. Org. Chem. 2021, 86, 9360–9383, https://doi.org/10.1021/acs.joc.1c00609.
  6. Boonya-udtayan, S.; Thasana, N.; Jarussophon, N.; Ruchirawat, S. Serratene Triterpenoids and their Biological Activities from Lycopodiaceae Plants. Fitoterapia 2019, 136, 104181, DOI: 10.1016/j.fitote.2019.104181.
  7. Nilsu, T.; Thaisaeng, W.; Thamnarak, W.; Eurtivong, C.; Jumraksa, A.; Thorroad S.; Khunnawutmanotham, N.; Ruchirawat, S.; Thasana, N. Three Lycopodium Alkaloids from Thai Club Mosses. Phytochemistry 2018, 156, 83–88, https://doi.org/10.1016/j.phytochem.2018.09.001.
  8. Pramthaisong, C.; Worayuthakarn, R.; Pharikornburee, V.; Duangthongyou, T.; Rattanakam, R.; Ruchirawat, S.; Thasana, N. Base-mediated Cascade Cyclization: Stereoselective Synthesis of Benzooxazocinone. Org. Lett. 2018, 20, 4015–4019, https://doi.org/10.1021/acs.orglett.8b01573.
  9. Pongpamorn, P.; Wan-erlor, S.; Ruchirawat, S.; Thasana, N. Semi-synthetic Studies of a-Onocerin Derivative for Cytotoxicity. Phytochemistry Lett. 2018, 23, 106–115, https://doi.org/10.1016/j.phytol.2017.11.017.
  10. Nealmongkol, P.; Calmes, J.; Ruchirawat, S.; Thasana, N. Synthesis of Phenanthridinones Using Cu- or Pd-mediated C-N Bond Formation. Tetrahedron 2017, 73, 735–741, https://doi.org/10.1016/j.tet.2016.12.051.
  11. Pongpamorn, P.; Wan-erlor, S.; Ruchirawat, S.; Thasana, N. Lycoclavatumide and 8β,11α-Dihydroxylycopodine, a New Fawcettimine and Lycopodine-type Alkaloid from Lycopodium clavatum. Tetrahedron 2016, 72, 7065–7069, https://doi.org/10.1016/j.tet.2016.09.046.
  12. Nilsu, T.; Thorroad, S.; Ruchirawat, S.; Thasana, N. Squarrosine A and Pyrrolhuperzine A, New Lycopodium Alkaloids from Thai and Philippine Huperzia squarrosa. Planta Med. 2016, 82, 1046–1050, DOI: 10.1055/s-0042-106904.
  13. Thorroad, S.; Worawittayanont, P.; Khunnawutmanotham, N.; Chimnoi, N.; Jumruksa, A.; Ruchirawat, S.; Thasana, N. Three New Lycopoium Alkaloids from Huperzia carinata and Huperzia squarrosa. Tetrahedron 2014, 70, 8017–8022, https://doi.org/10.1016/j.tet.2014.08.042.
  14. Worayuthakarn, R.; Boonya-udtayan, S.; Ruchirawat, S.; Thasana, N. Total Synthesis of Unsymmetric Benzils, Scandione and Calophione A. Eur. J. Org. Chem. 2014, 2496–2507, https://doi.org/10.1002/ejoc.201301722.
  15. Nealmongkol, P.; Tangdenpaisal, K.; Ruchirawat, S.; Thasana, N. Cu(I)-mediated Lactone Formation in Subcritical Water: A Benign Synthesis of Benzopyranones and Urolithins A-C. Tetrahedron 2013, 69, 9277–9283, https://doi.org/10.1016/j.tet.2013.08.045.
  16. Boonya-udtayan, S.; Eno, M.; Ruchirawat, S.; Mahidol, C.; Thasana, N. Palladium-catalyzed Intramolecular C-H Activation: Synthesis and Biological Activities of Indolobenzazocin-8-ones. Tetrahedron 2012, 68, 10293–10301, https://doi.org/10.1016/j.tet.2012.10.011.
  17. Worayuthakarn, R.; Nealmongkol, P.; Ruchirawat, S.; Thasana, N. Synthesis of Benzoindoloquinolizines via Cu(I)-mediated C-N Bond Formation. Tetrahedron 2012, 68, 2864–2875, https://doi.org/10.1016/j.tet.2012.01.094.
  18. Wittayalai, S.; Sathalalai, S.; Thorroad, S.; Worawittayanon, P.; Ruchirawat, S.; Thasana, N. Lycophlegmariols A-D: Cytotoxic Serratene Triterpenoids from the Club Moss Lycopodium phlegmaria L. Phytochemistry 2012, 76, 117–123, https://doi.org/10.1016/j.phytochem.2012.01.006.
  19. Boonya-udtayan, S.; Yotapan, N.; Woo, C.; Bruns, C. J.; Ruchirawat, S.; Thasana, N. Synthesis and Biological Activities of Azalamellarins. Chem. Asian J. 2010, 5, 2113–2123, https://doi.org/10.1002/asia.201000237.
  20. Thasana, N.; Prapagdee, B.; Rangkadilok, N.; Sallabhan, R.; Lwin Aye, S.; Ruchirawat, S.; Loprasert, S. Bacillus subtilis SSE4 Produces Subtulene A, a New Lipopeptide Possessing an Unusual C15 Unsaturated b-Amino Acid. FEBS Lett. 2010, 584, 3209–3214, https://doi.org/10.1016/j.febslet.2010.06.005.
  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, https://doi.org/10.1021/jo8013353.
  22. Thasana, N.; Bjerke-Kroll, B.; Ruchirawat, S. A Facile Synthesis of Telisatin A via Microwave-promoted Annulation and Reformatsky Reaction. Synlett 2008, 505–508, DOI: 10.1055/s-2008-1042764.
  23. Thasana, N.; Worayuthakarn, R.; Kradanrat, P.; Hohn, E.; Young, L.; Ruchirawat, S. Copper(I)-mediated and Microwave-assisted Caryl-Ocarboxylic Coupling: Synthesis of Benzopyaranones and Isolamellarin Alkaloids. J. Org. Chem. 2007, 72, 9379–9382, https://doi.org/10.1021/jo701599g.
  24. Worayuthakarn, R.; Thasana, N.; Ruchirawat, S. Three Distinct Reactions of 3,4-Dihydroisoquinolines with Azlactones: Novel Synthesis of Imidazoloisoquinolin-3-ones, Benzo[a]quinolizin-4-ones, and Benzo[d]azocin-4-ones. Org. Lett. 2006, 8, 5845–5848, https://doi.org/10.1021/ol062429m.
  25. Thasana, N.; Pisutjaroenpong, S.; Ruchirawat, S. Two Protocols for the Conversion of Biphenol to Binaphthol: Synthesis of Diospyrol. Synlett 2006, 1080–1084, DOI: 10.1055/s-2006-939075.
  26. Sahakitpichan, P.; Thasana, N.; Ruchirawat, S. Efficient Synthesis of Diospyrol via Suzuki-Miyaura and Modified in situ Cross-coupling. Synthesis 2005, 2934–2938, DOI: 10.1055/s-2005-872176.
  27. Thasana, N.; Ruchirawat, S. Directed Remote Metalation: The Synthesis of Wrightiadione. Synlett 2003, 1037–1039, DOI: 10.1055/s-2003-39313.
  28. Thasana, N.; Prachyawarakorn, V.; Tontoolarug, S.; Ruchirawat, S. Synthesis of Aryl a-Keto Esters via the Rearrangement of Aryl Cyanohydrin Carbonate Esters. Tetrahedron Lett. 2003, 44, 1019–1021, https://doi.org/10.1016/S0040-4039(02)02725-9.
  29. Thasana, N.; Ruchirawat, S. The Application of the Baker-Venkataraman Rearrangement to the Synthesis of Benz[b]indeno[2,1-e]pyran-10,11-dione. Tetrahedron Lett. 2002, 43, 4315–4317.
  30. Ruchirawat, S.; Thasana N. The First Synthesis of Wrightiadione. Synth. Commun. 2001, 31, 1765–1769, https://doi.org/10.1081/SCC-100104406.

Other Publications

  1. Ngernnak, C.; Thamnarak, W.; Thaisaeng, W.; Ruchirawat, S.; Thasana, N. Lycopodium Alkaloids from Thai Club Mosses. Prayogik Rasayan 2021, 5(1), 7–16, doi 10.53023/p.rasayan-20210326.
  2. Bag, B. G.; Hasan, S. N.; Pongpamorn, P.; Thasana, N. First Hierarchical Self-assembly of a Seco-triterpenoid a-Onocerin Yielding Supramolecular Architectures. ChemistrySelect 2017, 2, 6650–6657, https://doi.org/10.1002/slct.201701285.
  3. Boonya-udtayan, S.; Chaipattarakit, N.; Thasana, N.; Ruek-ngam, N.; Ruchuirawat, S.; Techasakul, S. Phytochemicals and Their Antibacterial Activity of Lycopodium nummullrifolium Blume. Sci. J. Petchaburi Rajabhat U., 2017, 14, 26–33.
  4. Thiengmag, T.; Whangsuk, W.; Chuencharoen, S.; Thasana, N.; Mongkolsuk, S.; Loprasert, S. Bacterial Consortium Expressing Surface Displayed, Intra and Extracellular Lipases and Pseudopyronine B for the Degradation of oil. Int. J. Environ. Sci. Tech. 2016, 13, 2067–2078, DOI 10.1007/s13762-016-1034-z.
  5. Noomnual, S.; Thasana, N.; Sungkeeree, P.; Mongkolsuk S.; Loprasert, S. Streptanoate, a New Anticancer Butanoate from Streptomyces sp. DC3. J. Antibiotics 2016, 69, 124–127, https://doi.org/10.1038/ja.2015.95.
  6. Isobe, M.; Murata, M.; Hanashima, S.; Nishida, A.; Loh, T. P.; Abd. Rahman, N.; Thasana, N.; Chittchang, M. JSPS Asian Core Program: 7th & 8th ICCEOCA (Phase II/NICCEOCA-3 &-4), 2nd & 3rd Junior ICCEOCA, and Partly IUPAC Asian Project. Chem. Asian J. 2014, 9, 1689–1696, https://doi.org/10.1002/asia.201402189.
  7. Worawittayanon, P.; Ruadree, J.; Disadee, W.; Sahakitpichan, P. Sitthimonchai, S.; Thasana, N.; Ruchirawat, S.; Kanchanapoom, T. Iridoid and Flavone Glycosides from Asystasia salicifolia and Their Antioxidant Activities. Biochemical Systematics and Ecology 2012, 40, 38–42, doi:10.1016/j.bse.2011.08.016.
  8. Adachi, M.; Higuchi, K. Thasana, N.; Yamada, H.; Nishikawa, T. Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain. Org. Lett. 2012, 14, 114–117, https://doi.org/10.1021/ol202895u.
  9. Kanintronkul, Y.; Worayuthakarn, R.; Thasana, N.; Winayanuwattikun, P.; Pattanapanyasat, K.; Surarit, R.; Ruchirawat, S.; Svasti, J. Overcoming Multidrug Resistance in Human Lung Cancer with Novel Benzo[a]quinolizin-4-one Chemomodulators. Anticancer Research 2011, 31, 921–927.
  10. 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. Monatshefte für Chemie 2011, 142, 97–109, https://doi.org/10.1007/s00706-010-0409-y.
  11. Athikomkulchai, S.; Prawat, H.; Thasana, N.; Ruangrungsi, N.; Ruchirawat, S. COX-1, COX-2 Inhibitors and Antifungal Agents from Croton hutchinsonianus. Chem. Pharm. Bull. 2006, 54, 262–264, https://doi.org/10.1248/cpb.54.262.
  12. Tempeam, A.; Thasana, N.; Pavaro, C.; Chuakul, W.; Siripong, P.; Ruchirawat, S. A New Cytotoxic Daphnane Diterpenoid, Rediocide G, from Trigonostermon reidioides. Chem. Pharm. Bull. 2005, 53, 1321–1323, https://doi.org/10.1248/cpb.53.1321.
  13. Kondo, N.; Kuse, M.; Mutarapat, T.; Thasana, N.; Isobe, M. Novel Synthetic Route of Coelenterazines-2-: Synthesis of Various Dehydrocoelenterazine Analogs. Heterocycles 2005, 65, 843–856.
  14. Chuankamnerdkarn, M.; Sutthivaiyakit, S; Thasana, N. Prenylated Isoflavones from Derris scandens. Heterocycles 2002, 57, 1901–1906.
  15. Karig, G.; Moon, M.-T.; Thasana, N.; Gallagher, T. C-H Activation and Palladium Migration within Biaryls under Heck Reaction Conditions. Org. Lett. 2002, 4, 3115–3118, https://doi.org/10.1021/ol026426v.
  16. Karig, G.; Thasana, N.; Gallagher, T. Directed Deprotonation-transmetalation of 4-Bromopyridine: Flexible Routes to Substituted Pyridines. Synlett 2002, 808–810, DOI: 10.1055/s-2002-25342.
  17. Tempeam, A.; Thasana, N.; Thavornkitcharat, A.; Pavaro, C.; Ruchirawat, S. In vitro Cytotoxicity of some Thai Medicinal Plants and Daphanane Diterpenoid from Trigonostemon redioides.  Mahidol U.  J. Pharm. Sci. 2002, 29, 25–31.
  18. Thasana, N.; Chuankamnerdkarn, M.; Ruchirawat, S. A New 12a-Hydroxyelliptone from the Stems of Derris malaccensis. Heterocycles 2001, 55, 1121–1125.

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