Nopporn Thasana, Ph.D.

Green chemistry, Microwave-assisted organic synthesis and organometallic chemistry
Research in Dr. Thasana’s lab focuses on the synthesis of bioactive lactone and lactam molecules. His group studies the Cu(I)-mediated/MW-assisted C-O/N bond formation under “subcritical water” conditions as “Green Chemistry” to synthesize bioactive benzopyranone (urolithins A-C), novobiocin, and indolo-2-carboxamide analogs. Moreover chemistry of oxazolone and coumarin derivatives has been studied to develop efficient synthetic routes for a wide range of structurally complex natural products using metal catalysis or metal-free condition in key step. The natural bioactive alkaloids, lamellarin, clausenamide and naucleamide derivatives, will be synthesized using the developed synthetic methodology.

Natural products chemistry
A part from his interest in organic synthesis, he is also interested the screening and isolation of Lycopodium alkaloids having complex skeleton characteristics from Lycopodaceae/Huperziaceae plants. Huperzine A (HupA), firstly isolated from Huperzia serrata a traditional Chinese folk medicine, is a well known biological activity for acetylcholinesterase (AChE) inhibition. The investigation of phytochemical constituents of club mosses in Thailand has been studied. As well as dimer and hybrid of huperzine A have been synthesized to develop a more potent AChE inhibitor.

1. Nilsu, T.; Thaisaeng, W.; Thamnarak, W.; Jumraksa, A.; Thorroad S.; Khunnawutmanotham, N.; Ruchirawat, S.; Thasana, N. Three Lycopodium alkaloids from Thai club mosses. Phytochemistry 2018, 156, 83-88. Full Text
2. 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. Full Text
3. Pongpamorn, P.; Wan-erlor, S.; Ruchirawat, S.; Thasana, N. Semi-synthetic studies of α-onocerin derivative for cytotoxicity. Phytochemistry Lett. 2018, 23, 106-115. Full Text
4. Bag, B. G.; Hasan, S. N.; Pongpamorn, P.; Thasana, N. First hierarchical self-assembly of a seco-triterpenoid α-onocerin yielding supramolecular architectures: entrapment and release of fluorophores including an anticancer drug. ChemistrySelect 2017, 2, 6650-6657. Full Text
5. Nealmongkol, P.; Calmes, J.; Ruchirawat, S.; Thasana, N. Copper and Palladium Mediated C-N bond Formation: Synthesis of Phenanthridinones. Tetrahedron 2017, 73, 735-741. Full Text
6. 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. Full Text
7. 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. Full Text
8. Nilsu, T.; Thorroad, S.; Ruchirawat, S.; Thasana, N. New Lycopodium alkaloids from Thai and Philippine Huperzia squarrosa. Planta Med. 2016, 82, 1046-1050. Full Text
9. 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. Full Text
10. Thorroad, S.; Worawittayanont, P.; Khunnawutmanotham, N.; Chimnoi, N.; Jumruksa, A.; Ruchirawat, S.; Thasana, N. Three new Lycopoium alkaloids from Huperzia carinata and H. squarrosa. Tetrahedron 2014, 70, 8017-8022, doi: 10.1026/j.tet.2014.08.042. Full Text
11. 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. Full Text
12. Worayuthakarn, R.; Boonya-udtayan, S.; Ruchirawat, S.; Thasana, N. Total synthesis of scandione and calophione A. Eur. J. Org. Chem. 2014, 2496-2507, doi: 10.1002/ejoc.201301722. Full Text
13. 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, doi: 10.1026/j.tet.2013.08.045. Full Text
14. 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, doi: 10.1026/j.tet.2012.10.011. Full Text
15. Worayuthakarn, R.; Nealmongkol, P.; Ruchirawat, S.; Thasana, N. Synthesis of benzoindoloquinolizines via Cu(I)-mediated C-N bond formation. Tetrahedron 2012, 68, 2864-2875, doi: 10.1026/j.tet.2012.01.094. Full Text
16. 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, doi: 10.1026/j.phytochem.2012.01.006. Full Text
17. 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. Full Text
18. 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, doi 10.1021/ol202895u.Full Text
19. 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.Full Text
20. 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.Full Text
21. 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. Full Text
22. 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 β-amino acid. FEBS Lett. 2010, 584, 3209-3214.Full Text
23. 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.Full Text
24. Thasana, N.; Bjerke-Kroll, B.; Ruchirawat, S. A facile synthesis of telisatin A via microwave-promoted annulation and Reformatsky reaction. Synlett 2008, 505-508. Full Text
25. 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.Full Text
26. 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.Full Text
27. Thasana, N.; Pisutjaroenpong, S.; Ruchirawat, S. Two protocols for the conversion of biphenol to binaphthol: Synthesis of diospyrol. Synlett 2006, 1080-1084. Full Text
28. 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. Full Text
29. Sahakitpichan, P.; Thasana, N.; Ruchirawat, S. Efficient synthesis of diospyrol via Suzuki-Miyaura and modified in situ cross-coupling. Synthesis 2005, 2934-2938.Full Text
30. 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.Full Text
31. 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.Full Text
32. Thasana, N.; Ruchirawat, S. Directed remote metalation: The synthesis of wrightiadione. Synlett 2003, 1037-1039.Full Text
33. Thasana, N.; Prachyawarakorn, V.; Tontoolarug, S.; Ruchirawat, S. Synthesis of aryl α-keto esters via the rearrangement of aryl cyanohydrin carbonate esters. Tetrahedron Lett. 2003, 44, 1019-1021.Full Text
34. Chuankamnerdkarn, M.; Sutthivaiyakit, S; Thasana, N.; Pisutjaroenpong, S. Prenylated isoflavones from Derris scandens. Heterocycles 2002, 57, 1901-1906.Full Text
35. 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.Full Text
36. 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, 4515-4517.Full Text
37. Karig, G.; Thasana, N.; Gallagher, T. Directed deprotonation-transmetalation of 4-bromopyridine: Flexible routes to substituted pyridines. Synlett 2002, 808-810.Full Text
38. Ruchirawat, S.; Thasana N. The first synthesis of wrightiadione. Synth. Commun. 2001, 31, 1765-1769.Full Text
39. Thasana, N.; Chuankamnerdkarn, M.; Ruchirawat, S. A new 12a-hydroxyelliptone from the stems of Derris malaccensis. Heterocycles 2001, 55, 1121-1125. Full Text