50333-13-6Relevant academic research and scientific papers
One-Pot Preparation of Pyranoquinolinones by Ytterbium(III) Trifluoromethanesulfonate-Catalyzed Reactions: Efficient Synthesis of Flindersine, N-Methylflindersine, and Zanthosimuline Natural Products
Lee, Yong Rok,Kweon, Hyuk Il,Koh, Wha Soo,Min, Kyung Rak,Kim, Youngsoo,Lee, Seung Ho
, p. 1851 - 1855 (2001)
An efficient synthesis of pyranoquinolinones is achieved by ytterbium(III) triflate-catalyzed reaction of 4-hydroxy-2-quinolones with a variety of α,β-unsaturated aldehydes in moderate yields. This new method has been applied to the synthesis of pyranoqui
A DIELS-ALDER ADDUCCT OF N-METHYLFLINDERSINE AND A QUINOLONE QUINONE METHIDE
Grundon, Michael F.,Ramachandran, V. N.,Sloan, Barbara M.
, p. 3105 - 3108 (1981)
A quinolone quinone methide (5; R=Me), prepared from 1,3-dimethyl-4-hydroxy-2-quinolone (7) and DDQ, reacted readily with N-methylflindersine (3) to give a single cyclo-addition product (4).
Efficient synthesis of substituted pyranoquinolinones from 2,4-dihydroxyquinoline: Total synthesis of zanthosimuline, cis-3′, 4′-dihydroxy-3′,4′-dihydroflindersine, and orixalone D
Wang, Xue,Yong, Rok Lee
, p. 3044 - 3050 (2007)
A convenient and efficient synthesis of pyranoquinolinones was achieved using the ethylenediamine diacetate catalyzed reactions of 2,4- dihydroxyquinoline and a variety of α,β-unsaturated aldehydes in good yield. The key feature of these reactions is the
Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)
Atangana, Albert Fouda,Fotso, Ghislain Wabo,Happi, Emmanuel Ngeufa,Lenta, Bruno Ndjakou,Mbahbou, Gabin Thierry Bitchagno,Ngadjui, Bonaventure Tchaleu,Noulala, Cédric Guy Tchatchouang,Ouete, Judith Laure Nantchouang,Sewald, Norbert,Stammler, Hans-Georg
, (2022/02/19)
The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2-10. In addition, six semi-synthetic derivatives 3a-c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2-4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1-7 and 9, and semi-synthetic derivatives 3a-c, 4b, 5a and 6a were evaluated for their cyto-toxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.
Asymmetric Total Synthesis and Biological Evaluation of the Natural PDE4 Inhibitor Toddacoumalone
Hou, Ke-Qiang,Chen, Xue-Ping,Huang, Yiyou,Chan, Albert S. C.,Luo, Hai-Bin,Xiong, Xiao-Feng
supporting information, p. 584 - 588 (2020/02/04)
We describe herein the first asymmetric total synthesis and biological evaluation of the natural PDE4 inhibitor toddacoumalone and its stereoisomers. The key step of the total synthesis is a formal asymmetric [4 + 2] cycloaddition reaction catalyzed by chiral secondary amine catalysts. A variety of pyranoquinolinones and 3-methylcrotonaldehyde are well tolerated under the optimized reaction conditions, which paved the way for further SAR studies. Further biological evaluation showed 1a′ with the best PDE4 inhibitory activity (IC50 = 0.18 μM).
Euodenine A: A small-molecule agonist of human TLR4
Neve, Juliette E.,Wijesekera, Hasanthi P.,Duffy, Sandra,Jenkins, Ian D.,Ripper, Justin A.,Teague, Simon J.,Campitelli, Marc,Garavelas, Agatha,Nikolakopoulos, George,Le, Phuc V.,De A. Leone, Priscila,Pham, Ngoc B.,Shelton, Philip,Fraser, Neil,Carroll, Anthony R.,Avery, Vicky M.,McCrae, Christopher,Williams, Nicola,Quinn, Ronald J.
, p. 1252 - 1275 (2014/03/21)
A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-κB reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-α, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.
Microwave-assisted solvent and catalyst free synthesis of 2H-Pyrans
Edayadulla, Naushad,Lee, Yong Rok
, p. 2963 - 2967 (2014/01/06)
This paper describes a simple and efficient method involving domino Knovenegal/6π electrocyclization for the preparation of a variety of 2H-pyrans using microwave irradiation under solvent- and catalyst-free conditions. This method offers the advantages of a green approach, high yields, and short reaction times. Sixteen compounds (9a-p) were obtained in good to excellent yields using the procedure.
Green one-pot synthesis of 2h-pyrans under solvent-free conditions catalyzed by ethylenediammonium diacetate
Riveira, Martin J.,Mischne, Mirta P.
, p. 208 - 220,13 (2020/09/02)
Ethylenediammonium diacetate readily catalyzes the Knoevenagel-type condensation between 1,3-dicarbonyl substrates and ,-unsaturated aldehydes at room temperature under solvent-free conditions. This rapid, efficient, and convenient one-pot approach to the
Synthesis of melicodenines C, D and e
Holla, Harish,Jenkins, Ian D.,Neve, Juliette E.,Pouwer, Rebecca H.,Pham, Ngoc,Teague, Simon J.,Quinn, Ronald J.
supporting information, p. 7101 - 7103 (2013/01/15)
A synthesis of the unusual cyclobutane-quinolinone alkaloids melicodenines C, D and E by intermolecular [2+2] cycloaddition is described.
Environmentally benign, one-pot synthesis of pyrans by domino Knoevenagel/6π-electrocyclization in water and application to natural products
Jung, Ene Jin,Park, Byung Ho,Lee, Yong Rok
experimental part, p. 2003 - 2011 (2011/02/19)
In water medium, environmentally benign, facile, and efficient synthesis of pyrans was achieved in good yields by the reactions of a variety of cyclic 1,3-dicarbonyls with several α,β-unsaturated aldehydes. The key strategy was a formal [3+3] cycloaddition by domino Knoevenagel/6π- electrocyclization. This methodology was applied to the synthesis of biologically interesting pyranocoumarin, pyranoquinolinone, and pyranonaphthoquinone derivatives along with selected natural and non-natural products. The Royal Society of Chemistry 2010.
