- Rhodium-Catalyzed Direct Arylation of Furopyridine: Synthesis and the Cardiac Effects of Dictamnine Derivatives
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Herein is reported a Rh2(OAc)4/IMes ? HCl system that promotes the chemoselective installation of aryl groups at the 2-position of furo[2,3-b]pyridine (53–94% yields). The method is applicable to the direct modification of the natura
- Du, Yufeng,Huang, Linyu,Wang, Neng,Li, Xiaohuan,Zhou, Xian-Li,Zhang, Lan,Huang, Shuai,Walsh, Patrick J.,Gao, Feng
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p. 1002 - 1008
(2022/02/07)
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- Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: Chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids
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Biotransformation of acridine, dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings.
- Boyd, Derek R.,Sharma, Narain D.,Carroll, Jonathan G.,Loke, Pui L.,O'Dowd, Colin R.,Allen, Christopher C. R.
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p. 10944 - 10955
(2013/09/02)
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- 4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3
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The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC50 of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC50s of 150 nM to 10 μM in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC50 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers.
- Bodendiek, Silke B.,Mahieux, Cedrick,Haensel, Wolfram,Wulff, Heike
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experimental part
p. 1838 - 1852
(2009/09/08)
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- Synthesis of (+)-myrtopsine, (+)-7,8-dimethoxymyrtopsine, and related 2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methyl-ethyl)benzofuran natural products
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The first syntheses of myrtopsine (8t) and 7,8-dimethoxymyrtopsine (9t) have been carried out by halogen-metal exchange of 3-iodo-4-methoxy-quinolin-2(1H)-ones (15) and (21) with i-PrMgCl followed by addition of 3,3-dimethyloxirane-2-carboxaldehyde (1). A two-step sequence leads selectively to trans-2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl)benzofurans (7t), (8t), (9t), (28), and (32) by conversion of a 2-iodophenol or a 3-iodo-4-methoxyquinolin-2(1H)-one to an aryl Grignard reagent and addition of 3-methyl-2-butenal, followed by threo selective epoxidation of the resulting allylic alcohol and cyclization with inversion.
- Snider, Barry B.,Wu, Xiaoxing
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p. 279 - 294
(2008/04/18)
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- New synthesis of linear furoquinoline alkaloids
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A new synthetic method for the synthesis of the linear furoquinoline alkaloids, dictamnine, γ-fagarine, evolitrine and pteliene from 3-oxiranylquinoline using dimethylsulfonium methylide is described.
- Bhoga, Umadevi,Mali,Adapa, Srinivas R.
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p. 9483 - 9485
(2007/10/03)
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- Natural Product Chemistry, 114. - Dictamnine and Derivatives by Pd/Cu-Catalysed Alkyne Coupling
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The Pd/Cu-catalysed reaction of 3-iodo-4-methoxy-2(1H)-quinolinone (6) with (trimethylsilyl)ethyne yields 2-(trimethylsilyl)dictamnine (4) or the coupling product 3.The furoquinoline alkaloid dictamnine (1) is obtained by addition of fluoride to 4.The deuteriodesilylation of 4 to dictamnine (1a) is also possible.Further 1-alkynes afford 2-substituted furoquinolines.With 2-methyl-3-butyn-2-ol the coupled quinoline 9 is available, too.Starting with ethyl propiolate, the N-vinyl adduct 12 is generated.
- Reisch, Johannes,Bathe, Andreas
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- A New Synthesis of Dictamnine, Evolitrine and 6-Methyldictamnine
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A new synthesis of dictamnine (2a), evolitrine (2b), and 6-methyldictamnine (2c) starting from 4-carboxy-3-vinyl-2-quinolones (1a-c) is reported.
- Rajamanickam, P.,Shanmugam, P.
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p. 910 - 913
(2007/10/02)
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- A NEW METHOD FOR INTRODUCING THE 2,2-DICHLOROETHYL GROUP AT THE 3-POSITION OF THE 2-QUINOLONE SYSTEM, AND THE SYNTHESIS OF DICTAMNINE
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A novel method is described for the introducing the 2,2-dichloroethyl group at the 2-quinolone ring.The method from 4-substituted 2-quinolone consists of 1) photoaddition of the quinolone to 1,1-dichloroethylene, 2) base treatment of the cross adduct giving a bicyclobutane, and 3) conversion of the latter to the final product with hydrogen chloride.By applying this reaction to 4-methoxy-2-quinolone, a short-step synthesis of dictamnine is accomplished.KEYWORDS - photo cycloaddition; 2,2-dichloroethylation; furoquinoline; dictamnine; 1,1a-methanocyclopropaquinoline; cyclobutaquinoline; 2-quinolone
- Sato, Masayuki,Kawakami, Katsuhiro,Kaneko, Chikara
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p. 1319 - 1321
(2007/10/02)
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