484-29-7

Usage

Uses

Used in Pharmaceutical Industry:
DICTAMNINE is used as an antifungal agent for its ability to inhibit the growth of fungi, making it a potential candidate for the development of antifungal medications.
DICTAMNINE is used as a vasal relaxant for its ability to relax blood vessels, which can be beneficial in treating conditions related to vascular constriction.
DICTAMNINE is used as a smooth muscle contractant for its ability to cause contraction in smooth muscles, which can be useful in various therapeutic applications.
Used in Agricultural Industry:
DICTAMNINE is used as a phytotoxic agent for its ability to exhibit anti-microbial activity against bacteria and fungi, making it a potential candidate for the development of biopesticides and other plant protection products.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 843, 1973 DOI: 10.1016/S0040-4039(01)95731-4

InChI:InChI=1/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 530-52-9 furo[2,3-b]quinolin-4(9H)-one 
• 63536-51-6 4-chloro-2,3-dihydro-furo[2,3-b]quinoline 
• 67-56-1 methanol 
• 95874-16-1 4-ethoxy-furo[2,3-b]quinoline 
• 51179-18-1 2,4-dimethoxy-3-formylquinoline 
• 2181-42-2 trimethylsulphonium iodide 
• 60623-06-5 trans-2,3-dihydro-3-hydroxy-4-methoxy-α,α-dimethylfuro[2,3-b]quinoline-2-methanol 
• 115881-29-3 2-Chloro-4-cyano-3-vinylquinoline 
• 30451-18-4 4-Carboxy-3-vinyl-2-quinolone 
• 115881-32-8 2-Methoxy-3-(2'-methoxyethyl)quinoline-4-carboxamide 
• 79105-87-6 4-Methoxy-3-(2-hydroxy-ethyl)-2-oxo-1,2-dihydro-chinolin 
• 51179-21-6 2,4-dimethoxy-3-(2-methoxyethenyl)quinoline 
• 703-61-7 2,4-dichloroquinoline 

Downstream Products

• 484-74-2 iso-dictamnine 
• 530-52-9 furo[2,3-b]quinolin-4(9H)-one 
• 523-61-5 Dictaminsaeure 
• 530-52-9 nordictamnine 
• 2255-50-7 robustine 
• 524-15-2 4,8-dimethoxyfuro[2,3-b]quinoline 
• 2221-41-2 pteleine 
• 627086-17-3 4-chlorofuro[3,2-c]quinoline 

Relevant academic research and scientific papers

Rhodium-Catalyzed Direct Arylation of Furopyridine: Synthesis and the Cardiac Effects of Dictamnine Derivatives

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

Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: Chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids

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.

4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

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.

Synthesis of (+)-myrtopsine, (+)-7,8-dimethoxymyrtopsine, and related 2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methyl-ethyl)benzofuran natural products

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.

New synthesis of linear furoquinoline alkaloids

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.

Natural Product Chemistry, 114. - Dictamnine and Derivatives by Pd/Cu-Catalysed Alkyne Coupling

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.

A NEW METHOD FOR INTRODUCING THE 2,2-DICHLOROETHYL GROUP AT THE 3-POSITION OF THE 2-QUINOLONE SYSTEM, AND THE SYNTHESIS OF DICTAMNINE

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

A New Synthesis of Dictamnine, Evolitrine and 6-Methyldictamnine

A new synthesis of dictamnine (2a), evolitrine (2b), and 6-methyldictamnine (2c) starting from 4-carboxy-3-vinyl-2-quinolones (1a-c) is reported.