1-O-Substituted derivatives of murrayafoline A and their antifungal properties

Abstract

The synthesis of some 1-oxygenated derivatives of murrayafoline A (1) and their antifungal properties is reported. Three derivatives, 1-hydroxy-3-methyl-9H-carbazole (2), 1-(3-methylbut-2-enyloxy)-3-methyl-9H-carbazole (3) and 1-(2,3,4,6,-tetra-O-acetyl-alpha-D-O-glucopyranosyl)-3-methyl-9H-carbazole (4), of murrayafoline A were synthesized. Compounds 1 and 2 exhibit strong fungicidal activity against Cladosporium cucumerinum at the dose of 12.5 microg.

Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles

“…Using carbazole 5bb as a precursor, we undertook the formal synthesis of murrayafoline A ( 8 , Scheme 5 ). Murrayafoline A is a monomeric carbazolic alkaloid that has been isolated from kilograms of the dried powdered roots of several species of the genus Murraya , Glycosmis , and Clausena in up to 3% yield [ 51 , 52 , 53 ]. Murrayafoline A was shown to exhibit a number of interesting biological activities including strong fungicidal activity (12.5 µg dose against C. cucumerinum ) [ 52 ], cancer growth inhibitory activity (HT-1080 cells) [ 53 ], and Wnt/β-catenin signaling antagonist activity [ 54 ].…”

“…Murrayafoline A is a monomeric carbazolic alkaloid that has been isolated from kilograms of the dried powdered roots of several species of the genus Murraya , Glycosmis , and Clausena in up to 3% yield [ 51 , 52 , 53 ]. Murrayafoline A was shown to exhibit a number of interesting biological activities including strong fungicidal activity (12.5 µg dose against C. cucumerinum ) [ 52 ], cancer growth inhibitory activity (HT-1080 cells) [ 53 ], and Wnt/β-catenin signaling antagonist activity [ 54 ]. It has been the target of numerous several syntheses due to its role as a precursor to access a variety of congeners and non-natural derivatives.…”

Synthesis of pyrophosphate analogues and their cytotoxic activities

“…The synthesis was initiated with acridone, 4-hydroxycoumarin, and two bioactive natural compounds, murrayafoline A and zerumbone, which can be easily isolated as the major active ingredients from the rhizomes of Glycosmis stenocarpa 15 and Zingiber zerumbet, 16 respectively. Compounds 4a-d were obtained from murrayafoline A and zerumbone using the procedures of Cuong et al 15 and Chinh et al 17 The Huisgen 1,3-dipolar cycloaddition was used as the key reaction for the preparation of the desired final products 6a-f.…”

“…Purification was performed on silica gel (CH 2 Cl 2 /acetone 3:1). 24.17 (dd, J = 6.5, 3.7 Hz, CH 3 ), 24.00 (dd, J = 8.9, 5.3 Hz, CH 3 ), 16.47 (d, J = 5.9 Hz, O-CH2-CH 3 ), 15 4-(((4E,8E)-1,5,10,10-tetramethyl-7-oxo-13-oxa-6-azabicyclo[10.1.0]trideca-4,8-dien-6-yl) methyl)-1H-1,2,3-triazol-1-yl)methyl)phosphoryl)methyl) phosphonate (6d): Compound 6d (300 mg, 49%) was obtained as a white oil from intermediate 3 (328 mg, 1 mmol) using the general procedure (24 h). Purification was performed on silica gel (CH 2 Cl 2 /acetone 3:1).…”

A Concise Synthesis of 1-Oxygenated Carbazole Alkaloids, Clausine E and Clausine F

“…Accordingly, O-prenylation of clausine E was attempted by heating with prenyl bromide in the presence of potassium carbonate in acetone, however no product formation was observed. Hence, we carried out O-prenylation of clausine E through a Mitsunobu reaction, 31 which provided the O-prenylated ether of clausine E 15 in good yield. Further heating of product 15 to reflux in diethylaniline gave clausine F through p-Claisen rearrangement with 54% yield in just 12 minutes (Scheme 3).…”