Unusual anthelminthic oxazoles from a marine sponge

Adamczeski, Madeline; Quiñoá, Emilio; Crews, Phillip

doi:10.1021/ja00213a037

Cited by 86 publications

(76 citation statements)

References 3 publications

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“…The latter also confirmed C(6')-C(7') bonding and established the C(2')-C( 1') and C(S')-C(7') bonds. On account of the remaining N-and 0-atoms, and NMR signals fitting for a 2,4-disubstituted oxazole [6], the entire side chain was thus elucidated.…”

mentioning

confidence: 99%

Leucascandrolide A, a New Type of Macrolide: The first powerfully bioactive metabolite of calcareous sponges (Leucascandra caveolata, a new genus from the coral sea)

D’Ambrosio¹,

Guerriero²,

Pietra³

et al. 1996

Helvetica Chimica Acta

142

110

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Leucascdndrolide A ((+)-l), a doubly 0-bridged 18-membered macrolide of a new type, i.e., showing little C,-branching vs. extensive 1,3-dioxygenation and a peculiar side chain, was isolated from a calcareous sponge of a new genus, Leucuscundra caveoluta BOROJEVIC and KLAUTAU from the Coral Sea. Transesterification of (+)-1 gave the methyl ester 3, derived from the side chain, and the 5-hydroxy derivative (+)-2, derived from the macrolide portion and with the natural configuration at C(5) (axial). Mosher's MTPA esters 4 and 5 obtained from (+)-2 showed scattered AS = (S(S) -6 ( R ) ) data. However, inversion of the configuration at C(5) led, via ketone (+)-6, to the less encumbered 5-equatorial hydroxy derivative (+)-7, whose MTPA esters 8 and 9 gave consistent AS data, allowing the assignment of the absolute configuration of (+)-7, and hence of (+)-1. The structural novelty of (+)-1 and its powerful antifungal and cytotoxic activities are likely to renew interest in calcareous sponges, previously limited to scarcely biologically active 2-aminoimidazoles.

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mentioning

confidence: 99%

Leucascandrolide A, a New Type of Macrolide: The first powerfully bioactive metabolite of calcareous sponges (Leucascandra caveolata, a new genus from the coral sea)

D’Ambrosio¹,

Guerriero²,

Pietra³

et al. 1996

Helvetica Chimica Acta

142

110

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show abstract

“…In order to confirm the configuration of the new stereocentersc yclic 1,3-dioxolane 37 was synthesized and ad etailed NMR study was performed, [25] in which the coupling constant (J 1,2 = 8.9 Hz) revealed a trans configuration at C1-C2. [26] It is important to emphasize that 31 presentsacomplementary relative stereochemistryt ot hat of 27 (Scheme 12). Thiss tereodivergency is an oteworthy accomplishmentofo ur methodology.…”

Section: Reactivity Of 14-diolsmentioning

confidence: 99%

Sulfinyl‐Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes

Colomer

Ureña

Viso

et al. 2020

Chemistry A European J

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The chemo‐ and stereocontrolled functionalization of conjugated sulfinyl dienes in a cascade process that involves a conjugate addition, diastereoselective protonation and a [2,3]‐sigmatropic rearrangement is reported. Enantioenriched 1,4‐diol and 1,4‐aminoalcohol derivatives are obtained in a very straightforward manner. Further functionalization of these structures, including highly stereoselective epoxidation, dihydroxylation and the stereodivergent synthesis of several polyols in a controlled fashion is described.

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“…The history of the bengazoles commences in 1988 when Crews and co-workers [34] isolated, from a huge amount of Jaspidae sponge collected from new locations in the Benga Lagoon, Fiji, two unusual oxazoles, bengazoles A ( 229 ) and B ( 230 ). Subsequently, in 1993, Crews et al [109] discovered, in a Papua New Guinea specimen an inseparable mixture of seven new bengazoles (C 2 , D 2 , C 3 , D 3 , C 4 , D 4 and C 9 ) accompanied by bengamides A and B.…”

Section: Chemistry and Biology Of The Bengazolesmentioning

confidence: 99%

“…In addition, bengazole A ( 229 ), exhibits anthelminthic activity against Nippostrongylus braziliensis at a concentration of 50 µg/mL [34]. Letourneux et al [29] evaluated the antifungal properties against Candida albicans CIP 118079, detecting a very active profile for bengazoles 245 – 250 , with MIC values from 0.8 to 1.5 µM.…”

Section: Chemistry and Biology Of The Bengazolesmentioning

confidence: 99%

Chemistry and Biology of Bengamides and Bengazoles, Bioactive Natural Products from Jaspis Sponges

García‐Ruiz

Sarabia

2014

Marine Drugs

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Sponges corresponding to the Jaspidae family have proved to be a prolific source of bioactive natural products. Among these, the bengamides and the bengazoles stand out by virtue of their unprecedented molecular architectures and impressive biological profiles, including antitumor, antibiotic and anthelmintic properties. As a consequence, intense research activity has been devoted to these compounds from both chemical and biological standpoints. This review describes in detail the research into these classes of natural products and the benefits they offer in chemistry and biology.

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Unusual anthelminthic oxazoles from a marine sponge

Cited by 86 publications

References 3 publications

Leucascandrolide A, a New Type of Macrolide: The first powerfully bioactive metabolite of calcareous sponges (Leucascandra caveolata, a new genus from the coral sea)

Leucascandrolide A, a New Type of Macrolide: The first powerfully bioactive metabolite of calcareous sponges (Leucascandra caveolata, a new genus from the coral sea)

Sulfinyl‐Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes

Chemistry and Biology of Bengamides and Bengazoles, Bioactive Natural Products from Jaspis Sponges

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