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1.
This review is focused on recent synthetic achievements and ongoing work in our laboratory using phenylglycinol-derived oxazolopiperidone lactams as starting materials for the enantioselective synthesis of piperidine-containing alkaloids: madangamines, 2,5-disubstituted decahydroquinoline and 1-substituted tetrahydroisoquinoline alkaloids, the indole alkaloids 20S- and 20R-dihydrocleavamine and quebrachamine, and indole alkaloids of the uleine and silicine groups. 相似文献
2.
[reaction: see text] Pyrrole-imidazole alkaloids are widely distributed in marine sponges of the orders Halichondrida and Agelasida. Chemical investigation of the Caribbean sponge Stylissa caribica led to the isolation of the first tetrameric pyrrole-imidazole alkaloids. The so-called stylissadines are the largest and most complex pyrrole-imidazole alkaloids discovered so far and are therefore a major challenge for the structure determination by NMR spectroscopy. Their isolation and structure elucidation are discussed in detail. 相似文献
3.
S Proto M Amat M Pérez R Ballette F Romagnoli A Mancinelli J Bosch 《Organic letters》2012,14(15):3916-3919
Using simplified model derivatives, the assembly of the macrocyclic rings of madangamines, including the 13- and 14-membered D rings of madangamines C-E, the all-cis-triunsaturated 15-membered D ring of madangamine A, and the (Z,Z)-unsaturated 11-membered E ring common to madangamines A-E, has been studied. 相似文献
4.
PolycycJic marine alkaloids containing 3-alkylpyridine or partially reduced 3-alkylpyridine as basic building blocks represent an emerging and intriguing group of bioactive natural products from marine sponges. Since halitoxin,2 the first example of this kind of alkaloid, was reported in 1978, many related alkaloids have been discovered from sponges of the order Haplosclerida. All of these alkaloids, in spite of formally exhibiting quite different frameworks, could biogeneticaliy derive from bis-3-alkylpyridine or reduced bis-3-alkylpyridine units. In the last decade, the knowledge of this fascinating group of compounds has increased remarkably. A recent review has exhaustively studied occurrence, distribution, plausible biogenetic origin and relatedness, as well as biological activities, of 3-alkylpyridine derived marine alkaloids.3 相似文献
5.
Michael JP 《Natural product reports》2002,19(6):719-741
This review covers the isolation, structure determination, synthesis and biological activity of indolizidine and quinolizidine alkaloids from microbial, plant and animal sources. Included in the review are slaframine; hydroxylated indolizidines and their analogues; alkaloids from ants and amphibians; metabolites of the genera Prosopis, Streptomyces and Nuphar and the Lythraceae; phenanthroindolizidines and related alkaloids; lupin alkaloids; and alkaloids from sponges. tunicates and coccinellid beetles. The literature from July 2000 to June 2001 is reviewed, and 172 references are cited. 相似文献
6.
Philip Crews Xing-Chung Cheng Madeline Adamczeski Jaime Rodríguez Marcel Jaspars Francis J. Schmitz Sarah C. Traeger Evamarie O. Pordesimo 《Tetrahedron》1994,50(48):13567-13574
The isolation and characterization of two new sponge alkaloids, 1,2,3,4-tetrahydro-2-N-methyl-8-hydroxymanzamine A (2) and 1,2,3,4-tetrahydro-8-hydroxymanzamine A (3), is described. These compounds were obtained from Papua New Guinea sponges of the genera Petrosia and Cribochalina, which are in different families of the order Haplosclerida. These new manzamines are close in structure to 8-hydroxymanzamine (4) recently reported from Pachypellina, a Haplosclerid sponge belonging to a different family than that of the two preceding sponges. The cytotoxicity of 2 is described and the biogenetic relationship of 2 or 3 to manzamine A (1) and to nine other related polycyclic diamine and one monoamine type alkaloids is described. 相似文献
7.
Siguara B. L. Silva Franois Oberhnsli Marie‐Aude Tribalat Grgory Genta‐Jouve Jean‐Louis Teyssi Marie‐Yasmine Dechraoui‐Bottein Jean‐Franois Gallard Laurent Evanno Erwan Poupon Olivier P. Thomas 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(2):530-535
Among the outstanding chemical diversity found in marine sponges, cyclic guanidine alkaloids, present in species of the family Crambeidae, are particularly attractive, not only because of their unique chemical features, but also due to a broad range of biological activities. Despite a growing interest in these natural products as therapeutic agents, their metabolic pathway has not been experimentally investigated. Ex situ feeding experiments using radiolabeled precursors performed on the Mediterranean sponge Crambe crambe suggest arginine and fatty acids as precursors in the metabolic pathway of crambescins. A subsequent bio‐inspired approach supported the change of paradigm in the metabolic pathway of cyclic guanidine alkaloids. A large part of the chemical diversity of this family would therefore originate from a tethered Biginelli‐like reaction between C‐2/C‐3 activated fatty acids and a central guanidinylated pyrrolinium. 相似文献
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9.
Marine sponges belonging to the Calcarea family have been studied for some time and have yielded a wide variety of structurally unique secondary metabolites. In particular, these sponges have produced a large number of bioactive alkaloids containing an imidazole heterocycle, typically substituted with two benzylic fragments at various locations around the azole nucleus and at various oxidation states. This review will describe the isolation, structural determination and synthetic studies towards this growing class of natural products. 相似文献
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11.
Calter MA Phillips RM Flaschenriem C 《Journal of the American Chemical Society》2005,127(42):14566-14567
Pyrimidine derivatives of the cinchona alkaloids function as excellent asymmetric catalysts for the "Interrupted" Feist-Bénary Reaction. This reaction produces highly substituted hydroxydihydrofurans from simple starting materials under mild conditions. The asymmetric reaction gives high enantioselectivities with unsubstituted bromoketones, and high enantio- and diastereoselectivities with substituted substrates. Mechanistic experiments suggest that the hydrobromide salt of the alkaloid derivative is the active catalyst for the reaction. 相似文献
12.
This review presents the structure, biological activity, biosynthetic studies and, where applicable, references to syntheses of 81 marine alkaloids containing either tetra-, hexa- or octa-hydrogenated variants of pyrrolo[4,3,2-de]quinoline, pyrrolo[4,3,2-de]pyrrolo[2,3-h]quinoline and pyrido[2,3-h]pyrrolo[4,3,2-de]quinoline core skeletons. The literature describing the isolation of pyrroloiminoquinones, and related metabolites, from marine sponges is littered with taxonomic inconsistencies and recent efforts to clarify the taxonomy of the sponges that produce this group of metabolites are discussed. 相似文献
13.
Weinreb SM 《Natural product reports》2007,24(5):931-948
This Highlight describes some of the recent synthetic work on imidazole-containing alkaloids isolated from marine sponges. Target molecules have been chosen which demonstrate synthetic strategies leading towards metabolites containing intact imidazole moieties as well as systems bearing modified imidazole rings. 相似文献
14.
Sabrin R. M. Ibrahim Sana A. Fadil Haifa A. Fadil Rawan H. Hareeri Hossam M. Abdallah Gamal A. Mohamed 《Molecules (Basel, Switzerland)》2022,27(18)
Marine sponges continue to attract remarkable attention as one of the richest pools of bioactive metabolites in the marine environment. The genus Smenospongia (order Dictyoceratida, family Thorectidae) sponges can produce diverse classes of metabolites with unique and unusual chemical skeletons, including terpenoids (sesqui-, di-, and sesterterpenoids), indole alkaloids, aplysinopsins, bisspiroimidazolidinones, chromenes, γ-pyrones, phenyl alkenes, naphthoquinones, and polyketides that possessed diversified bioactivities. This review provided an overview of the reported metabolites from Smenospongia sponges, including their biosynthesis, synthesis, and bioactivities in the period from 1980 to June 2022. The structural characteristics and diverse bioactivities of these metabolites could attract a great deal of attention from natural-product chemists and pharmaceuticals seeking to develop these metabolites into medicine for the treatment and prevention of certain health concerns. 相似文献
15.
Stout EP Wang YG Romo D Molinski TF 《Angewandte Chemie (International ed. in English)》2012,51(20):4877-4881
Game-SET-match: Pyrrole aminoimidazole alkaloids (PAIs) are metabiosynthesized from chlorinated analogues of oroidin by cell-free enzyme preparations from PAI-producing sponges. Evidence and implications for the biosynthesis of PAIs include putative single-electron transfers (SETs) that promote C-C bond-forming reactions of precursors. 相似文献
16.
The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many are now being tested in various phases of clinical trials. Recently, marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities including anti-angiogenic, anti-proliferative, inhibition of topoisomerase activities and tubulin polymerization, and induction of apoptosis and cytotoxicity. Two tunicate-derived alkaloids, aplidin and trabectedin, offer promising drug profiles, and are currently in phase II clinical trials against several solid and hematologic tumors. This review sheds light on the rich array of anti-cancer alkaloids in the marine ecosystem and introduces the most investigated compounds and their mechanisms of action. 相似文献
17.
Direct Synthesis of Protoberberine Alkaloids by Rh‐Catalyzed C−H Bond Activation as the Key Step
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Dr. Jayachandran Jayakumar Prof. Dr. Chien‐Hong Cheng 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(5):1800-1804
A one‐pot reaction of substituted benzaldehydes with alkyne–amines by a Rh‐catalyzed C?H activation and annulation to afford various natural and unnatural protoberberine alkaloids is reported. This reaction provides a convenient route for the generation of a compound library of protoberberine salts, which recently have attracted great attention because of their diverse biological activities. In addition, pyridinium salt derivatives can also be formed in good yields from α,β‐unsaturated aldehydes and amino–alkynes. This reaction proceeds with excellent regioselectivity and good functional group compatibility under mild reaction conditions by using O2 as the oxidant. 相似文献
18.
[structure: see text] Pyridinium alkaloids are widely distributed in marine sponges of different genera. Chemical investigation of the Arctic sponge Haliclona viscosa led to the isolation of a new trimeric 3-alkyl pyridinium alkaloid (viscosamine). Trimers have not been described as natural products yet. The isolation and the structure elucidation of viscosamine are discussed in detail. 相似文献
19.
3-Alkylpyridine alkaloids are very common secondary metabolites from marine sponges of the order Haplosclerida. Here, we report on the identification and synthesis of the first cyclic monomeric 3-alkylpyridinium alkaloid from natural sources. Due to the lack of a pure sample of the new compound, structure elucidation had to rely on HPLC and MS(n). 相似文献
20.
Viscosaline: new 3-alkyl pyridinium alkaloid from the Arctic sponge Haliclona viscosa 总被引:2,自引:0,他引:2
Polycyclic pyridinium alkaloids are widely distributed in several sponges of the order Haplosclerida. So far, studies on Haliclona and related genera were mainly concentrated on warm or tropical waters. Here, we describe the chemical investigation of the Arctic sponge Haliclona viscosa and structure elucidation of the acyclic 1,3-dialkyl pyridinium alkaloid viscosaline. A novel structural motif of viscosaline is that beta-alanine is covalently bound to one alkyl chain. 相似文献