Stereoselective Synthesis and Biological Evaluation of C1-Epimeric and Desmethyl Monomeric Nuphar Analogues

Li, Hui; Cooke, Timothy J.; Korotkov, Alexander; Chapman, Charles W.; Eastman, Alan; Wu, Jimmy

doi:10.1021/acs.joc.6b03052

Cited by 13 publications

(6 citation statements)

References 39 publications

(80 reference statements)

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“…Phlorotannins possessed therapeutic properties [85][86][87]. Phlorotannins are specifically present as the only group of phenolic compounds in brown algae.…”

Section: Phaeophyceaementioning

confidence: 99%

Review POTENT PHARMACEUTICAL PRODUCTS FROM AQUATIC PLANTS – REVIEW

Saxena¹,

Singh²,

Kumar³

et al. 2021

Asian J Pharm Clin Res

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Several biologically active secondary metabolites from aquatic plants have been extracted and identified using modern instrumental BioTechniques and used in various ways as flavors, food, additives, coloring agents, nutraceuticals, cosmetics, and also as unique source of pharma industries for the discovery or development of new drugs. From algae to aquatic macrophytes belonging to various categories, aquatic plants produce a variety of compounds such as polyketides, peptides, alkaloids, flavonoids, phenolic compounds, terpenes, steroids, quinones, tannins, coumarins, and essential oils commercially involving in antibiotic, antiviral, antioxidant, antifouling, anti-inflammatory, anticancer, cytotoxic, and antimitotic activities; thus making them a rich source of medicinal compounds. Moreover, they are comprehensively used in human therapy, veterinary, agriculture, scientific research, and in countless areas. Importantly these chemicals are exercised for developing new antimicrobial and cancer drugs. Furthermore, antioxidant molecules in aquatic plants and seaweeds have recently been acknowledged. This review contains a consolidated contemporary document consisting of entire knowledge available on pharmaceutical products of aquatic plants and highlights major differences among secondary metabolites found in aquatic (algae) and terrestrial plants.

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“…Phlorotannins possessed therapeutic properties [85][86][87]. Phlorotannins are specifically present as the only group of phenolic compounds in brown algae.…”

Section: Phaeophyceaementioning

confidence: 99%

Review POTENT PHARMACEUTICAL PRODUCTS FROM AQUATIC PLANTS – REVIEW

Saxena¹,

Singh²,

Kumar³

et al. 2021

Asian J Pharm Clin Res

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“…Oxoesters 1a,b have also been employed in three-component vinylogous Mannich (VM) reactions as the electrophilic acceptors upon reaction with an aromatic amine followed by several steps to obtain the indolizidine and quinolizidine frameworks with very high enantio-and diastereoselectivity (Scheme 1, eq. a) [15][16][17]. To the best of our knowledge, we are aware of only one example featuring a Mannich reaction of oxoesters 1a,b, in which these compounds behave as nucleophilic donor.…”

Section: Alkylmentioning

confidence: 99%

Experimental and Computational Studies Unraveling the Peculiarity of Enolizable Oxoesters in the Organocatalyzed Mannich-Type Addition to Cyclic N-Acyl Iminium Ions

et al. 2020

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γ− and δ-Oxoesters are easily available starting materials that have been sparingly used in some organocatalyzed reactions proceeding with a high enantioselectivity. In our experimentation we found that the use of these compounds as the enolizable (nucleophilic) component in organocatalyzed Mannich-type reactions using in situ-generated cyclic N-acyl iminium ions gave low diastereoselectivity and low to moderate values of enantioselectivity. This significant drop of facial selectivity with respect to simple aliphatic aldehydes has been rationalized by means of density functional theory (DFT) calculations.

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“…Recently, synthetic studies of nuphar alkaloids, including unnatural-type alkaloids, have been reported, [30][31][32][33][34][35][36] and several of these studies are aimed at developing new anti-cancer agents. Despite the unique stereostructures of dimeric sesquiterpene thioalkaloids have been determined in the 1970s, their total synthesis was not completed until 2013 by Jansen and Shenvi 30) and Korotkov et al in 2015.…”

Section: Synthesis Of Nuphar Alkaloids and Their Development As Anti-cancer Agentsmentioning

confidence: 99%

Biofunctional Effects of Thiohemiaminal-Type Dimeric Sesquiterpene Alkaloids from <i>Nuphar</i> Plants

Matsuda

Nakamura

Nakashima

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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Dimeric sesquiterpene thioalkaloids from the rhizomes of Nuphar pumilum exhibited immunosuppressive effects using a sheep erythrocyte plaque forming cell (PFC) assay, as well as an anti-metastasis effect, and rapid apoptosis-inducing effects in tumor cell lines. In particular, dimeric sesquiterpene thioalkaloids with a hydroxy group (6-hydroxythiobinupharidine, 6,6′-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B) showed substantial effects, whereas dimeric sesquiterpene thioalkaloids lacking the hydroxy group (thiobinupharidine, thionuphlutine B, 6′-hydroxythionuphlutine B, neothiobinupharidine, thionuphlutine B β-sulfoxide, neothiobinupharidine β-sulfoxide) and monomeric sesquiterpene alkaloids (nupharidine, 7-epideoxynupharidine, nupharolutine) showed weak activity. In this review, we summarize our studies of the biofunctional effects of these alkaloids.

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Stereoselective Synthesis and Biological Evaluation of C1-Epimeric and Desmethyl Monomeric Nuphar Analogues

Cited by 13 publications

References 39 publications

Review POTENT PHARMACEUTICAL PRODUCTS FROM AQUATIC PLANTS – REVIEW

Review POTENT PHARMACEUTICAL PRODUCTS FROM AQUATIC PLANTS – REVIEW

Experimental and Computational Studies Unraveling the Peculiarity of Enolizable Oxoesters in the Organocatalyzed Mannich-Type Addition to Cyclic N-Acyl Iminium Ions

Biofunctional Effects of Thiohemiaminal-Type Dimeric Sesquiterpene Alkaloids from <i>Nuphar</i> Plants

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