scholarly journals Marine Pyrrole Alkaloids

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 514
Author(s):  
Kevin Seipp ◽  
Leander Geske ◽  
Till Opatz
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Marine Environment ◽  
Biological Activities ◽  
Nitrogen Heterocycles ◽  
Important Class ◽  
Chemical Machinery ◽  
Terrestrial Habitats ◽  
Pyrrole Alkaloids ◽  
Broad Overview

Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats but can also frequently be found as natural products in the marine environment. This review highlights the important class of marine pyrrole alkaloids, well-known for their diverse biological activities. A broad overview of the marine pyrrole alkaloids with a focus on their isolation, biological activities, chemical synthesis, and derivatization covering the decade from 2010 to 2020 is provided. With relevant structural subclasses categorized, this review shall provide a clear and timely synopsis of this area.

scholarly journals Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2095 ◽  
Author(s):  
Yi Qiu ◽  
Wen-Jian Lan ◽  
Hou-Jin Li ◽  
Liu-Ping Chen
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Chemical Structure ◽  
Biological Activities ◽  
Structural Diversity ◽  
Structure Identification ◽  
Important Class ◽  
Soft Corals ◽  
Wide Range ◽  
New Challenges

Linear triquinane sesquiterpenoids represent an important class of natural products. Most of these compounds were isolated from fungi, sponges, and soft corals, and many of them displayed a wide range of biological activities. On account of their structural diversity and complexity, linear triquinane sesquiterpenoids present new challenges for chemical structure identification and total synthesis. 118 linear triquinane sesquiterpenoids were classified into 8 types, named types I–VIII, based on the carbon skeleton and the position of carbon substituents. Their isolation, structure elucidations, biological activities, and chemical synthesis were reviewed. This paper cited 102 articles from 1947 to 2018.

scholarly journals Chemical Synthesis of (+)-Brevianamide a Supports a Diels–Alderase-Free Biosynthesis

2019 ◽  
Author(s):  
Robert Godfrey ◽  
Nicholas Green ◽  
Gary Nichol ◽  
Andrew Lawrence
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Scientific Community ◽  
Biological Activities ◽  
Alder Reaction ◽  
Diels Alder ◽  
Compelling Evidence ◽  
Diels Alder Reaction ◽  
Significant Interest

<div> <div> <div> <p>The fungal-derived bicyclo[2.2.2]diazaoctane alkaloids are of significant interest to the scientific community for their potent and varied biological activities. Within this large and diverse family of natural products the insecticidal metabolite (+)-brevianamide A is particularly noteworthy for its synthetic intractability and inexplicable biogenesis. Despite five decades of research, this alkaloid has never succumbed to chemical synthesis. It has been suggested that a proposed Diels–Alder reaction in the biosynthesis of (+)-brevianamide A requires a Diels–Alderase enzyme. We herein report the first chemical synthesis of (+)-brevianamide A (7 steps, 8.0% overall yield, 750 mg scale), which provides compelling evidence in support of a Diels–Alderase-free biosynthesis; a significant departure from the established biosynthesis of related alkaloids. </p> </div> </div> </div>

Chemical Synthesis of (+)-Brevianamide a Supports a Diels–Alderase-Free Biosynthesis

2019 ◽  
Author(s):  
Robert Godfrey ◽  
Nicholas Green ◽  
Gary Nichol ◽  
Andrew Lawrence
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Scientific Community ◽  
Biological Activities ◽  
Alder Reaction ◽  
Diels Alder ◽  
Compelling Evidence ◽  
Diels Alder Reaction ◽  
Significant Interest

<div> <div> <div> <p>The fungal-derived bicyclo[2.2.2]diazaoctane alkaloids are of significant interest to the scientific community for their potent and varied biological activities. Within this large and diverse family of natural products the insecticidal metabolite (+)-brevianamide A is particularly noteworthy for its synthetic intractability and inexplicable biogenesis. Despite five decades of research, this alkaloid has never succumbed to chemical synthesis. It has been suggested that a proposed Diels–Alder reaction in the biosynthesis of (+)-brevianamide A requires a Diels–Alderase enzyme. We herein report the first chemical synthesis of (+)-brevianamide A (7 steps, 8.0% overall yield, 750 mg scale), which provides compelling evidence in support of a Diels–Alderase-free biosynthesis; a significant departure from the established biosynthesis of related alkaloids. </p> </div> </div> </div>

scholarly journals Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

2017 ◽  
Vol 13 ◽  
pp. 1670-1692 ◽  
Author(s):  
Santanu Hati ◽  
Ulrike Holzgrabe ◽  
Subhabrata Sen
Keyword(s):  
Natural Products ◽  
Oxidative Dehydrogenation ◽  
Scientific Community ◽  
Nitrogen Heterocycles ◽  
Building Blocks ◽  
Important Class ◽  
Heteroaromatic Compounds ◽  
Synthetic Drugs ◽  
Convenient Approach ◽  
Synthetic Drug

Nitrogen heteroarenes form an important class of compounds which can be found in natural products, synthetic drugs, building blocks etc. Among the diverse strategies that were developed for the synthesis of nitrogen heterocycles, oxidative dehydrogenation is extremely effective. This review discusses various oxidative dehydrogenation strategies of C–C and C–N bonds to generate nitrogen heteroarenes from their corresponding heterocyclic substrates. The strategies are categorized under stoichiometric and catalytic usage of reagents that facilitate such transformations. The application of these strategies in the synthesis of nitrogen heteroarene natural products and synthetic drug intermediates are also discussed. We hope this review will arouse sufficient interest among the scientific community to further advance the application of oxidative dehydrogenation in the synthesis of nitrogen heteroarenes.

scholarly journals Unified Total Synthesis of the Brevianamide Alkaloids Enabled by Chemical Investigations into their Biosynthesis.

2021 ◽  
Author(s):  
Robert C. Godfrey ◽  
Helen E. Jones ◽  
Nicholas J. Green ◽  
Andrew L. Lawrence
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Total Synthesis ◽  
Scientific Community ◽  
Biological Activities ◽  
Focus Of Attention ◽  
Complex Structures ◽  
Biosynthetic Pathways ◽  
Synthetic Strategy ◽  
Synthetic Studies

The bicyclo[2.2.2]diazaoctane alkaloids are a vast group of natural products which have been the focus of attention from the scientific community for several decades. This interest stems from their broad range of biological activities, their diverse biosynthetic origins, and their topologically complex structures, which combined make them enticing targets for chemical synthesis. In this article, full details of our synthetic studies into the chemical feasibility of a proposed network of biosynthetic pathways towards the brevianamide family of bicyclo[2.2.2]diazaoctane alkaloids are disclosed. Insights into issues of reactivity and selectivity in the biosynthesis of these structures have aided the development of a unified biomimetic synthetic strategy, which has resulted in the total synthesis of all known bicyclo[2.2.2]diazaoctane brevianamides and the anticipation of an as-yet-undiscovered congener.

scholarly journals Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Zhe Chang ◽  
Jialin Huang ◽  
Si Wang ◽  
Geshuyi Chen ◽  
Heng Zhao ◽  
...  
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Late Stage ◽  
Nitrogen Heterocycles ◽  
Pharmaceutical Chemistry ◽  
Nitrogen Heterocycle ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Modern Chemical

AbstractNitrogen heterocycle represents a ubiquitous skeleton in natural products and drugs. Late-stage C(sp3)-H bond functionalization of N-heterocycles with broad substrate scope remains a challenge and of particular significance to modern chemical synthesis and pharmaceutical chemistry. Here, we demonstrate copper-catalysed late-stage C(sp3)-H functionalizaion of N-heterocycles using commercially available catalysts under mild reaction conditions. We have investigated 8 types of N-heterocycles which are usually found as medicinally important skeletons. The scope and utility of this approach are demonstrated by late-stage C(sp3)-H modification of these heterocycles including a number of pharmaceuticals with a broad range of nucleophiles, e.g. methylation, arylation, azidination, mono-deuteration and glycoconjugation etc. Preliminary mechanistic studies reveal that the reaction undergoes a C-H fluorination process which is followed by a nucleophilic substitution.

Pyrone-derived Marine Natural Products: A Review on Isolation, Bio-activities and Synthesis

2020 ◽  
Vol 24 (4) ◽  
pp. 354-401 ◽  
Author(s):  
Keisham S. Singh
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Marine Fungi ◽  
Kojic Acid ◽  
Biological Activities ◽  
Biological Significance ◽  
Pyrone Ring ◽  
Enol Ethers ◽  
Bioactive Natural Products ◽  
Marine Metabolites

Marine natural products (MNPs) containing pyrone rings have been isolated from numerous marine organisms, and also produced by marine fungi and bacteria, particularly, actinomycetes. They constitute a versatile structure unit of bioactive natural products that exhibit various biological activities such as antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic and anti-tyrosinase. The two structure isomers of pyrone ring are &#947;- pyrone and &#945;-pyrone. In terms of chemical motif, &#947;-pyrone is the vinologous form of &#945;- pyrone which possesses a lactone ring. Actinomycete bacteria are responsible for the production of several &#945;-pyrone compounds such as elijopyrones A-D, salinipyrones and violapyrones etc. to name a few. A class of pyrone metabolites, polypropionates which have fascinating carbon skeleton, is primarily produced by marine molluscs. Interestingly, some of the pyrone polytketides which are found in cone snails are actually synthesized by actinomycete bacteria. Several pyrone derivatives have been obtained from marine fungi such as Aspergillums flavus, Altenaria sp., etc. The &#947;-pyrone derivative namely, kojic acid obtained from Aspergillus fungus has high commercial demand and finds various applications. Kojic acid and its derivative displayed inhibition of tyrosinase activity and, it is also extensively used as a ligand in coordination chemistry. Owing to their commercial and biological significance, the synthesis of pyrone containing compounds has been given attention over the past years. Few reviews on the total synthesis of pyrone containing natural products namely, polypropionate metabolites have been reported. However, these reviews skipped other marine pyrone metabolites and also omitted discussion on isolation and detailed biological activities. This review presents a brief account of the isolation of marine metabolites containing a pyrone ring and their reported bio-activities. Further, the review covers the synthesis of marine pyrone metabolites such as cyercene-A, placidenes, onchitriol-I, onchitriol-II, crispatene, photodeoxytrichidione, (-) membrenone-C, lihualide-B, macrocyclic enol ethers and auripyrones-A & B.

Advances in Synthesis and Medicinal Applications of Compounds Derived from Phthalimide

2020 ◽  
Vol 17 (4) ◽  
pp. 252-270
Author(s):  
Marcel L. Almeida ◽  
Maria C.V.A. Oliveira ◽  
Ivan R. Pitta ◽  
Marina G.R. Pitta
Keyword(s):  
Chemical Synthesis ◽  
Biological Activities ◽  
Sedative Effects ◽  
Phthalimide Derivative ◽  
Anti Inflammatory

Phthalimide derivatives have been presenting several promising biological activities in the literature, such as anti-inflammatory, analgesic, antitumor, antimicrobial and anticonvulsant. The most well-known and studied phthalimide derivative (isoindoline-1,3-dione) is thalidomide: this compound initially presented important sedative effects, but it is now known that thalidomide has effectiveness against a wide variety of diseases, including inflammation and cancer. This review approaches some of the recent and efficient chemical synthesis pathways to obtain phthalimide analogues and also presents a summary of the main biological activities of these derivatives found in the literature. Therefore, this review describes the chemical and therapeutic aspects of phthalimide derivatives.

A Mini Review on the Chemical Synthesis of Resveratrol

2020 ◽  
Vol 17 (5) ◽  
pp. 546-558
Author(s):  
Hong Huang ◽  
Ruonan Liu ◽  
Wenhua Ou
Keyword(s):  
Cardiovascular Disease ◽  
Chemical Synthesis ◽  
Neurodegenerative Diseases ◽  
Biological Activities ◽  
Polyphenolic Compound ◽  
Chemical Methods

Resveratrol is a polyphenolic compound and has been shown to possess numerous biological activities, which could possibly be applied to the prevention and/or treatment of cancer, cardiovascular disease, and neurodegenerative diseases. This review summarizes the progress of different chemical methods in the preparation of resveratrol.

scholarly journals Natural products isolated from Casimiroa

2020 ◽  
Vol 18 (1) ◽  
pp. 778-797
Author(s):  
Khun Nay Win Tun ◽  
Nanik Siti Aminah ◽  
Alfinda Novi Kristanti ◽  
Hnin Thanda Aung ◽  
Yoshiaki Takaya
Keyword(s):  
Natural Products ◽  
Spectral Data ◽  
Aromatic Compounds ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Quinoline Alkaloids

AbstractAbout 140 genera and more than 1,600 species belong to the Rutaceae family. They grow in temperate and tropical zones on both hemispheres, as trees, shrubs, and herbs. Casimiroa is one of the genera constituting 13 species, most of which are found in tropical and subtropical regions. Many chemical constituents have been derived from this genus, including quinoline alkaloids, flavonoids, coumarins, and N-benzoyltyramide derivatives. This article reviews different studies carried out on aromatic compounds of genus Casimiroa; their biological activities; the different skeletons of coumarins, alkaloids, flavonoids, and others; and their characteristic NMR spectral data.

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