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Special Issue "Natural Product Inspired Scaffolds Designs"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products".

Deadline for manuscript submissions: closed (30 April 2017)

Special Issue Editor

Guest Editor
Dr. Kamal Kumar

Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn Str. 11, 44227-Dortmund, Germany
Website | E-Mail
Interests: scaffold diversity synthesis; annulation reactions; asymmetric catalysis; cascade reactions; chemical biology of small molecules

Special Issue Information

Dear Colleagues,

The Special Issue on “Natural Product Inspired Scaffold Designs” intends to bring together some wonderful ideas, offering natural product-derived or natural products-based molecular architectures either through or for a synthesis project. Natural products have been an immensely useful source of drug candidates, as well as a great motivation for the chemists to realize laboratory access to them. Diverse forms of life have created and improved the chemical entities through the evolution and optimized them for their physiological requirements that help them cope with some of the toughest of environments. Biological relevance of the molecular frameworks of these natural products is an open secret that remains underexplored and calls to exploit the potential of natural scaffolds to deliver novel modulators of diverse biological functions. Concise synthesis strategies that employ few synthetic steps, by incorporating domino or cascade reactions, as well as one-pot multicomponent reactions, provide highly efficient access to natural product-based structural complexity. The state-of-art chemical transformations, for instance, C–H activations, that can modify a highly complex natural product or its analogues, have recently seen a surge in their applications towards building natural product-like small molecules. Natural product-core structures can either be the target or the starting points in the synthesis journey to create novel chemical matter. A known biological target of a natural product ligand can also offer important structural insights and help in designing novel scaffolds towards better inhibitors, activators or binders of the same target. Therefore, chem- and bioinformatics approaches with their power to predict biological targets for various molecular scaffolds based on natural products are important and desired contributions to advance this field of research. Biological screenings and evaluation of the compound collections developed around natural product core scaffolds provides the necessary medicinal or biological direction to a class of small molecules and depict the first stage of the journey of a novel natural product based chemical entity to become a drug or a tool candidate.
In conclusion, this Special Issue embodies the chemistry around natural product core frameworks or scaffolds, and the applications of the small molecules based on natural scaffolds in biological and material sciences. We hope that the contributions will be able to garner your attention and will further empower the scientific community to take full advantage of nature’s tool box.

Dr. Kamal Kumar
Guest Editor

Keywords

•    natural products
•    privileged scaffolds
•    divergent synthesis
•    natural-product like small molecules
•    scaffold design
•    biologically relevant chemical entities
•    natural-product modifications
•    complexity generating reactions
•    cascade and domino reactions
•    asymmetric synthesis

Published Papers (5 papers)

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Research

Open AccessArticle Hydronopylformamides: Modification of the Naturally Occurring Compound (-)-β-Pinene to Produce Insect Repellent Candidates against Blattella germanica
Molecules 2017, 22(6), 1004; doi:10.3390/molecules22061004
Received: 5 May 2017 / Revised: 12 June 2017 / Accepted: 13 June 2017 / Published: 16 June 2017
PDF Full-text (529 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The development of a novel repellent plays an important role in the integrated control of Blattella germanica. A series of novel hydronopylformamides derivatives were synthesized from a naturally occurring compound (-)-β-pinene. The structures of these hydronopylformamides derivatives were characterized by Fourier transform
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The development of a novel repellent plays an important role in the integrated control of Blattella germanica. A series of novel hydronopylformamides derivatives were synthesized from a naturally occurring compound (-)-β-pinene. The structures of these hydronopylformamides derivatives were characterized by Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (1H-NMR and 13C-NMR), and electron impact mass spectrometry (EI-MS). Repellency of these hydronopylformamides derivatives against Blattella germanica was evaluated by the using petri dish arena method. The results showed that four derivatives (compounds 8a, 8b, 8c and 8e) exhibited repellency against Blattella germanica at a concentration of 20 mg/mL. Compound 8a was the most active compound among these derivatives, where the repelling ratios of compound 8a against Blattella germanica were 66.10%, 50.46%, 48.26%, at concentrations of 20 mg/mL, 10 mg/mL, and 5 mg/mL, respectively. In addition, compound 8a showed better repellency than the traditional insect repellent N, N-diethyl-3-methylbenzamide (DEET), which indicated that compound 8a had a good application prospect in the prevention of Blattella germanica. This research hopes to promote the value-added utilization of (-)-β-pinene and the development of novel German cockroach repellents. Full article
(This article belongs to the Special Issue Natural Product Inspired Scaffolds Designs)
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Open AccessArticle New Strigolactone Mimics as Exogenous Signals for Rhizosphere Organisms
Molecules 2017, 22(6), 961; doi:10.3390/molecules22060961
Received: 28 April 2017 / Revised: 6 June 2017 / Accepted: 7 June 2017 / Published: 9 June 2017
PDF Full-text (5518 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The importance of strigolactones in plant biology prompted us to synthesize simplified strigolactone mimics effective as exogenous signals for rhizosphere organisms. New strigolactone mimics easily derived from simple and available starting materials in significant amounts were prepared and fully characterized. These compounds contain
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The importance of strigolactones in plant biology prompted us to synthesize simplified strigolactone mimics effective as exogenous signals for rhizosphere organisms. New strigolactone mimics easily derived from simple and available starting materials in significant amounts were prepared and fully characterized. These compounds contain an aromatic or heterocyclic ring, usually present in various bioactive molecules, connected by an ether link to a furan-2-one moiety. The new synthesized strigolactone mimics were confirmed to be active on plant pathogenic fungi and parasitic weed seeds. Full article
(This article belongs to the Special Issue Natural Product Inspired Scaffolds Designs)
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Open AccessArticle Highly Stereoselective Synthesis of a Compound Collection Based on the Bicyclic Scaffolds of Natural Products
Molecules 2017, 22(5), 827; doi:10.3390/molecules22050827
Received: 12 April 2017 / Revised: 11 May 2017 / Accepted: 12 May 2017 / Published: 18 May 2017
Cited by 1 | PDF Full-text (2627 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Despite the great contribution of natural products in the history of successful drug discovery, there are significant limitations that persuade the pharmaceutical industry to evade natural products in drug discovery research. The extreme scarcity as well as structural complexity of natural products renders
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Despite the great contribution of natural products in the history of successful drug discovery, there are significant limitations that persuade the pharmaceutical industry to evade natural products in drug discovery research. The extreme scarcity as well as structural complexity of natural products renders their practical synthetic access and further modifications extremely challenging. Although other alternative technologies, particularly combinatorial chemistry, were embraced by the pharmaceutical industry to get quick access to a large number of small molecules with simple frameworks that often lack three-dimensional complexity, hardly any success was achieved in the discovery of lead molecules. To acquire chemotypes beholding structural features of natural products, for instance high sp3 character, the synthesis of compound collections based on core-scaffolds of natural products presents a promising strategy. Here, we report a natural product inspired synthesis of six different chemotypes and their derivatives for drug discovery research. These bicyclic hetero- and carbocyclic scaffolds are highly novel, rich in sp3 features and with ideal physicochemical properties to display drug likeness. The functional groups on the scaffolds were exploited further to generate corresponding compound collections. Synthesis of two of these collections exemplified with ca. 350 compounds are each also presented. The whole compound library is being exposed to various biological screenings within the European Lead Factory consortium. Full article
(This article belongs to the Special Issue Natural Product Inspired Scaffolds Designs)
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Open AccessArticle Design, Synthesis and Antifungal Activity of Coumarin Ring-Opening Derivatives
Molecules 2016, 21(10), 1387; doi:10.3390/molecules21101387
Received: 3 September 2016 / Revised: 30 September 2016 / Accepted: 13 October 2016 / Published: 17 October 2016
Cited by 1 | PDF Full-text (996 KB) | HTML Full-text | XML Full-text
Abstract
Based on our initial design, we synthesized two series of coumarin ring-opening derivatives by the reactions of hydrolysis and methylation. Results of antifungal screening in vitro showed that the target compounds exhibited potent activity against the six common pathogenic fungi. Compounds 6b,
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Based on our initial design, we synthesized two series of coumarin ring-opening derivatives by the reactions of hydrolysis and methylation. Results of antifungal screening in vitro showed that the target compounds exhibited potent activity against the six common pathogenic fungi. Compounds 6b, 6e, 6g, 6i, 7b and 7c were identified as the most active ones, and the EC50 values of these active compounds were further tested. Compared to the commonly used fungicide Azoxystrobin (0.0884 µM), compounds 6b (0.0544 µM) and 6e (0.0823 µM) displayed improved activity against Botrytis cinerea. Full article
(This article belongs to the Special Issue Natural Product Inspired Scaffolds Designs)
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Open AccessArticle Synthesis and Antimicrobial Characterization of Half-Calycanthaceous Alkaloid Derivatives
Molecules 2016, 21(9), 1207; doi:10.3390/molecules21091207
Received: 3 July 2016 / Revised: 6 September 2016 / Accepted: 6 September 2016 / Published: 9 September 2016
Cited by 1 | PDF Full-text (539 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A total of 29 novel tetrahydropyrroloindol-based calycanthaceous alkaloid derivatives were synthesized from indole-3-acetonitrile in good yields. The synthesized compounds were evaluated against nine strains of bacteria and a wide range of plant pathogen fungi. Bioassay results revealed that majority of the compounds displayed
[...] Read more.
A total of 29 novel tetrahydropyrroloindol-based calycanthaceous alkaloid derivatives were synthesized from indole-3-acetonitrile in good yields. The synthesized compounds were evaluated against nine strains of bacteria and a wide range of plant pathogen fungi. Bioassay results revealed that majority of the compounds displayed similar or higher in vitro antimicrobial activities than the positive control. The biological activities also indicated that substituents at R4 and R5 significantly affect the activities. Notably, compound c4 was found to be most active among the tested calycanthaceous analogues and might be a novel potential leading compound for further development as an antifungal agent. The results could pave the way for further design and structural modification of calycanthaceous alkaloids as antimicrobial agents. Full article
(This article belongs to the Special Issue Natural Product Inspired Scaffolds Designs)
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