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Molecules
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Alkaloid Derivatives: Synthesis and Application
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Alkaloid Derivatives: Synthesis and Application

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

Deadline for manuscript submissions: closed (1 March 2021) | Viewed by 9094

Special Issue Editor

Prof. Dr. Jacek Skarzewski

E-Mail Website
Guest Editor
Faculty of Chemistry, Wrocław University of Science and Technology, Wyb. Wyspianskiego 27, 50-370 Wrocław, Poland
Interests: organic synthesis; asymmetric catalysis; catalyzed oxidations

Special Issue Information

Dear Colleagues,

Alkaloids belong to a class of naturally-occurring organic compounds, containing basic nitrogen atoms. They are produced by the secondary metabolism of living organisms. Many of them have an outstanding pharmacological activity and are used in traditional as well as modern medicine. Their essential chemical frameworks are often considered as pharmacophores and starting points for new drug discoveries. This stimulates the development of synthetic methodologies for further transformations of native alkaloids, mostly isolated from plants. Another synthetic approach adopted in medicinal chemistry applies the semi-total syntheses of the alkaloid precursors. These derivatives are transformed into libraries of compounds for biological screening.

Yet another use of the easily available natural alkaloids is a chiral recognition process. This includes separation of racemates and their application as chiral catalysts. Cinchona alkaloids have especially found many prominent applications in this field. Among them are Cinchona dimers used in the metal-catalyzed reaction, e.g., the Sharpless dihydroxylation as well as thioureas and square acid amides exploited as organocatalysts.

Both fields are still under viable development and new manuscripts (articles or reviews) that discuss innovative synthetic methodologies for assembling or transforming alkaloids with potential applications in catalysis and medicine are therefore welcome.

Prof. Jacek Skarżewski
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Alkaloid
  • Biological activity
  • Alkaloid precursor
  • Organic synthesis
  • Chiral recognition
  • Cinchona alkaloids
  • Asymmetric catalysis
  • Metal-catalyzed reactions
  • Organocatalysts
  • Functional group transformations
  • Chemo-, regio-, and stereoselective reactions

Published Papers (3 papers)

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Research

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20 pages, 3802 KiB  
Article
Hybrides of Alkaloid Lappaconitine with Pyrimidine Motif on the Anthranilic Acid Moiety: Design, Synthesis, and Investigation of Antinociceptive Potency
by Kirill P. Cheremnykh, Victor A. Savelyev, Sergey A. Borisov, Igor D. Ivanov, Dmitry S. Baev, Tatyana G. Tolstikova, Valentin A. Vavilin and Elvira E. Shults
Molecules 2020, 25(23), 5578; https://doi.org/10.3390/molecules25235578 - 27 Nov 2020
Cited by 9 | Viewed by 2490
Abstract
Convenient and efficient routes to construct hybrid molecules containing diterpene alkaloid lappaconitine and pyrimidine fragments are reported. One route takes place via first converting of lappaconitine to 1-ethynyl-lappaconitine, followed by the Sonogashira cross-coupling-cyclocondensation sequences. The other involves the palladium-catalyzed carbonylative Sonogashira reaction of [...] Read more.
Convenient and efficient routes to construct hybrid molecules containing diterpene alkaloid lappaconitine and pyrimidine fragments are reported. One route takes place via first converting of lappaconitine to 1-ethynyl-lappaconitine, followed by the Sonogashira cross-coupling-cyclocondensation sequences. The other involves the palladium-catalyzed carbonylative Sonogashira reaction of 5′-iodolappaconitine with aryl acetylene and Mo (CO)6 as the CO source in acetonitrile and subsequent cyclocondensation reaction of the generated alkynone with amidines. The reaction proceeded cleanly in the presence of the PdCl2-(1-Ad)2PBn∙HBr catalytic system. The protocol provides mild reaction conditions, high yields, and high atom and step-economy. Pharmacological screening of lappaconitine-pyrimidine hybrids for antinociceptive activity in vivo revealed that these compounds possessed high activity in experimental pain models, which was dependent on the nature of the substituent in the 2 and 6 positions of the pyrimidine nucleus. Docking studies were undertaken to gain insight into the possible binding mode of these compounds with the voltage-gated sodium channel 1.7. The moderate toxicity of the leading compound 12 (50% lethal dose (LD50) value was more than 600 mg/kg in vivo) and cytotoxicity to cancer cell lines in vitro encouraged the further design of therapeutically relevant analogues based on this novel type of lappaconitine–pyrimidine hybrids. Full article
(This article belongs to the Special Issue Alkaloid Derivatives: Synthesis and Application)
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10 pages, 2272 KiB  
Article
Total Synthesis of Novel Skeleton Flavan-Alkaloids
by Jing Zhen, James E. Simon and Qingli Wu
Molecules 2020, 25(19), 4491; https://doi.org/10.3390/molecules25194491 - 30 Sep 2020
Cited by 4 | Viewed by 2852
Abstract
The first total synthesis of novel skeleton natural compounds kinkeloids A and B, a group of newly discovered flavan alkaloids isolated from the African plant Combretum micranthum, are described in this study. The key and final step are achieved by Mannich reaction, [...] Read more.
The first total synthesis of novel skeleton natural compounds kinkeloids A and B, a group of newly discovered flavan alkaloids isolated from the African plant Combretum micranthum, are described in this study. The key and final step are achieved by Mannich reaction, through which the piperidine moiety couples to the flavan moiety. The identities of synthesized kinkeloids were further confirmed through a comparison with the ones in the plant leaves extract using LC/MS. Full article
(This article belongs to the Special Issue Alkaloid Derivatives: Synthesis and Application)
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Review

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14 pages, 5298 KiB  
Review
Strategies and Efforts towards the Total Synthesis of Palhinine Alkaloids
by Yu-Yan Liang, Shi-Chao Lu, Ya-Ling Gong and Shu Xu
Molecules 2020, 25(18), 4211; https://doi.org/10.3390/molecules25184211 - 14 Sep 2020
Cited by 2 | Viewed by 3092
Abstract
The palhinine family of Lycopodium alkaloids were first reported in 2010, which feature an intriguing isotwistane carbon cage and a nine-membered azonane ring. It is noteworthy that the tetracyclic 5/6/6/9 skeleton was unprecedented in Lycopodium alkaloids before their seminal discovery. Over the past [...] Read more.
The palhinine family of Lycopodium alkaloids were first reported in 2010, which feature an intriguing isotwistane carbon cage and a nine-membered azonane ring. It is noteworthy that the tetracyclic 5/6/6/9 skeleton was unprecedented in Lycopodium alkaloids before their seminal discovery. Over the past decade, extensive synthetic efforts stemming from seven research groups have resulted in two racemic total syntheses to date. This review article takes the opportunity to survey these efforts and achievements so as to promote further research towards the asymmetric total synthesis of palhinine alkaloids. Full article
(This article belongs to the Special Issue Alkaloid Derivatives: Synthesis and Application)
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