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Natural Organic Substances as Starting Bricks for the Semi-synthesis of New Compounds II

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

Deadline for manuscript submissions: closed (1 July 2023) | Viewed by 1752

Special Issue Editors

Department of Environmental Biology, University of Rome, La Sapienza, Rome, Italy
Interests: HPLC and NMR analysis; phytochemistry; synthesis of natural products; chemotaxonomy; ethnopharmacology; nutraceutics
Special Issues, Collections and Topics in MDPI journals
Dipartimento di Chimica, Università di Roma “La Sapienza” Piazzale Aldo Moro, Roma, Italy
Interests: semi-synthesis; natural products; phytochemical analysis; biological activities; medicinal plants

Special Issue Information

Dear Colleagues,

We are pleased to invite you to contribute to this Special Issue, which is a continuation from a very successful Volume I on the topic of “Natural Organic Substances as Starting Bricks for the Semi-Synthesis of New Compounds”.

The main objective of this Special Issue is to collect and disseminate papers on the concept of using natural products as starting bases for the semi-synthesis of new compounds.

Compounds based on natural products have proven to be an important and interesting tool to remedy two specific limitations often associated with natural products, i.e., their little recovery from natural sources, plants, and so on, and their little pharmacological effects due to general, pharmacokinetic, and pharmacodynamic problems.

The main and probably most well-known example in the former context is surely that of taxol. In fact, the decision to obtain it through a semi-synthesis process from 10-deacetylbaccatin III has made history in the field and serves as an inspiration for this Special Issue, which will focus on examining the potential of this approach In particular, the goal of the issue is to highlight how often a simple and safe semi-synthetic procedure can greatly increase the potential of natural organic compounds as pharmacologically active substances in contrast to being used as recovered from their natural sources. A typical example of this is salicylic acid and acetyl–salicylic acid. There are no restrictions regarding the kind of compounds and the pharmacological effects studied, but the differences in the pharmacological activity between the natural compound and its semi-synthetic derivative or derivatives must be shown and explained.

Dr. Claudio Frezza
Dr. Marco Franceschin
Guest Editors

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

  • natural products
  • plant sources
  • isolation
  • semi-synthesis
  • active substances
  • pharmacology

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Published Papers (1 paper)

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Research

15 pages, 2266 KiB  
Article
Stereoselective Epoxidation of Triterpenic Allylic Alcohols and Cytotoxicity Evaluation of Synthesized Compounds
by Gulnaz Krainova, Yulia Beloglazova, Maksim Dmitriev and Victoria Grishko
Molecules 2023, 28(2), 550; https://doi.org/10.3390/molecules28020550 - 05 Jan 2023
Viewed by 1435
Abstract
The epoxidation process of semi-synthetic triterpenoids 2-methyl-3-oxo-19β,28-epoxy- 18α-olean-1-ene, and its allylic alcohol derivatives were examined. 1,2α-epoxide, as the main product, was found to be formed from the starting enone exposed to m-chloroperbenzoic acid (mCPBA). In the case of hydroxy-directed mCPBA-oxidation of triterpenic [...] Read more.
The epoxidation process of semi-synthetic triterpenoids 2-methyl-3-oxo-19β,28-epoxy- 18α-olean-1-ene, and its allylic alcohol derivatives were examined. 1,2α-epoxide, as the main product, was found to be formed from the starting enone exposed to m-chloroperbenzoic acid (mCPBA). In the case of hydroxy-directed mCPBA-oxidation of triterpenic allyl alcohols and their 3α-alkyl-substituted derivatives, inversion of C1 and C2 asymmetric centers with the formation of 1,2β-epoxyalcohols took place. The synthesis of 2,3α-epoxides was fulfilled from 2,3-dialkyl-substituted C(3) allyl alcohols by the action of pyridinium chlorochromate under [1,3]-oxidative rearrangement conditions. The transformations brought about enabled chiral oleanane derivatives with an oxygen-containing substituent at the C1, C2, and C3 atoms to be obtained. The study also provides information on in silico PASS prediction of pharmacological effects and in vitro evaluation of the cytotoxic activity of the synthesized compounds. Full article
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