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Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications 2.0

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Biochemistry".

Deadline for manuscript submissions: closed (15 April 2024) | Viewed by 2375

Special Issue Editor

Prof. Dr. Elena K. Beloglazkina

E-Mail Website
Guest Editor
Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1-3, 119991 Moscow, Russia
Interests: cycloaddition reactions; organic ligands; medicinal chemistry; functional organic-inorganic materials
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues, 

Organic spiro derivatives are extremely attractive molecules for the development of novel structural types of biologically active molecules, and for the fabrication of new materials. The rigidity of spiro junctions in molecular frameworks makes it possible to fix the required spatial arrangement of exocyclic substituents, which are crucial to enabling with biological targets and the properties of developed materials. It is also vital that spiro-linked carbo- and heterocyclic compounds can be obtained via various types of cyclization reactions with high regio- and stereoselectivity, as well as atomic precision; such reactions are atom-economical and make it possible to significantly complicate the molecular structure in one synthetic step.

This Special Issue of International Journal of Molecular Sciences focuses on the synthesis and physico-chemical and biological investigation of spiro-conjugated organic compounds, and welcomes both original research articles and review papers addressing with both practical and mechanistic aspects of the preparation and reactivity of title compounds, as well as prospects for their possible application. In its Volume I, 10 papers were published. We sincerely encourage you to read these papers and welcome your contributions to Volume II.

Prof. Dr. Elena K. Beloglazkina
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. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. 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

  • bioactivity
  • carbocycles
  • cyclization
  • cycloaddition
  • heterocycles
  • low molecular weight materials
  • spiro-compounds
  • synthetic methods

Published Papers (3 papers)

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Research

11 pages, 1759 KiB  
Communication
Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step
by Arina Y. Obydennik, Alexander A. Titov, Anna V. Listratova, Tatiana N. Borisova, Victor B. Rybakov, Leonid G. Voskressensky and Alexey V. Varlamov
Int. J. Mol. Sci. 2024, 25(2), 1085; https://doi.org/10.3390/ijms25021085 - 16 Jan 2024
Viewed by 550
Abstract
Here, An efficient approach to obtaining previously unknown furo[2′,3′:2,3]pyrrolo[2,1-a]isoquinoline derivatives from readily available 1-R-1-ethynyl-2-vinylisoquinolines is described. The reaction features a simple procedure, occurs in hexaflouroisopropanol and does not require elevated temperatures. It has been found that the addition of glacial acetic [...] Read more.
Here, An efficient approach to obtaining previously unknown furo[2′,3′:2,3]pyrrolo[2,1-a]isoquinoline derivatives from readily available 1-R-1-ethynyl-2-vinylisoquinolines is described. The reaction features a simple procedure, occurs in hexaflouroisopropanol and does not require elevated temperatures. It has been found that the addition of glacial acetic acid significantly increases the yields of the target spirolactone products. Using trifluoroethanol instead of hexaflouroisopropanol results in the formation of pyrido[2,1-a]isoquinolines. Full article
(This article belongs to the Special Issue Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications 2.0)
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25 pages, 4695 KiB  
Article
[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones
by Juliana V. Kuznetsova, Varvara T. Tkachenko, Lada M. Petrovskaya, Maria E. Filkina, Dmitry E. Shybanov, Yuri K. Grishin, Vitaly A. Roznyatovsky, Viktor A. Tafeenko, Anna S. Pestretsova, Vera A. Yakovleva, Vadim S. Pokrovsky, Maxim E. Kukushkin and Elena K. Beloglazkina
Int. J. Mol. Sci. 2024, 25(1), 18; https://doi.org/10.3390/ijms25010018 - 19 Dec 2023
Viewed by 831
Abstract
Approximately 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile [...] Read more.
Approximately 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using the recently proposed diffusion mixing technique, which led to ~5–15% increases in target compound yields. It was found that the addition of nitrile imines to C=S or C=N exocyclic double bonds led to 1,2,4-thiazolines or triazolines and occurred regioselectively in accordance with the ratio of FMO coefficients of reactants. The yield of the resulting spiro-compound depended on the presence of alkyl substituents in the nitrile imine structure and was significantly decreased in reactions with imines with strong electron donor or electron-withdrawing groups. Some of the obtained compounds showed reasonable in vitro cytotoxicity. IC50 values were calculated for HCT116 (colon cancer) cells using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test. Full article
(This article belongs to the Special Issue Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications 2.0)
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22 pages, 2901 KiB  
Article
Diastereoselective Synthesis of Dispiro[Imidazothiazolotriazine-Pyrrolidin-Oxindoles] and Their Isomerization Pathways in Basic Medium
by Alexei N. Izmest′ev, Dmitry B. Vinogradov, Angelina N. Kravchenko, Natalya G. Kolotyrkina and Galina A. Gazieva
Int. J. Mol. Sci. 2023, 24(22), 16359; https://doi.org/10.3390/ijms242216359 - 15 Nov 2023
Viewed by 637
Abstract
Highly diastereoselective methods for the synthesis of two series of regioisomeric polynuclear dispyroheterocyclic compounds with five or six chiral centers, comprising moieties of pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine of linear structure or imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine of angular structure, have [...] Read more.
Highly diastereoselective methods for the synthesis of two series of regioisomeric polynuclear dispyroheterocyclic compounds with five or six chiral centers, comprising moieties of pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine of linear structure or imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine of angular structure, have been developed on the basis of a [3+2] cycloaddition of azomethine ylides to functionalized imidazothiazolotriazines. Depending on the structure of the ethylenic component, cycloaddition proceeds as an anti-exo process for linear derivatives, while cycloaddition to angular ones resulted in a syn-endo diastereomer. Novel pathways of isomerization for the synthesized anti-exo products upon treatment with sodium alkoxides have been found, which resulted in two more series of diastereomeric dispiro[imidazothiazolotriazine-pyrrolidin-oxindoles] inaccessible with the direct cycloaddition reaction. For the first series, the inversion of the configuration of one stereocenter, i.e., C-4′ atom of the pyrrolidine cycle, (epimerization) was established. For the second one, configuration of the obtained diastereomer formally corresponded to the syn-endo approach of the azomethine ylide in the case of cycloaddition to the ethylenic component. Full article
(This article belongs to the Special Issue Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications 2.0)
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