Synthesis and in vitro cytotoxic evaluation of spiro-β-lactone-γ-lactam scaffolds
A successful approach to the construction of spiro-β-lactone-γ-lactam synthons 5 and ent-5 as a similar structural motif present in natural products such as oxazolomycins was developed. Two chirons, the protected 3-isothiocyanato-3-C-vinyl-α-d-xylofuranose and its antipode, were employed as the star...
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| Published in: | Tetrahedron Vol. 76; no. 18; p. 131144 |
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| Format: | Journal Article |
| Language: | English |
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01-05-2020
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| Abstract | A successful approach to the construction of spiro-β-lactone-γ-lactam synthons 5 and ent-5 as a similar structural motif present in natural products such as oxazolomycins was developed. Two chirons, the protected 3-isothiocyanato-3-C-vinyl-α-d-xylofuranose and its antipode, were employed as the starting material. In order to obtain a lactone-pyrrolidine cyclic framework, a ring-closing metathesis, a highly diastereoselective reduction of a double bond and the formation of a β-lactone skeleton were involved as the key transformations. The final enantiomeric pharmacophores were screened for their capacity to alter the viability of cancer cells.
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•Synthesis of spiro-β-lactone-γ-lactam scaffolds was accomplished.•Developed strategy relied on a RCM reaction and highly diastereoselective catalytic hydrogenation.•A single crystal X-ray analysis of the key substructure was performed.•The target lactone-pyrrolidine cyclic systems demonstrate the interesting cytotoxic activity. |
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| AbstractList | A successful approach to the construction of spiro-β-lactone-γ-lactam synthons 5 and ent-5 as a similar structural motif present in natural products such as oxazolomycins was developed. Two chirons, the protected 3-isothiocyanato-3-C-vinyl-α-d-xylofuranose and its antipode, were employed as the starting material. In order to obtain a lactone-pyrrolidine cyclic framework, a ring-closing metathesis, a highly diastereoselective reduction of a double bond and the formation of a β-lactone skeleton were involved as the key transformations. The final enantiomeric pharmacophores were screened for their capacity to alter the viability of cancer cells.
[Display omitted]
•Synthesis of spiro-β-lactone-γ-lactam scaffolds was accomplished.•Developed strategy relied on a RCM reaction and highly diastereoselective catalytic hydrogenation.•A single crystal X-ray analysis of the key substructure was performed.•The target lactone-pyrrolidine cyclic systems demonstrate the interesting cytotoxic activity. |
| ArticleNumber | 131144 |
| Author | Pilátová, Martina Bago Gonda, Jozef Fábian, Martin Jáger, Dávid Jacková, Dominika Martinková, Miroslava |
| Author_xml | – sequence: 1 givenname: Martin surname: Fábian fullname: Fábian, Martin organization: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic – sequence: 2 givenname: Jozef surname: Gonda fullname: Gonda, Jozef organization: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic – sequence: 3 givenname: Dominika surname: Jacková fullname: Jacková, Dominika organization: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic – sequence: 4 givenname: Miroslava surname: Martinková fullname: Martinková, Miroslava email: miroslava.martinkova@upjs.sk organization: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic – sequence: 5 givenname: Martina Bago surname: Pilátová fullname: Pilátová, Martina Bago organization: Institute of Pharmacology, Faculty of Medicine, P.J. Šafárik University, SNP 1, 040 66, Košice, Slovak Republic – sequence: 6 givenname: Dávid surname: Jáger fullname: Jáger, Dávid organization: Institute of Geotechnics, Slovak Academy of Sciences, Watsonova 45, 040 01, Košice, Slovak Republic |
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| Keywords | Antiproliferative activity [3,3]-Sigmatropic rearrangement Oxazolomycins Spiro-β-lactone-γ-lactam framework |
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| SubjectTerms | [3,3]-Sigmatropic rearrangement Antiproliferative activity Oxazolomycins Spiro-β-lactone-γ-lactam framework |
| Title | Synthesis and in vitro cytotoxic evaluation of spiro-β-lactone-γ-lactam scaffolds |
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