From natural to artificial antitumor lipidic alkynylcarbinols: Asymmetric synthesis, enzymatic resolution, and refined SARs
Identifieur interne : 000070 ( Hal/Corpus ); précédent : 000069; suivant : 000071From natural to artificial antitumor lipidic alkynylcarbinols: Asymmetric synthesis, enzymatic resolution, and refined SARs
Auteurs : Dymytrii Listunov ; Etienne Joly ; Pauline Rulliere ; H. Gaspard ; V. Bernardes-Genisson ; Y. Genisson ; V. Maraval ; R. ChauvinSource :
- SYNTHESIS [ 0039-7881 ] ; 2018.
Abstract
A review. Among acetylenic natural products, chiral lipidic alkynylcarbinol (LAC) metabolites, mostly extd. from marine sponges, have revealed a broad spectrum of biol. activities, in particular, remarkable antitumor cytotoxicity. With ref. to one of the simplest natural representatives, [( S)-eicos-(4 E)-en-1-yn-3-ol], and a given cancer cell line (HCT116), combined extensive efforts in chem. synthesis (relying on the use of a large chem. toolbox) and biol. anal. ( in vitrotests), have provided systematic structure-activity relationships (SARs) where the initially selected four structural parameters appear as independent principal components: (i) and (ii) the sp/sp 2content and extent of the terminal and internal unsaturations adjacent to the carbinol center, (iii) the abs. configuration of the latter, (iv) the length of the n-aliph. backbone. Two key criteria have also been established regarding the functional alkynylcarbinol pharmacophore: the alkynylcarbinol unit must be both secondaryand terminal(i.e., substituted by a short ethynyl or ethenyl C 2group). This review is intended to provide a further illustration of the value of a simple rational approach for drug design, and to act as a benchmark for future optimization of LACs as antitumor agents. 1 Introduction 2 2C 2-Unsatd. Pharmacophore Candidates 2.1 Alkenylalkynylcarbinols (AACs) 2.2 Dialkynylcarbinols (DACs or DACys) 2.3 Alkynylalkenylcarbinols (iso-AACs) and Dialkenylcarbinols (DACes) 2.4 Oxidn.-Protected Dialkynylcarbinols and Dialkynylketones 2.5 Fluorophore-Labeled Lipidic Dialkynylcarbinols 3 C 2/C 3-Unsatd. Pharmacophore Candidates 3.1 Cyclopropylalkynylcarbinols (CACs) 3.2 Allenylalkynylcarbinols (AllACs) 4 C 2/C 4- and 3C 2-Unsatd. Pharmacophore Candidates 4.1 Butadiynylalkynylcarbinols (BACs) 4.2 Trialkynylcarbinols (TACs) 5 Double-AC-Headed Pharmacophore Candidates 6 Screening on the Lipidic Chain Length 7 Conclusion.
Url:
DOI: 10.1055/s-0037-1610006
Links to Exploration step
Hal:hal-01952874Le document en format XML
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<front><div type="abstract" xml:lang="en"> <p>A review. Among acetylenic natural products, chiral lipidic alkynylcarbinol (LAC) metabolites, mostly extd. from marine sponges, have revealed a broad spectrum of biol. activities, in particular, remarkable antitumor cytotoxicity. With ref. to one of the simplest natural representatives, [( S)-eicos-(4 E)-en-1-yn-3-ol], and a given cancer cell line (HCT116), combined extensive efforts in chem. synthesis (relying on the use of a large chem. toolbox) and biol. anal. ( in vitrotests), have provided systematic structure-activity relationships (SARs) where the initially selected four structural parameters appear as independent principal components: (i) and (ii) the sp/sp 2content and extent of the terminal and internal unsaturations adjacent to the carbinol center, (iii) the abs. configuration of the latter, (iv) the length of the n-aliph. backbone. Two key criteria have also been established regarding the functional alkynylcarbinol pharmacophore: the alkynylcarbinol unit must be both secondaryand terminal(i.e., substituted by a short ethynyl or ethenyl C 2group). This review is intended to provide a further illustration of the value of a simple rational approach for drug design, and to act as a benchmark for future optimization of LACs as antitumor agents. 1 Introduction 2 2C 2-Unsatd. Pharmacophore Candidates 2.1 Alkenylalkynylcarbinols (AACs) 2.2 Dialkynylcarbinols (DACs or DACys) 2.3 Alkynylalkenylcarbinols (iso-AACs) and Dialkenylcarbinols (DACes) 2.4 Oxidn.-Protected Dialkynylcarbinols and Dialkynylketones 2.5 Fluorophore-Labeled Lipidic Dialkynylcarbinols 3 C 2/C 3-Unsatd. Pharmacophore Candidates 3.1 Cyclopropylalkynylcarbinols (CACs) 3.2 Allenylalkynylcarbinols (AllACs) 4 C 2/C 4- and 3C 2-Unsatd. Pharmacophore Candidates 4.1 Butadiynylalkynylcarbinols (BACs) 4.2 Trialkynylcarbinols (TACs) 5 Double-AC-Headed Pharmacophore Candidates 6 Screening on the Lipidic Chain Length 7 Conclusion.</p>
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<abstract xml:lang="en"> <p>A review. Among acetylenic natural products, chiral lipidic alkynylcarbinol (LAC) metabolites, mostly extd. from marine sponges, have revealed a broad spectrum of biol. activities, in particular, remarkable antitumor cytotoxicity. With ref. to one of the simplest natural representatives, [( S)-eicos-(4 E)-en-1-yn-3-ol], and a given cancer cell line (HCT116), combined extensive efforts in chem. synthesis (relying on the use of a large chem. toolbox) and biol. anal. ( in vitrotests), have provided systematic structure-activity relationships (SARs) where the initially selected four structural parameters appear as independent principal components: (i) and (ii) the sp/sp 2content and extent of the terminal and internal unsaturations adjacent to the carbinol center, (iii) the abs. configuration of the latter, (iv) the length of the n-aliph. backbone. Two key criteria have also been established regarding the functional alkynylcarbinol pharmacophore: the alkynylcarbinol unit must be both secondaryand terminal(i.e., substituted by a short ethynyl or ethenyl C 2group). This review is intended to provide a further illustration of the value of a simple rational approach for drug design, and to act as a benchmark for future optimization of LACs as antitumor agents. 1 Introduction 2 2C 2-Unsatd. Pharmacophore Candidates 2.1 Alkenylalkynylcarbinols (AACs) 2.2 Dialkynylcarbinols (DACs or DACys) 2.3 Alkynylalkenylcarbinols (iso-AACs) and Dialkenylcarbinols (DACes) 2.4 Oxidn.-Protected Dialkynylcarbinols and Dialkynylketones 2.5 Fluorophore-Labeled Lipidic Dialkynylcarbinols 3 C 2/C 3-Unsatd. Pharmacophore Candidates 3.1 Cyclopropylalkynylcarbinols (CACs) 3.2 Allenylalkynylcarbinols (AllACs) 4 C 2/C 4- and 3C 2-Unsatd. Pharmacophore Candidates 4.1 Butadiynylalkynylcarbinols (BACs) 4.2 Trialkynylcarbinols (TACs) 5 Double-AC-Headed Pharmacophore Candidates 6 Screening on the Lipidic Chain Length 7 Conclusion.</p>
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