Synthesis and germination activity study of novel strigolactam/strigolactone analogues

Ge, Yuhua; Chen, Xingyue; Khan, Shah Nawaz; Jia, Shuhe; Chen, Gang

doi:10.1016/j.tetlet.2022.154315

Cited by 4 publications

(8 citation statements)

References 34 publications

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“… [51] Analogs with low and no bioactivity (Figure 3C) have been developed in order to understand the limits of the structural changes and to subsequently putatively develop inhibitors of SL receptor(s) (Figure 6). It has been possible to develop SL analogs simply possessing the 3′‐methylbutenolide (D‐ring) linked by the enol ether function to a wide variety of simplified motifs that deviate from the structures of natural molecules such as AR36 ( 75 ) [52] and Nijmegen‐1 ( 63 ), [53] lactam derivatives ( 67 – 69 ), [54] lactone derivatives ( 62 ), [55] ketone derivatives ( 70 ), [56] cyclic keto enols ( 71 ), [57] and SL analogs based on guaianolides, eudesmadolides, sclarerolides and named guaianestrigolactones ( 76 ), [58] eudesmanestrigolactones ( 77 ), [59] and sclareolide analogs [ e. g ., AB1 ( 78 )], [54d,60] respectively. Analogs with significant hormonal activity and reduced germination activity on the seeds of parasitic plants have also been obtained.…”

Section: Analogs Mimics and Stable Isotope‐labeled Standardsmentioning

confidence: 99%

“…A new category of SL analogs, strigolactams, [54] emerged in 2013 with the introduction of nitrogen into the C‐ring. The synthesis of this type of analogs has been extensively studied with the development of series of strigolactams Type I ( 67 ), and Type II ( 68 ) with cis / trans fused B/C rings [54d,119] . A synthesis of strigolactam type I was carried out by Lachia, et al .…”

Section: Synthesis Of Natural Sls Analogs Mimics and Isotope‐labeled ...mentioning

confidence: 99%

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Chemistry of Strigolactones, Key Players in Plant Communication

Daignan‐Fornier,

Keita,

Boyer

2024

ChemBioChem

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Today, the use of artificial pesticides is questionable and the adaptation to global warming is a necessity. The promotion of favorable natural interactions in the rhizosphere offers interesting perspectives for changing the type of agriculture. Strigolactones (SLs), the latest class of phytohormones to be discovered, are also chemical mediators in the rhizosphere. We present in this review the diversity of natural SLs, their analogs, mimics, and probes essential for the biological studies of this class of compounds. Their biosynthesis and access by organic synthesis are highlighted especially concerning noncanonical SLs, the more recently discovered natural SLs. Organic synthesis of analogs, stable isotope‐labeled standards, mimics, and probes are also reviewed here. In the last part, the knowledge about the SL perception is described as well as the different inhibitors of SL receptors that have been developed.

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Section: Analogs Mimics and Stable Isotope‐labeled Standardsmentioning

confidence: 99%

Section: Synthesis Of Natural Sls Analogs Mimics and Isotope‐labeled ...mentioning

confidence: 99%

Chemistry of Strigolactones, Key Players in Plant Communication

Daignan‐Fornier,

Keita,

Boyer

2024

ChemBioChem

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“…Subsequently, the β-orientated (red) C-ring and the α-orientated (blue) C-ring render the strigol- and orobanchol-types, respectively (Figure ). A wide variety of analogues of orobanchol 205a have been identified all sharing the hydroxy group in ring B, e.g., 7-oxoorobanchol 204 , 7-hydroxyorobanchol 205b , and fabacol 206 . Furthermore, fabacol 206 and solanacol 201 bear structural modifications in ring A with solanacol’s aromatic motif being discussed further in a separate section below.…”

Section: Strigolactonesmentioning

confidence: 99%

“…The researchers determined that some of the trans-fused compounds (198) showed good activity (Figure 36). 172 As exemplified thus far, the structures of SL analogues and mimics nearly all have the unmodified D-ring portion tethered via an enol-ether bridge. McErlean and co-workers recently reported a potent SL antagonist for Striga, called dormirazine (DOZ) 199.…”

Section: ■ Strigolactonesmentioning

confidence: 99%

Inspired by Nature: Isostere Concepts in Plant Hormone Chemistry

Frackenpohl

Abel

Alnafta

et al. 2023

J. Agric. Food Chem.

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Chemical concepts such as isosteres and scaffold hopping have proven to be powerful tools in agrochemical innovation processes. They offer opportunities to modify known molecular lead structures with the aim to improve a range of parameters, including biological efficacy and spectrum, physicochemical properties, stability, and toxicity. While recent biochemical insights into plant-specific receptors and signaling pathways trigger the discovery of the first lead structures, the disclosure of such a new chemical structure sparks a broad range of synthesis activities giving rise to diverse chemical innovation and often a considerable boost in biological activity. Herein, recent examples of isostere concepts in plant-hormone chemistry will be discussed, outlining how synthetic creativity can broaden the scope of natural product chemistry and giving rise to new opportunities in research fields such as abiotic stress tolerance and growth promotion.

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“…The cross-enolate-type coupling reaction of sclareolide with amide carbonyl could also realize alkylation via the use of 2-iodopyridine and 2,6-lutidine N -oxide in the presence of NaH ( Scheme 1 c) [ 31 ]. In the presence of sodium hydride, the α-formylation of sclareolide was achieved via a treatment with ethyl formate in ether ( Scheme 1 d) [ 32 , 33 ]. Despite there being excellent reports on the α-functionalization of lactone unit of sclareolide, the installation of amino functionality in this position still remains unexplored.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Aminoalkyl Sclareolide Derivatives and Antifungal Activity Studies

Gao

Mei

et al. 2023

Molecules

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Sclareolide was developed as an efficient C-nucleophilic reagent for an asymmetric Mannich addition reaction with a series of N-tert-butylsulfinyl aldimines. The Mannich reaction was carried out under mild conditions, affording the corresponding aminoalkyl sclareolide derivatives with up to 98% yield and 98:2:0:0 diastereoselectivity. Furthermore, the reaction could be performed on a gram scale without any reduction in yield and diastereoselectivity. Additionally, deprotection of the obtained Mannich addition products to give the target sclareolide derivatives bearing a free N-H group was demonstrated. In addition, target compounds 4–6 were subjected to an antifungal assay in vitro, which showed considerable antifungal activity against forest pathogenic fungi.

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Synthesis and germination activity study of novel strigolactam/strigolactone analogues

Cited by 4 publications

References 34 publications

Chemistry of Strigolactones, Key Players in Plant Communication

Chemistry of Strigolactones, Key Players in Plant Communication

Inspired by Nature: Isostere Concepts in Plant Hormone Chemistry

Synthesis of Aminoalkyl Sclareolide Derivatives and Antifungal Activity Studies

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