Total synthesis of anithiactins A-C and thiasporine A

Vaaland, I. Caroline; Lindbäck, Emil; Sydnes, Magne O.

doi:10.1016/j.tetlet.2019.01.038

Cited by 5 publications

(3 citation statements)

References 10 publications

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“…It seemed that the methyl group linked to an amino group decreased the activity. Afterward, Suzuki–Miyaura cross-coupling was applied in the total synthesis of these four metabolites (Vaaland et al 2019 ).…”

Section: Thioethersmentioning

confidence: 99%

The intriguing chemistry and biology of sulfur-containing natural products from marine microorganisms (1987–2020)

Hai

Wei

Wang

et al. 2021

Mar Life Sci Technol

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Natural products derived from marine microorganisms have received great attention as a potential resource of new compound entities for drug discovery. The unique marine environment brings us a large group of sulfur-containing natural products with abundant biological functionality including antitumor, antibiotic, anti-inflammatory and antiviral activities. We reviewed all the 484 sulfur-containing natural products (non-sulfated) isolated from marine microorganisms, of which 59.9% are thioethers, 29.8% are thiazole/thiazoline-containing compounds and 10.3% are sulfoxides, sulfones, thioesters and many others. A selection of 133 compounds was further discussed on their structure–activity relationships, mechanisms of action, biosynthesis, and druggability. This is the first systematic review on sulfur-containing natural products from marine microorganisms conducted from January 1987, when the first one was reported, to December 2020.

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Section: Thioethersmentioning

confidence: 99%

The intriguing chemistry and biology of sulfur-containing natural products from marine microorganisms (1987–2020)

Hai

Wei

Wang

et al. 2021

Mar Life Sci Technol

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“…Shortly thereafter, a marine-derived bacterium, Actinomycetospora sp., has also produced anithiactins A and C along with thiasporine A [7,8]. Several studies regarding the synthesis of these secondary metabolites have been reported [6,[9][10][11]. Intensive investigation of the chemical components of the culture broth of the strain 10A085 has led to the isolation of a new 2-phenylthiazole natural product, anithiactin D (1).…”

Section: Introductionmentioning

confidence: 99%

Anithiactin D, a Phenylthiazole Natural Product from Mudflat-Derived Streptomyces sp., Suppresses Motility of Cancer Cells

Pulat,

Yang,

Lee

et al. 2024

Marine Drugs

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Anithiactin D (1), a 2-phenylthiazole class of natural products, was isolated from marine mudflat-derived actinomycetes Streptomyces sp. 10A085. The chemical structure of 1 was elucidated based on the interpretation of NMR and MS data. The absolute configuration of 1 was determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectral data. Anithiactin D (1) significantly decreased cancer cell migration and invasion activities at a concentration of 5 μM via downregulation of the epithelial-to-mesenchymal transition (EMT) markers in A549, AGS, and Caco-2 cell lines. Moreover, 1 inhibited the activity of Rho GTPases, including Rac1 and RhoA in the A549 cell line, suppressed RhoA in AGS and Caco-2 cell lines, and decreased the mRNA expression levels of some matrix metalloproteinases (MMPs) in AGS and Caco-2 cell lines. Thus 1, which is a new entity of the 2-phenylthiazole class of natural products with a unique aniline-indole fused moiety, is a potent inhibitor of the motility of cancer cells.

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“…1(A)), as a natural product, was first isolated from the metabolite of Actinomycetospora chlora SNC‐032 by MacMillan in 2015 13 . Studies on the activities of thiasporine A and its analogs are mainly focused on the field of medicine, although a few studies on agricultural applications have been reported 14,15 . The structure of thiasporine A is a typical thiazole heterocycle, which is found in many commercial pesticides, such as ethaboxam, thifluzamide and thiamethoxam (Fig.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antifungal evaluation of phenylthiazole‐1,3,4‐oxadiazole thione (ketone) derivatives inspired by natural thiasporine A

Shi

Tian

Chen

et al. 2023

Pest Management Science

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BACKGROUNDPlant pathogenic fungal infections have become a severe threat to the yield and quality of agricultural products, and new green antifungal agents with high efficiency and low toxicity are needed. In this study, a series of thiasporine A derivatives containing phenylthiazole‐1,3,4‐oxadiazole thione (ketone) structures were designed and synthesized, and their antifungal activities against six invasive and highly destructive phytopathogenic fungi were evaluated.RESULTSThe results found that all compounds showed moderate to potent antifungal activity against six phytopathogenic fungi, and most of the E series compounds showed remarkable antifungal activity against Sclerotinia sclerotiorum and Colletotrichum camelliaet. In particular, compounds E1–E5, E7, E8, E13, E14, E17, and E22 showed more significant antifungal activity against S. sclerotiorum, with half‐maximal effective concentration (EC50) values of 0.22, 0.48, 0.56, 0.65, 0.51, 0.39, 0.60, 0.56, 0.60, 0.63, and 0.45 μg mL−1, respectively, which were superior to that of carbendazim (0.70 μg mL−1). Further activity studies showed that compound E1 possessed superior curative activities against S. sclerotiorum in vivo and better inhibitory effects on sclerotia germination and the formation of S. sclerotiorum compared with those of carbendazim.CONCLUSIONSThis study indicates that these thiasporine A derivatives containing phenylthiazole‐1,3,4‐oxadiazole thione structures might be used as antifungal agents against S. sclerotiorum. © 2023 Society of Chemical Industry.

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Total synthesis of anithiactins A-C and thiasporine A

Cited by 5 publications

References 10 publications

The intriguing chemistry and biology of sulfur-containing natural products from marine microorganisms (1987–2020)

The intriguing chemistry and biology of sulfur-containing natural products from marine microorganisms (1987–2020)

Anithiactin D, a Phenylthiazole Natural Product from Mudflat-Derived Streptomyces sp., Suppresses Motility of Cancer Cells

Design, synthesis and antifungal evaluation of phenylthiazole‐1,3,4‐oxadiazole thione (ketone) derivatives inspired by natural thiasporine A

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