Synthesis of 4-methylthio-1,2-dithiolane and 5-methylthio-1,2,3-trithiane. Two naturally occurring bioactive compounds

Anthoni, Uffe; Christophersen, Carsten; Jacobsen, Niels; Svendsen, Axel

doi:10.1016/0040-4020(82)87022-1

Cited by 31 publications

(6 citation statements)

References 10 publications

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“…The hydrolysable polyphenols in M. spicatum comprise all those activities (Choi et al, 2002;Leu et al, 2002;Walenciak et al, 2002). The cyclic sulphur compounds considered responsible for allelopathic activity in Chara have insecticidal properties (Anthoni et al, 1982;Jacobsen & Pedersen, 1983). In plant-herbivore and plant-pathogen interactions, defensive compounds might be constitutively present in the plant or can be induced upon feeding damage.…”

Section: Discussionmentioning

confidence: 99%

Searching for allelopathic effects of submerged macrophytes on phytoplankton—state of the art and open questions

Gross

Hilt

Lombardo

et al. 2007

Shallow Lakes in a Changing World

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Allelopathy, here defined as biochemical interactions between aquatic primary producers, has always been intriguing as a process explaining the dominance of certain plant or algal species over others. Negative chemical interference has been invoked as one of the steering mechanisms behind mutual dominance of either submerged macrophytes or phytoplankton in shallow eutrophic lakes. Yet, despite much effort, convincing evidence for allelopathic interactions in situ is still missing. Also, laboratory approaches often lack reality. Inspired by a series of talks at the Shallow Lakes 2005 meeting in Dalfsen, the Netherlands, we argue that there is circumstantial but strong evidence that allelopathic interference between submerged macrophytes and phytoplankton may indeed exist in aquatic ecosystems despite the problems associated with research in this field. We first discuss experimental approaches combining laboratory and field studies, based on examples presented at this meeting. We then discuss the impact of nutrient status of both producing and target organism and biotic factors such as herbivory or pathogens that might affect allelopathy. Further topics are the potential seasonality of effects and the species-specificity of certain allelochemicals. We conclude with some thoughts why a final First publ. in: Hydrobiologia 584 (2007), pp. 77-88 proof for allelopathy in situ might remain difficult or even inaccessible in some cases, and why we nevertheless should not abandon this idea.

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Section: Discussionmentioning

confidence: 99%

Searching for allelopathic effects of submerged macrophytes on phytoplankton—state of the art and open questions

Gross

Hilt

Lombardo

et al. 2007

Shallow Lakes in a Changing World

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“…7,8 Conversion of 2 into 1 was assumed to proceed through a mechanism involving in situ formation of 1,5,3,7-dithiadiazabicyclo[3.3.0]octane-type mesocyclic dications 3 [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] followed by ring contraction and sulfur insertion. [27][28][29][30] Scheme 2 Preparation of N-aryl-1,2,3,4,5,7-pentathiazocanes 1.…”

Section: Resultsmentioning

confidence: 99%

Novel Thiofomylation of Primary and Secondary Amines Using N-Aryl-1,2,3,4,5,7-Pentathiazocanes

Shimada

Shibuya

Makino

et al. 2010

Phosphorus, Sulfur, and Silicon and the Related Elements

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Heating of N-aryl-1,2,3,4,5,7-pentathiazocanes 1 in the presence of primary and secondary amines afforded N-Alkyl or N,N-dialkylthioformamides 5, and similar heating of 1 in the absence of amines afforded an inseparable mixture of acyclic polysulfides 4 bearing a thioformanilide moiety on each terminal. Bisthioformanilides 4 were also converted into 5 by treating with these amines, and the thioformylation was assumed to proceed through a pathway involving the ring fission of 1 and the subsequent nucleophilic attack of these amines onto the thioformyl group of 4.

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“…The brominated indole (38), derived from Laurencia brongniartii, has been shown to possess cytotoxic and antimicrobial properties (76). A further indole-based compound isolated from Prionitis lanceolata is 3-(hydroxyacetyl)indole (39). Prior to its isolation as a natural product this compound had been obtained synthetically and was shown to be a potent stimulant of the central nervous system (77).…”

Section: Charaminmentioning

confidence: 97%

“…Phytochemical investigations of this alga yielded two biologically active compounds, charatoxin (18) (38)(39)(40), and 4-azoniaspiro [3,3]heptane-2,6-diol (19, charamin) (41). Charatoxin (18) is structurally similar to nereistoxin, an insecticide obtained from an annelid worm which is suggested to block acetylcholine receptors.…”

Section: Konig and Wrightmentioning

confidence: 98%

Algal Secondary Metabolites and Their Pharmaceutical Potential

König

Wright

1993

ACS Symposium Series

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Algae are a rich and varied source of pharmacologically active natural products. In this paper the biological properties of natural products derived from algae of the divisions Chlorophyta, Rhodophyta, Phaeophyta and Cyanophyta are discussed. The compounds described belong to a wide range of structural classes, e.g., alkaloids, aromatic compounds, macrolides, peptides and terpenes, all of which exhibit some biological activity.This paper provides an overview of the literature relating to algae of the divisions Chlorophyta, Rhodophyta, Phaeophyta and Cyanophyta that have afforded biologically active natural products. Within each division, information is subdivided according to the structural classes in which the active compounds belong. It is considered beyond the scope of this paper to mention every algal metabolite shown to possess some biological activity. Thus, examples were chosen in such a way as to demonstrate the range of chemical structures and biological activities encountered in algae, with an emphasis on the more recent literature. Prior to this compilation, many interesting and detailed reports have been published relating either to algal metabolites (1-10) or to marine natural products in general (11, 12), but no recent report has attempted to provide an overall view of bioactive secondary metabolites from algae.

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Synthesis of 4-methylthio-1,2-dithiolane and 5-methylthio-1,2,3-trithiane. Two naturally occurring bioactive compounds

Cited by 31 publications

References 10 publications

Searching for allelopathic effects of submerged macrophytes on phytoplankton—state of the art and open questions

Searching for allelopathic effects of submerged macrophytes on phytoplankton—state of the art and open questions

Novel Thiofomylation of Primary and Secondary Amines Using N-Aryl-1,2,3,4,5,7-Pentathiazocanes

Algal Secondary Metabolites and Their Pharmaceutical Potential

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