Synthesis and Reactions of New Dithiolopyrroles

Stachel, Hans‐Dietrich; Eckl, E.; Immerz-Winkler, Elisabeth; Kreiner, Christine; Weigand, Wolfgang; Robl, Christian; Wünsch, Ralf; Dick, Stefan; Drescher, N.

doi:10.1002/hlca.200290022

Cited by 18 publications

(11 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…) (Jiang et al ). Depending on the nature of R1, two dithiolopyrrolone groups are mainly distinguished: pyrrothins (R1 = CH 3 ) and holothins (R1 = H) that differ from each other by the side chain R2 (Stachel et al ). These compounds have been found to be produced by few species of actinobacteria ( Streptomyces and Saccharothrix ), Xenorhabdus and some marine bacteria such as Alteromonas rava , Photobacterium halotolerans , Yersinia ruckeri and Pseudoalteromonas sp.…”

Section: Introductionmentioning

confidence: 99%

A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium

Merrouche

Yekkour

Coppel

et al. 2019

Lett Appl Microbiol

View full text Add to dashboard Cite

Saccharothrix algeriensis NRRL B‐24137 is an actinobacterium isolated from Algerian Saharan soil. It produces bioactive compounds belonging to the dithiolopyrrolone class of antibiotics, which are characterized by the possession of a unique pyrrolinonodithiole nucleus. Dithiolopyrrolones are known for their strong antibacterial and antifungal activities. This class of antibiotics generated great interest after the discovery of their anticancer properties. In this study, an antibiotic named PR11, produced after a long bacterial fermentation (11 days) in sorbic acid‐containing culture broth, was characterized as a new dithiolopyrrolone derivative. After HPLC analysis and purification, the chemical structure of this antibiotic was determined by 1H‐ and 13C‐nuclear magnetic resonance, mass and UV‐visible data. PR11 was thus characterized as an iso‐hexanoyl‐pyrrothine, a novel dithiolopyrrolone derivative. The minimum inhibitory concentrations of the new induced antibiotic were determined against several pathogenic micro‐organisms. A moderate to strong activity was noted against all Gram‐positive bacteria, filamentous fungi and yeasts tested. Significance and Impact of the Study Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. In the future investigation for novel dithiolopyrrolone discovery, fermentation duration should be regarded as a key parameter as well.

show abstract

Section: Introductionmentioning

confidence: 99%

A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium

Merrouche

Yekkour

Coppel

et al. 2019

Lett Appl Microbiol

View full text Add to dashboard Cite

show abstract

“…In conclusion, we have demonstrated that it is possible to activate a NÀS(O) bond in the pyrroloisothiazolone S-oxides 18a and 20a by oxidative addition of the Pt 0 complexes 24a ± c. The products isolated and characterized were the cis-amidosulfenato platinum(II) complexes 25 and 26a ± c. Compared with the analogous reactions of the isoelectronic 1,2-dithiolo [4,3-b]pyrrolone S-oxide (21) [14] …”

mentioning

confidence: 88%

Metal Complexes of Functionalized Sulfur‐Containing Ligands. Part XIX

Stachel¹,

Immerz-Winkler²,

Poschenrieder³

et al. 2003

Helvetica Chimica Acta

Self Cite

View full text Add to dashboard Cite

Dedicated to Professor Heinrich Nˆth on the occasion of his 75th birthdayThe title compounds were prepared starting from the dihydropyrrolones 4 ± 6. Nucleophilic displacement and ring closure yielded the 1H-pyrrolo[3,2-c]isothiazol-5(4H)-ones 8 and 10. The fused systems formed salts with strong acids and electrophiles (15, 16), as well as with bases. Oxidation led either to S(2)-oxides (18a, 20a) or to the corresponding bicyclic sultams (18b, 20b), depending on the reaction conditions. The sulfinamide 18a was also obtained from the known 1,2-dithiolopyrrolone S-oxide 21 by a ring-opening/ring-closure reaction sequence. O-Methylation of 8 furnished the −azafulvene× 17. The oxidative addition of [Pt(h 2 -C 2 H 4 )L 2 ] (24a: L Ph 3 P, 24b: L 1/2 dppf, 24c: L 1/2 (R,R)-diop) to 18a and 20a led to the cis-amido-sulfenato Pt complexes 25 and 26a ± c, respectively.

show abstract

“…Compound 1 was prepared as previously described in the literature. [35] Unfortunately, treatment of equimolar amounts of Fe 3 (CO) 12 and compound 1 in boiling THF for 3 hours does not afford the binuclear complex 2 (Scheme 1). In contrast, stirring a mixture of equimolar amounts of Fe 3 (CO) 12 and compound 1 in THF at 25°C followed by column chromatography afforded the binuclear complex 2 in moderate yield, as illustrated in Scheme 1.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and Electrochemical Investigations of the [FeFe]‐Hydrogenase H‐Cluster Mimics Mediated by Bicyclic Dithiols Derivative

Daraosheh

Abul‐Futouh

Abdel‐Rahem

et al. 2021

Zeitschrift anorg allge chemie

Self Cite

View full text Add to dashboard Cite

Biomimic of the active site of [FeFe]-hydrogenase containing bicyclic dithiols as bridging linker has been synthesized and characterized using different spectroscopic methods. The influence of this linker on the redox properties and the catalytic behavior of the resulted binuclear complex was investigated using cyclic voltammetry, showing that it can catalyze the reduction of protons to H 2 in the presence of acetic acid (AcOH). Moreover, the results revealed that the bicyclic dithiolene linker has improved the chemical stability of the reduced species and caused a shift to less negative potential in comparison to the synthetic models that mimic the active site of [FeFe]-hydrogenase reported in the literature. In addition, the structure of the resulted binuclear complex mediated by bicyclic dithiols as bridging linker was confirmed by X-ray diffraction analysis.

show abstract

Synthesis and Reactions of New Dithiolopyrroles

Cited by 18 publications

References 39 publications

A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium

A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium

Metal Complexes of Functionalized Sulfur‐Containing Ligands. Part XIX

Synthesis and Electrochemical Investigations of the [FeFe]‐Hydrogenase H‐Cluster Mimics Mediated by Bicyclic Dithiols Derivative

Contact Info

Product

Resources

About