Synthesis and in vitro evaluation of pseudosaccharinamine derivatives as potential elastase inhibitors

Rode, Haridas B.; Koerbe, Stefanie; Besch, A.; Methling, Karen; Loose, Jutta; Otto, Hans‐Hartwig

doi:10.1016/j.bmc.2005.11.057

Cited by 9 publications

(6 citation statements)

References 22 publications

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“…Sulfatecontaining glycolipids have been characterized as platelet aggregating factors [13]. Sulfated heparin and its analogues present in blood are strong neutrophil elastase inhibitors [14]. Possibly sulfated di-pentose also has the same function, and the ceramide moiety helps this molecule to bind to the membranes.…”

Section: Resultsmentioning

confidence: 99%

Partial Purification and Characterization of an Elastase-inhibitory Lipid Derivative from a Cyanobacterium, Microcystis Ku2

Bagchi

Ghosh

2011

Indian J Microbiol

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A unicyanobacterial isolate of cyanobacterium, identified as Microcystis Ku2, produced a mammalian elastase-inhibitory lipid derivative. Protease inhibitors in cyanobacteria are unequivocally peptides. Since this metabolite appeared in lipid phase, we worked on a hypothesis that whether metabolite other than peptides could be responsible for the characteristic inhibition. It was purified by saponification and reverse phase column chromatography. The resulting compound was tentatively characterized as a glycolipid with structure of sulfated dipentose derivative of ceramide (MW = 956 Da). The apparent IC 50 for elastase was 1.3 lM.

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Section: Resultsmentioning

confidence: 99%

Partial Purification and Characterization of an Elastase-inhibitory Lipid Derivative from a Cyanobacterium, Microcystis Ku2

Bagchi

Ghosh

2011

Indian J Microbiol

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“…Bode et al (1989); Edwards & Bernstein, 1994;Rode et al, 2005). The detailed description of these biochemical assays is reported in our earlier work (Rode et al, 2006). It is important to note that compound 3 inhibited 32% activity of PPE at 100 µM concentration and 15% activity of HLE at 200 µM concentrations.…”

Section: General Description and Spectral Propertiesmentioning

confidence: 99%

“…For general information on elastases, see: Bode et al (1989); Edwards & Bernstein (1994). For biochemical assays of HLE inhibition, see: Rode et al (2005Rode et al ( , 2006. For information on the synthesis, see: Wade et al (1979); Gupta et al (1999).…”

Section: Related Literaturementioning

confidence: 99%

“…Of interest are the heterocyclic inhibitors as these small molecules potentially offer advantages over the larger, peptide based inhibitors due to their increased proteinase stability, increased oral absorption and decreased structural complexity. In our earlier reports, we described peptidic and heterocyclic elastase inhibitors and illustrated that the pseudosaccharin amine derivatives are potential inhibitors of elastase (Rode et al 2005, Rode et al 2006. Pseudosaccharin amines were further explored to synthesize analogues containing thiophene and thiazole components.…”

Section: S1 Commentmentioning

confidence: 99%

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Methyl 3-[(1,1-dioxo-1λ⁶,2-benzothiazol-3-yl)amino]-5-nitrothiophene-2-carboxylate

Rode¹,

Chojnacki²,

Otto³

2012

Acta Cryst E

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The title nitrothiophene compound, C13H9N3O6S2, crystallizes with two independent molecules in the asymmetric unit; the molecular structure of each is stabilized by an intramolecular N—H⋯O hydrogen bond. The two molecules adopt flattened but slightly different conformations, viz. the dihedral angle between the thiophene ring and the essentailly planar 1,2-benzisothiazole fragment (r.m.s. deviations = 0.0227 and 0.0108 Å, respectively) is 15.62 (11)° in one molecule and 5.46 (11)° in the other. In the crystal, molecules are arranged into layers parallel to (-111) with weak Car—H⋯O interactions formed within the layer. N—H⋯O hydrogen bonds also occur. There are π–π stacking interactions between the molecules in neighbouring layers, the distance between the centroids of the 1,2-benzisothiazole benzene rings being 3.8660 (16) Å. Moreover, dipolar S=O⋯C=O interactions with an O⋯C distance of 2.893 (3) Å are observed between the symmetry-independent molecules in different layers. The title compound showed weak inhibition of HLE (human leukocyte elastase).

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“…Based on numerous reports revealing saccharin derivatives as elastase inhibitors, a series of pseudosaccharinamine derivatives was envisaged, synthesized and evaluated for elastase inhibitory activity. Some of those were found to be potent and reversible inhibitors of HLE in the low micromolar range [56,57].…”

Section: Biologically Active Derivativesmentioning

confidence: 99%

Advances in the Chemistry of Saccharins: From Synthetic Novelties Towards Biologically Active Compounds

Ms¹

2010

CMC

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The saccharin ring system has gained considerable attention in the past decades, especially in the field of medicinal chemistry. The wide applicability of saccharin derivatives remains the driving force behind the constant development of novel routes and methods that provide new access to the construction of saccharin. Since the functionalization of this heterocycle has proved difficult, except for N- and O-alkylation, novel strategic approaches are much sought-after and thus constitute a great value to any medicinal chemist. In addition to the synthetic novelties introduced into the synthesis and functionalization of this particular heterocycle, the numerous newly discovered biological activities of saccharin and its derivatives are also reviewed. Saccharin may be considered to constitute a privileged framework on account of its role as a key structural element in several biologically active compounds ranging from enzyme inhibitors to receptor ligands and beyond.

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Synthesis and in vitro evaluation of pseudosaccharinamine derivatives as potential elastase inhibitors

Cited by 9 publications

References 22 publications

Partial Purification and Characterization of an Elastase-inhibitory Lipid Derivative from a Cyanobacterium, Microcystis Ku2

Partial Purification and Characterization of an Elastase-inhibitory Lipid Derivative from a Cyanobacterium, Microcystis Ku2

Methyl 3-[(1,1-dioxo-1λ⁶,2-benzothiazol-3-yl)amino]-5-nitrothiophene-2-carboxylate

Advances in the Chemistry of Saccharins: From Synthetic Novelties Towards Biologically Active Compounds

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Synthesis and in vitro evaluation of pseudosaccharinamine derivatives as potential elastase inhibitors

Cited by 9 publications

References 22 publications

Partial Purification and Characterization of an Elastase-inhibitory Lipid Derivative from a Cyanobacterium, Microcystis Ku2

Partial Purification and Characterization of an Elastase-inhibitory Lipid Derivative from a Cyanobacterium, Microcystis Ku2

Methyl 3-[(1,1-dioxo-1λ6,2-benzothiazol-3-yl)amino]-5-nitrothiophene-2-carboxylate

Advances in the Chemistry of Saccharins: From Synthetic Novelties Towards Biologically Active Compounds

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Product

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Methyl 3-[(1,1-dioxo-1λ⁶,2-benzothiazol-3-yl)amino]-5-nitrothiophene-2-carboxylate