Fibrin-stabilizing factor inhibitors. 12. 5-Dibenzylaminopentylamine and related compounds, a new type of FSF [fibrin-stabilizing factor] inhibitors

Hoffmann, K. J.; Stenberg, P.; Ljunggren, C; Svensson, U; Nilsson, Jonas; Eriksson, Olle; Hartkoorn, A; Lundén, Ragnar

doi:10.1021/jm00237a014

Cited by 18 publications

(11 citation statements)

References 6 publications

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“…The crude product was purified by column chromatography (SiO2: CHCl3/ MeOH, 9:1; Rf 0.17) to provide 7a (1.21 g, 4.5 mmol, 56%) as a colorless oil. 21 1 H NMR (CDCl3, 200 MHz) δ 1.37-1.50 (m, 4H), 1.81 (br, 2H), 2.40 (t, J ) 6.8 Hz, 2H), 2.57 (t, J ) 6.7 Hz, 2H), 3.52 (s, 4H), 7.16-7.37 (m, 10H). 13 C NMR (CDCl3, 50 MHz) δ 24.2, 30.9, 41.7, 52.9, 58.1, 126.6, 127.9, 128.6, 139.7.…”

Section: Resultsmentioning

confidence: 99%

Efficient Syntheses of Oncinotine and Neooncinotine

2004

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We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components: 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage: the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.

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Section: Resultsmentioning

confidence: 99%

Efficient Syntheses of Oncinotine and Neooncinotine

2004

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“…According to the procedure of Abdel-Monem et al,11 0.11 mol of methyl p-toluenesulfonate, ethyl iodide, 1-bromopentane, chloroacetone, or 5-chloro-2-pentanone was added to 0.1 mol of potassium phthalimide in DMF and heated to 100 °C for 8 h to afford compound 2 (41%), 3 (63%), 6 (51%), 10 (50%), or 12 (12%). Method B. Equimolar amounts of phthalic anhydride and a primary amine were mixed in toluene and heated according to the method of Sterk et al6 to synthesize compounds 4 (79%), 5 (88%), 7 (83%), 8 (61%), 9 (85%), 15 (90%), 16 (39%), 17 (75%), 18 (70%), and 19 (70%). l-jV-Phthalimidobutan-3-one (11).…”

Section: Methodsmentioning

confidence: 99%

“…Preliminary data from our laboratory indicated that potassium phthalimide (1) possessed hypolipidemic activity in mice. Subsequently, a series of N-substituted phthalimides including alkyl (2)(3)(4)(5)(6)(7)(8)(9), methyl ketone (10)(11)(12)(13)(14), carboxylic acid (15)(16)(17)(18)(19), and acetate ester (20)(21)(22)(23) substituents of various chain lengths were synthesized.…”

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confidence: 99%

Hypolipidemic activity of phthalimide derivatives. 1. N-Substituted phthalimide derivatives

Chapman¹,

Cocolas²,

Hall³

1979

J. Med. Chem.

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The general lipid-lowering action of the N-substituted phthalimide derivatives reported herein, as well as the activity of potassium phthalimide, implicates the phthalimide moiety as possessing hypolipidemic activity in rodents. Compounds containing substituents with chain lengths of four carbon or oxygen atoms showed the best hypolipidemic activity in the series tested. Tests involving 1-N-phthalimidobutan-3-one demonstrated a dose-dependent hypolipidemic action free of estrogenic side effects, with no apparent deposition of cholesterol in body organs, and with a high therapeutic index. Further work on the hypolipidemic activity of phthalimido, as well as other imido compounds, is underway.

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“…However, when labelled they can be used to identify specific glutamine residues on various proteins that are TG substrates [56]. In an attempt to develop more selective and less toxic compounds, a series of tTG pseudo-substrate amine donors have been synthesized, i.e., -dibenzylaminoalkylamines [85] and phenylthiourea derivatives of , -diaminoalkanes [86]. The thiol esters of carboxylic acids 2-benzyldiethylammonioethyl 3-phenylthiolpropionate and 2-benzyldiethylammonioethyl 4-phenylthiolbutyrate have also been used as pseudo-substrates amine acceptors in in vitro experiments [87].…”

Section: Competitive Non-peptidic Substratesmentioning

confidence: 99%

New Therapeutic Strategies for Coeliac Disease: Tissue Transglutaminase as a Target

Esposito

Caputo²,

Troncone³

2007

CMC

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Coeliac disease is a multifactorial disease characterized by a dysregulated immune response to ingested wheat gluten and related cereal proteins. With an incidence of about 1% of the general population, it is considered the most common food intolerance disorder. The mainstay of coeliac disease treatment is strict lifelong adherence to a gluten-free diet. Elimination of gluten and related proteins from the diet leads to clinical and histological improvement. However, some patients do not respond to dietary therapy and others have poor dietary compliance. This has prompted the search for a therapy alternative to a gluten-free diet. Tissue transglutaminase is a crucial factor in coeliac disease because it promotes the gluten-specific T-cell response and is also the target of the autoimmune response. Tissue transglutaminase induces changes in gluten, which in turn, cause the generation of a series of gluten peptides that bind to HLA-DQ2 or DQ8 molecules with high affinity. The resulting HLA-DQ2 (DQ8)-gluten peptide interaction triggers the proinflammatory T cell response. Tissue transglutaminase is also involved in other non-T-cell-mediated biological activities of gliadin peptides. For these reasons, tissue transglutaminase is a potential target for therapeutic intervention. In this paper we review the state-of-the-art of tissue transglutaminase inhibition, and examine known and new-generation inhibitors and their activity in in vitro and in vivo models. We also examine their potential as therapeutic tools for coeliac disease.

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Fibrin-stabilizing factor inhibitors. 12. 5-Dibenzylaminopentylamine and related compounds, a new type of FSF [fibrin-stabilizing factor] inhibitors

Cited by 18 publications

References 6 publications

Efficient Syntheses of Oncinotine and Neooncinotine

Efficient Syntheses of Oncinotine and Neooncinotine

Hypolipidemic activity of phthalimide derivatives. 1. N-Substituted phthalimide derivatives

New Therapeutic Strategies for Coeliac Disease: Tissue Transglutaminase as a Target

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