- N,O-bis(trifluoroacetyl)hydroxylamine as a useful electrophilic nitrogen source: Catalytic synthesis of N-(trifluoroacetyl)sulfilimines
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(equation presented) In the presence of catalytic quantites of Cu(OTf)2 the novel hydroxamic acid anhydride salt functions competently in the trifluoroacetamidation of sulfides to afford N-(trifluoroacetyl)sulfilimines. The salient features of this salt include its ease of synthesis from the inexpensive, commercially available starting materials trifluoroacetic anhydride and hydroxylamine hydrochloride.
- Tomooka,LeCloux,Sasaki,Carreira
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- New jasmonate analogues as potential anti-inflammatory agents
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In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-α) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone (1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA1, PGA2, and 15-deoxy-Δ12,14-PGJ2). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that α-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads.
- Dang, Hung The,Lee, Hye Ja,Yoo, Eun Sook,Hong, Jongki,Bao, Baoquan,Choi, Jae Sue,Jung, Jee H.
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experimental part
p. 10228 - 10235
(2009/04/10)
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- ENCHAINEMENTS HETEROATOMIQUES ET LEURS PRODUITS DE CYCLISATION - VIII METHYLENE-2-DIHYDRO-3,6-2H-THIAZINES-1,3-FONCTIONNALISEES EN POSITION 4 PAR SUBSTITUTION NUCLEOPHILE D'UN GROUPEMENT BROMOMETHYLE ET PAR CONVERSION D'UN GROUPEMENT DIBROMOMETHYLENE EN ALDEHYDE, NITRILE ET ESTER
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Treatment with NBS of 2-methylene-3,6-dihydro-2H-1,3-thiazines carrying an ester function on 5 and a methyl on 4 gives the corresponding 4-bromomethyl and 4,4-dibromomethyl derivatives in a perfectly selective manner.The monobromo compounds give access to 4-aminomethyl, 4-alkoxymethyl, 4-alkylthiomethyl, 4-acetoxymethyl and 4-formyl thiazines.These aldehydes, also prepared from the dibromo derivatives, are converted into 4-cyano and 4-alkoxycarbonyl thiazines.In certain cases, interactions with the neighbouring ester group, leading to lactones are observed.
- Reliquet, F.,Reliquet, A.,Sharrard, F.,Meslin, J. C.,Quiniou, H.
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p. 361 - 370
(2007/10/02)
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- Therapeutically active 3-amino-1-halogenated phenyl-2-pyrazolines and their C4 and C5 analogs
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A method of meliorating the inflammation and/or the progressive joint deterioration characteristic of arthritic disease, preventing the onset of asthmatic symptoms and allergic diseases, treating pain or treating bacterial and fungal infections in mammals using 3-amino-1-halogenated phenyl-2-pyrazolines and their C4 and C5 analogs.
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- Trifluoroacetonitrile Oxide
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Trifluoroacetonitrile oxide (1) is a reactive intermediate that can be generated by the dehydrochlorination of trifluoroacetohydroximoyl chloride (2) with base.It reacts with mercaptans and amines in a stereospecific manner to give Z oximes 3 and 15 and forms a cycloadduct (10) with benzonitrile.In the absence of trapping agents, it dimerizes to give either the expected furoxan dimer 7 or the unusual dioxadiazine dimer 8, depending upon conditions.A convenient synthesis for 2 based on hydroxylamine hydrochloride, trifluoroacetic anhydride, and PCl3 was developedto make 1 easily accessible.
- Middleton, William J.
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p. 919 - 922
(2007/10/02)
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