- Photodegradation of sulfamethazine, sulfamethoxypiridazine, amitriptyline, and clomipramine drugs in aqueous media
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The photochemical transformation of two antibacterial sulfonamides, namely sulfamethazine (SMT) and sulfamethoxypyridazine (SMP), and two tricyclic antidepressants, namely amitriptyline (AMT) and clomipramine (CMP) were investigated. Experiments conducted in river water under artificial sunlight irradiation show an acceleration of the degradation for SMT, SMP, and CMP of a factor 1.6–7.7 by comparison to purified water. This acceleration is, at least partially, due to photosensitized reactions which can occur in river water. The photodegradation of CMP was particularly fast. In addition, no degradation was observed for AMT in purified water while photosensitized reaction occurs. Under ultra-violet (254?nm) irradiation in purified water, the four drugs were degraded. Calculated quantum yields of photodegradation were of 4.3?×?10?3, 5.1?×?10?3, 7.6?×?10?3, and 65.0?×?10?3 respectively for SMT, SMP, AMT, and CMP. UV coupled with hydrogen peroxide (UV/H2O2) was used as an advanced oxidation process for water depollution. The calculated second order rate constants of reaction with hydroxyl radicals were of 5.0?×?109, 5.0?×?109, 8.0?×?109 and 9.5?×?109?L?mol?1?s?1 for SMT, SMP, AMT and CMP, respectively. Finally, the structures of photoproducts were proposed according to LC–MS/MS analyses. The elimination of SO2 was the main photochemical process for SMT and SMP. In the case of AMT and CMP, hydration and hydroxylation, respectively, were observed.
- Nassar, Rania,Trivella, Aurélien,Mokh, Samia,Al-Iskandarani, Mohamad,Budzinski, Hélène,Mazellier, Patrick
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- Multiple organolithium generation in the continuous flow synthesis of amitriptyline
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A continuous flow protocol for the preparation of the tricyclic antidepressant (TCA) amitriptyline is reported. The advantages of flow chemistry when handling organometallic agents as well as when performing reaction with gases are demonstrated. Continuous multilithiation combined with carboxylation and the Parham cyclization, a Grignard addition and thermolytic water elimination by inductive heating are key features of the multistep protocol. Copyright
- Kupracz, Lukas,Kirschning, Andreas
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p. 3375 - 3380
(2013/12/04)
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- Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2
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The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [3H]-BTX binding site and sodium currents of hNav1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Nav1.2 currents at 10 μM, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNav1.2 activity and modification of the amine portion is detrimental to sodium channel block.
- Hudgens, Debjani P.,Taylor, Catherine,Batts, Timothy W.,Patel, Manoj K.,Brown, Milton L.
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p. 8366 - 8378
(2008/02/05)
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- Benzo-cyclitolamines
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Compounds having the formula STR1 and the pharmaceutically acceptable salts thereof, wherein n is 1 or 2; m is 2, 3 or 4; R1 is alkanoyl; and R2 is a tertiary amino group; have hypotensive activity.
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