- Synthesis of Allocolchicine Conjugates with a Cetirizine Analog
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Conjugates of allocolchicine and a cetirizine analog have been synthesized as potential anti-inflammatory and anti-allergic drugs.
- Zotov,Shchegravina,Fedorov, A. Yu.
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- Sulphide as a leaving group: Highly stereoselective bromination of alkyl phenyl sulphides
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A conceptionally novel nucleophilic substitution approach to synthetically important alkyl bromides is presented. Using molecular bromine (Br2), readily available secondary benzyl and tertiary alkyl phenyl sulphides are converted into the corresponding bromides under exceptionally mild, acid- and base-free reaction conditions. This simple transformation allows the isolation of elimination sensitive benzylic β-bromo carbonyl and nitrile compounds in mostly high yields and purities. Remarkably, protic functionalities such as acids and alcohols are tolerated. Enantioenriched benzylic β-sulphido esters, readily prepared by asymmetric sulpha-Michael addition, produce the corresponding inverted bromides with high stereoselectivities, approaching complete enantiospecificity at -40 °C. Significantly, the reported benzylic β-bromo esters can be stored without racemisation for prolonged periods at -20 °C. Their synthetic potential was demonstrated by the one-pot preparation of γ-azido alcohol (S)-5 in 90% ee. NMR studies revealed an initial formation of a sulphide bromine adduct, which in turn is in equilibrium with a postulated dibromosulphurane intermediate that undergoes C-Br bond formation.
- Canestrari, Daniele,Cioffi, Caterina,Biancofiore, Ilaria,Lancianesi, Stefano,Ghisu, Lorenza,Ruether, Manuel,O'Brien, John,Adamo, Mauro F.A.,Ibrahim, Hasim
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p. 9042 - 9050
(2019/10/22)
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- Anti-inflammatory effects of two new methyl and morpholine derivatives of diphenhydramine on rats
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Diphenhydramines are one of the first-generation histamine H1-receptor antagonists of the ethanolamine class that demonstrate many pharmacological properties including anti-inflammatory effects. In this research, bromo (II) and two new tolyl derivatives of I, (Di [p-tolyl] [dimethylaminoethoxy] methane, III) and (Di [p-tolyl] [2-morpholinoethoxy] methane, IV) were synthesized. Their acute and chronic anti-inflammatory activities were evaluated with the formalin and histamine-induced rat paw edema. The vascular permeability in formalin and histamine-induced paw edema, in xylene-induced ear edema, and in peritonitis after acetic acid application into peritoneal cavity were also measured and compared to II. Cotton pellet-induced granuloma model was selected for inducing chronic inflammations in rats. The newly synthesized analogs of diphenhydramine seemed effective to decrease acute inflammations. It was concluded that the prominent anti-phlogistic effects of the new drugs could be related to its reduction vascular permeability mechanism(s) or to its antagonistic effects on H1 histamine receptors. Springer Science+Business Media, LLC 2011.
- Ahmadi, Abbas,Khalili, Mohsen,Hajikhani, Ramin,Safari, Narjes,Nahri-Niknafs, Babak
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p. 3532 - 3540
(2013/02/25)
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- N-heterocyclic carbene-catalyzed cross-coupling of aromatic aldehydes with activated alkyl halides
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N-Heterocyclic carbene-catalyzed umpolung of aldehydes followed by their interception with diarylbromomethanes has been reported. This conceptually novel transition-metal-free cross-coupling of aldehydes with alkyl halides works well at low catalyst loadings and under mild reaction conditions leading to the formation of diaryl acetophenone derivatives in good yields. In addition, α-halo ketones and esters can also be used as aldehyde reaction partners.
- Padmanaban, Mohan,Biju, Akkattu T.,Glorius, Frank
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- Synthesis and anticonvulsant activity of some cinnamylpiperazine derivatives
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A series of cinnamylpiperazine derivatives was synthesized using different benzophenone as starting material. The structures of the compounds were proved by their IR, 1H-NMR spectroscopic data and mass spectra data. The anticonvulsant activities of these compounds were evaluated with maximal electroshock (MES) test and rotarod test with intraperitoneal injection on KunMing mice. Among all the flunarizine analogues, no one exhibited better anticonvulsant activity than flunarizine. Flunarizine (4i) exhibited anticonvulsant activity with ED50 of 38.1 mg/kg, TD50 of 164.3 mg/kg and PI of 4.3 through administration intraperitoneal, and with ED50 of 56.8 mg/kg, TD50 of 456.3 mg/kg and PI of 8.0 through oral administration.
- Hu, Chuan,Sun, Zhi-Gang,Wei, Cheng-Xi,Quan, Zhe-Shan
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p. 661 - 664
(2011/11/29)
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