20141-47-3Relevant academic research and scientific papers
Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
, p. 1008 - 1016 (2015/08/18)
Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
Synthesis, anti-inflammatory activity and COX-1/COX-2 inhibition of novel substituted cyclic imides. Part 1: Molecular docking study
Abdel-Aziz, Alaa A.-M.,Eltahir, Kamal E.H.,Asiri, Yousif A.
scheme or table, p. 1648 - 1655 (2011/05/06)
A group of cyclic imides (1-13) was designed for evaluation as selective COX-2 inhibitors and investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model. Compounds 5b, 6b, 11b, 11c, 12b and 12c were proved to be potent COX-2 inhibitors with IC50 range of 0.1-1.0 μM. In vitro COX-1/COX-2 inhibition structure-activity studies identified compound 5b as a highly potent (IC50 = 0.1 μM), and an extremely selective [COX-2 (SI) = 400] comparable to celecoxib [COX-2 (SI) > 333.3], COX-2 inhibitor that showed superior anti-inflammatory activity (ED 50 = 104 mg/kg) relative to diclofenac (ED50 = 114 mg/kg). A Virtual screening was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. Molecular modeling (docking) study showed that the CH3O substituents of 5b inserted deep inside the 2°-pocket of the COX-2 active site, where the O-atoms of such group underwent a H-bonding interaction with His90 (2.43, 2.83 ), Arg513 (2.89 ) and Tyr355 (3.34 ). Docking study of the synthesized compound 5b into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.
Tandem Diels-Alder/cross-coupling reactions of generated in situ organoindium reagents in a one-pot process
Mo, Juntae,Kim, Sung Hong,Lee, Phil Ho
supporting information; experimental part, p. 424 - 427 (2010/04/24)
[Chemical equation presented] Tandem Diels-Alder/ cross-coupling reactions with organoindium reagents generated in situ from 1-bromo-2,3-butadiene and indium were developed in a one-pot process. [4 + 2] Cycloaddition reactions using organoindium reagents and subsequent Pd-catalyzed cross-coupling reactions provided the rapid synthesis of six-membered carbocycles starting from 1-bromo-2,3-butadiene.
Preparation of 2-Trialkylsiloxy-substituted 1,3-dienes and their Diels - Alder/cross-coupling reactions
Pidaparthi, Ramakrishna R.,Welker, Mark E.,Day, Cynthia S.,Wright, Marcus W.
, p. 1623 - 1626 (2008/02/02)
2-Triethylsiloxy-substituted 1,3-butadiene has been prepared in gram quantities from chloroprene via a simple synthetic procedure. Silatrane and catechol-substituted analogues of this main group element substituted diene were prepared by ligand exchange a
Antifungal properties of novel N- and α,β-substituted succinimides against dermatophytes
Lopez, Silvia N.,Sortino, Maximiliano,Escalante, Andrea,De Campos, Fatima,Correa, Rogerio,Cechinel Filho,Nunes, Ricardo J.,Zacchino, Susana A.
, p. 280 - 288 (2007/10/03)
The synthesis and antifungal properties of a series of new N-aryl α,β-substituted succinimides against a panel of dermatophytes of clinical relevance are reported. Among those compounds possessing a N-phenyl substituent, 7-thia-2-azabicyclo[2,2,1]hept-2-en-3-amine[5,6-c]succinimide was the better inhibitor of Trichophyton rubrum, the major ethiological agent of all infections produced by dermatophytes. In contrast, succinimides containing a N-(p-sulfonylphenyl) substituent, only inhibited Epidermophyton floccosum, all active compounds possessing an oxabicyclo group in positions α,β of the imide. Substituents on the oxabicyclo group were important for the activity. Regarding the mechanism of action, N-(p-N′-4-methoxyphenylsulfamoylphenyl) -8-oxabicyclo[2,2,1]hept-4-en-3-methyl[5,6-c]succinimide produced a mottled inhibition halo in the Neurospora crassa assay, showing that it would act by inhibiting the synthesis or assembly of the fungal cell wall.
Comparative Study of the Reactions of Dilithiated Vicinal Diesters and Dilithiated 1,2-Dicarboximides with Methyl Iodide, α,ω-Dihalides, α,ω-Ditosylates, and ω-Bromo Esters
Bilyard, Kevin G.,Garratt, Peter J.,Hunter, Roger,Lete, Ester
, p. 4731 - 4736 (2007/10/02)
The reactions od dilithiated dimethyl cyclohexane-1,2-dicarboxylate (1), dimethyl 4-cyclohexene-1,2-dicarboxylate (2), N-substituted cyclohexane-1,2-dicarboximides 11a-c, and N-phenyl-4-cyclohexene-1,2-dicarboximides 18 with a variety of substrates have b
