Total synthesis of the two series of new pentacycilc cycloalk[g]indolo[2,3-a]quinolizine alkaloids (modified sempervirine possessing the wide range of activity), has been elaborated in five steps from 5-acetyl-3-methylthio-1,2,4-triazine (obtained from the simple acyclic materials). In the two k...
The title ketone, a supposed metabolite of 9-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine (MIQ), was prepared and found different on chromatographic comparison from the isolated metabolite M 4 . However, the pharmacological screening of this compound evidenced, among other...
Synthesis of indole alkaloid related compounds using Schiff base formation, intramolecular cyclization (or N-alkylation), and Pictet–Spengler reaction as a cascade one pot condensation has been reported. The cascade chemistry has been applied to the synthesis of (±)-harmicine as a key step.
Pentacarbonyl(2-alkynylanilinocarbene) complexes of chromium undergo a novel intramolecular tandem alkyne insertion/carbene annulation sequence to give 9H-carbazoles and 11H-benzo[a]carbazoles in a one-pot reaction. The yields of the cyclization products depend on the substitution pattern both ...
Density functional theory calculations show that the heightened stability of α-keto radicals, the derivatives of perfluorinated α-diketones of general formula CF3C(O)C(O)RF (RF = i-C3F7; t-C4F9), in perfluoro-tert-butanol can be caused by the H-bond-imposed formation of cation radicals of vici...
In the presence of n-BuLi in THF at low temperature, the phenomena of ring opening of symmetric substituted dithieno[2,3-b:3′,2′-d]thiophenes were observed. After quenching the organolithium intermediates with dry DMF, a series of substituted novel bithiophenyl aldehydes were prepared in good ...
In situ scanning tunneling microscopy (STM) has been used to examine the spatial structures of mixed molecular adlayers of dithieno[2,3-b:3,2-d]thiophene diphenyl (C6H5–DTT–C6H5, 1), 2-pentafluorophenyl-6-phenyldithieno [2,3-b:3′,2′-d]thiophene (C6F5–DTT–C6H5, 2), and 2,6-bis(pentafluoroph...
A series of dithieno[2,3-b:3′,2′-d]thiophene (DTT; 1) derivatives were synthesized and characterized. Facile, one-pot [2+1] and [1+1+1] synthetic methods of DTT were developed, which enabled the efficient realization of a new DTT-based semiconductor series for organic thin-film transistors (OT...
General methods are descibed for the synthesis of mesoionic derivatives of [1,2,3]triazolo[1,5-a]quinoline, [1,2,3]triazolo[1,5-a]quinazoline, [1,2,3]triazolo[1,5-a]quinoxaline and [1,2,3]triazolo[5,1-c]benzotriazine.
Preparation and structure of salts and ylides derived from triazolo[1,5-a]quinoline 2 and triazolo[5,1-a]isoquinoline 3 are described. Reactions with methyl propiolate of ylides 6-9 give pyrrolo[1,2-a]quinolines 13, 18 and pyrrolo[2,1-a]isoquinolines 12, 19.
New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalog...
The synthesis of a series of 1,2,4-triazolo[4,3-a]quinoline derivatives is described; their structures were assigned by 1 H NMR and analytical data. The new compounds were tested in vivo for their antiinflammatory and analgesic activities, as well as for their ulcerogenic action. Some of...
In spite of the development of new anticancer drugs by the pharmaceutical industry, melanoma and T lymphomas are diseases for which medical advances remain limited. Thus, there was an urgent need of new therapeutics with an original mechanism of action. Since several years, our group develops qu...
Imidazoquinoxaline and pyrazoloquinoxaline derivatives, analogues of imiquimod, were synthesized, and their in vitro cytotoxic and pharmacodynamic activities were evaluated. In vitro cytotoxicity studies were assessed against melanoma (A375, M4Be, RPMI-7591), colon (LS174T), breast (MCF7), and l...
The inhibition of the NF-κB-dependent pathways by IKK inhibitors plays an important role in immunity, inflammation, and cancer. New imidazoquinoxalines tricyclic derivatives are prepared using microwave assistance and their biological activities as IKK inhibitors are described. Compounds 6a pre...
In the presence of base, ethyl 2,2-dihydropoly(per)fluoroalkanoate(2) reacted with N-phenacyl benzimidazole bromide(1a-1b),N-acetonyl benzimidazole bromide(1c) and N-ethoxycarbonylmethyl benzimidazole bromide(1d) in DMF to give pyrrolo[1,2-a]quinoxaline derivatives(3ae-3dg) respectively.
Herein we describe the synthesis and properties of substituted phenylaminopyrrolo[1,2-a]quinoxaline-carboxylic acid derivatives as a novel class of potent inhibitors of the human protein kinase CK2. A set of 15 compounds was designed and synthesized using convenient and straightforward synthesis...
The synthesis of 3-(4-alkyl-4,5-dihydropyrrolo[1,2-a]quinoxalin-4-yl)-2H-chromen-2-one derivatives by a three-component reaction of salicylaldehyde, β-keto esters, and 1-(2-aminophenyl)pyrrole using piperidine–iodine as a dual system catalyst is reported. Good yields, mild reaction conditions,...
Four series of [1,2,4]triazolo[3,4-a]phthalazine and tetrazolo[5,1-a]phthalazine derivatives bearing substituted piperazine moieties were synthesized and evaluated for their positive inotropic activity by measuring the left atrium stroke volume in isolated rabbit-heart preparations. Several comp...
A general method is reported for the solid-phase synthesis of [1,2,4]triazolo[3,4-a]phthalazine and tetrazolo[5,1-a]phthalazine derivatives based on the cyclization of resin-bound chlorophthalazines 4 with various hydrazides or sodium azide. The resin-bound chlorophthalazines 4, produced by nucl...
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