Indolo 2,3quinodimethanes and stable cyclic analogs for regio and stereocontrolled syntheses of bannelated indoles. The present study describes synthesis of a series of 2phenyl benzimidazole1acetamide derivatives and their evaluation for anthelmintic activity using indian adult earthworms, pheretima posthuma. The present invention relates to novel substituted indole compounds of formula i having pharmacological activity, to processes for their preparation, to a combinatorial library and solid phase methods for preparing libraries of the compounds, to utilizing libraries of the compounds for drug discovery, and to pharmaceutical compositions thereof. Thus, we began the synthesis of nhydroxyalkyl3acetoxy2phenyl indoles. Electrocatalytic intramolecular dehydrogenative annulation for the synthesis of indoles. For the most biologically relevant derivatives, the effect on human. Azttreated control done at the same time 5 2phenyl3gndolal 2thiohydantoin which contains under identical conditions.
Synthesis and studies on some pharmacologically active sulpha substituted indoles kumar a department of chemistry, maharaj singh college, saharanpur, uttar pradesh, india research article abstract some pharmacologically active sulphasubstituted indoles were. The efficient synthesis of 2phenyl1hindoles was achieved by fischer indole synthesis with addition of phenyl hydrazine and acetophenone. Pdf synthesis of pharmacologically activity 2phenyl sulpha. Functional group interconversion, protection, alkylation on nitrogen, and bocprotection on nitrogen gave intermediate 23. Scheme 4 synthesis of 2phenylindole building blocks 3 and 5 from common precursor 6. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. A group of 5substituted24azido or methylsulfonylphenyl1hindoles were designed and synthesized as selective cyclooxygenase cox2 inhibitors. Synthesis and studies on some pharmacologically active. Initially, to evaluate the effect of the catalyst sbmimhso 4 under different reaction conditions, the reaction of indole and 1phenyl32phenyl1,2,3triazol4ylpropan1one was selected as a model reaction. Design and synthesis of some 5substituted24azido or. A series of hybrid molecules comprising of indole and imidazolone moieties 4ag and 5a,b was synthesized with a view to obtain promising anticonvulsant molecules.
Synthesis, antimicrobial, and antioxidant activities of n. Indole is a ubiquitous structural motif with important applications in many areas of chemistry. This is followed by the insertion of the appropriate benzyl or benzoyl fragment. The catalyst was characterized using tem, xrd and xps. Dk144655b 2phenylindole derivatives for use as heat.
It is the parent structure of a group of nonsteroidal selective estrogen receptor modulators serms that includes zindoxifene, bazedoxifene, and pipendoxifene, as well as the nonsteroidal estrogen d15414 the major metabolite of zindoxifene references. Synthesis of 2phenylindole nderivatives under conditions of. The pk a values were determined and are discussed in terms of substituent effects using hammett substituent constants. Pdf synthesis of pharmacologically activity 2phenyl. Synthesis and antiinflammatory activities of some nacetyl2 phenylindole mannich bases.
Links to pubmed are also available for selected references. Synthesis of the desired 1,3disubstituted2phenyl indoles 26. In this study, we report that the novel clay material was found to catalyze electrophilic substitution reaction of 2phenyl1hindoles with a variety of aromatic aldehydes to excellent yields of bis indolyl methanes at room temperature. Nalkylation of 2phenyl and 2pfluorophenyl indole 4 with tbsprotected bromoalcohols proceeded in modest yield using nah in dmf, followed by acetoxylation with lta and removal of the tbs protecting group to give alcohols 9 scheme 4. The newly synthesized compounds were tested for antibacterial andantiinflammatory activity. Onepot synthesis of 3substituted indole derivatives. The synthesis of indole 3aldehyde and its homologues. The structure of the title compounds was elucidated by. A highly active and recyclable catalyst for the synthesis. Synthesis, antiproliferative effect, and topoisomerase ii.
Synthesis of 2phenylindole from phenyl hydrazine labmonk. The present invention relates to 2phenyl indole derivatives and processes for preparing the said 2phenyl indole derivatives. It was found that primary condensation occurs only on aminogroups and produces the corresponding enaminoketones, which under conditions of enamine acidic cyclization on the basis of dibenzoylmethane, turn into. Author links open overlay panel cigdem karaaslan a b hachemi kadri b tulay coban c sibel suzen a andrew d. Triazoles26 and 28 were synthesised from azide3 by copper catalysed. Excellent selectivity and good functional group tolerance of this transformation were observed. The fischer indole synthesis is an organic reaction used to convert a phenyl hydrazine and an aldehyde or ketone to an indole using an acid catalyst. A series of 17 phenyl substituted derivatives of 2phenyl1,1,3,3tetramethylguanidine was synthesized. An ullmann reaction with bromobenzene converted 1h. Application of novel clay catalyst for the synthesis of bisindole. Synthesis and biological evaluation of some novel 2phenyl.
Pdf the synthesis of 2phenylindole nderivatives was accomplished. The 2phenyl indole derivatives with which the present invention is concerned are the substances represented by the formula. The product structure represents a scaffold that could be exploited in a pharmaceutical or academic setting. It could be used as an efficient catalyst for the synthesis of both indole and phenyl ether. Hence, considerable research is underway to develop indole based therapeutic agents. Application of novel clay catalyst for the synthesis of. Serotonin is known to exhibit antimigrane activity, so serotoninlike compounds have been synthesized as receptor agonists for the treatment of migrane headaches.
Fisher indole synthesis with phenyl hydrazine using the procedure of hutchins and chapman 18 gave the propionic acid intermediate 21. Some interesting enhancements have been published recently. Synthesis and evaluation of acrylate resins suspending indole derivative structure in the side chain for marine antifouling. Synthesis and biological evaluation of some novel 2phenyl benzimidazole1acetamide derivatives as potential anthelmintic agents. Synthesis of diverse amide linked bisindoles and indole. Synthesis of biologically active new indole and pyrazole derivatives has earned a. Synthesis and properties of phenyl substituted derivatives. The synthesis of indole3aldehyde and its homologues. Indoles with various substituents in the 2 and 3 position can be synthesized via the fisher indole synthesis which involves two steps and utilizes a phenylhydrazine and an aliphatic or aromatic aldehyde or ketone as starting materials. Herein we report the results on synthesis of new 2substituted phenyl1h indole derivatives via sulfuric acid catalyzed fischer indole reaction. A facile, mild and efficient onepot synthesis of 2. As a part of systematic investigation of synthesis and biological activity, some new indole compounds 3a c and 4a c were prepared and screened for. Synthesis of 2phenyl5sulphasubstituted3 substituted.
A series of 2phenyl sulphasubstituted indoles have been synthesized by the interaction of sulphasubstituted anilines and phenacyl halide. The mechanism begins with formation of a phenylhydrazone through the acid catalyzed reaction of the hydrazine with the carbonyl. In a new group of 3methyl2phenyl1substituted indole derivatives 10af, the indomethacin analogs were prepared via the fisher indole synthesis reaction of propiophenone with appropriately substituted phenylhydrazine hydrochloride. The gi50 values of the most potent compounds 32 and 33 were lower than 5. The synthesis of a series of indole and carbazole derivatives from 2fluorophenyl imines is reported. The synthesis of 2 and 3substituted indoles tlabo caiphus leboho a dissertation submitted to the faculty of science, university of the witwatersrand, johannesburg, in fulfilment of the requirement for the degree of master of science. It has been found that 2phenyl indole derivatives of formula i, all of which have a substituent r, which is linked through a heteroatom, has a significantly better stabilizing effect than 2phenyl indole and from the description of the abovementioned french patent no. The fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a substituted phenylhydrazine and an aldehyde or ketone under acidic conditions. It was clear that the best solvent was acetonitrile and the best molar ratio of ilsubstrate is 10% table 1, entry 3. Thus it was our aim to synthesize a series of 22346substituted phenyl 1h indoles. The indole scaffold 6 can be obtained by the fischer rearrangement between a phenylhydrazine 4 and a phenone 5. Electrocatalytic intramolecular dehydrogenative annulation. A series of 3methyl2phenyl1hindoles was prepared and investigated for antiproliferative activity on three human tumor cell lines, hela, a2780, and msto211h, and some structureactivity relationships were drawn up. Piperidine and diethylamine as catalysts in the condensation of aromatic.
The reaction of 4amino2phenyl and 4aminolmethyl2phenylindoles with a free. Synthesis and antioxidant properties of substituted 2. Finally by fischer indole synthesis the arylhydrazone acetophenone phenylhydrazone converts into the indole 2phenylindole in the presence of an acid catalyst. A novel fourstep domino process for the synthesis of 32arylalkylsulfonylethylindoles starting from readily available 2iodoanilines is reported. Given this, a simple and efficient ruiicatalyzed synthesis of indole via intermolecular annulation of naryl2aminopyridines and sulfoxonium ylides was proposed and accomplished. Synthesis and evaluation of acrylate resins suspending. Scheme 5 gargs synthesis of aspidophylline using a fischer indole approach. The synthesis of the 2phenyl derivative prepared in this. This strategy provides a unique organocatalytic atroposelective route to axially chiral aryl. Synthesis, pharmacology and molecular modeling of n. The second step of the synthesis is an acylation between the indole 6 and a chloroacetamide 9, obtained by coupling between chloroacetic acid 7. Translated from khimiya geterotsiklicheskikh soedinenii, no.
Synthesis of pharmacologically activity 2phenyl sulphasubstituted indoles. The reaction was discovered in 1883 by emil fischer. Get a printable copy pdf file of the complete article 993k, or click on a page image below to browse page by page. Anticonvulsant activity of the title compounds was determined in mes and scptz animal models. All tests were compared with at least one herein we report the results of the antihiv assay of positive e. Pdc catalyzed synthesis of indoles under ultrasound irradiation. In addition, a newly indole derivatives 1416 incorporated or fused with coumarin moieties have been prepared through the reaction of 9 or 11 with 4chloro3formylcoumarin a or 4chloro3nitrocoumarin b. New amide linked bisindoles 10a, b, and 12 have been synthesized by treatment of tryptamine 9 or 5aminoindole 11 with oxalyl chloride or adipoyl chloride. An ultrasoundbased approach for the synthesis of indoles under pd. Synthesis of 2benzyl4phenyl2,4dihydropyrrolo3,4bindole. Pdf a series of 2phenyl sulphasubstituted indoles have been synthesized by the interaction of sulphasubstituted. Rutheniumcatalyzed synthesis of indole derivatives from n.