Synthesis and biological significance of some 2azetidinone derivatives 141 148. Some new 2azetidinone derivatives possessing benzimidazole nucleus were synthesized and characterized by ir, nmr and mass spectral analysis. Xray photoelectron spectra of 2azetidinone was investigated. The completion of the reaction was monitored by silica gelg coated. Rapid and stereocontrolled synthesis of racemic and optically pure highly functionalized pyrrolizidine systems via rearrangement of 1,3dipolar cycloadducts derived from 2azetidinonetethered azomethine ylides. In silico design, synthesis, characterization and biological. The first step is synthesis of benzohydrazide through nucleophilic substitution reaction between methyl benzoate and hydrazine hydrate. Molecules free fulltext novel penicillintype analogues. Procedure for synthesis synthesis of schiff base equimolar quantities of substituted benzaldehydes and substituted anilines dissolved in ethanol are taken in a round bottom flask. Some new 2 azetidinone derivatives possessing benzimidazole nucleus were synthesized and characterized by ir, nmr and mass spectral analysis. Insilico design, synthesis, characterization and biological. A practical synthesis of 4acetoxy2azetidinone useful for the preparation of carbapenem and penemtype antibiotics is described. The overall yield of the product is greatly improved and the process is also more economical for largescale. The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin a4 are described which contain the 1,4diaryl2 azetidinone.
Synthesis and antifungal activity of azetidinone and thiazolidinones derivatives of 2amino62naphthalenylthiazolo3,2dthiadiazole. Full chirality transfer has been accomplished from the enantiomerically pure 2azetidinones. Xray photoelectron spectra of 2 azetidinone was investigated. The pyrimidine synthesis is a similar process than that of purinespurines synthesis. In this paper we propose the synthesis of 4anthracen10yl1cyclohexyl3phenoxyazetidin2one. Process for synthesis of a chiral 3beta hydrogen 3r 4aroyloxy azetidinone. Department of pharmaceutical chemistry, maratha mandals college of pharmacy, belgaum 590016, karnataka, india. Chloroacetylchloride was added drop wise to schiffs base 0. The key transformation is the reaction between electron. Synthesis of some new azetidinones derived from heterocyclics. Synthesis, characterization of new azetidinone derivatives. The reaction mixture was then stirred for 20 hours and kept at room temperature for three days.
Sigmaaldrich offers a number of 2azetidinone products. Process for the preparation of azetidinonethiazoline. A highly stereoselective synthesis of the novel tryptase inhibitor bms262084 was developed. Stereoselective allylation of 4oxoazetidine2carbaldehydes. Synthesis of lactone, oxetane, and azetidinone analogs from the naturally occurring lactone l. The application relates to a process for preparing a compound of formula i this compound is an intermediate used to produce compounds that are useful as hypocholesterolemic agents in the treatment and prevention of atheroschlerosis. This research involved synthesis of some new azetidinone derivatives from azo compound4amino34methoxy2nitrophenyldiazenylnpyrimidine2ylbenzenesulfonamiden1by two routsone of. The preparation of a novel hmg coa synthase inhibitor. The synthesis has advantages such as avoiding the tedious and costly column chromatographic or recrystallized separation steps for diastereomers. Synthesis of novel azetidinone derivatives as antitubercular. The synthesis and antimicrobial study of some azetidinone. Synthesis and antimicrobial evaluation of some2azetidinone. New substituted azetidinones as antiinflammatory and antidegenerative agents.
Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans azetidinone. Synthesis and antimicrobial screening of 4thiazolidinone. The addition of lithium acetylides to 4oxoazetidine2carbaldehydes at. The structures of the newly synthesized compounds have been established on the basis of their spectral data and elemental analysis. A process is described for the stereocontrolled synthesis of 3 r 31. Saundane 1 and prabhaker walmik 1 1 department of postgraduate studies and research in chemistry. Lactams via free radical cyclization of 2azetidinonetethered bromohomoallylic alcohols.
Pdf synthesis and antifungal activity of azetidinone and. Nearly all of these antibiotics work by inhibiting bacterial cell wall biosynthesis. The synthesis and the biological activity of novel semisynthetic. Pyrimidine rings are assembled from bicarbonate, aspartate, and ammonia. Synthesis of the isothiazolidinone 2a2f and azetidinone 3a and 3b compounds the structure of the formed compounds 2af and 3a,3b were confirmed by elemental analysis, ir and nmr spectral.
The free aldehyde reacts with different free amide rnh 2 group to form imines cn which on react with chloro acetyl chloride and triethylamine to give 2azetidinone derivatives. Synthesis of the azetidinone derivatives by the described method resulted in good yields of the products, as can be seen from table i, which also lists the physical data of compounds 4ah. Bms262084 was prepared in 10 steps from dornithine in 30% overall yield. Synthesis and evaluation of azetidinone analogues of. This invention relates to the preparation of azetidinonethiazoline precursors for cephalosporin synthesis.
Synthesis of quinoline substituted 2azetidinones 623 these schiff bases 3ac were then reacted with acid chlorides in the pre sence of a base to yield the 1,3,4trisubstituted2azetidinones 4ah. Read free radical synthesis of benzofused tricyclic. Synthesis, characterization and biological aspects of. A new approach to the synthesis of selectively protected 2s1,2,4triaminobutane derivatives.
Patel science college, sardar patel university, anand, gujarat, india 2chemistry department, government science college, gandhinagar, gujarat, india. Enantioselective synthesis of azetidinone intermediate. Us6627757b2 us10105,710 us10571002a us6627757b2 us 6627757 b2 us6627757 b2 us 6627757b2 us 10571002 a us10571002 a us 10571002a us 6627757 b2 us6627757 b2 us 6627757b2 authority us united states prior art keywords process compound acid formula ii catalyst prior art date 20010328 legal status the legal status is an assumption and is not a legal conclusion. A stereoselective synthesis of bms262084, an azetidinone. Synthesis and antimicrobial studies of azetidinone.
The cover picture shows novel scaffolds for drug discovery, 6 azaspiro4. All synthesized compounds were screened for antimicrobial activity using cup plate method. Oct 06, 2015 the new series of 39were synthesis by reaction of schiff base 1014 with chloroacetyl chloride, triethyl amine as an catalyst and 1,4dioxane as a solvent. The synthesized compounds were screened for their in vitro antimicrobial activity against a panel of gram positive and gram negative pathogens and environmental. Practical synthetic approach to 4acetoxy2azetidinone for. Apr 18, 1978 this invention relates to the preparation of azetidinone thiazoline precursors for cephalosporin synthesis. Pdf synthesis and antimicrobial evaluation of some2. The cyclic 2azetidinone skeleton has been extensively used as a template to build the heterocyclic structure fused to the four membered rings. Results and discussion chemistry 2 azetidinone derivatives 118 were synthesized according to synthetic procedure described in scheme 1. Ep0269236a1 process for synthesis of a chiral azetidinone. The breaking and formation of bonds occur simultaneously and thus the reaction proceeds via a single cyclic as show in scheme 2. Rapid and efficient synthesis of newer heterocyclic 2. The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin a4 are described which contain the 1,4diaryl2azetidinone.
Pdf synthesis, characterization of some new 2azetidinone. Synthesis of some azetidi2ones and thiazolidin4ones as potential antimicrobial agents. Synthesis and antimicrobial evaluation of some 2azetidinone. This research involved synthesis of some new azetidinone derivatives from azo compound4amino34 methoxy2nitrophenyldiazenylnpyrimidine2ylbenzenesulfonamiden1by two routsone of.
Synthesis of quinolone substituted 2 azetidinone derivatives uday c. Physical state melting point 0c molecular formula %yield. All the compounds showed moderate to good antimicrobial activity and anti fungal activity. The synthesis and antimicrobial study of some azetidinone derivatives with the paraanisidine moiety. Synthesis and antimicrobial activity of azetidinone and. Mar 14, 2005 read free radical synthesis of benzofused tricyclic. Synthesis and antimicrobial evaluation of some2azetidinone derivatives article pdf available in international journal of chemtech research 12. Synthesis of quinolone substituted 2azetidinone derivatives. Practical synthetic approach to 4acetoxy2azetidinone. 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. The overall yield of the product is greatly improved and the process is also more economical for largescale production.
Ep0269236a1 ep87309104a ep87309104a ep0269236a1 ep 0269236 a1 ep0269236 a1 ep 0269236a1 ep 87309104 a ep87309104 a ep 87309104a ep 87309104 a ep87309104 a ep 87309104a ep 0269236 a1 ep0269236 a1 ep 0269236a1 authority ep european patent office prior art keywords process azetidinone selected imine chiral prior art date 19861024 legal status the legal status is an. Synthesis of strained tricyclic lactams by intramolecular. This has a lethal effect on bacteria, although any given bacteria population will. Synthesis, characterization and antimicrobial activity of 2. The free aldehyde reacts with different free amide rnh 2 group to form imines cn which on react with chloro acetyl chloride and triethylamine to give 2 azetidinone derivatives. This research involved synthesis of some new azetidinone derivatives from azo compound4amino34methoxy2nitrophenyldiazenylnpyrimidine2ylbenzenesulfonamiden1by two routsone of them conversion the free amino group in an azo comp. A convenient and highyielding route to these compounds was developed and optimized.
A synthesis of optically pure densely functionalized. A practical synthesis of 4acetoxy2 azetidinone useful for the preparation of carbapenem and penemtype antibiotics is described. Synthesis and physical characterization of 4 anthracen 10yl1cyclohexyl3phenoxyazetidin2one as a new trans 2azetidinone by aliasghar jarrahpour 1, mohammad nazari 1 and abraham f. An efficient catalytic synthetic strategy towards beta. Lactams via free radical cyclization of 2azetidinone. To this added 2 drops of glacial acetic acid and was refluxed for 3 hours and the completion of reaction monitered by tlc. Patkar college, goregaon west, mumbai 400 062, india received 17 june, revised 30 july 2012 abstract. Keri rs, hosamani km, shingalapur rv, reddy hrs 2009 2azetidinone derivatives. Synthesis and antimicrobial screening of 4thiazolidinone and.
Synthesis, characterization and antimicrobial activity of. Us6627757b2 enantioselective synthesis of azetidinone. The ir spectra of compounds 4ah showed the absorption for one carbonyl. The synthesized compounds were screened for their in vitro antimicrobial activity against a panel of gram positive and gram negative pathogens and. Rapid and stereocontrolled synthesis of racemic and optically pure highly functionalized pyrrolizidine systems via rearrangement of 1,3dipolar cycloadducts derived from 2 azetidinone tethered azomethine ylides. Procedure for the synthesis of compound 2 the compound. Pilar ruiz, free radical synthesis of benzofused tricyclic. Synthesis of 4thiazolidinones and 2azetidinones section aresearch paper eur. The reaction mechanism of the synthesis of azetidinones the c. Synthesis, antitubercular and anticancer activities of pnitrophenylethylenediamine derived schiff bases medicinal chemistry.
Synthesis, characterization and biological aspects of novel. In the 1h nmr spectra, two doublets for c3h and c4h were present. Synthesis of novel azetidinone derivatives as antitubercular agents volume. Acetanilide was converted into 2chloro3formylquinoline by reac. Synthesis, antioxidant, antimicrobial, antimycobacterial, and cytotoxic activities of azetidinone and thiazolidinone moieties linked to indole nucleus a. The obtained product was filtered, dried and recrystallized by.
Physical data of the synthesized azetidinone compounds 4a4h compound no. Synthesis, antioxidant, antimicrobial, antimycobacterial. The indolylaldehyde 4, 1 mmol, 4aryloxazole2amine 4arylthiazole 2amine 4aryl imidazole2amine 123, 1 mmol, acetic acid 2 drops and methanol 10 ml were sonicated at 30c for 1014 min at a frequency of 46 khz. The structure of synthesized compounds was confirmed by nmr and ir spectra. Synthesis of the isothiazolidinone 2a2f and azetidinone 3a and 3b compounds the structure of the formed compounds 2af and 3a,3b. R hydroxyethyl4 r benzoyl2oxo1azetidines and their derivatives which are useful intermediates in the synthesis of carbapenem antibiotics. Synthesis, characterization and biological aspects of novel azetidinone derivatives 1suresh p. The precursors have the general formula ii below and may be used in the synthesis of derivatives of 7aminocephalosporanic acid 7aca and 7aminodesacetoxycephalosporanic acid 7adca. General procedure for the synthesis of schiffs bases 567. Thus, derivatization of 6apa led to higher coupling reaction yields and easier isolation of target compounds. In addition to its synthesis am1 calculations to characterize.
The mechanism of the synthesis of azetidinone compounds from the reaction of schiff bases and chloroacetyl chloride in the presence triethylamine can be illustrated in scheme 2. The free amine 10 was so added to a preformed mixture of acid 6 and dcc in order to afford compound 11 as mixture of diastereomers, with the 2azetidinone ring directly coniugated to 6apa residue. Our synthesis of the enantiomerically pure 2azetidinone analogs 4ac were based on an asymmetric synthesis of ezetimibe as depicted in scheme 3. Synthesis and physical characterization of 4anthracen10. These novel compounds are also substituted at position 3 of the. Volume 61, issue 11, 14 march 2005, pages 27672778.
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