Physical state melting point 0c molecular formula %yield. Oxidation of 2,3cis2sulfonamidenbutenoate azetidinone 3 and 2,3trans2acetoxynbutenoate azetidinone 6 led to the formation of azetidinone oxiranes 5 and 7. 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. Synthesis, biochemical and molecular modelling studies of antiproliferative azetidinones causing microtubule disruption and mitotic catastrophe, european journal of medicinal chemistry 2011, doi. Synthesis of some new azetidinone derivatives containing. 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. Chiral donoracceptor azetines as powerful reactants for. 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 study of antitubercular activity of some. 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. Physical data of the synthesized azetidinone compounds 4a4h compound no. Chiral 3azetidinones are structural analogues of medicinally relevant.
Synthesis and antimicrobial screening of 4thiazolidinone and. Rapid and efficient synthesis of newer heterocyclic 2. Synthesis and antimicrobial screening of 4thiazolidinone. Synthesis and antibacterial activity of some azetidinone derivatives. General procedures for catalytic asymmetric synthesis of.
Our synthesis of the enantiomerically pure 2azetidinone analogs 4ac were based on an asymmetric synthesis of ezetimibe as depicted in scheme 3. Center of drug discovery, china pharmaceutical university, 24 tongjiaxiang, nanjing 29, china. Read synthesis of pyrazole imines and azetidinone compounds using conventional and microwave technique and studies of their antibacterial activity. The breaking and formation of bonds occur simultaneously and thus the reaction proceeds via a single cyclic as show in scheme 2. Staudinger reaction, anticancer activity, azetidinone, sulphadiazine. Girges department of chemistry, mansoura and bdamiatta faculties of science, mensoura university, 355 16 mansoura, egypt. The cover picture shows novel scaffolds for drug discovery, 6 azaspiro4. The pyrimidine synthesis is a similar process than that of purinespurines synthesis.
Paclitaxel total synthesis in organic chemistry is a major ongoing research effort in the total synthesis of paclitaxel taxol. Synthesis and bioactivities of 2azetidinone derivatives. This has a lethal effect on bacteria, although any given bacteria population will. Pyrimidine rings are assembled from bicarbonate, aspartate, and ammonia. The synthesis has advantages such as avoiding the tedious and costly column chromatographic or recrystallized separation steps for diastereomers. Nm, carr m, greene lm, bergin o, nathwani sm, mccabe t, lloyd dg, zisterer dm, meegan mj, synthesis and evaluation of azetidinone analogues of combretastatin a4 as tubulin targeting agents. The 2azetidinones are of immense attention in diverse areas of medicinal chemistry because of their different pharmacological activities like antimicrobial 3, 4. Synthesis and bioactivities of 2azetidinone derivatives as.
Pdf on jan 1, 2014, munther abduljaleel mohammedali and others published synthesis, characterization of new azetidinone derivatives and evaluation of. The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin a4 are described which contain the 1,4diaryl2azetidinone. Synthesis and study of antitubercular activity of some newly. Synthesis of novel azetidinone derivatives as antitubercular agents volume. Synthesis and antibacterial activity of some azetidinone.
An efficient synthesis and antibacterial activity of some. Pdf synthesis, characterization of some new 2azetidinone. An efficient synthesis and antibacterial activity of some novel 2. The completion of the reaction was monitored by silica gelg coated. Recrystallization was carried out with ethanol and physical data was noted. The 4sulfonyloxy aniline derivative 2 has been prepared by reaction of 4nitro phenol sodium salt with nacetyl sulfanilyl chloride asc followed by hydrolysis by ethanolic hcl. Oxidation of 2,3cis2sulfonamidenbutenoateazetidinone 3 and 2,3trans2acetoxynbutenoateazetidinone 6 led to the formation of azetidinoneoxiranes 5 and 7. Synthesis and antifungal activity of azetidinone and thiazolidinones. Stereoselective transformations of 4vinyl2azetidinone derivative 4 into a variety of highly functionalized 6 and 5membered carbocyclic compounds 7 and 9 were carried out using sequences involving sequential c1n bond cleavage and rucatalyzed ringclosing metathesis. Synthesis and biological evaluation of new 3amino2. Synthesis and bioactivities of 2azetidinone derivatives as cholesterol absorption inhibitors volume. Stereoselective synthesis of highly functionalized 5 and 6. Synthesis, characterisation of some 2 azetidinone derivatives from 2,6diaminopyridine and evaluation of their antimicrobial activity 1kasem murad, 1adnan deeb, 1farouk kandil 1department of chemistry, faculty of sciences, damascus university, syria. Synthesis, characterization of new azetidinone derivatives.
A new efficient and environmental friendly procedure for the synthesis of a series of salicylaldehydebased schiff bases under microwave irradiation is described. Synthesis and evaluation of azetidinone analogues of combretastatin a4 as tubulin targeting agents. The obtained product was filtered, dried and recrystallized by. The method is compared with the conventional method also. The pdf file you selected should load here if your web browser has a pdf reader plugin installed for example, a recent version of adobe acrobat reader if you would like more information about how to print, save, and work with pdfs, highwire press provides a helpful frequently asked questions about pdfs alternatively, you can download the pdf file directly to your computer. Pdf on jan 1, 2014, munther abduljaleel mohammedali and others published synthesis, characterization of new azetidinone derivatives and evaluation of their antimicrobial activity. Enamino esters synthesis of pyranopyrimidine, pyranopyridine, and vpyran2ylazetidinone ring systems aa.
Dec 23, 2010 the synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin a4 are described which contain the 1,4diaryl2azetidinone. Synthesis and antimicrobial evaluation of some 2azetidinone. The pyrimidine synthesis is a similar process than that of purines purines synthesis. Thus thiazole derivatives playes pivotal role in medicinal chemistry. Silveri salts as useful reagents in pyrazole synthesis. Synthesis of the isothiazolidinone 2a2f and azetidinone 3a and 3b compounds the structure of the formed compounds 2af and 3a,3b. Design, synthesis and bioactivity of catechinepicatechin. Our next task was to introduce the alkyne and the azide functionalities separately in protected polyphenol and. 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 practical synthesis of 4acetoxy2azetidinone useful for the preparation of carbapenem and penemtype antibiotics is described.
Synthesis of the 2 azetidinone derivatives 5a e world scientific news 922 2018 247259 250 on cooling the product, acid hydrazide separates out. Synthesis, characterization and biological aspects of novel azetidinone derivatives 1suresh p. Synthesis, biochemical and molecular modelling studies of. Darlin quine2, 1department of chemistry, periyar government arts college, cuddalore 607001, india 2department of chemistry, government arts college, chidambaram 608102, india. The present work involves condensation of salicylaldehyde with various aromatic amines in water under microwave irradiation. Department of chemistry, faculty of sciences, university of kufa, iraq. These novel compounds are also substituted at position 3 of the. Zimam department of chemistry, faculty of educations for girls, university of kufa, iraq. The bands were visualized under a uvtransilluminator by virtue of the ethidium bromide final concentration 0.
Not only is the synthetic reproduction of the compound itself of. Synthesis, structure elucidation and reactivity of novel. Synthesis and biological evaluation of new 3amino2azetidinone derivatives as anticolorectal cancer agents farida tripodi, a federico dapiaggi, b fulvia orsini, b roberto pagliarin, b guido sello b and paola coccetti a. As part of interest in hetrocycles that have been explored for developing pharmaceutically. Patel science college, sardar patel university, anand, gujarat, india 2chemistry department, government science college, gandhinagar, gujarat, india. The reaction mechanism of the synthesis of azetidinones the c. Synthesis and antimicrobial evaluation of some2azetidinone. Synthesis and evaluation of azetidinone analogues of. Synthesis, characterization and study biological screening of some new azetidinone derivatives from azo sulphadiazine radhiyah a. Yubin wang, hai qian, jinpei zhou, huibin zhang, jianfeng ji and wenlong huang affiliation. Then schiff bases on reaction with acid chloride gave different azetidinones. A convenient and highyielding route to these compounds was developed and optimized. Synthesis, antimicrobial, anticancer evaluation and qsar studies a series of 2 azetidinone derivatives was synthesized from hippuric acid and evaluated.
Here, the authors show a highly enantioselective copper. Practical synthetic approach to 4acetoxy2azetidinone. Department of pharmaceutical chemistry, maratha mandals college of pharmacy, belgaum 590016, karnataka, india. 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. Scheme 2 all new synthesis compounds have been characterized by their melting points, uv spectra, ft.
Synthesis and antimicrobial activity of new pyridine. The overall yield of the product is greatly improved and the process is also more economical for largescale. Synthesis of some salicylaldehydebased schiff bases in. Pdf synthesis, characterization of new azetidinone. Pdf new series of 2azetidinone 4a4f were synthesized, the structure of these new derivativeswereconfirmed using spectral methods. The structure of the new derivatives was confirmed by the spectral data and elemental analyses. Chloroacetylchloride was added drop wise to schiffs base 0. Twentyfour 2 azetidinone derivatives have been designed and synthesized as cholesterol absorption inhibitors.
Comparison of the gel pattern in various lanes indicated that these catechin and epicatechin and 2azetidinone chimeric molecules are also good inhibitors of rnase a. This diterpenoid is an important drug in the treatment of cancer but, also expensive because the compound is harvested from a scarce resource, namely the pacific yew taxus brevifolia. A series of 2 azetidinone derivatives was synthesized from hippuric acid and evaluated for its in vitro antimicrobial and anticancer activities. So, all of authors and contributors must check their papers before submission to making assurance of following our antiplagiarism policies. A group of ten 3amino2azetidinone derivatives, as combretastatin a4 analogues, was selected through docking experiments, synthesized and tested for their antiproliferative. Molecular structure of 5, including its absolute configuration, was unambiguously determined by x. Nearly all of these antibiotics work by inhibiting bacterial cell wall biosynthesis. This research involved synthesis of some new azetidinone derivatives from azo compound4amino34methoxy2nitrophenyldiazenylnpyrimidine2ylbenzenesulfonamiden1by two routsone of. The most important nitrogen containing heterocycles of pyridine containing substituted phenyl azetidine2ones have found pharmacological application such as antibiotics and these compounds also have practical importance. Synthesis, antitubercular and anticancer activities of pnitrophenylethylenediamine derived schiff bases medicinal chemistry. Synthesis, characterization and biological aspects of novel. Apr 23, 2004 some novel azetidinone derivatives containing aryl sulfonyloxy group have been prepared. Design, synthesis and bioactivity of catechinepicatechin and. Ijcr is following an instant policy on rejection those received papers with plagiarism rate of more than 20%.
Synthesis, characterization and biological activities of. This compound 2 undergoes facile condensation reaction with aromatic aldehydes to yield different schiffs bases 3ah. We used dabco as a good homogenous, ecofriendly, highly reactive, easy t. Synthesis of 4thiazolidinones and 2azetidinones section aresearch paper eur. General procedure for the synthesis of schiffs bases 567.
Synthesis of novel azetidinone derivatives as antitubercular. Synthesis of some azetidi2ones and thiazolidin4ones as potential antimicrobial agents. 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. Keri rs, hosamani km, shingalapur rv, reddy hrs 2009 2azetidinone derivatives. The pdf file you selected should load here if your web browser has a pdf reader plugin installed for example, a recent version of adobe acrobat reader if you would like more information about how to print, save, and work with pdfs, highwire press provides a helpful frequently asked questions about pdfs. These schiff bases were then reacted with acid chlorides in toluene in the presence of a base to give 1,3,4trisubstituted2 azetidinones. Synthesis, characterization and biological activities of some azetidin2one as potential antifungal agents r. An efficient catalytic synthetic strategy towards beta. Synthesis, characterization and biological aspects of. Procedure for the synthesis of compound 2 the compound. Molecular structure of 5, including its absolute configuration, was unambiguously determined by xray structure analysis. The reaction mixture was then stirred for 20 hours and kept at room temperature for three days. All new compounds were evaluated for their activity to inhibit cholesterol absorption in hamsters, and most of them showed considerable effects in lowering the levels of total cholesterol in the serum, especially compound 2d, 4a, 4f, 4i and 4j. Several synthetic combretastatin a4 ca4 derivatives were recently prepared to increase the drug efficacy and stability of the natural product isolated from the south african tree combretum caffrum.
Synthesis of some new azetidinone derivatives containing aryl. The use of azetidinone compounds that are inhibitors of cholesterol absorption as tools for discovering and characterizing proteins involved in trafficking or absorption of cholesterol andor cholesteryl esters in biological systems is presented. Moreover they have been studied extensively because of their ready. For the alkyne component, tetrabenzyl catechin tbc or epicatechin tbec 10 was converted to 3opropargyl catechin or epicatechin by reacting with propargyl bromide in presence of sodium hydride. Synthesis and antimicrobial evaluation of some2azetidinone derivatives article pdf available in international journal of chemtech research 12. Girges department of chemistry, mansoura and bdamiatta faculties of science, mensoura university, 355 16 mansoura, egypt received 30 september 1991. These compounds can serve as tools for competitive binding assays to discover and characterize other chemical agents useful as. Synthesis and antimicrobial activity of azetidinone and.
Practical synthetic approach to 4acetoxy2azetidinone for. Antimicrobial properties of the title compounds were investigated against gram positive and gram negative bacterial as well as fungal strains. 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. This compound 2 undergoes facile condensation reaction with aromatic aldehydes to yield. Some novel azetidinone derivatives containing aryl sulfonyloxy group have been prepared.
Synthesis and antimicrobial studies of azetidinone. Sigmaaldrich offers a number of 2azetidinone products. Synthesis and biological significance of some 2azetidinone derivatives 141 148. Synthesis, characterization and biological activities of some. The final derivatives of the azetidinones were obtained by reaction. Pdf synthesis, characterization of new azetidinone derivatives.
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