Synthesis, characterization and biological studies of novel azetidinones r. Chemistry synthesis of gamma lactam analogues of combretastatin a4 1. Synthesis, characterization of some new 2 azetidinone derivatives monther faisal mahdi, rafah fadhel alsmaism and ammar ihsan mahmood department of pharmaceutical chemistry, collage of. The indole framework is a medicinally relevant scaffold and has become widely. Kolaus et al14 prepared several 2 azetidinones which were proved to. All above facts strongly indicate the synthesis of all above compounds. 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. A series of schiff derivatives 5aq and azetidinone by way of amide linkage analogues 6aq containing 2amino benzthiazole have been synthesized. A group of ten 3amino2azetidinone derivatives, as combretastatin a4 analogues, was.
Rapid and efficient synthesis of newer heterocyclic 2 azetidinone and 5benzylidine4oxothiazolidine compounds and their pharmacological studies. Synthesis and antimicrobial screening of 4thiazolidinone. Synthesis, characterization and biological aspects of novel azetidinone derivatives 1suresh p. The synthesis has advantages such as avoiding the tedious and costly column chromatographic or recrystallized separation steps for diastereomers. 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. Herein we described the synthesis of a series of novel.
Synthesis and antimicrobial evaluation of some 2azetidinone derivatives s. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the transazetidinone. This article focuses on the various pharmacological profile of 2azetidinone scaffold and development of novel derivatives with their potential activity. Gang lu d3 n n o n o azetidines azetidin3ones azetidin2ones. Synthesis and biological evaluation of new 3amino2. The chloro, bromo and nitro substituted imidazolyl azetidinones 6c, 6d, 6f and nitro substituted imidazolyl triazole 5f exhibited excellent. Bms262084 was prepared in 10 steps from dornithine in 30% overall yield. 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. Some novel azetidinone derivatives containing aryl sulfonyloxy group have been prepared. Pdf synthesis and antimicrobial studies of azetidinone. Synthesis of some new azetidinone derivatives containing. Study on synthesis of some novel azetidinone derivatives. The structures of all the synthesized compounds were confirmed by chemical and spectral analyses such as ir, 1h nmr, c nmr and fabmass.
Rapid entry to enantiopure carbacepham derivatives via. Synthesis, antimicrobial, anticancer evaluation and qsar studies a series of 2azetidinone derivatives was synthesized from hippuric acid and evaluated. A practical synthesis of 4acetoxy2azetidinone useful for the preparation of carbapenem and penemtype antibiotics is described. The microwave assisted synthesis of 2azetidinone derivatives. Synthesis and biological evaluation of azetidinone derivatives from. Antibacterial agentschemical synthesis antibacterial agentspharmacology. Amide linkage were adapted from acid via reaction with hydrazine hydrate followed by reaction with different substituted aldehyde derived various arylidene derivatives comprising with various donor and acceptor functional group. Synthesis and pharmaceutical importance of 2azetidinone. All the new compounds were evaluated for their activity to inhibit cholesterol absorption in rats, and most of them showed comparable effects in lowering the levels of total cholesterol in the serum. A highly stereoselective synthesis of the novel tryptase inhibitor bms262084 was developed.
The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin a4 are described which contain the 1,4diaryl2 azetidinone. Vyas c ams shree tirupati industries, palanpur, gujarat india bgovernment science college, gandhinagar, gujarat india csheth l. Physical data of the synthesized azetidinone compounds 4a4h compound no. 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. Pdf synthesis of novel schiff base and azetidinone derivatives. These novel compounds are also substituted at position 3 of the.
Southgate november 5, 2015 introduction since the discovery of the potent antibiotic activity of penicillium notatum cultures against many strains of bacteria1, the importance of the. Synthesis of 2azetidinone derivatives of 6nitro1hindazole and. An efficient synthesis and antibacterial activity of some novel 2. Synthesis and antimicrobial studies of azetidinone derivatives from naphthylamine moiety ajay bagherwal, ashish baldi, rakesh kumar nagar, dinesh kumar patidar dr. Practical synthetic approach to 4acetoxy2azetidinone. Synthesis and biological significance of some 2azetidinone derivatives 141 148. Procedure for the synthesis of compound 2 the compound. The first step is synthesis of benzohydrazide through nucleophilic substitution reaction between methyl benzoate and hydrazine hydrate. Synthesis, characterization and biological activities of some azetidin2one as potential antifungal. Synthesis and antimicrobial studies of azetidinone.
It is named as such because the nitrogen atom is attached to the. Synthesis, characterization of new azetidinone derivatives and evaluation of their antimicrobial activity hussam hamza salman,munther abduljaleel mohammedali and alyaa ahmed albader department of pharmaceutical chemistrycollege of pharmacybasrah university iraq department of biology college of science basrah university iraq. Synthesis and antifungal activity of azetidinone and thiazolidinones derivatives of 2amino62naphthalenylthiazolo3,2dthiadiazole. Synthesis of new 2azetidinone derivatives and related schiff bases from 3 phenyl2,3,6,7tetrahydroimidazo 2,1b thiazolo 5,4d isoxazole. Synthesis and medicinal evaluation of mannich bases a ra. 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. Syntheses of azetidines and azetidin2ones literature seminar on apr. Synthesis, molecular properties prediction and antimicrobial activity. Synthesis of some thiazolidinone and azetidinone from dapsone r heterocyclic or aromatic aldehyde o s o. A new series of n21h1,2,3benzotriazol1ylethyl4substitutedphenyl3chloro2oxo1iminoazetidine, compounds 4aj were synthesized. The completion of the synthesis of target compounds were confirmed by tlc. Spasov et al have reported synthesis and bactericidal property of different 2azetidinones.
Physical state melting point 0c molecular formula %yield. In this work, new schiff bases, their acetyl oxadiazole, and azetidinone derivatives derived from pyromelliticdiimide were synthesized via multistep synthesis. Development of the asymmetric kinugasa reaction reported by emma h. Synthesis, characterization and biological studies of. Department of chemistry, faculty of sciences, university of kufa, iraq. V 07 remarks of the guide the mentioned title compound will be synthesized and screened for the activity. The compounds 4aj were screened for their antibacterial, antifungal and antitubercular activities and. Patel science college, sardar patel university, anand, gujarat, india 2chemistry department, government science college, gandhinagar, gujarat, india. The breaking and formation of bonds occur simultaneously and thus the reaction proceeds via a single cyclic as show in scheme 2. Synthesis and characterization of new 2amino pyridine. Introduction over the past years, potency of antimicrobial therapy is somewhat in hesitate due to bacterial resistance to. Overall antimicrobial activity results indicated that compound 4 pmic 1.
The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin a4 are described which contain the 1,4diaryl2azetidinone. The synthetic route explored to make gamma lactams utilizes beta lactams, the active ring system in penicillin, as precursors. Pdf a series of five novel azetidinones saz1 5 were synthesized by cyclocondensation of various schiff bases of naphthylamine with. International journal of chemical and pharmaceutical. Pyrimidine rings are assembled from bicarbonate, aspartate, and ammonia. Sigmaaldrich offers a number of 2azetidinone products. The overall yield of the product is greatly improved and the process is also more economical for largescale. Synthesis and biological activity studies of some thiazolidinones and azetidinones p. Fourteen new derivatives of the 2azetidinone cholesterol absorption inhibitors have been synthesized, and three of them were enantiomerically pure. Indoles are considered as the most promising bicyclic heteroaromatic nucleus in the field of medicinal chemistry.
Chandra jnns, sadashiva ct, kavitha cv, rangappa ks 2006 synthesis and in vitro antimicrobial studies of medicinally important novel nalkyl and nsulfonyl derivatives of 1bis4fluorophenylmethylpiperazine. Synthesis, characterization of new azetidinone derivatives. Pdf synthesis and antifungal activity of azetidinone and. 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. Rapid and efficient synthesis of newer heterocyclic 2. Synthesis, characterization of some new 2azetidinone derivatives monther faisal mahdi, rafah fadhel alsmaism and ammar ihsan mahmood department of. Synthesis of 4thiazolidinones and 2azetidinones section aresearch paper eur. Synthesis of benzthiazole derivatives grouping with. Zimam department of chemistry, faculty of educations for girls, university of kufa, iraq. A stereoselective synthesis of bms262084, an azetidinone. Abstract the goal of this research is to access gamma lactam combretastatin a4 analogues. Synthesis and antimicrobial activity of azetidinone and. The completion of the reaction was monitored by silica gelg coated. Synthesis of new 2azetidinone derivatives and related schiff.
The 2azetidinone ring system is commonly found in a number of. Synthesis, characterization and biological aspects of. Lewis acid promoted types i and ii carbonylene cyclizations of 2azetidinonetethered alkenylaldehydes are used for the rapid, highly diastereoselective synthesis of polyfunctionalized, enantiomerically pure carbacepham derivatives. Synthesis of 3amino3methyl2azetidinone1sulfonic acid and its derivatives. Synthesis of new 2azetidinone derivatives and related. Synthesis, characterization and biological activities of. The pyrimidine synthesis is a similar process than that of purinespurines synthesis. Synthesis of new 2azetidinone derivatives and related schiff bases from 3phenyl2,3,6,7tetrahydroimidazo 2,1b thiazolo 5,4d isoxazole.
519 247 461 1159 1154 227 477 86 846 1124 908 1040 423 721 37 1304 1093 860 836 71 89 1245 66 928 1137 375 29 792 759 690 1340 937 1484 1159 952 806 672 348 1296 466 587 1208 1153