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Synthesis of Some New Phthalimides As Anti-Metabolic Agents with Chemotherapeutic Effects

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Synthesis of Some New Phthalimides As Anti-Metabolic Agents with Chemotherapeutic Effects British Journal of Pharmaceutical Research 4(16): 1923-1936, 2014 SCIENCEDOMAIN international www.sciencedomain.org Synthesis of Some New Phthalimides as Anti-metabolic Agents with Chemotherapeutic Effects Fathy A. Yassin 1* , Amal F. Seleim 2, Ali M. Hassan 3, Atif F. Hadad 4, Nahed M. Fathy 5 and M. Fayad 3 1Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt. 2Department of Chemistry, Faculty of Science, Najran Univeristy, Saudi Arabia. 3Department of Chemistry, Faculty of Science, Al-Azhar University, Cairo, Egypt. 4Department of Chemistry, Faculty of Science, Helwan University, Helwan, Egypt. 5Department of Chemistry, National Research Center, Cairo, Egypt. Authors’ contributions This work was carried out in collaboration between all authors. Authors FAY and MF designed the study, performed the statistical analysis, wrote the protocol, and wrote the first draft of the manuscript. Authors AFS, AMH, AFH managed the analyses of the study and managed the literature searches. All authors read and approved the final manuscript. Received 11 th August 2013 rd Original Research Article Accepted 3 July 2014 Published 8th August 2014 ABSTRACT A series of new phthalimides 1(a-f) were synthesized via reaction phthalic anhydride with different amino acids under fusion conditions. Esterification of N-phthaloyl acid derivatives 1(a-f) with methanol in the presence of SOCl 2 to producing the corresponding esters 2(a-f). Which on reaction with hydrazine hydrate in boiling n-butanol afforded the corresponding N-phthaloyl acid hydrazides 4(a-f) Reaction of compound (4a) with different aldehydes and ketones yielded the corresponding hydrazone derivatives 5(a-d). Some new phthalimides linked to hetero cyclic moieties such as benzimidazoles, benzoxazines and quinazolines were synthesized. The structure of the synthesized compounds was confirmed from their analytical and spectral data such as, IR spectra, 1H-NMR and mass spectra. Antimicrobial against two types of bacteria and anticancer activity for some of the synthesized imides were evaluated. The results showed that most of them have a good antimicrobial and anticancer activities. ____________________________________________________________________________________________ *Corresponding author: Email: [email protected]; British Journal of Pharmaceutical Research, 4(16): 1923-1936, 2014 Keywords: Phthalimide; phthaloyl ethyl glycinate; benzimidazoles; benzoxazines quinzolinones; anti-inflammatory; antihypertensive activity; antimicrobial; anticancer activities. 1. INTRODUCTION Imide group is an interesting functionality, due to its wide presence in natural products and in the pharmacologically active compounds. Compounds containing phthalimide moiety are distinguished by their potent antimicrobial action [1-3]. Phthalimides were found to possess anti-inflammatory, antiviral, anxiolytic, antibacterial and antitumor properties [4,5]. Also, phthalimides are important synthetic intermediate to prepare primary amines, agriculture pesticides. The use of phthalimide as primary amine protecting group is extensively documented in the chemical literature, especially for peptides, α-amino acids, amino glycosides and β-lactam antibiotics [6]. 2. EXPERIMENTAL All melting points were measured on a Gallenkamp melting point apparatus and are uncorrected. The infrared spectra were recorded on a PVE Unicam SP 3300 and Shimadzu FT IR 8101 PC infrared spectrophotometers. The NMR spectra were recorded on a Varian Mercury VXR-300 NMR spectrometer at 300 MHz (DMSO-d6). Chemical shifts were related to that of the solvent. The biological and pharmaceutical activities were carried out at The Regional Center for Mycology & Biotechnology in Al-Azhar University, Cairo, Egypt, National Research Center, Giza, Egypt, Cairo University, Giza, Egypt and at Faculty of Science, Zagazig University, Zagazig, Egypt. 2.1 Synthesis of N-phthaloyl Amino Acids 1(a-f) Method (A): A mixture of equimolecular quantities of phthalic anhydride, appropriate amino acids (glycine, alanine, asparagine, methionine, tyrosine, and valine) was heated under fusion condition in an oil bath at 170-190ºC for 30 minutes. The reaction mixture was kept at room temperature, overnight. The unreacted raw material removed by repeatedly shaking with 50 ml portions of benzene and then with 50 ml portions of chloroform. The solid separated was filtered, dried and recrystallized from the proper solvents. Method (B): A mixture of phthalic anhydride 74 g (0.5 mole) and (0.5 mole) of respective amino acids namely, glycine, alanine, asparagine, methionine, tyrosine, and valine was refluxed in 100 ml toluene/and or acetic acid in presence of 6.5 ml of triethylamine for 2 hours, the organic solvents were removed in vacuum, then 100 ml of H 2O and 10 ml of concentrated HCl were added. The solid separated was filtered, dried and recrystallized from the proper solvents. 1924 British Journal of Pharmaceutical Research, 4(16): 1923-1936, 2014 2.2 Synthesis of N-phthaloyl Amino Acid Methyl Esters 2(a-f) Method A: To a stirred solution of N-phthaloyl amino acids 1(a-f) (0.1 mole) in absolute methanol (30 ml), thionyl chloride (0.02 mole) was added dropwise with stirred at room temperature for 4 hours. The reaction, the mixture was allowed to stay overnight then poured on crushed ice. The solid separated recrystallized with petroleum ether. Method B: A mixture of N-phthaloyl amino acids 1(a-f) (0.03 mole) in acetone, dimethyl sulphate (0.07 mole) anhydrous potassium carbonate (0.02 mole) was refluxed on a water bath for 2 hours with occasional stirring. After the completion of the reaction, the mixture was allowed to cool at room temperature and poured into crushed ice. The solid separated was recrystallized with petroleum ether. 2.3 Synthesis of N-phthaloyl Acetyl Chloride Derivatives 3(a-f) Method (A): A mixture (0.01 mole) of phthaloyl acetic acid derivatives 1(a-f) and 10 ml of thionyl chloride was heated on water bath till evolution of hydrogen chloride gas ceased. The excess of thionyl chloride was distilled off under reduced pressure using vacuum pump. The acid chloride left behind as residue was used in the next experiment without further purification. Method (B): To a stirred solution of N-phthaloyl amino acids 1(a-f) (0.1 mole) in cyclohexane-benzene (1:1) (40 ml), oxalyl chloride (0.02 mole) was added dropwise and then freshly distilled DMF (0.02 mole) was added. The reaction mixture was stirred at room temperature for 4 hours. The solvents were evaporated to dryness under vacuum to give acid chlorides 3(a-f). 2.4 Synthesis of N-phthaloyl Amino Acid Hydrazides 4(a-f) Method A: To a solution of the phthaloyl aectic acid esters 2(a-f) (0.02 mole) in absolute n-butanol (20 ml) hydrazine hydrate (0.02 mole) was added. The reaction mixture was refluxed for 5hours. The solid separated was filtered washed with water, dried and crystallized from ethanol. Method B: To a solution of the acid chloride 3(a-f) (0.02 mole) in absolute ethanol (20 ml) hydrazine hydrate (0.02 mole) was added. The reaction mixture was refluxed for 5hours. The solid separated was filtered washed with water, dried and crystallized from ethanol. 2.5 Synthesis of N-phthaloyl Amino Acid Hydrazones 5(a-d) To a solution of the acid hyrazide 4a (0.01 mole) in 30 ml ethanol and few drops of acetic acid, (0.02 mole) of aromatic aldehydes namely salicyaldhyde, o-chlorobenzaldehyde and p- methoxybenzaldehyde also with ketone as acetyl acetone was added. The reaction mixture was heated under reflux for 5 hours and then cooled. The solid separated was filtered, dried and crystallized from the proper solvents. 2.6 Synthesis of Benzimidazoles 6(a-f) Method (A): A mixture of (0.0l mole) of 0-Phenylenediamine, (0.01 mole) N-phthaloyl amino acids 1(a-f), 5ml of dilute hydrochloric acid were taken into a 250ml round bottomed flask. The mixture was refluxed for two hours. The reaction mixture 1925 British Journal of Pharmaceutical Research, 4(16): 1923-1936, 2014 was cooled and 10% sodium hydroxide solution was added slowly with constant stirring of the flask, until the mixture was just alkaline to litmus paper. The solid separated was filtered, washed with ice cold water, dried and recrystallized from ethanol. Method B: A mixture of o-phenyldiamine (0.01 mole) p-nitrobenzaldehyde (0.01 mole) and zinc acetate (0.03 mole) was stirred magnetically at room temperature. The reaction mixture was poured up on cooled water and extracted with ethyl acetates. The combined ethyl acetates were evaporated under vacuum and the solid separated was dried and recrystallized from ethanol. 2.7 Synthesis of Bezoxazinone 7(a-f) To a solution anthranilic acid (0.01 mole) in 30 ml dry pyridine and (0.01 mole) each of N- phthaloyl amino acids 1(a-f). The reaction mixture was heated under reflux for 5 hours, and then cooled. Then the reaction mixtures were poured upon ice /HCl. The solid separated was filtered, dried and crystallized from the proper solvents. 2.8 Synthesis of Quinazolinones 8(a-d) To a solution of the bezoxazinone 7a (0.01 mole) in 30 ml n-butanol and (0.02 mole) of different amines namely formamide, hydrazine hydrate, phenyl hydrazine and aniline was added. The reaction mixture was heated under reflux for 5hours and then cooled. The solid separated was filtered, dried and crystallized from the proper solvents. 3. RESULTS AND DISCUSSION In view of tremendous importance of phthalimides due to their medicinal and bioactive properties for both phthalimide moiety and the side chain hetero
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