Abeer Shaddy | National Research Centre (original) (raw)

Papers by Abeer Shaddy

Research paper thumbnail of THE REACTIONS OF ALKYL PHOSPHITES WITH αβ-UNSATURATED CARBON-NITROGEN MULTIPLE-BONDS: 2-BENZYLIDENECYANOMETHYL-1,3-BENZOTHIAZOLE AND α-BENZIL MONOXIME

Phosphorus, Sulfur, and Silicon and the Related Elements, 1998

2-Benzylidenecyanomethyl-1,3-benzothiazole (1) reacts with trialkyl phosphites (6) to give a mixt... more 2-Benzylidenecyanomethyl-1,3-benzothiazole (1) reacts with trialkyl phosphites (6) to give a mixture of the corresponding-phosphonates 9 (E & Z) with 6a, b or 16c (E & Z) with 6c (∼50%) and -[2,1-b]-fused pyrido-derivative 12 (∼20%), meanwhile, with dialkyl phosphonates 7 affords only the phosphonates 16 (E & Z) in high yields (∼80%). Only E-isomer of both types of phosphonates could be

Research paper thumbnail of Synthesis and Antimicrobial Evaluation of Newly Synthesized N,S -Bisphosphonate Derivatives

Journal of Heterocyclic Chemistry, 2015

With the aim of producing new biologically active compounds, a series of New Pyridine Imidazo [2,... more With the aim of producing new biologically active compounds, a series of New Pyridine Imidazo [2,1b]-1,3,4-thiadiazole derivatives 4(a-k) were synthesized. All the compounds were characterized via IR, 1 H-NMR and Mass spectral studies. The antimicrobial activity of newly synthesized compounds against various bacteria; Bacillus pumillus, Staphylococcus aureus, Vibrio cholera, Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, and fungi; Candida albicans were evaluated. Among the compounds tested, 4(a), 4(b), 4(f), 4(h) and 4(k) exhibited good antimicrobial activity while others responded moderately with reference to standard drugs ampicillin and amphotericin B.

Research paper thumbnail of ChemInform Abstract: Novel Microwave-Assisted One-Pot Synthesis of Heterocycle Phosphor Esters and Cyclic Oxophospholes with Antibiotic Activity

Research paper thumbnail of ChemInform Abstract: Synthesis, Quantitative Structure-Activity Relationship, and Antiinflammatory Profiles of Substituted 5- and 6-N-Heterocycle Bisphosphonate Esters

ChemInform, 2013

ABSTRACT A series of substituted N-heterocyclic aminomethylene bisphosphonates are synthesized vi... more ABSTRACT A series of substituted N-heterocyclic aminomethylene bisphosphonates are synthesized via a modified one-pot Kabachnik—Fields reaction.

Research paper thumbnail of Synthesis, Quantitative Structure–Activity Relationship, and Anti-Inflammatory Profiles of Substituted 5- and 6- N -Heterocycle Bisphosphonate Esters

Synthetic Communications, 2013

ABSTRACT A modified multi-component reaction in a one pot synthesis of a new series of substitute... more ABSTRACT A modified multi-component reaction in a one pot synthesis of a new series of substituted N-heterocyclic aminomethylene bisphosphonates, in high rates, was described. Accordingly, synthesis of α-aminobisphosphonates, via Kabachnik-Fields reaction, from the substituted amine with triethyl orthoformate, and followed by treating the product mixture with a toluene solution containing diethyl phosphite-sodium salt. The design of potentially anti-inflammatory bisphosphonates (BPs) was relied on the results of the prediction that carried out using computer-assisted molecular modeling (CAMM). Later on, new BPs were evaluated in animal model of chronic inflammation using the delayed-type hypersensitivity granuloma reaction (DTH-GRA).

Research paper thumbnail of ChemInform Abstract: A New Conjugated Addition of Trialkyl Phosphites and Alkylidenephosphoranes to 3-ω-Azidoacetyl Coumarin. Synthesis of Some 1,2,3,4-Triazaphospholes, Triazoles, and Azido-Coumarin Derivatives

Research paper thumbnail of A new conjugated addition of trialkyl phosphites and alkylidenephosphoranes to 3-ω-azideoacetyl coumarin synthesis of some 1,2,3,4-triazaphospholes, triazoles, and azido-coumarin derivatives

ABSTRACT A new and efficient conjugate addition of trimethyl and triethyl phosphites to 3-omega-a... more ABSTRACT A new and efficient conjugate addition of trimethyl and triethyl phosphites to 3-omega-azidoacetylcoumarin (1) has been studied. The reaction proceeded smoothly at r. t. furnishing 1,2,3,4-triazaphosphole coumarin derivatives 4a,b in similar to 75% yields. Linear substituted triazoles 10a,b were also obtained from the reactions of 1 with alpha-keto ylides, acetyl- and benzoylmethylene triphenylphosphoranes. Contrary to these results, Wittig reaction was occurred when 1 was allowed to react with a-alkoxycarbonylmethylene- and cyanomethylenetriphenylphosphoranes 7c-e as well as with methylidene-and benzylidenetriphenylphosphoranes 8a,b resulting in the formation of the corresponding olefins either as an intermediate 14b or as final products 11a-c.

Research paper thumbnail of ChemInform Abstract: Application of Dialkyl Cyanomethylphosphonates in Synthesis of Biologically Active Phosphono-Substituted Heterocycles and Vinylphosphonates

Research paper thumbnail of ChemInform Abstract: Use of Phosphonyl Carbanions in the Synthesis of Antiinflammatory Active Phosphorus-Containing Fused Heterocycles and Relevance Phosphonates

ChemInform, 2011

bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran... more bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran (I) or -thiophene (V). Compounds (VIIIa)-(VIIIc) and (XI) are found to exhibit good antiinflammatory activity. -(ABDOU*, W. M.; KAMEL, A. A.; SHADDY, A. A.; Eur. J. Med. Chem. 45 (2010) 11, 5217-5224, http://dx.

Research paper thumbnail of ChemInform Abstract: Synthesis of Tetrazoloquinoline-Based Mono- and Bisphosphonate Esters as Potent Antiinflammatory Agents

ChemInform, 2013

ABSTRACT Three different types of new phosphono-substituted tetrazolo quinolines are synthesized ... more ABSTRACT Three different types of new phosphono-substituted tetrazolo quinolines are synthesized by reacting 2-azidoquinoline-3-carboxaldehydes (I) with phosphites, phosphines, and Horner—Emmons reagent.

Research paper thumbnail of ChemInform Abstract: The Development of Bisphosphonates for Therapeutic Uses and Bisphosphonate Structure-Activity Consideration

Research paper thumbnail of Selective addition of Wittig reagents to bifunctionalized compounds. Condensation of 3-phenyl (2-benzothiazolyl)acrylonitrile with some phosphorus ylides

Tetrahedron, 1998

The behaviour of the acryionitriic 1 toward different types of phosphorus ylides such a.s alkoxyc... more The behaviour of the acryionitriic 1 toward different types of phosphorus ylides such a.s alkoxycarbonyl-7,a,b and ~-keto-alkylidene phosphoranes 2c..e as well as arylidenephosphorane 3 has been studied. The reactions take different pathways leading to unusual products, depending only on the nature of the substituents of ylldes used. All reA,-tions proceed only in the presence of a Imse whereby a variety of 1.3-henzothiazolyl-[l,2-x] fused compounds, e.g. 6, 16 and 18; cyclolm3pene-15 and cyclopropane-19 derivatives as well as different types of new ylides: 7, 10 and 17.a,b were isolated and established on chemical and physical evidence.

Research paper thumbnail of APPLICATION OF DIALKYL CYANOMETHYLPHOSPHONATES IN SYNTHESIS OF BIOLOGICALLY ACTIVE PHOSPHONO SUBSTITUTED-HETEROCYCLES AND VINYLPHOSPHONATES

Synthetic Communications, 2001

An efficient method has been developed for the synthesis of phosphono substituted-heterocycles an... more An efficient method has been developed for the synthesis of phosphono substituted-heterocycles and vinylphosphonates. The procedure involves coupling reactions between α,α-dihalo-, α-monohalo- and β-monohalo-carbonyl substrates with the sodium salt of diethyl cyanomethylphosphonate.

Research paper thumbnail of Regioselective Condensation of Alkylidenephosphoranes with Bifunctionalized Compounds: New Approach to the Synthesis of Fused O - and N -Heterocycles

Phosphorus, Sulfur, and Silicon and the Related Elements, 2005

Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy-and N-Anilino-1H Isoindole-1,3... more Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy-and N-Anilino-1H Isoindole-1,3-(2H)-diones. -Some of the monoolefinated phthalimide derivatives obtained are found to be potent antiinflammatory agents. In particular, potassium salts of phthalimide derivatives (VII) appear to be good candidates for lead molecules. -(ABDOU*, W. M.; KHIDRE, R. E.; BARGHASH, R. F.; Synth. Commun. 42 (2012Commun. 42 ( ) 13, 1967Commun. 42 ( -1978

Research paper thumbnail of Addition-Cyclization Reactions Of Alkylidene Phosphoranes With α-Benzoinoxime

Phosphorus, Sulfur, and Silicon and the Related Elements, 2000

ABSTRACT

Research paper thumbnail of Symmetrical and Asymmetrical Bisphosphonate Esters. Synthesis, Selective Hydrolysis, and Isomerization

Monatshefte für Chemie - Chemical Monthly, 2006

Two simple and efficient one-pot procedures for the synthesis of a series of -branched N-heterocy... more Two simple and efficient one-pot procedures for the synthesis of a series of -branched N-heterocycle-substituted methane-1,1-bisphosphonates are outlined. In the first method, the parent halosubstrates were reacted with cyanomethylphosphonate followed by reaction with dialkyl phosphonates to give asymmetrical or symmetrical bisphosphonates (BPs). In the second approach, the same halocompounds were reacted with tetraethyl methyl-1,1-bisphosphonate to give the requisite BPs. Partial and complete hydrolysis of the prepared BPs were also investigated. The products contain functional groups advantageous for further synthetic modification as structural units for coupling with the drug. Scheme 1 Formula 1 106 W. M. Abdou et al.

Research paper thumbnail of Novel Microwave-Assisted One-Pot Synthesis of Heterocycle Phosphor Esters and Cyclic Oxophospholes with Antibiotic Activity

Letters in Organic Chemistry, 2008

... aThe 1H and 13C NMR spectra were measured on a Joel ECA-500 MHz instrument using SiMe4 as an ... more ... aThe 1H and 13C NMR spectra were measured on a Joel ECA-500 MHz instrument using SiMe4 as an internal reference; bThe 31P NMR spectra were ... ions 2a, 2b, 7 and 13 as well as their phosphonium counter-parts [3] in their initial chemical attack toward the carboni-trile 1 ...

Research paper thumbnail of Synthesis of Tetrazoloquinoline-Based Mono- and Bisphosphonate Esters as Potent Anti-Inflammatory Agents

Journal of Heterocyclic Chemistry, 2013

ABSTRACT Several new a-alkoxy- and a-hydroxyphosphonate derivatives of tetrazole-quinolines were ... more ABSTRACT Several new a-alkoxy- and a-hydroxyphosphonate derivatives of tetrazole-quinolines were synthesized from the reaction of 2-azidoquinolines 3-carboxaldehyde 1a,b with trialkyl phosphites and dialkyl phosphites. On the other hand, azaphospholes 12a,b were obtained by treating 1a,b with tris(dimethylamino)phosphine. Furthermore, Perkin-type condensation of 1a,b and tetraethyl methylenebisphosphonate provided the corresponding tetrazoloquinoline-based bisphosphonate esters 14a,b. Based on the prediction results (PASS program), the anti-inflammatory activity of the prepared compounds was determined in vivo by the acute carrageenin-induced paw edema in rats. Many of the new compounds exhibit considerable anti-inflammatory properties at a dose of 50 mg/kg body weight. Especially 14a and 14b revealed remarkable activities compared with indomethacin, which was used as a reference standard in this study.

Research paper thumbnail of Antimicrobial activity of novel fused nitrogen, sulfur and phosphorus containing-heterocycles and relevant phosphonates with difurylpyridazine Species

Journal of Chemical Research, 2009

ABSTRACT Treatment of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with phosphon... more ABSTRACT Treatment of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with phosphonate carboanions stabilised with electron withdrawing group (CO2R, CN, SR′) led, under microwave irradiation and the effect of basic catalysis, to excellent yields of a variety of condensed sulfur, nitrogen and phosphorus-containing heterocycles as major products, along with fused thieno- and thiazole ring systems bearing a phosphonate moiety. On the other hand, fused thiazaphosphinine oxide and thiopyranone phosphonate were obtained in equal yields from the reaction of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with diethyl vinylphosphonate. Screening results of antimicrobial potency for the products were discussed in terms of structure-activity relationships (SAR), and an attempt was made to define the structural features for lead compounds.

Research paper thumbnail of Use of phosphonyl carbanions in the synthesis of anti-inflammatory active phosphorus-containing fused heterocycles and relevance phosphonates

European Journal of Medicinal Chemistry, 2010

bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran... more bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran (I) or -thiophene (V). Compounds (VIIIa)-(VIIIc) and (XI) are found to exhibit good antiinflammatory activity. -(ABDOU*, W. M.; KAMEL, A. A.; SHADDY, A. A.; Eur. J. Med. Chem. 45 (2010) 11, 5217-5224, http://dx.

Research paper thumbnail of THE REACTIONS OF ALKYL PHOSPHITES WITH αβ-UNSATURATED CARBON-NITROGEN MULTIPLE-BONDS: 2-BENZYLIDENECYANOMETHYL-1,3-BENZOTHIAZOLE AND α-BENZIL MONOXIME

Phosphorus, Sulfur, and Silicon and the Related Elements, 1998

2-Benzylidenecyanomethyl-1,3-benzothiazole (1) reacts with trialkyl phosphites (6) to give a mixt... more 2-Benzylidenecyanomethyl-1,3-benzothiazole (1) reacts with trialkyl phosphites (6) to give a mixture of the corresponding-phosphonates 9 (E & Z) with 6a, b or 16c (E & Z) with 6c (∼50%) and -[2,1-b]-fused pyrido-derivative 12 (∼20%), meanwhile, with dialkyl phosphonates 7 affords only the phosphonates 16 (E & Z) in high yields (∼80%). Only E-isomer of both types of phosphonates could be

Research paper thumbnail of Synthesis and Antimicrobial Evaluation of Newly Synthesized N,S -Bisphosphonate Derivatives

Journal of Heterocyclic Chemistry, 2015

With the aim of producing new biologically active compounds, a series of New Pyridine Imidazo [2,... more With the aim of producing new biologically active compounds, a series of New Pyridine Imidazo [2,1b]-1,3,4-thiadiazole derivatives 4(a-k) were synthesized. All the compounds were characterized via IR, 1 H-NMR and Mass spectral studies. The antimicrobial activity of newly synthesized compounds against various bacteria; Bacillus pumillus, Staphylococcus aureus, Vibrio cholera, Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, and fungi; Candida albicans were evaluated. Among the compounds tested, 4(a), 4(b), 4(f), 4(h) and 4(k) exhibited good antimicrobial activity while others responded moderately with reference to standard drugs ampicillin and amphotericin B.

Research paper thumbnail of ChemInform Abstract: Novel Microwave-Assisted One-Pot Synthesis of Heterocycle Phosphor Esters and Cyclic Oxophospholes with Antibiotic Activity

Research paper thumbnail of ChemInform Abstract: Synthesis, Quantitative Structure-Activity Relationship, and Antiinflammatory Profiles of Substituted 5- and 6-N-Heterocycle Bisphosphonate Esters

ChemInform, 2013

ABSTRACT A series of substituted N-heterocyclic aminomethylene bisphosphonates are synthesized vi... more ABSTRACT A series of substituted N-heterocyclic aminomethylene bisphosphonates are synthesized via a modified one-pot Kabachnik—Fields reaction.

Research paper thumbnail of Synthesis, Quantitative Structure–Activity Relationship, and Anti-Inflammatory Profiles of Substituted 5- and 6- N -Heterocycle Bisphosphonate Esters

Synthetic Communications, 2013

ABSTRACT A modified multi-component reaction in a one pot synthesis of a new series of substitute... more ABSTRACT A modified multi-component reaction in a one pot synthesis of a new series of substituted N-heterocyclic aminomethylene bisphosphonates, in high rates, was described. Accordingly, synthesis of α-aminobisphosphonates, via Kabachnik-Fields reaction, from the substituted amine with triethyl orthoformate, and followed by treating the product mixture with a toluene solution containing diethyl phosphite-sodium salt. The design of potentially anti-inflammatory bisphosphonates (BPs) was relied on the results of the prediction that carried out using computer-assisted molecular modeling (CAMM). Later on, new BPs were evaluated in animal model of chronic inflammation using the delayed-type hypersensitivity granuloma reaction (DTH-GRA).

Research paper thumbnail of ChemInform Abstract: A New Conjugated Addition of Trialkyl Phosphites and Alkylidenephosphoranes to 3-ω-Azidoacetyl Coumarin. Synthesis of Some 1,2,3,4-Triazaphospholes, Triazoles, and Azido-Coumarin Derivatives

Research paper thumbnail of A new conjugated addition of trialkyl phosphites and alkylidenephosphoranes to 3-ω-azideoacetyl coumarin synthesis of some 1,2,3,4-triazaphospholes, triazoles, and azido-coumarin derivatives

ABSTRACT A new and efficient conjugate addition of trimethyl and triethyl phosphites to 3-omega-a... more ABSTRACT A new and efficient conjugate addition of trimethyl and triethyl phosphites to 3-omega-azidoacetylcoumarin (1) has been studied. The reaction proceeded smoothly at r. t. furnishing 1,2,3,4-triazaphosphole coumarin derivatives 4a,b in similar to 75% yields. Linear substituted triazoles 10a,b were also obtained from the reactions of 1 with alpha-keto ylides, acetyl- and benzoylmethylene triphenylphosphoranes. Contrary to these results, Wittig reaction was occurred when 1 was allowed to react with a-alkoxycarbonylmethylene- and cyanomethylenetriphenylphosphoranes 7c-e as well as with methylidene-and benzylidenetriphenylphosphoranes 8a,b resulting in the formation of the corresponding olefins either as an intermediate 14b or as final products 11a-c.

Research paper thumbnail of ChemInform Abstract: Application of Dialkyl Cyanomethylphosphonates in Synthesis of Biologically Active Phosphono-Substituted Heterocycles and Vinylphosphonates

Research paper thumbnail of ChemInform Abstract: Use of Phosphonyl Carbanions in the Synthesis of Antiinflammatory Active Phosphorus-Containing Fused Heterocycles and Relevance Phosphonates

ChemInform, 2011

bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran... more bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran (I) or -thiophene (V). Compounds (VIIIa)-(VIIIc) and (XI) are found to exhibit good antiinflammatory activity. -(ABDOU*, W. M.; KAMEL, A. A.; SHADDY, A. A.; Eur. J. Med. Chem. 45 (2010) 11, 5217-5224, http://dx.

Research paper thumbnail of ChemInform Abstract: Synthesis of Tetrazoloquinoline-Based Mono- and Bisphosphonate Esters as Potent Antiinflammatory Agents

ChemInform, 2013

ABSTRACT Three different types of new phosphono-substituted tetrazolo quinolines are synthesized ... more ABSTRACT Three different types of new phosphono-substituted tetrazolo quinolines are synthesized by reacting 2-azidoquinoline-3-carboxaldehydes (I) with phosphites, phosphines, and Horner—Emmons reagent.

Research paper thumbnail of ChemInform Abstract: The Development of Bisphosphonates for Therapeutic Uses and Bisphosphonate Structure-Activity Consideration

Research paper thumbnail of Selective addition of Wittig reagents to bifunctionalized compounds. Condensation of 3-phenyl (2-benzothiazolyl)acrylonitrile with some phosphorus ylides

Tetrahedron, 1998

The behaviour of the acryionitriic 1 toward different types of phosphorus ylides such a.s alkoxyc... more The behaviour of the acryionitriic 1 toward different types of phosphorus ylides such a.s alkoxycarbonyl-7,a,b and ~-keto-alkylidene phosphoranes 2c..e as well as arylidenephosphorane 3 has been studied. The reactions take different pathways leading to unusual products, depending only on the nature of the substituents of ylldes used. All reA,-tions proceed only in the presence of a Imse whereby a variety of 1.3-henzothiazolyl-[l,2-x] fused compounds, e.g. 6, 16 and 18; cyclolm3pene-15 and cyclopropane-19 derivatives as well as different types of new ylides: 7, 10 and 17.a,b were isolated and established on chemical and physical evidence.

Research paper thumbnail of APPLICATION OF DIALKYL CYANOMETHYLPHOSPHONATES IN SYNTHESIS OF BIOLOGICALLY ACTIVE PHOSPHONO SUBSTITUTED-HETEROCYCLES AND VINYLPHOSPHONATES

Synthetic Communications, 2001

An efficient method has been developed for the synthesis of phosphono substituted-heterocycles an... more An efficient method has been developed for the synthesis of phosphono substituted-heterocycles and vinylphosphonates. The procedure involves coupling reactions between α,α-dihalo-, α-monohalo- and β-monohalo-carbonyl substrates with the sodium salt of diethyl cyanomethylphosphonate.

Research paper thumbnail of Regioselective Condensation of Alkylidenephosphoranes with Bifunctionalized Compounds: New Approach to the Synthesis of Fused O - and N -Heterocycles

Phosphorus, Sulfur, and Silicon and the Related Elements, 2005

Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy-and N-Anilino-1H Isoindole-1,3... more Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy-and N-Anilino-1H Isoindole-1,3-(2H)-diones. -Some of the monoolefinated phthalimide derivatives obtained are found to be potent antiinflammatory agents. In particular, potassium salts of phthalimide derivatives (VII) appear to be good candidates for lead molecules. -(ABDOU*, W. M.; KHIDRE, R. E.; BARGHASH, R. F.; Synth. Commun. 42 (2012Commun. 42 ( ) 13, 1967Commun. 42 ( -1978

Research paper thumbnail of Addition-Cyclization Reactions Of Alkylidene Phosphoranes With α-Benzoinoxime

Phosphorus, Sulfur, and Silicon and the Related Elements, 2000

ABSTRACT

Research paper thumbnail of Symmetrical and Asymmetrical Bisphosphonate Esters. Synthesis, Selective Hydrolysis, and Isomerization

Monatshefte für Chemie - Chemical Monthly, 2006

Two simple and efficient one-pot procedures for the synthesis of a series of -branched N-heterocy... more Two simple and efficient one-pot procedures for the synthesis of a series of -branched N-heterocycle-substituted methane-1,1-bisphosphonates are outlined. In the first method, the parent halosubstrates were reacted with cyanomethylphosphonate followed by reaction with dialkyl phosphonates to give asymmetrical or symmetrical bisphosphonates (BPs). In the second approach, the same halocompounds were reacted with tetraethyl methyl-1,1-bisphosphonate to give the requisite BPs. Partial and complete hydrolysis of the prepared BPs were also investigated. The products contain functional groups advantageous for further synthetic modification as structural units for coupling with the drug. Scheme 1 Formula 1 106 W. M. Abdou et al.

Research paper thumbnail of Novel Microwave-Assisted One-Pot Synthesis of Heterocycle Phosphor Esters and Cyclic Oxophospholes with Antibiotic Activity

Letters in Organic Chemistry, 2008

... aThe 1H and 13C NMR spectra were measured on a Joel ECA-500 MHz instrument using SiMe4 as an ... more ... aThe 1H and 13C NMR spectra were measured on a Joel ECA-500 MHz instrument using SiMe4 as an internal reference; bThe 31P NMR spectra were ... ions 2a, 2b, 7 and 13 as well as their phosphonium counter-parts [3] in their initial chemical attack toward the carboni-trile 1 ...

Research paper thumbnail of Synthesis of Tetrazoloquinoline-Based Mono- and Bisphosphonate Esters as Potent Anti-Inflammatory Agents

Journal of Heterocyclic Chemistry, 2013

ABSTRACT Several new a-alkoxy- and a-hydroxyphosphonate derivatives of tetrazole-quinolines were ... more ABSTRACT Several new a-alkoxy- and a-hydroxyphosphonate derivatives of tetrazole-quinolines were synthesized from the reaction of 2-azidoquinolines 3-carboxaldehyde 1a,b with trialkyl phosphites and dialkyl phosphites. On the other hand, azaphospholes 12a,b were obtained by treating 1a,b with tris(dimethylamino)phosphine. Furthermore, Perkin-type condensation of 1a,b and tetraethyl methylenebisphosphonate provided the corresponding tetrazoloquinoline-based bisphosphonate esters 14a,b. Based on the prediction results (PASS program), the anti-inflammatory activity of the prepared compounds was determined in vivo by the acute carrageenin-induced paw edema in rats. Many of the new compounds exhibit considerable anti-inflammatory properties at a dose of 50 mg/kg body weight. Especially 14a and 14b revealed remarkable activities compared with indomethacin, which was used as a reference standard in this study.

Research paper thumbnail of Antimicrobial activity of novel fused nitrogen, sulfur and phosphorus containing-heterocycles and relevant phosphonates with difurylpyridazine Species

Journal of Chemical Research, 2009

ABSTRACT Treatment of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with phosphon... more ABSTRACT Treatment of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with phosphonate carboanions stabilised with electron withdrawing group (CO2R, CN, SR′) led, under microwave irradiation and the effect of basic catalysis, to excellent yields of a variety of condensed sulfur, nitrogen and phosphorus-containing heterocycles as major products, along with fused thieno- and thiazole ring systems bearing a phosphonate moiety. On the other hand, fused thiazaphosphinine oxide and thiopyranone phosphonate were obtained in equal yields from the reaction of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with diethyl vinylphosphonate. Screening results of antimicrobial potency for the products were discussed in terms of structure-activity relationships (SAR), and an attempt was made to define the structural features for lead compounds.

Research paper thumbnail of Use of phosphonyl carbanions in the synthesis of anti-inflammatory active phosphorus-containing fused heterocycles and relevance phosphonates

European Journal of Medicinal Chemistry, 2010

bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran... more bicyclic 5,5-and 5,6-membered systems are synthesized by Horner-Emmons reactions of 2-acetylfuran (I) or -thiophene (V). Compounds (VIIIa)-(VIIIc) and (XI) are found to exhibit good antiinflammatory activity. -(ABDOU*, W. M.; KAMEL, A. A.; SHADDY, A. A.; Eur. J. Med. Chem. 45 (2010) 11, 5217-5224, http://dx.