Samir Bondock - Academia.edu (original) (raw)
Papers by Samir Bondock
ChemInform, May 18, 2004
From 3-methylbutyraldehyde (0.43 g, 5 mmol) according to the general procedure. Distillation of t... more From 3-methylbutyraldehyde (0.43 g, 5 mmol) according to the general procedure. Distillation of the solvent under vaccum afforded 0.85 g of the oxetane 8f as a pale yellow oil.
![Research paper thumbnail of Synthesis, antitumor evaluation and microarray study of some new pyrazolo[3,4- d ][1,2,3]triazine derivatives](https://attachments.academia-assets.com/108084341/thumbnails/1.jpg)
](European journal of medicinal chemistry, Dec 1, 2017
New pyrazolo[3,4-d][1,2,3]triazine derivatives were synthesized and evaluated in vitro for their ... more New pyrazolo[3,4-d][1,2,3]triazine derivatives were synthesized and evaluated in vitro for their anticancer activity. Compound 6c showed excellent anticancer activity. In this study we provide new anticancer scaffolds to overcome drug resistance problem.-Potent antitumor agents against Huh-7 cell line.-Induces apoptosis due to, in part, activation of caspases 3/7.-Up-and down-regulates many genes related to apoptosis, metabolism, cell cycle, tumor growth and suppressor.
RSC Advances
A novel series of 2,4,5- and 2,3,4-trisubstituted thiazole hybrids with 1,3,4-thiadiazolylbenzene... more A novel series of 2,4,5- and 2,3,4-trisubstituted thiazole hybrids with 1,3,4-thiadiazolylbenzenesulfonamide was designed following the tail approach as possible hCAIX inhibitors.
Current Organic Chemistry, 2011
Australian Journal of Chemistry, 2008
The photocycloaddition of carbonyl compounds (aldehydes and keto esters, respectively) with 5-met... more The photocycloaddition of carbonyl compounds (aldehydes and keto esters, respectively) with 5-methoxyoxazoles bearing substituents at C2 and C4 is described with respect to regio- and diastereoselectivity. In all cases the reactions proceed with excellent regioselectivity and with high to moderate (exo) diastereoselectivity independent of the nature of the excited carbonyl compound. The products can be easily ring-opened to give α-amino, β-hydroxy carboxylic acid derivatives.
Angewandte Chemie, 2001
Diese Arbeit wurde durch die Deutsche Forschungsgemeinschaft und den Fonds der Chemischen Industr... more Diese Arbeit wurde durch die Deutsche Forschungsgemeinschaft und den Fonds der Chemischen Industrie gefˆrdert. S.B. bedankt sich f¸r ein Promotionsstipendium der ‰gyptischen Regierung. Hintergrundinformationen zu diesem Beitrag sind im WWW unter http://www.angewandte.de zu finden oder kˆnnen beim Autor angefordert werden.
Accounts of Chemical Research, 2004
Arkivoc, 2006
This review describes the synthesis and reactions of cyanoacetic acid hydrazide as building block... more This review describes the synthesis and reactions of cyanoacetic acid hydrazide as building block for the synthesis of polyfunctionalized heterocyclic compounds with pharmacological interest.
The XeCl excimer 308 nm radiation system is described as a powerful tool for synthetic organic ph... more The XeCl excimer 308 nm radiation system is described as a powerful tool for synthetic organic photochemistry involving carbonyl and carbonyl-type chromophores. Scaleable photochemical reactions which have been tested and optimized for this system were photodecarboxylation, [2 ϩ 2]-photocycloaddition, and Type III (electron transfer) photooxygenation reactions.
Photochemical & Photobiological Sciences, 2002
The simple diastereoselectivity of the photocycloaddition of aliphatic aldehydes to (Z)-and (E)-c... more The simple diastereoselectivity of the photocycloaddition of aliphatic aldehydes to (Z)-and (E)-cyclooctene was analyzed as a function of the substrate concentrations and applied to spin mapping.
Organic Letters, 2000
The concentration dependence of the Paternò −Bu 1chi photocycloaddition of the two cyclic enoleth... more The concentration dependence of the Paternò −Bu 1chi photocycloaddition of the two cyclic enolethers 2,3-dihydrofuran and 2,3-dihydropyran, respectively, with aromatic as well as aliphatic aldehydes was studied. For aliphatic aldehydes, a sharp transition from low to high diastereostereoselectivity was observed, indicating a switch from singlet to triplet photocycloaddition with different selectivity controlling mechanisms.
The Journal of Organic Chemistry, 2003
A new photoaldol route to R-amino-hydroxy carboxylic acid esters is initiated by the photocycload... more A new photoaldol route to R-amino-hydroxy carboxylic acid esters is initiated by the photocycloaddition of aromatic or aliphatic aldehydes to 5-methoxyoxazoles. The 4-unsubstituted 5-methyloxazole 1 gave the cycloadducts 8a-f in high yields and excellent exo-diastereoselectivities. Hydrolysis of 8a-f gives the N-acetyl R-amino-hydroxy esters 9a-f, which could be subsequently converted into the corresponding Z-didehydro R-amino acids 10a-f. Quartenary R-amino-hydroxy esters 12, 14, 16, 18, and 20, which are stable against dehydration, were obtained from the 4-alkylated 5-methoxyoxazoles 2-6, in most cases highly erythro-selective due to the high degree of stereocontrol (exo) at the photocycloaddition (to give 11, 13, 15, 17, and 19) level. The relative configurations of the N-acetyl R-amino-hydroxy esters were determined by NMR spectroscopy and comparison with chiral pool-derived compounds as well as by X-ray structure determination of the ester 23, formed by hydrolysis of the cycloadduct 22, derived from photocycloaddition of propionaldehyde to the isoleucine-derived oxazole 21.
Journal of Chemical Research, 2005
A solvent-free photooxygenation of 5-methoxyoxazoles 1a–j embedded in porphrin-loaded polystyrene... more A solvent-free photooxygenation of 5-methoxyoxazoles 1a–j embedded in porphrin-loaded polystyrene beads as solid support is described and applied for the synthesis of 3H-1,2,4-dioxazole derivatives 2a–j. Acid catalysed hydrolysis of 3H-1,2,4-dioxazole derivatives gave α-amino-α-hydroxy carboxylic acid derivatives 3a–j. The structural elucidation of the new compounds were carried on the basis of spectral and X-ray analyses.
Angewandte Chemie International Edition, 2001
RSC Advances
Toward finding potential and novel anticancer agents, we designed and prepared novel differently ... more Toward finding potential and novel anticancer agents, we designed and prepared novel differently substituted unsymmetrical azine-modified thiadiazole sulfonamide derivatives using the “combi-targeting approach”.
Russian Journal of General Chemistry, 2021
The title of Supplementary Information should read as "Synthesis and Antimicrobial Activity of Ne... more The title of Supplementary Information should read as "Synthesis and Antimicrobial Activity of New 4-Methyl-2-(3-pyridyl)thiazolyl Chalcones and Pyrazolines.
Journal of the Korean Chemical Society, 2012
Novel azopyrazolin-5-one dyes 4a-f were synthesized by the regioselective reaction of phenylhydra... more Novel azopyrazolin-5-one dyes 4a-f were synthesized by the regioselective reaction of phenylhydrazine with 2,3,4-chromantrione-3-arylhydrazones 2a-f. The acid dissociation constants pKa for the series prepared were determined and correlated by the Hammett equation. The results of such correlation together with the spectral data indicated that the studied compounds exist predominantly in the hydrazone keto structure, (D) as the Z-configuration. The dyes were applied to polyester fabrics, affording orange-yellow shades and assessments of their dyeing performance are considered. Further, the compounds 4a-f were screened for their antimicrobial activity against various microorganisms.
Journal of the Korean Chemical Society, 2012
In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series... more In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series of novel bisazo dyestuffs based on 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones 3a-f were prepared by diazocoupling of p-nitrophenyl diazonium chloride with 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones 2a-f. Compounds 3a-f were subsequently reacted with acetic anhydride in the presence of p-toluenesulfonic acid afford the corresponding O-acetyl derivatives 4a-f. The latter products as well as spectral data indicated that compounds 3a-f exist predominantly in the azo-hydrazone tautomeric form (H) as the ZE-configuration. Additionally, two series of the synthesized dyes 3a-f and 4a-f were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also the position of color in CIELAB coordinates (L*, a*, b*, H*, C*) was assessed.
Advances in Biological Chemistry, 2017
Purpose: Aim of this study is to assess the anti-proliferative effect of the thiazole analogue (5... more Purpose: Aim of this study is to assess the anti-proliferative effect of the thiazole analogue (5-acetyl-4-methyl-2-(3-pyridyl) thiazole) with different human carcinoma cell lines and to postulate its possible mechanism of action using molecular modeling. Methods: Three different human carcinoma cell lines were used namely hepatocyte carcinoma (HEPG2), breast adenocarcinoma (MCF7) and colon cancer (HCT116). Molecular docking simulations for tested thiazole analogue and its virtual analogues against the cytochrome P-450 2A6 enzyme and mutated SOD were performed. Results: Cell lines cytotoxicity revealed that the tested thiazole analogue exerts a significant anti-proliferative activity in all the used human carcinoma cell lines with a pronounced anti-proliferative effect in liver carcinoma cell line HEPG2 (IC 50 = 23.8 µg/ml) whereas the anti-proliferative effect in colon carcinoma and breast cancer cell lines was poor with IC 50 = 50 µg/ml and IC 50 > 50 µg/ml respectively. The postulated mechanism of action revealed the high affinity to inhibit SOD and CYP2A6 enzymes in the liver. Conclusion: The thiazole analogue (5-acetyl-4-methyl-2-(3-pyridyl)thiazole) is a potential liver specific anticancer agent capable of interfering with both apoptotic signaling pathway and the free radical processing in liver which leads to more studies on liver cancer from different perspective rather than the apoptotic signaling pathway.
ChemInform, May 18, 2004
From 3-methylbutyraldehyde (0.43 g, 5 mmol) according to the general procedure. Distillation of t... more From 3-methylbutyraldehyde (0.43 g, 5 mmol) according to the general procedure. Distillation of the solvent under vaccum afforded 0.85 g of the oxetane 8f as a pale yellow oil.
European journal of medicinal chemistry, Dec 1, 2017
New pyrazolo[3,4-d][1,2,3]triazine derivatives were synthesized and evaluated in vitro for their ... more New pyrazolo[3,4-d][1,2,3]triazine derivatives were synthesized and evaluated in vitro for their anticancer activity. Compound 6c showed excellent anticancer activity. In this study we provide new anticancer scaffolds to overcome drug resistance problem.-Potent antitumor agents against Huh-7 cell line.-Induces apoptosis due to, in part, activation of caspases 3/7.-Up-and down-regulates many genes related to apoptosis, metabolism, cell cycle, tumor growth and suppressor.
RSC Advances
A novel series of 2,4,5- and 2,3,4-trisubstituted thiazole hybrids with 1,3,4-thiadiazolylbenzene... more A novel series of 2,4,5- and 2,3,4-trisubstituted thiazole hybrids with 1,3,4-thiadiazolylbenzenesulfonamide was designed following the tail approach as possible hCAIX inhibitors.
Current Organic Chemistry, 2011
Australian Journal of Chemistry, 2008
The photocycloaddition of carbonyl compounds (aldehydes and keto esters, respectively) with 5-met... more The photocycloaddition of carbonyl compounds (aldehydes and keto esters, respectively) with 5-methoxyoxazoles bearing substituents at C2 and C4 is described with respect to regio- and diastereoselectivity. In all cases the reactions proceed with excellent regioselectivity and with high to moderate (exo) diastereoselectivity independent of the nature of the excited carbonyl compound. The products can be easily ring-opened to give α-amino, β-hydroxy carboxylic acid derivatives.
Angewandte Chemie, 2001
Diese Arbeit wurde durch die Deutsche Forschungsgemeinschaft und den Fonds der Chemischen Industr... more Diese Arbeit wurde durch die Deutsche Forschungsgemeinschaft und den Fonds der Chemischen Industrie gefˆrdert. S.B. bedankt sich f¸r ein Promotionsstipendium der ‰gyptischen Regierung. Hintergrundinformationen zu diesem Beitrag sind im WWW unter http://www.angewandte.de zu finden oder kˆnnen beim Autor angefordert werden.
Accounts of Chemical Research, 2004
Arkivoc, 2006
This review describes the synthesis and reactions of cyanoacetic acid hydrazide as building block... more This review describes the synthesis and reactions of cyanoacetic acid hydrazide as building block for the synthesis of polyfunctionalized heterocyclic compounds with pharmacological interest.
The XeCl excimer 308 nm radiation system is described as a powerful tool for synthetic organic ph... more The XeCl excimer 308 nm radiation system is described as a powerful tool for synthetic organic photochemistry involving carbonyl and carbonyl-type chromophores. Scaleable photochemical reactions which have been tested and optimized for this system were photodecarboxylation, [2 ϩ 2]-photocycloaddition, and Type III (electron transfer) photooxygenation reactions.
Photochemical & Photobiological Sciences, 2002
The simple diastereoselectivity of the photocycloaddition of aliphatic aldehydes to (Z)-and (E)-c... more The simple diastereoselectivity of the photocycloaddition of aliphatic aldehydes to (Z)-and (E)-cyclooctene was analyzed as a function of the substrate concentrations and applied to spin mapping.
Organic Letters, 2000
The concentration dependence of the Paternò −Bu 1chi photocycloaddition of the two cyclic enoleth... more The concentration dependence of the Paternò −Bu 1chi photocycloaddition of the two cyclic enolethers 2,3-dihydrofuran and 2,3-dihydropyran, respectively, with aromatic as well as aliphatic aldehydes was studied. For aliphatic aldehydes, a sharp transition from low to high diastereostereoselectivity was observed, indicating a switch from singlet to triplet photocycloaddition with different selectivity controlling mechanisms.
The Journal of Organic Chemistry, 2003
A new photoaldol route to R-amino-hydroxy carboxylic acid esters is initiated by the photocycload... more A new photoaldol route to R-amino-hydroxy carboxylic acid esters is initiated by the photocycloaddition of aromatic or aliphatic aldehydes to 5-methoxyoxazoles. The 4-unsubstituted 5-methyloxazole 1 gave the cycloadducts 8a-f in high yields and excellent exo-diastereoselectivities. Hydrolysis of 8a-f gives the N-acetyl R-amino-hydroxy esters 9a-f, which could be subsequently converted into the corresponding Z-didehydro R-amino acids 10a-f. Quartenary R-amino-hydroxy esters 12, 14, 16, 18, and 20, which are stable against dehydration, were obtained from the 4-alkylated 5-methoxyoxazoles 2-6, in most cases highly erythro-selective due to the high degree of stereocontrol (exo) at the photocycloaddition (to give 11, 13, 15, 17, and 19) level. The relative configurations of the N-acetyl R-amino-hydroxy esters were determined by NMR spectroscopy and comparison with chiral pool-derived compounds as well as by X-ray structure determination of the ester 23, formed by hydrolysis of the cycloadduct 22, derived from photocycloaddition of propionaldehyde to the isoleucine-derived oxazole 21.
Journal of Chemical Research, 2005
A solvent-free photooxygenation of 5-methoxyoxazoles 1a–j embedded in porphrin-loaded polystyrene... more A solvent-free photooxygenation of 5-methoxyoxazoles 1a–j embedded in porphrin-loaded polystyrene beads as solid support is described and applied for the synthesis of 3H-1,2,4-dioxazole derivatives 2a–j. Acid catalysed hydrolysis of 3H-1,2,4-dioxazole derivatives gave α-amino-α-hydroxy carboxylic acid derivatives 3a–j. The structural elucidation of the new compounds were carried on the basis of spectral and X-ray analyses.
Angewandte Chemie International Edition, 2001
RSC Advances
Toward finding potential and novel anticancer agents, we designed and prepared novel differently ... more Toward finding potential and novel anticancer agents, we designed and prepared novel differently substituted unsymmetrical azine-modified thiadiazole sulfonamide derivatives using the “combi-targeting approach”.
Russian Journal of General Chemistry, 2021
The title of Supplementary Information should read as "Synthesis and Antimicrobial Activity of Ne... more The title of Supplementary Information should read as "Synthesis and Antimicrobial Activity of New 4-Methyl-2-(3-pyridyl)thiazolyl Chalcones and Pyrazolines.
Journal of the Korean Chemical Society, 2012
Novel azopyrazolin-5-one dyes 4a-f were synthesized by the regioselective reaction of phenylhydra... more Novel azopyrazolin-5-one dyes 4a-f were synthesized by the regioselective reaction of phenylhydrazine with 2,3,4-chromantrione-3-arylhydrazones 2a-f. The acid dissociation constants pKa for the series prepared were determined and correlated by the Hammett equation. The results of such correlation together with the spectral data indicated that the studied compounds exist predominantly in the hydrazone keto structure, (D) as the Z-configuration. The dyes were applied to polyester fabrics, affording orange-yellow shades and assessments of their dyeing performance are considered. Further, the compounds 4a-f were screened for their antimicrobial activity against various microorganisms.
Journal of the Korean Chemical Society, 2012
In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series... more In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series of novel bisazo dyestuffs based on 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones 3a-f were prepared by diazocoupling of p-nitrophenyl diazonium chloride with 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones 2a-f. Compounds 3a-f were subsequently reacted with acetic anhydride in the presence of p-toluenesulfonic acid afford the corresponding O-acetyl derivatives 4a-f. The latter products as well as spectral data indicated that compounds 3a-f exist predominantly in the azo-hydrazone tautomeric form (H) as the ZE-configuration. Additionally, two series of the synthesized dyes 3a-f and 4a-f were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also the position of color in CIELAB coordinates (L*, a*, b*, H*, C*) was assessed.
Advances in Biological Chemistry, 2017
Purpose: Aim of this study is to assess the anti-proliferative effect of the thiazole analogue (5... more Purpose: Aim of this study is to assess the anti-proliferative effect of the thiazole analogue (5-acetyl-4-methyl-2-(3-pyridyl) thiazole) with different human carcinoma cell lines and to postulate its possible mechanism of action using molecular modeling. Methods: Three different human carcinoma cell lines were used namely hepatocyte carcinoma (HEPG2), breast adenocarcinoma (MCF7) and colon cancer (HCT116). Molecular docking simulations for tested thiazole analogue and its virtual analogues against the cytochrome P-450 2A6 enzyme and mutated SOD were performed. Results: Cell lines cytotoxicity revealed that the tested thiazole analogue exerts a significant anti-proliferative activity in all the used human carcinoma cell lines with a pronounced anti-proliferative effect in liver carcinoma cell line HEPG2 (IC 50 = 23.8 µg/ml) whereas the anti-proliferative effect in colon carcinoma and breast cancer cell lines was poor with IC 50 = 50 µg/ml and IC 50 > 50 µg/ml respectively. The postulated mechanism of action revealed the high affinity to inhibit SOD and CYP2A6 enzymes in the liver. Conclusion: The thiazole analogue (5-acetyl-4-methyl-2-(3-pyridyl)thiazole) is a potential liver specific anticancer agent capable of interfering with both apoptotic signaling pathway and the free radical processing in liver which leads to more studies on liver cancer from different perspective rather than the apoptotic signaling pathway.