A. E. Amr

Steroidal pyrazolines evaluated as aromatase and quinone reductase-2 inhibitors for chemoprevention of cancer

The aromatase and quinone reductase-2 inhibition of synthesized heterocyclic pyrazole derivatives fused with steroidal structure for chemoprevention of cancer is reported herein. All compounds were interestingly less toxic than the reference drug (Cyproterone(®)). The aromatase inhibitory activities of these compounds were much more potent than the lead compound resveratrol, which has an IC(50) of 80 μM. In addition, all the compounds displayed potent quinone reductase-2 inhibition. Initially the acute toxicity of the compounds was assayed via the determination of their LD(50). The aromatase and quinone reductase-2 inhibitors resulting from this study have potential value in the treatment and prevention of cancer.

5α-reductase inhibitors, antiviral and anti-tumor activities of some steroidal cyanopyridinone derivatives.

We herein report the 5α-reductase inhibitors, antiviral and anti-tumor activities of some synthesized heterocyclic cyanopyridone and cyanothiopyridone derivatives fused with steroidal structure. Initially the acute toxicity of the compounds was assayed via the determination of their LD(50). All the compounds, except 3b, were interestingly less toxic than the reference drug (Prednisolone(®)). Seventeen heterocyclic derivatives containing a cyanopyridone or cyanothiopyridone rings fused to a steroidal moiety were synthesized and screened for their 5α-reductase inhibitors, antiviral and anti-tumor activities comparable to that of Anastrozole, Bicalutamide, Efavirenz, Capravirine, Ribavirin, Oseltamivir and Amantadine as the reference drugs. Some of the compounds exhibited better 5α-reductase inhibitors, antiviral and anti-tumor activities than the reference drugs. The detailed 5α-reductase inhibitors, antiviral and anti-tumor activities of the synthesized compounds were reported.

A new investigation for some steroidal derivatives as anti-Alzheimer agents

We herein report the anti-Alzheimer activity of some synthesized heterocyclic pyrimidine and thiopyrimidine derivatives fused with steroidal structure. Twenty-one of these compounds were synthesized and conveniently screened for their anti-Alzheimer activities using of Flurbiprofen as the reference drug. Some of these compounds were demonstrated to exhibit remarkable activity and their β-amyloid (Aβ) lowering results as IC(50) values reported.

Synthesis, reactions, and antimicrobial activity of some novel fused thiazolo[3,2-a]pyrimidine-5H-indeno[1,2-d]pyrimidine derivatives

Series of novel substituted thioxopyrimidine and thiazolo[3,2-a]pyrimidine compounds that combine various heteroaryl rings have been synthesized via Biginelli one-pot three-component reaction and elucidated with chemical and spectral analysis. Several products were tested for their antimicrobial properties.

Synthesis of novel substituted pyridines from 1-(3-aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one and their anticancer activity

A series of novel substituted pyridine derivatives have been synthesized via the reaction of 3-indole carboxaldehyde with 3-aminoacetophenone. The products structures have been elucidated from elemental analysis as well as IR, 1H NMR, 13C NMR, and MS spectroscopy data. All the synthesized compounds have shown anticancer activity against HEPG2 and MCF-7 in vitro; some of them have exhibited the in vivo activity.

Synthesis of chiral linear and macrocyclic candidates: VI. Synthesis and antibacterial activity of some macrocyclic tripeptides and linear dipeptide Schiff bases

A series of macrocyclic tripeptides and linear dipeptide Schiff base derivatives has been synthesized using pyridine-3,5-dicarboxylic acid and L-phenyalanine methyl ester as starting materials. Treatment of pyridine-3,5-dicarbonyl dichloride with L-phenylalanine methyl ester gave N,N′-(pyridine-3,5-diyldicarbonyl)bis(L-phenyalanine methyl ester) which was hydrolyzed with 1N sodium hydroxide to the corresponding bis-acid, and the latter was cyclized with diamino acids to afford macrocyclic tripeptide derivatives. The reaction of the bis ester with hydrazine hydrate gave bis-hydrazide, which was condensed with aldehydes to obtain the corresponding Schiff base derivatives. The structures of the newly synthesized compounds were confirmed by IR, 1H and 13C NMR, and MS spectral data and elemental analyses. The antimicrobial activities of some of the newly synthesized compounds were comparable with that of Streptomycin used as control.

Synthesis and antiviral activity of 1,2,3-triazole glycosides based substituted pyridine via click cycloaddition

Novel conjugates of substituted pyridine and carbohydrate moieties linked by 1,2,3-triazoles were synthesized. The propargyl group was introduced by O-propargylation of pyridone derivatives. Attachment of carbohydrate molecules to the substituted pyridine core was performed by Cu-catalyzed cycloaddition of propargyl sugars with azidoethoxypyridine derivative or azido-sugars with substituted (propargyl)oxypyridines which afforded the corresponding 1,2,3-triazoles in high yields. Antiviral activity of synthesized compounds was studied against H5N1 influenza virus and triazolyl glycoside 7 demonstrated high activity in addition to its low toxicity. The effect of attachment of glycosyl triazole moieties to pyridinyl system was studied, in SAR correlation, which has been found to enhance antiviral activity.

2-Amino-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carbonitrile

In the title molecule, C21H15FN2O2, the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109u2005(2)u2005Å] is 83.35u2005(7)°. The pyran ring adopts a slight sofa conformation with the tertiary C(H) atom forming the flap. The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −4.3u2005(3)°]. In the crystal, molecules are linked by intermolecular N—H⋯N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.7713u2005(9)u2005Å].

Synthesis of some novel S-alkylated and S-glycosylated hydantoin derivatives containing pyrene moiety

Abstract3-Aryl-5-[(Z)-pyrenylmethylene]-2-alkylthiohydantoins and 3-Aryl-5-[(Z)-pyrenylmethylene]-2-(D-glycosyl)-2-thiohydantoins functionalized with different aromatic and glycoside substituents have been synthesized by the reaction of (Z)-3-(4-methoxyphenyl)-5-[(pyren-8-yl)methylene]-2-thiohydantoin with alkyl halides, cyclic and acyclic nucleosides via various routes with moderate to good yields and characterized by 1H, 13C NMR and mass spectra and elemental analysis

Synthesis and characterization of novel 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) and dihydro-alkylthio-benzyloxopyrimidine (S-DABO) analogs containing a benzo[d]thiazol moiety

A series of novel dihydro-alkylthio-benzyloxopyrimidine (S-DABO) and 1-[(2-hydroxyethoxy) methyl]-6-(phenylthio)thymine (HEPT) analogs bearing a (benzo[d]thiazol-2-yl)methyl moiety at the C6 position of the pyrimidine core have been synthesized. 5-Allyl-6-{(benzo[d]thiazol-2-yl)methyl}-2-thiouracil and 5-allyl-6-{(benzo-[d]thiazol-2-yl)methyl}uracil were alkylated to give, respectively, S2- and N1- ethoxymethyl and -methylthiomethyl uracil derivatives. 5-Allyl-6-[(benzo[d]thiazol-2-yl)methyl]-2-thiouracil was also alkylated by S2 with methyl bromoacetate and hydrolyzed to the corresponding acid.