Publications by authors named "Hanaa M Hosni"

9 Publications

  • Page 1 of 1

Synthesis and Characterization of Macrocyclic Chiral Tröger's Base Phenhomazine Candidates as Anticancer Agent.

Front Chem 2020 28;8:633065. Epub 2021 Jan 28.

Bioproducts Research Chair, Zoology Department, Faculty of Science, King Saud University, Riyadh, Saudi Arabia.

1,4,7,10-Tetraoxa[10](2,8)trögerophane was synthesized from its corresponding precursors. Heating of with p-nitrophenoxide afforded bis(p-nitrophenyl)ether , which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether . Treatment of with paraformaldehyde and triflouroacetic anhydride gave trögerophane . Reaction of with trifluroacetic anhydride afforded phenhomazine derivative , which was treated with potassium carbonate to afford tetrahydrophenhomazine . Finally, reaction of with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds and , respectively. The synthesized trögerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa[10](2,8)trögerophane had a promising selectivity towards colon cancer cell line with an IC of 92.7 µg/ml.
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http://dx.doi.org/10.3389/fchem.2020.633065DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7976657PMC
January 2021

In Vitro and In Vivo Anti-Breast Cancer Activities of Some Newly Synthesized 5-(thiophen-2-yl)thieno-[2,3-d]pyrimidin-4-one Candidates.

Molecules 2019 Jun 17;24(12). Epub 2019 Jun 17.

Zoology Department, Bioproducts Research Chair, Faculty of Science, King Saud University, Riyadh 11451, Saudi Arabia.

In this study, some of new thiophenyl thienopyrimidinone derivatives - were prepared and tested as anti-cancer agents by using thiophenyl thieno[2,3-d]pyrimidinone derivative as a starting material, which was prepared from cyclization of ethyl ester derivative with formamide. Treatment of with ethyl- chloroacetate gave thienopyrimidinone -ethylacetate , which was reacted with hydrazine hydrate or anthranilic acid to afford acetohydrazide and benzo[d][1,]oxazin-4-one respectively. Condensation of with aromatic aldehydes or phenylisothiocyanate yielded Schiff base derivatives , and thiosemicarbazise , which were treated with 2-mercaptoacetic acid or chloroacetic acid to give the corresponding thiazolidinones , and phenylimino-thiazolidinone , respectively. Treatment of with ethylacetoacetate or acetic acid/acetic anhydride gave pyrazole and acetyl acetohydrazide derivatives, respectively. The latter compound was reacted with ethyl cycno-acetate or malononitrile to give and , respectively. In this work, we have studied the anti-cancer activity of the synthesized thienopyrimidinone derivatives against MCF-7 and MCF-10A cancer cells. Furthermore, in vivo experiments showed that the synthesized compounds significantly reduced tumor growth up to the 8 day of treatment in comparison to control animal models. Additionally, the synthesized derivatives showed potential inhibitory effects against pim-1 kinase activities.
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http://dx.doi.org/10.3390/molecules24122255DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6631792PMC
June 2019

Synthesis and Molecular Docking of New Thiophene Derivatives as Lactate Dehydrogenase-A Inhibitors.

Mini Rev Med Chem 2019 ;19(10):833-841

Drug Exploration & Development Chair (DEDC), Pharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.

Background & Objective: A series of novel derivatives possessing the thiophene moiety were synthesized using ethyl 5'-amino-2,3'-bithiophene-4'-carboxylate as the starting material.

Methods: The new synthesized derivatives were screened as lactate dehydrogenase (LDH) inhibitors. LDH plays an important role in glucose metabolism in cancer cells and can affect tumor genesis and metastasis.

Results: 3-Substituted p-tolylthieno[2,3-d]pyrimidin-4(3H)-ones 4 were the most potent inhibitors in this study compared to Galloflavin reference drug.

Conclusion: Molecular docking studies on the Human Lactate Dehydrogenase active site were carried out on the synthesized compounds and the MolDock scores ranged between -127 to -171.
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http://dx.doi.org/10.2174/1389557519666190212165302DOI Listing
August 2019

Synthesis and antimicrobial evaluation of some new cyclooctanones and cyclooctane-based heterocycles.

Arch Pharm (Weinheim) 2012 Mar 2;345(3):231-9. Epub 2011 Nov 2.

Applied Organic Chemistry Department, National Research Center, Dokki-Cairo, Egypt.

The versatile synthon (E)-2-((dimethyl amino)methylene)cyclooctanone (2) was used as a key intermediate for the synthesis of cyclooctanones and cyclooctane-based heterocycles with pyrazole, isoxazole, pyrimidine, pyrazolopyrimidine, triazolopyrimidine and imidazopyrimidine derivatives via its reactions with several nitrogen nucleophiles. The newly synthesized compounds were screened in vitro for their antimicrobial activity against pathogenic microorganisms (Listeria monocytogenes, methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans). Most of the tested compounds showed moderate to high antibacterial and antifungal effects against the tested pathogenic microorganisms. Among the synthesized compounds, 2-((p-sulfonamidophenyl)methylene)cyclooctanone (5) showed excellent activity against Listeria monocytogenes.
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http://dx.doi.org/10.1002/ardp.201100186DOI Listing
March 2012

Anti-inflammatory and analgesic activities of some newly synthesized pyridinedicarbonitrile and benzopyranopyridine derivatives.

Acta Pharm 2008 Jun;58(2):175-86

Pesticide Chemistry Department, National Research Centre Doki, Cairo, Egypt.

In continuation of our search for new substituted pyridine based anti-inflammatories, reaction of 1-(2-thienyl or furanyl)-3-(2-hydroxyphenyl)-2-propen-1-ones (1) with malononitrile in alcoholic KOH solution afforded a mixture of 4-alkoxy-2-(2-thienyl or furanyl)-5H-[1]benzopyrano[3,4-c]pyridine-5-ones (2) and 2-alkoxy-4-amino-6- (2-thienyl or furanyl)-3,5-pyridinedicarbonitriles (3). Some of the synthesized compounds were evaluated for their anti-inflammatory and analgesic activities compared to diclofenac potassium as positive control. Detailed synthesis, spectroscopic and toxicity data are reported.
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http://dx.doi.org/10.2478/v10007-008-0005-4DOI Listing
June 2008

Novel synthesis of [1]-benzothiepino[5,4-b]pyridine-3-carbonitriles and their anti-inflammatory properties.

Bioorg Med Chem 2007 Mar 17;15(6):2403-13. Epub 2007 Jan 17.

Pesticide Chemistry Department, National Research Centre, Dokki, 12622 Cairo, Egypt.

Reaction of 4-arylmethylene-3,4-dihydro-[1]-benzothiepin-5(2H)-ones 1 with malononitrile in the appropriate alcohol in the presence of sodium afforded the 2-alkoxy-4-aryl-5,6-dihydro-[1]-benzothiepino[5,4-b]pyridine-3-carbonitriles 2 and not the isomeric forms [1]-benzothiepino[4,5-c]pyridine-1-carbonitriles 3 in high regioselective manner. The assumed structure of 2 was inferred through independent synthetic reaction of 3,4-dihydro-[1]-benzothiepin-5(2H)-one (4) with ylidenemalononitriles 5 under the same applied reaction conditions and confirmed by single crystal X-ray diffraction studies. However, reaction of 4 with arylidenecyanothioacetamides 6 in refluxing ethanol in the presence of basic catalyst (piperidine or morpholine) does not afford the expected 4-aryl-3-cyano-5,6-dihydro-[1]-benzothiepino[5,4-b]pyridine-2(1H)-thiones 7 and instead 4-aryl-3,5-dicyano-6-thioxo-2(1H)-pyridinethiolate monohydrates were isolated as piperidinium or morpholinium salts 8. On the other hand, reaction of 6 with cyanothioacetamide in the presence of a sufficient amount of basic catalyst yielded exclusively 2-amino-4-aryl-3,5-dicyano-2-pyridinethiolates as piperidinium or morpholinium salts 9. Meanwhile, 7 were prepared through the reaction of 1 with cyanothioacetamide in refluxing ethanol in the presence of a catalytic amount of piperidine. Anti-inflammatory activity screening of the prepared compounds using in vivo acute carrageenan-induced paw oedema in rats exhibited that all the tested compounds possess considerable activity. In addition, few synthesized derivatives reveal remarkable anti-inflammatory properties (2d, k, l) comparable with indomethacin which was used as a reference standard during the pharmacological activity screening studies.
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http://dx.doi.org/10.1016/j.bmc.2007.01.015DOI Listing
March 2007

Novel synthesis of nicotinamide derivatives of cytotoxic properties.

Bioorg Med Chem 2006 Jul 9;14(13):4466-76. Epub 2006 Mar 9.

Pesticide Chemistry Department, National Research Centre, Dokki, Cairo, Egypt.

A variety of 2-substituted-4,6-diaryl-3-pyridinecarboxamides 5 were synthesized through aromatic nucleophilic substitution reaction of secondary amines with 2-bromo analogues 4. The latter were obtained via bromination of 2-cyano-3,5-diaryl-5-oxo-N-substituted pentamides 3 in glacial acetic acid. Moreover, pentamide derivatives 3 were prepared through base-catalyzed Michael addition of cyanacetanilides 2 with 1,3-diaryl-2-propen-1-ones 1. Otherwise, reaction of 2-bromo-3-pyridinecarboxamides 4 with primary aromatic amines in refluxing pyridine afforded the corresponding 2-(arylamino)-3-pyridinecarboxamides 6 besides the unexpected 2-unsubstituted amino analogues 7. Antitumor properties of the synthesized pyridinecarboxamides utilizing 59 different human tumor cell lines, representing leukemia, melanoma, and cancers of the lung, colon, brain, ovary, breast, prostate as well as kidney, were screened. Many of the tested compounds show considerable in vitro antitumor properties especially 5c and 7a, which reveal moderate activities against most of the used human tumor cell lines. It has also been achieved that, all the tested nicotinamide derivatives reveal promising antitumor properties against MDA-MB-231/ATCC (breast cancer).
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http://dx.doi.org/10.1016/j.bmc.2006.02.031DOI Listing
July 2006

Novel bis(1-acyl-2-pyrazolines) of potential anti-inflammatory and molluscicidal properties.

Bioorg Med Chem 2006 Jun 7;14(11):3929-37. Epub 2006 Feb 7.

Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo, Egypt.

A variety of bis[3-aryl-4,5-dihydro-1H-pyrazol-1-carboxaldehydes] 4a-h were obtained via reaction of bis[1-aryl-2-propen-1-ones] 3a-h with hydrazine hydrate in refluxing formic acid. In addition, the corresponding bis[1-acetyl-3-aryl-4,5-dihydro-1H-pyrazoles] 4i-m were formed through conducting the reaction of 3 with hydrazine hydrate in refluxing acetic acid. The starting bis(2-propen-1-ones) 3a-h were prepared stereoselectively as E,E'-geometric isomer via condensation of bisbenzaldehydes 1a,b with (un)substituted acetophenones 2 in ethanolic KOH solution. Anti-inflammatory as well as ulcerogenic activities of the prepared pyrazolines were evaluated in vivo and compared with that of a standard drug (indomethacin). Many of the tested compounds show remarkable anti-inflammatory properties with an ulcerogenic liability (especially 4f, g, j, and k) lower than that of the standard used drug. Compound 4f was established to be the best effectively prepared anti-inflammatory active pyrazoline derivative and safer than indomethacin with respect to its ulcerogenic liability. Molluscicidal activity of the prepared compounds against Biomphalaria alexandrina snails (the intermediate host of Schistosoma mansoni) was screened. Where, some of the prepared compounds show considerable activities.
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http://dx.doi.org/10.1016/j.bmc.2006.01.042DOI Listing
June 2006

Novel nicotinate esters of vasodilatation activity.

Boll Chim Farm 2004 Dec;143(10):365-75

Pesticide Chemistry Dept, National Research Centre, Dokki, Cairo, Egypt.

A variety of 2-substituted-4, 6-diaryl-3-pyridinecarboxylates 4 were obtained through aromatic nucleophilic substitution. reaction of secondary amines with 2-bromo-3-pyridinecarboxylate derivatives 3. The latters were obtained through bromination of 3-aryl-4-benzoyl-2-cyanobutyrates 2 in glacial acetic acid. However; reaction of primary aromatic amines with 2-bromopyridines 3 afforded 2-arylamino-3-pyridinecarboxylates 5 beside the unexpected 2-amino analogues 6. On the other hand, 3-hydroxy-1H-pyrazolo[3,4-b]pyridines 7 were isolated via reaction of 3 with hydrazine hydrate. Good to complete muscle relaxation of rabbit's jejunium, rat's uterus and rabbits aorta was observed during screening representative examples (3a, 4c, Sd, 5f and 6b) of the newly synthesized 3-pyridinecarboxylates indicating the vasodilatation and antihypertension activity for the tested compounds.
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December 2004
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