Rafat M. Mohareb
Cairo University
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Featured researches published by Rafat M. Mohareb.
Molecules | 2010
Rafat M. Mohareb; Daisy H. Fleita; Ola K. Sakka
The reaction of cyanoacetyl hydrazine (1) with 3-acetylpyridine (2) gave the hydrazide-hydrazone derivative 3. The latter compound undergoes a series of heterocyclization reactions to give new heterocyclic compounds. The antitumor evaluation of the newly synthesized products against three cancer cell lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) was performed. Most of the synthesized compounds showed high inhibitory effects.
Steroids | 2012
Rafat M. Mohareb; Fatima Al-Omran
Pregnenolone (1) was used as a template to develop new anticancer compounds. Ring D modification of 1 through its reaction with cyanoacetylhydrazine (2) gave the hydrazide-hydrazone derivative 3. The latter compound underwent heterocyclization reactions to give the pyrazole, pyridine, thiazole and thiophene derivatives of pregnenolone. The cytotoxicity of the newly synthesized heterocyclic steroids against three human tumor cell lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were studied. Some of tested compounds were found to exhibit much higher inhibitory effects towards the three tumor cell lines than the reference drug, doxorubicin.
Molecules | 2010
Hoda Z. Shams; Rafat M. Mohareb; M.H. Helal; Amira E. Mahmoud
The reaction of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene with ethyl cyanoacetate gave 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. The latter was used to synthesize different heterocyclic derivatives comprising thiophene, thiazole, pyrazole, pyridine, pyrimidine, and coumarin rings. The mechanistic and synthetic pathways depended on regioselective attack and/or cyclization by the cyanoacetamido moiety in the key precursor on various chemical reagents. The competition of the reaction pathways including dipolar cyclization, dinucleophilic-bielectrophilic attack, β-attack, Gewald-type attack, and condensation reactions led to the diversity of the synthesized products. The antitumor activities of the synthesized products were studied and evaluated. Most of the compounds revealed high inhibitory effects when screened in vitro for their antiproliferative activity. Three human cancer cell lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were used in the screening tests. The simplicity of the synthetic procedures which mainly involved one-pot reactions under mild reaction conditions, the convenience of yield production and the diversity of the reactive sites in the produced systems play a valuable role for further heterocyclic transformations and further biological investigations.
Steroids | 2012
Rafat M. Mohareb; Wagnat W. Wardakhan; Gamal A. Elmegeed; Rehab M.S. Ashour
Pregnenolone (1) was used as a template to develop new anticancer compounds. Ring D modification of 1 through its reaction with 4-phenyl-3-thiosemicarbazide gave the thiosemicarbazone derivative 3. The latter compound underwent heterocyclization reactions to give the thiazolyl hydrazonoandrostane and pyrazolyl semicarbazidoandrostane derivatives 5a-d, and 9a-d, respectively. On the other hand compound 1 reacted with either malononitrile or ethyl cyanoacetate to give the Knoevenagel condensated products 11a and 11b, respectively. Compounds 11a,b afforded the thiophenyl pregnane derivatives 12a and 12b, respectively, their reactivity toward some chemical reagents was studied. The cytotoxicity of the newly synthesized heterocyclic steroids against three human tumor cell lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were studied. Some of tested compounds were found to exhibit much higher inhibitory effects toward the three tumor cell lines than the reference drug, doxorubicin.
Bioorganic & Medicinal Chemistry | 2011
Gamal A. Elmegeed; Wagdy K.B. Khalil; Rafat M. Mohareb; Hanaa H. Ahmed; Mervat M. Abdelhalim; Ghada H. Elsayed
Anti-cancer agents which combine two biologically active compounds in one such as steroidal heterocyclic derivatives attain both hormone and cytotoxic effects on cancer cells. The aim of the present study is to synthesize and evaluate new potential chemotherapeutic anti-breast cancer agents. Several pyridazino-, pyrimido-, quinazolo-, oxirano- and thiazolo-steroid derivatives were synthesized. The structure of the novel steroid derivatives was confirmed using the analytical and spectral data. The most structurally promising of the novel synthesized steroid derivatives, compounds 8, 12, 17, 20, 22c, 24c, 30a and 30b, were investigated individually as anti-breast cancer agents against human breast cancer cells (MCF-7) using sulforhodamine B (SRB) assay. The tested compounds 17, 20, 22c and 8 showed potent broad spectrum cytotoxic activity in vitro after 48 h incubation. Compound 17 (IC(50)=2.5 μM) exhibited more inhibitory influence on MCF-7 growth than the reference drug doxorubicin (Dox) (IC(50)=4.5 μM) after 48 h incubation. Also, the present study showed that all the tested steroid derivatives exhibited significant depletion with various intensities in gene expression of breast cancer related genes (VEGF, CYP19 and hAP-2γ). Noteworthy, compounds 17, 20 and 22c showed the most pronounced effect in this respect.
Phosphorus Sulfur and Silicon and The Related Elements | 2007
Hoda Z. Shams; Rafat M. Mohareb; M.H. Helal; Amira E. Mahmoud
Aiming to produce cyclized systems with potential bioactivity, a variety of fused and/or pendant thiophene, pyrazole, imidazole, thiazole, triazole, triazine, and coumarin systems were synthesized based on a cyanoacetic 2-[(benzoylamino)thi- oxomethyl] hydrazide precursor. The structure of the synthesized compounds was established based on elemental analysis and spectral data. The antibacterial and antifungal activities of the compounds are discussed and evaluated.
Steroids | 2015
Rafat M. Mohareb; Mayssoune Y. Zaki; Nermeen S. Abbas
The reaction of androstenedione with bromine gave the 16-bromo derivative 2. The latter reacted with either cyanothioacetamide or thiourea to give the 2-cyanomethylthiazole derivative 4 and the 2-aminothiazole derivative 13. Compound 4 and 13 were used underwent some condensation, coupling and heterocyclization reactions to give thiophene, pyridine and pyran derivatives. The anti-inflammatory and anti-ulcer evaluations of the newly synthesized products were evaluated and the results showed that 23f showed the maximum antiulcer activity. In addition, toxicity of the most active compounds was studied against shrimp larvae and showed that compounds 2, 23c and 23f showed non-toxicity against the tested organisms.
Medicinal Chemistry Research | 2014
Rafat M. Mohareb; Amira E. M. Abdallah; Mahmoud A. Abdelaziz
The reaction of cyanoacetylhydrazine (1) with acetylchloride (2) gave the N-acyl derivative 3. The latter underwent ready cyclization in sodium ethoxide to give the pyrazole derivative 4 which was the key compound for the synthesis of thiophene, thieno[2,3-b]pyridine, and thiazole derivatives. The anti-tumor evaluations of the newly synthesized products against the three human tumor cell lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460), and CNS cancer (SF-268), were studied. Some of these compounds were found to exhibit much higher inhibitory effects toward the three tumor cell lines than the reference doxorubicin. Molecular modeling of the four compounds 12c, 12f, 16a, and 16d, which showed the maximum inhibitory effect, were done.
Molecules | 2011
Hoda Zaki Shams; Rafat M. Mohareb; M.H. Helal; Amira E. Mahmoud
A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide or 2-phenylcarbamoyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide systems as precursors. The latter compounds were used to synthesize polyfunctional thiophene-, thiazole-, pyrazole, pyridine-, pyrimidine-, oxazine-, as well as acyclic moieties. The dyes and dye precursors were characterized by elemental analysis and spectral methods. All dyes and their precursors were screened in vitro and evaluated for both their antibacterial and antifungal activities. MIC data of the novel dye systems and their respective precursors showed significant antimicrobial activity against most tested organisms. Some compounds exhibited comparable or even higher efficiency than selected standards. Dyes were applied at 5% depth for disperse dyeing of nylon, acetate and polyester fabrics. Their spectral characteristics and fastness properties were measured and evaluated.
Tetrahedron-asymmetry | 1999
Claus Herdeis; Rafat M. Mohareb; Reinhard B Neder; Franz Schwabenländer; Joachim Telser
Abstract Sugar lactones were converted to 3,4-disubstituted azepanes and caprolactam derivatives by selective deoxygenation, functionalization and reductive cyclization. The cyclization proved troublesome with 6-azidolactols but led to good results with the corresponding lactones. A formal synthesis of (+)- and (−)-balanol is reported.