Structure-activity relationships and molecular docking studies of chromene and chromene based azo chromophores

The design of novel materials with significant biological properties is a main target in drug design research. Chromene compounds represent an interesting medicinal scaffold in drug replacement systems. This report illustrates a successful synthesis and characterization of two novel series of chromene compounds using multi-component reactions. The synthesis of the first example of azo chromophores containing chromene moieties has also been established using the same methodology. The antimicrobial activity of the new molecules has been tested against seven human pathogens including two Gm+ve, two Gm-ve bacteria, and four fungi, and the results of the inhibition zones with minimum inhibitory concentrations were reported as compared to reference drugs. All the designed compounds showed significant potent antimicrobial activities, among of them, four potent compounds 4b, 4c, 13e, and 13i showed promising MIC from 0.007 to 3.9 μg/mL. In addition, antiproliferative analysis against three target cell lines was examined for the novel compounds. Compounds 4a, 4b, 4c, and 7c possessed significant antiproliferative activity against three cell lines with an IC50 of 0.3 to 2 μg/mL. Apoptotic analysis was performed for the most potent compounds via caspase enzyme activity assays as a potential mechanism for their antiproliferative effects. Finally, the computational 2D QSAR and docking simulations were accomplished for structure-activity relationship analyses

Polymerization of olefinic monomers functionalized with cationic cyclopentadienyliron arene complexes.

abstract: A review presents some of the results obtained on the polymn. of cyclopentadienyliron complexes functionalized with olefins. Methacrylate-, styrene-, and norbornene-substituted organoiron monomers are considered. [on SciFinder(R)] Cited Reference: Citations: 1) Arimoto, F; J Am Chem Soc 1955, 77, 6295|2) Baumert, M; Macromol Rapid Commun 1999, 20, 203|3) Kuramoto, N; J Polym Sci Part A, Polym Chem 1997, 35, 1967|4) Yang, Y; Macromolecules 2002, 35, 3426|5) Wright, M; Macromolecules 1994, 27, 3016|6) Wiesemann, A; Acta Polym 1995, 46, 25|7) Deschenaux, R; Macromolecules 1997, 30, 3759|8) Pittman, C; Macromolecules 1970, 3, 105|9) Lai, J; Macromolecules 1971, 4, 155|10) Pittman, C; Macromolecules 1971, 4, 291|11) Pittman, C; J Polym Sci Part A1 1971, 9, 3175|12) Cowan, D; J Am Chem Soc 1972, 94, 5110|13) Pittman, C; J Am Chem Soc 1974, 96, 7916|14) Albagli, D; J Am Chem Soc 1992, 114, 4150|15) Albagli, D; J Am Chem Soc 1993, 115, 7328|16) Mapolie, S; J Inorg Organomet Polym 1997, 7, 233|17) Pittman, C; J Macromol Sci Chem 1973, A7(8), 1563|18) Pittman, C; Macromolecules 1974, 7, 396|19) Abd-El-Aziz, A; J Inorg Organomet Polym 1998, 8, 127|20) Abd-El-Aziz, A; J Polym Sci Part A: Polym Chem 2001, 39, 1216|21) de Denus, C; J Inorg Organomet Polym 2000, 10, 189|22) Abd-El-Aziz, A; Macromolecules 2002, 35, 8929|23) Abd-El-Aziz, A; Macromol Rapid Commun 2002, 23, 743|24) Funaki, H; Synth Met 1995, 74, 59|25) Abd-El-Aziz, A; Polym Prepr (Am Chem Soc, Div Polym Chem) 2001, 42(2), 450|26) Abd-El-Aziz, A; Macromol Rapid Commun 2002, 23, 113|27) Abd-El-Aziz, A; Macromolecules 2000, 33, 5000|28) Abd-El-Aziz, A; New J Chem 1999, 23, 569|29) Abd-El-Aziz, A; Can J Chem 1999, 77, 1797|30) Abd-El-Aziz, A; Macromol Rapid Commun 2000, 21, 598|31) Abd-El-Aziz, A; J Inorg Organomet Polym 2000, 10, 265|32) Abd-El-Aziz, A; Polym Mater Sci Eng 2002, 86(1), 103|33) Abd-El-Aziz, A; J Polym Sci Part A, Polym Chem 2001, 39, 2716|34) Abd-El-Aziz, A; Polym Mater Sci Eng 2002, 86(1), 91|35) Abd-El-Aziz, A; Manuscript in preparation|36) Schwab, P; Angew Chem Int Ed Engl 1995, 34, 203

Successful Green Synthesis of Gold Nanoparticles using a Corchorus olitorius Extract and Their Antiproliferative Effect in Cancer Cells

A facile bottom-up “green” synthetic route of gold nanoparticles (Au NPs) is described, using a leaf extract of the Malvaceae plant Corchorus olitorius as a reducing and stabilizing agent. The size and shape of the obtained nanoparticles were modulated by varying the amounts of the metal salt and the broth extract in the reaction medium. Only one hour was required for the complete conversion to Au NPs, suggesting that the reaction rate was higher or comparable to those of nanoparticles synthesized by chemical methods. The obtained nanoparticles were characterized by UV–visible spectroscopy, transmission electron microscopy (TEM), X-ray diffraction (XRD), Fourier-transform infrared (FTIR) spectroscopy, and thermal gravimetric analysis (TGA). While infrared spectroscopy was employed to characterize the various functional groups in the organic layer that stabilized the particles, TEM images were used to optimize the conditions for NPs growth. A low concentration of the C. olitorius extract yielded mixed triangular and hexagonal shapes; in contrast, quasi-spherical shapes of Au NPs with an average size of 37–50 nm were obtained at a higher extract broth concentration. The Au NPs displayed Surface Plasmon Resonance (SPR) bands at 535 nm. An in vitro cytotoxic assay of the biocompatible Au NPs revealed a strong cytotoxic activity in three human cancer cell lines, namely, colon carcinoma HCT-116, hepatocellular carcinoma HepG-2, and breast adenocarcinoma MCF-7. In-silico bioactivity, drug-likeness, and ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) predictions were conducted in order to examine the pharmacokinetic behavior of the compounds present in the C. olitorius extract

Design of Novel Oligomeric Mixed Ligand Complexes: Preparation, Biological Applications and the First Example of Their Nanosized Scale

A successful oligomerization of ternary metal complexes, cobalt (II), nickel (II), copper (II), zinc (II), chromium (III) and ferric sulfate (III) with nitrilotriacetic acid (NTA) as a primary ligand and glutamic acid as a secondary ligand, has been demonstrated. The formation of oligomers arose from the presence of the sulfate moiety, which operates as a bridged bidentate ligand that coordinates with other metal moieties. The novel oligomers exhibited octahedral structures, which bonded together through the sulfate moiety. In silico predictions were conducted to gauge the bioactivity, physico-chemical and pharmacokinetic properties. The biological activities of these oligomers as well as their tumor inhibitory behavior have been explored. This work also presents a facile and novel method of preparing these materials in nanosize, using Cetyltrimethylammonium bromide (CTAB) and polyvinyl alcohol (PVA) as capping ligands. The size and shape of the nanomaterials have been confirmed using the transmission electron microscope (TEM) and the scanning electron microscope (SEM)

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

New modified acidic catalysts were prepared from the treatment of silica, titania and silica prepared from hydrolyzed tetraethyl orthosilicate (TEOS) with sulfuric and phosphoric acid. The sulfated and phosphated silica synthesized from TEOS were calcined at 450 and 650 °C. These catalysts were characterized by X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), transmission electron microscope (TEM), and scanning electron microscope (SEM). The surface areas, total pore volume, and mean pore radius of the acidic catalysts were investigated, while the pore size distribution was determined by the Barrett, Joyner and Halenda (BJH) method. The catalytic activity of the sulfated and phosphated silica and/or titania were examined with the Pechmann condensation reaction, in which different phenols reacted with ethyl acetoacetate as a neat reaction to obtain the corresponding coumarin derivatives. The results indicated that the treatment of the catalysts with sulfuric or phosphoric acid led to a decrease in the phases’ crystallinity to a certain degree. The morphology and the structure of the acidified catalysts were examined and their particle size was calculated. Furthermore, the amount of the used catalysts played a vital role in controlling the formation of the products as well as their performance was manipulated by the number and nature of the active acidic sites on their surfaces. The obtained results suggested that the highest catalytic conversion of the reaction was attained at 20 wt % of the catalyst and no further increase in the product yield was detected when the amount of catalyst exceeded this value. Meanwhile the phenol molecules were a key feature in obtaining the final product

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

New modified acidic catalysts were prepared from the treatment of silica, titania and silica prepared from hydrolyzed tetraethyl orthosilicate (TEOS) with sulfuric and phosphoric acid. The sulfated and phosphated silica synthesized from TEOS were calcined at 450 and 650 °C. These catalysts were characterized by X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), transmission electron microscope (TEM), and scanning electron microscope (SEM). The surface areas, total pore volume, and mean pore radius of the acidic catalysts were investigated, while the pore size distribution was determined by the Barrett, Joyner and Halenda (BJH) method. The catalytic activity of the sulfated and phosphated silica and/or titania were examined with the Pechmann condensation reaction, in which different phenols reacted with ethyl acetoacetate as a neat reaction to obtain the corresponding coumarin derivatives. The results indicated that the treatment of the catalysts with sulfuric or phosphoric acid led to a decrease in the phases’ crystallinity to a certain degree. The morphology and the structure of the acidified catalysts were examined and their particle size was calculated. Furthermore, the amount of the used catalysts played a vital role in controlling the formation of the products as well as their performance was manipulated by the number and nature of the active acidic sites on their surfaces. The obtained results suggested that the highest catalytic conversion of the reaction was attained at 20 wt % of the catalyst and no further increase in the product yield was detected when the amount of catalyst exceeded this value. Meanwhile the phenol molecules were a key feature in obtaining the final product

Ferrocene-based polymers containing azo groups in their backbone: Synthesis, electrochemical and thermal analysis.

abstract: Ferrocene-based polymers contg. azo groups in their backbone were synthesized by condensation polymn. of a cationic organometallic monomer contg. two azo dye moieties and ferrocene in the backbone as well as pendent cationic iron groups with 1,3-diaminopropane, 4,4'-thiobisbenzenethiol or bisphenol A in the presence of K2CO3. The pendent cationic cyclopentadienyl moieties were then photolytically removed from the polymers yielding neutral polyferrocene analogs. The neutral polyferrocenes had mol. wts. ranging from 8000-12,000. Thermogravimetric anal. of the cationic polymers showed two defined wt. losses, with degrdn. of the azo dye overlapped with the loss of the cyclopentadienyliron moiety at temps. between 210°-300° and degrdn of the polymer backbone at 400°-500°. The neutral polyferrocenes displayed a wt. loss assocd. with the degrdn. of the azo dye around 210°-300°. Degrdn. of the polymer backbone occurred between 400°-500°. The cationic polymers showed glass transition temps. between 126°-164°, whereas the neutral polymer displayed glass transition temps. at significantly lower temps., i.e., 85°-92°. UV-visible studies of the polymers showed they displayed a λmax similar to that of the unreacted azo dye. [on SciFinder(R)] Cited Reference: Citations: 1) Abd-El-Aziz, A; Macromolecules Containing Metal and Metal-Like Elements 2003, 1|2) Abd-El-Aziz, A; Metal-Containing Polymers, in "Ency-clopedia of Polymer Science and Technology", 3rd Edition 2002|3) Abd-El-Aziz, A; Macromol Rapid Commun 2002, 23, 995|4) Abd-El-Aziz, A; Coord Chem Rev 2003, 246, 3|5) Abd-El-Aziz, A; Macromol Chem Phys 2003, 204, 555|6) Abd-El-Aziz, A; Macromolecules 2002, 35, 8929|7) Abd-El-Aziz, A; Macromol Rapid Commun 2004, 25, 1497|8) Natansohn, A; Chem Rev 2002, 102, 4139|9) Hasegawa, M; J Appl Polym Sci 2002, 86, 17|10) Huang, K; Macromolecules 2002, 35, 8653|11) Uznanski, P; J Appl Polym Sci 2002, 86, 1456|12) Samyn, C; Macromol Rapid Commun 2000, 21, 1|13) Iftime, G; Chem Mater 2002, 14, 168|14) Tawa, K; Macromolecules 2001, 34, 8232|15) Wu, L; Macro-molecules 2001, 34, 8005|16) Nguyen, P; Chem Rev 1999, 99, 1515|17) Hudson, R; J Organomet Chem 2001, 47, 63

Redox-active η6-arene-η5-cyclopentadienyliron-containing macromolecules.

abstract: There has been tremendous interest in organoiron macromols. This interest stems from their application as chem. sensors, electrocatalysts, modified electrodes and photo-active mol. devices. Herein, we report the synthesis and characterization of a no. of different classes of organoiron macromols. contg. η6-arene-η5--cyclopentadienyliron complexes, and ferrocene. The electrochem. behavior of these materials has been investigated and showed the redn. of the cationic iron moieties and the oxidn. of the ferrocene moieties. The synthesis properties and the electrochem. studies of these iron-contg. macromols. will be presented. [on SciFinder(R)] Cited Reference: Citations: 1) Manners, I; Synthetic Metal Containing Polymers 2004|1b) Abd-El-Aziz, A; Macromolecules Containing Metal and Metal-Like Elements 2003, 1|1c) Abd-El-Aziz, A; Macromol Rapid Commun 2002, 23, 995|1d) Archer, R; Inorganic and Organometallic Polymers 2001|1e) Nguyen, P; Chem Rev 1999, 99, 1515|2) Abd-El-Aziz, A; Coord Chem Rev 2003, 246, 3|2b) Kulbaba, K; Macromol Rapid Commun 2001, 22, 711|2c) Astruc, D; Acc Chem Res 2000, 33, 287.2|3a) Anon; Ferrocenes 1995|3b) Astruc, D; Electron Transfer and Radical Processes in Transition-Metal Chemistry 1995|4) Plaulat, L; Angew Chem Int Ed 2004, 43, 2924|5) Wang, X; Macromol Rapid Commun 2003, 24, 403|6) Daniel, M; Chem Eur J 2003, 9, 4371|7) Nlate, S; Chem Eur J 2002, 8, 171|8) Ruiz, J; J Am Chem Soc 2003, 125, 7250|9) Daniel, M; J Am Chem Soc 2003, 125, 1150|10) Casado, C; Inorg Chem 1995, 34, 1668|11) Valerio, C; J Org Chem 2000, 65, 1996|12) Constable, E; Organometallics 1999, 18, 2565|13) Ruiz, J; J Organomet Chem 1999, 582, 139|14) Casado, C; Organometallics 1995, 14, 2618|15) Nlate, S; Chem Commun 2000, 417|16) Constable, E; Chem Commun 1996, 33|17) Lohmeijer, B; J Polym Sci Part A: Polym Chem 2003, 41, 1413|18) Abd-El-Aziz, A; J Polym Sci Part A: Polym Chem 2005, 43, 1382|19) Deschenaux, R; Chem Commun 1997, 1577|20) Ruiz, J; Chem Commun 2002, 1108|21) Martinez, V; Org Lett 2002, 4, 651|22) Zhou, M; Anal Chem 2003, 75, 6708|23) Johnson, R; Biomacromolecules 2004, 5, 580|24) Alonso, B; Organometallics 2002, 21, 1001|25) Serroni, S; Chem Soc Rev 2001, 30, 367|26) Constable, E; Chem Commun 1997, 1073|27) Newkome, G; Chem Eur J 2003, 9, 3367|28) Albrecht, M; Chem Eur J 2000, 6, 1431|29) Albrecht, M; Chem Commun 2001, 1874|30) Abd-El-Aziz, A; Macromolecules 2005, 38, 9411|31) Abd-El-Aziz, A; unpublished wor

Novel oxazolones incorporated azo dye: Design, synthesis photophysical-DFT aspects and antimicrobial assessments with In-silico and In-vitro surveys

New derivatives of the oxazolone compounds 4(a-j) and (7a-e) containing azo dye moieties have been prepared via the Erlenmeyer reaction of their azo dye precursors. The characterization of all the synthesized compounds was confirmed by the FT-IR, 1HNMR 13CNMR and MS spectroscopic techniques. The UV-visible examination of the new molecules revealed λmax values in the range of 392–464 nm, depending on the coupling component as well as the various substituents of the benzaldehyde derivatives. All the new chromophores demonstrated an acid chromism behavior, which impacted their usage as potential acid sensors. A detailed study of the azo and hydrazo tautomerism of the prepared dyes 3a-c has been executed through the theoretical DFT calculations. Moreover, the energy levels of the FMOs and their energy difference were predicted by the DFT for all the synthesized molecules to be affected by the geometrical isomerism along with the type of the couplers. These data were employed to elucidate the UV–visible spectral measurements. Furthermore, a detailed study of the substituent effect on the UV absorbance has been achieved by the quantitative structural-activity relationship of the prepared compounds 4f-g and 7a-e. The oxazolone azo dyes were evaluated for their in-vitro antifungal and antibacterial activities and displayed potency in comparison with the reference drugs. Furthermore, the in-silico prediction methodology was contemplated for foretelling the physicochemical, drug likeliness, and ADME traits of all the synthesized compounds, where their respective docking scores were contrasted with their biological activity results