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Fulltext Kinetic resolution of complexity of reaction paths in the alkaline hydrolysis of N-(2’-Hydroxyphenyl) phthalimide in mixed H2O-CH3CN solvent

Ariffin, A., Khan, M.N., Sim, Y.L.

ASM Science Journal, 2008;2(1):83-92.
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The rate of aqueous cleavage of N-(2’-hydroxyphenyl)phthalimide (A), monitored at 320 nm, 1.0  10–3 M NaOH, 35ºC and within CH3CN content range 1% – 80% v/v in mixed aqueous solvents, follows the reaction scheme: A + HO-/H2O ➝ B + HO-/H2O ➝ P1 + P2 where B, P1 and P2 represent N-(2’-hydroxyphenyl)phthalamic acid, phthalic acid and 2-hydroxyaniline, respectively. The values of k1 and k2 at different content of CH3CN have been calculated from a kinetic equation based upon a reaction scheme with two irreversible pseudo-first-order consecutive reaction paths. The values of k1/k2 are > 104 within CH3CN content range 1% – 80% v/v in mixed aqueous solvents. The intermediate hydrolysis product (B) exists in 72% dianionic, 27.9% monoanionic and 0.1% nonionic form under the present experimental conditions. Both dianionic and monoanionic forms of B are non-reactive while the nonionic form of B is reactive towards hydrolysis under such conditions.

Matched MeSH terms: Aminophenols
Fulltext Synthesis of new azo compounds based on N-(4-hydroxypheneyl)maleimide and N-(4-methylpheneyl)maleimide

Mohammed IA, Mustapha A

Molecules, 2010;15(10):7498-509.
PMID: 20975631 DOI: 10.3390/molecules15107498

Maleic anhydride was reacted with p-aminophenol and p-toluidine in the presence of di-phosphorus pentoxide (P₂O₅) as a catalyst to produce two compounds: N-(4-hydroxy-phenyl)maleimide (I) and N-(4-methylphenyl)maleimide (II). The new azo compounds I(a-c) and II(a-c) were prepared by the reaction of I and II with three different aromatic amines, namely aniline, p-aminophenol and p-toluidine. The structures of these compounds were confirmed by CHN, FT-IR, ¹H-NMR, ¹³C-NMR, mass spectrum and UV/Vis spectroscopy.

Matched MeSH terms: Aminophenols/chemistry
Synthesis and characterization of a new heterocyclic azo pigment

Asniza M, Issam A, Abdul Khalil H

Sains Malaysiana, 2011;40:1123-1127.

A new heterocyclic coupling agent has been produced from the reaction of maleic anhydride and p-aminophenol, namely N-(4-hydroxylpheneyl)maleimide. The coupling agent underwent azo coupling reaction with aromatic amine, which is p-aminophenol to produce a new heterocyclic azo pigment. The pigment was then subjected to solubility, hiding power and light fastness test. Fourier Transform Infrared Spectroscopy (FTIR), Ultraviolet/Visible (UV/Vis) Spectroscopy, and Nuclear Magnetic Resonance Spectroscopy (1H-NMR, 13C-NMR) were used to obtain the characteristics and structural features of the pigment.

Matched MeSH terms: Aminophenols
Synthesis and functionalization of chitosan built hydrogel with induced hydrophilicity for extended release of sparingly soluble drugs

Ullah F, Javed F, Othman MBH, Khan A, Gul R, Ahmad Z, et al.

J Biomater Sci Polym Ed, 2018 03;29(4):376-396.
PMID: 29285989 DOI: 10.1080/09205063.2017.1421347

Addressing the functional biomaterials as next-generation therapeutics, chitosan and alginic acid were copolymerized in the form of chemically crosslinked interpenetrating networks (IPNs). The native hydrogel was functionalized via carbodiimide (EDC), catalyzed coupling of soft ligand (1,2-Ethylenediamine) and hard ligand (4-aminophenol) to replace -OH groups in alginic acid units for extended hydrogel- interfaces with the aqueous and sparingly soluble drug solutions. The chemical structure, Lower solution critical temperature (LCST ≈ 37.88 °C), particle size (Zh,app ≈ 150-200 nm), grain size (160-360 nm), surface roughness (85-250 nm), conductivity (37-74 mv) and zeta potential (16-32 mv) of native and functionalized hydrogel were investigated by using FT-IR, solid state-13C-NMR, TGA, DSC, FESEM, AFM and dynamic light scattering (DLS) measurements. The effective swelling, drug loading (47-78%) and drug release (53-86%) profiles were adjusted based on selective functionalization of hydrophobic IPNs due to electrostatic complexation and extended interactions of hydrophilic ligands with the aqueous and drug solutions. Drug release from the hydrogel matrices with diffusion coefficient n ≈ 0.7 was established by Non- Fickian diffusion mechanism. In vitro degradation trials of the hydrogel with a 20% loss of wet mass in simulated gastric fluid (SGF) and 38% loss of wet mass in simulated intestinal fluid (SIF), were investigated for 400 h through bulk erosion. Consequently, a slower rate of drug loading and release was observed for native hydrogel, due to stronger H-bonding, interlocking and entanglement within the IPNs, which was finely tuned and extended by the induced hydrophilic and functional ligands. In the light of induced hydrophilicity, such functional hydrogel could be highly attractive for extended release of sparingly soluble drugs.

Matched MeSH terms: Aminophenols/chemistry
Fulltext Cytotoxic effects of Benzodioxane, Naphthalene diimide, Porphyrin and Acetamol derivatives on HeLa cells

Jeyamogan S, Khan NA, Anwar A, Shah MR, Siddiqui R

SAGE Open Med, 2018;6:2050312118781962.
PMID: 30034805 DOI: 10.1177/2050312118781962

Objectives: To synthesize novel compounds belonging to Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrin classes and test their potential anticancer properties.
Methods: Several compounds were synthesized and their molecular identity was confirmed using nuclear magnetic resonance. Potential anticancer properties were determined using cytopathogenicity assays and growth inhibition assays using cervical cancer cells (HeLa). Cells were incubated with different concentrations of compounds belonging to Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrins and effects were determined. HeLa cells cytopathogenicity was determined by measuring lactate dehydrogenase release using cytotoxicity detection assay. Growth inhibition assays were performed by incubating 50% semi-confluent HeLa cells with Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrin compounds and HeLa cell proliferation was observed. Growth inhibition and host cell death were compared in the presence and absence of drugs.
Results: Cytopathogenicity assays showed that the selected compounds were cytotoxic against HeLa cells, killing up to 90% of cells. Growth inhibition assays exhibited 100% growth inhibition. These effects are likely via oxidative stress, production of reactive oxygen species, changes in cytosolic and intracellular calcium/adenine nucleotide homeostasis, inhibition of ribonucleotide reductase/cyclooxygenase and/or glutathione depletion.
Conclusions: Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrins exhibited potent anticancer properties. These findings are promising and should pave the way in the rationale development of anticancer drugs. Using different cancer cell lines, future studies will determine their potential as anti-tumour agents as well as their precise molecular mode of action.

Matched MeSH terms: Aminophenols