Mannich base Research Papers - Academia.edu (original) (raw)

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- Chemistry, Organic Chemistry, Antitubercular, Mannich base

Aim: Cancer is a serious disease that not fully defined now-a-days. The problem of cancer is the metastatis, and the unnatural proliferation of the cell. Many chemotherapeutic agents are used to treat cancer, but they failed to cure the cancer patient. They may prevent some of the portion but not totally defend against cancer. So our work devoted to design a novel chemotherapeutic agent with minimal sideeffects against prostate cancer.

- by Vijey Aanandhi M
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- Prostate Cancer, Docking, Mannich base

This report gives an insight into the recent applications of Mannich reaction and its variants in the construction of bioactive molecules. Emphasis is given to the Mannich reaction that provides bioactive molecules and/or modifies the property of an existing bioactive molecule. The role of Mannich reaction in the construction of antimalarial, antitumor, antimicrobial, antitubercular, antiinflammatory and anticonvulsant molecules and also the significance of aminoalkyl Mannich side chain on the biological property of molecules is discussed here

- by Edaetii Bassey
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- Mannich base

Chemistry and pharmacological activity of various types of Mannich bases and their derivatives were well documented. A survey of the literature revealed extensive studies on the synthesis and reactivity of Mannich bases derived from ketones, amides, enamines, phenols and indoles of widely different structures, while comparatively little attention has been given to Mannich bases derived from nitroalkanes and related nitrocompounds. Mannich reactions using nitroalkanes and related compounds as substrates are of synthetic relevance and the products are promising as biologically active substances. It is known that the nitro group is an important constituent of many biologically significant heterocycles such as antibiotic drugs (nitrofurantoin and nitrofurazone). A number of nitro-heterocycles of pharmacological interest were also synthesized by Mannich reactions with suitable nitro-substrates. In view of this, and because of the widespread and increasing interest in the chemistry of Mannich bases, the present work is concerned with attempts to extend the scope of Mannich reactions with nitroalkanes to include the synthesis of a variety of nitro N-and S-heterocycles.

- by Mardia Teleb
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- Chemistry, Asymmetric catalysis, Mannich base

Medicinal chemistry’s roots can be found in the fertile mix of ancient folk medicine and early natural product chemistry and hence its name. As appreciation for the links between chemical structure and observed biological activity grew, medicinal chemistry began to emerge about 150 years ago as a distinct discipline intending to explore these relationships via chemical modification.

- by ITIRJ Editor
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- Active, Drugs, Mannich base, Bio

These acetophenone derivatives of mannich bases were synthesized by the reaction between the acetophenone, formaldehyde and alkanes(1). They were
evaluated for the analgesic, anti inflammatory and anticonvulsant activity. Phenytoin and its derivatives have shown good anticonvulsant activity by minimum
electro shock method. Indomethacin and its derivatives have shown good anti inflammatory activity by raw paw edema method. Indomethacin and its
derivatives have also shown good analgesic activity which can be observed by eddy’s hot plate method.
Key words: Mannich bases of acetophenone, anticonvulsant, and formaldehyde, anti-inflammatory.

- by Palani Shanmugasundaram
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- Anticonvulsant, Mannich base, Formaldehyde Production, Formaldehyde
- by Editor CSRL
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- Pharmacology, Chemistry, Inorganic Chemistry, Pharmacy

A new method for synthesizing phenolic N-benzylazacyclophanes starting from tyramine is presented here. Computational calculations showed that macrocyclization is favored by the formation of hydrogen bond-based templates; these templates are not affected by including benzyl groups in the nitrogen atom of the tyramine moiety. The results showed that N-benzyl groups with electron-donating substituents have more nucleophilic nitrogen atoms, thereby favoring macrocyclization, while electron-withdrawing groups favor polymerization.

Treatment of cycloalkanones 1a-c with benzalaniline or dibenzal -p-phenylenediamine gave the corresponding cycloalkanone sec-Mannich bases 2a-c and 4.Whereas, the reaction of 1a or b with benzal-1naphthylamine afforded the condensed systems 7 and 8. 2,6-di(p-anisal)cyclohexanone (10) was obtained from 1b and N,N'-bis(p-anisal)ethylenediamine 9.On the other hand, treatment of the bis-(Mannich base) 12 with benzalaniline gave the mixed Mannich base 13. The tetra-base 14 was obtained by treating 2b with ammonium chloride and formaldehyde, or from the tris -(Mannich base) 15 and benzalaniline.Schmidt reaction of 2a-c and 4 gave N-phenyl-α-aminobenzyl derivatives of piperidin-2-one 16, azepan-2-one 17, azocan-2-one 18 and the bis-(azepan-2-one) derivative 19, respectively. The potential of compounds 16 and 17 as precursors to fused heterocycles containing a nitrogen atom at a ring-junction was investigated. The 1,2,4-triazepine derivatives 25 and 26 were obtained by treating 2a,b with hydrazine and formaldehyde.

- by Elsayed Mohamed Afsah
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- Organic Chemisrty, Mannich base

A series of 1,3,4-oxadiazole and pyrazole derivatives have been synthesized and evaluated for antitubercular activity. All the structures of the newly synthesized compounds have been supported by IR, 1 H NMR, MS and CHN analysis. All the... more

- by Atheer Majeed
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- Chemistry, Organic Chemistry, Antitubercular, Mannich base

Tyrosinase inhibitors have become increasingly important as whitening agents and for the treatment of pigmentary disorders. In this study, the synthesis of kojic acid derivatives having... more

Tyrosinase inhibitors have become increasingly important as whitening agents and for the treatment of pigmentary disorders. In this study, the synthesis of kojic acid derivatives having 2-substituted-3-hydroxy-6-hyroxymethyl/chloromethyl/methyl/morpholinomethylpiperidinyl- methyl/pyrrolidinylmethyl-4H-pyran-4-one structure (compounds 1-30) with inhibitory effects on tyrosinase enzyme were described. One-pot Mannich reaction was carried out by using kojic acid/chlorokojic acid/allomaltol and substituted benzylpiperazine derivatives in presence of formaline. Subsequently, cyclic amine (morpholine, piperidine and pyrrolidine) derivatives of the 6th-position of chlorokojic acid were obtained with nucleophilic substitutions in basic medium. The structures of new compounds were identified by FT-IR, 1H- and 13C NMR, ESI-MS and elemental analysis data. The potential mushroom tyrosinase inhibitory activity of the compounds were evaluated by the spectrophotometric method using l-DOPA as a substrate and kojic acid as the control agent. The potential inhibitory activity was also investigated in silico using molecular docking simulation method. Tyrosinase inhibitory action was significantly more efficacious for several compounds (IC50: 86.2-362.1 µM) than kojic acid (IC50: 418.2). Compound 3 bearing 3,4-dichlorobenzyl piperazine moiety was proven to have the highest inhibitory activity. The results of docking studies showed that according to the predicted conformation of compound 3 in the enzyme binding site, hydroxymethyl group provides a metal complex with copper ions and enzyme. Thus, this interaction explain the high inhibitory activities of the compounds 1, 3 and 4 possessing hydroxymethyl substituent supporting the mushroom assay results with docking studies. In accordance with the results, it is suggested that Mannich bases of kojic acid bearing substituted benzyl piperazine groups (compounds 1, 3, 4, 11, 13, 14, 23, 24, 28, and 29) could be promising antityrosinase agents. Additionally, considering the relationship between tyrosinase inhibitory activity results and molecular docking, a new tyrosinase inhibition mechanism can be proposed.

- by Gülşah Karakaya
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- Organic Chemistry, Bioorganic Chemistry, Kojic Acid, Mannich base

A new Mannich base ligand: N-[Morpholino(phenyl)methyl]acetamide(MBA) was synthesized and characterized by elemental analyses, IR, UV, NMR and mass spectral studies. A few complexes of this ligand with Mn(II), Fe(II), Zn(II), Cd(II) and Hg(II) were prepared and characterized by elemental and chemical analyses, IR, electronic absorption and 1 H NMR spectral studies and magnetic susceptibility measurements. The ligand behaved as a bidentate/tridentates chelating in nature. Tetrahedral geometry was proposed for Cd II sulphato complex. Octahedral geometry was assigned for the remaining complexes. Antimicrobial studies were carried out which showed that the Zn(II) complex was more active than the other complexes.

- by Editor CSRL
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- Pharmacology, Chemistry, Inorganic Chemistry, Pharmacy

Tyrosinase inhibitors have become increasingly important as whitening agents and for the treatment of pigmentary disorders. In this study, the synthesis of kojic acid derivatives having... more

Tyrosinase inhibitors have become increasingly important as whitening agents and for the treatment of pigmentary disorders. In this study, the synthesis of kojic acid derivatives having 2-substituted-3-hydroxy-6-hyroxymethyl/chloromethyl/methyl/morpholinomethylpiperidinyl-methyl/pyrrolidinylmethyl-4H-pyran-4-one structure (compounds 1-30) with inhibitory effects on tyrosinase enzyme were described. One-pot Mannich reaction was carried out by using kojic acid/chlorokojic acid/allomaltol and substituted benzylpiperazine derivatives in presence of formaline. Subsequently, cyclic amine (morpholine, piperidine and pyrrolidine) derivatives of the 6th-position of chlorokojic acid were obtained with nucleophilic substitutions in basic medium. The structures of new compounds were identified by FT-IR, 1 Hand 13 C NMR, ESI-MS and elemental analysis data. The potential mushroom tyrosinase inhibitory activity of the compounds were evaluated by the spectrophotometric method using L-DOPA as a substrate and kojic acid as the control agent. The potential inhibitory activity was also investigated in silico using molecular docking simulation method. Tyrosinase inhibitory action was significantly more efficacious for several compounds (IC 50 : 86.2-362.1 µM) than kojic acid (IC 50 : 418.2). Compound 3 bearing 3,4-dichlorobenzyl piperazine moiety was proven to have the highest inhibitory activity. The results of docking studies showed that according to the predicted conformation of compound 3 in the enzyme binding site, hydroxymethyl group provides a metal complex with copper ions and enzyme. Thus, this interaction explain the high inhibitory activities of the compounds 1, 3 and 4 possessing hydroxymethyl substituent supporting the mushroom assay results with docking studies. In accordance with the results, it is suggested that Mannich bases of kojic acid bearing substituted benzyl piperazine groups (compounds 1, 3, 4, 11, 13, 14, 23, 24, 28, and 29) could be promising antityrosinase agents. Additionally, considering the relationship between tyrosinase inhibitory activity results and molecular docking, a new tyrosinase inhibition mechanism can be proposed.

- by Mutlu Aytemir
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- Kojic Acid, Mannich base