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Synthesis and pharmacological evaluation of schiff bases of 4-(2-aminophenyl)-morpholines.

Panneerselvam P, Priya MG, Kumar NR, Saravanan G - Indian J Pharm Sci (2009)

Bottom Line: In the present study, a novel series of 4-(2-aminophenyl)morpholines were synthesized and characterized by IR, (1)H-NMR, (13)C NMR and mass spectral analysis.The synthesized compounds were screened for analgesic (100 and 200 mg/kg), antiinflammatory (200 and 400 mg/kg), antibacterial (Bacillus subtilis, Bacillus cereus, Staphylococcus epidermidis, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli) and antifungal (Candida albicans and Aspergillus niger) activities.N-benzylidine-2-morpholoino benzenamine (1) and N-(3-nitro benzylidine)-2-morpholino benzenamine (3) exhibited significant analgesic, antiinflammatory and antimicrobial activities.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, C. L. Baid Mehta College of Pharmacy, Jyothi Nagar, Old Mahabaliupuram Road, Thoraipakkam, Chennai-600 096, India.

ABSTRACT
In the present study, a novel series of 4-(2-aminophenyl)morpholines were synthesized and characterized by IR, (1)H-NMR, (13)C NMR and mass spectral analysis. The synthesized compounds were screened for analgesic (100 and 200 mg/kg), antiinflammatory (200 and 400 mg/kg), antibacterial (Bacillus subtilis, Bacillus cereus, Staphylococcus epidermidis, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli) and antifungal (Candida albicans and Aspergillus niger) activities. The minimum inhibitory concentrations of the compounds were also ascertained by agar streak dilution method. N-benzylidine-2-morpholoino benzenamine (1) and N-(3-nitro benzylidine)-2-morpholino benzenamine (3) exhibited significant analgesic, antiinflammatory and antimicrobial activities.

No MeSH data available.


Related in: MedlinePlus

Synthetic route for the preparation of 4-(2-aminophenyl)-morpholines1: R = C6H5, 2: R = furyl, 3: R = m-NO2C6H4, 4: R = o-ClC6H5 and 5: R = -CH=CHC6H5
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Figure 0001: Synthetic route for the preparation of 4-(2-aminophenyl)-morpholines1: R = C6H5, 2: R = furyl, 3: R = m-NO2C6H4, 4: R = o-ClC6H5 and 5: R = -CH=CHC6H5

Mentions: Morpholine and 1-chloro-2-nitrobenzene was refluxed to yield 4-(2-nitrophenyl) morpholine, which was then reduced using zinc and hydrochloric acid affords 4-(2-aminophenyl) morpholine[16]. An equimolor mixture of 1.78 g (0.01 mol) of 4-(2-aminopheny1) morpholine and substituted aldehydes (aromatic/heterocyclic) in absolute ethanol was refluxed using dean stark apparatus for 2 h (Scheme 1). The reaction mixture was cooled for a while and solid separated was filtered and recrystallised from ethanol (99%) yield the title compounds (1-5). The structural assignment of the products was based on their IR,1H-NMR, 13C-NMR and mass spectral data.


Synthesis and pharmacological evaluation of schiff bases of 4-(2-aminophenyl)-morpholines.

Panneerselvam P, Priya MG, Kumar NR, Saravanan G - Indian J Pharm Sci (2009)

Synthetic route for the preparation of 4-(2-aminophenyl)-morpholines1: R = C6H5, 2: R = furyl, 3: R = m-NO2C6H4, 4: R = o-ClC6H5 and 5: R = -CH=CHC6H5
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2865815&req=5

Figure 0001: Synthetic route for the preparation of 4-(2-aminophenyl)-morpholines1: R = C6H5, 2: R = furyl, 3: R = m-NO2C6H4, 4: R = o-ClC6H5 and 5: R = -CH=CHC6H5
Mentions: Morpholine and 1-chloro-2-nitrobenzene was refluxed to yield 4-(2-nitrophenyl) morpholine, which was then reduced using zinc and hydrochloric acid affords 4-(2-aminophenyl) morpholine[16]. An equimolor mixture of 1.78 g (0.01 mol) of 4-(2-aminopheny1) morpholine and substituted aldehydes (aromatic/heterocyclic) in absolute ethanol was refluxed using dean stark apparatus for 2 h (Scheme 1). The reaction mixture was cooled for a while and solid separated was filtered and recrystallised from ethanol (99%) yield the title compounds (1-5). The structural assignment of the products was based on their IR,1H-NMR, 13C-NMR and mass spectral data.

Bottom Line: In the present study, a novel series of 4-(2-aminophenyl)morpholines were synthesized and characterized by IR, (1)H-NMR, (13)C NMR and mass spectral analysis.The synthesized compounds were screened for analgesic (100 and 200 mg/kg), antiinflammatory (200 and 400 mg/kg), antibacterial (Bacillus subtilis, Bacillus cereus, Staphylococcus epidermidis, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli) and antifungal (Candida albicans and Aspergillus niger) activities.N-benzylidine-2-morpholoino benzenamine (1) and N-(3-nitro benzylidine)-2-morpholino benzenamine (3) exhibited significant analgesic, antiinflammatory and antimicrobial activities.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, C. L. Baid Mehta College of Pharmacy, Jyothi Nagar, Old Mahabaliupuram Road, Thoraipakkam, Chennai-600 096, India.

ABSTRACT
In the present study, a novel series of 4-(2-aminophenyl)morpholines were synthesized and characterized by IR, (1)H-NMR, (13)C NMR and mass spectral analysis. The synthesized compounds were screened for analgesic (100 and 200 mg/kg), antiinflammatory (200 and 400 mg/kg), antibacterial (Bacillus subtilis, Bacillus cereus, Staphylococcus epidermidis, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli) and antifungal (Candida albicans and Aspergillus niger) activities. The minimum inhibitory concentrations of the compounds were also ascertained by agar streak dilution method. N-benzylidine-2-morpholoino benzenamine (1) and N-(3-nitro benzylidine)-2-morpholino benzenamine (3) exhibited significant analgesic, antiinflammatory and antimicrobial activities.

No MeSH data available.


Related in: MedlinePlus