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Novel 3,4-Methylenedioxybenzene Scaffold Incorporated 1,3,5-Trisubstituted-2-pyrazolines: Synthesis, Characterization and Evaluation for Chemotherapeutic Activity.

Deshpande SR, Nagrale SN, Patil MV, Chavan PS - Indian J Pharm Sci (2015 Jan-Feb)

Bottom Line: A series of novel 3, 4-methylenedioxybenzene scaffold incorporated 1,3,5-trisubstituted-2-pyrazoline derivatives was synthesised as potent antitubercular agents via chalcone intermediates by reaction with hydrazines.The structures of the compounds were confirmed by IR, 1HNMR, 13CNMR and mass spectral data.All the compounds exhibited excellent activity that could be due to the presence of 3,4-methylenedioxybenzene frame work in the molecules.

View Article: PubMed Central - PubMed

Affiliation: Department of Medicinal and Pharmaceutical Chemistry, H. S. K. College of Pharmacy, BVVS Campus, Bagalkote-587 101, India.

ABSTRACT
A series of novel 3, 4-methylenedioxybenzene scaffold incorporated 1,3,5-trisubstituted-2-pyrazoline derivatives was synthesised as potent antitubercular agents via chalcone intermediates by reaction with hydrazines. The structures of the compounds were confirmed by IR, 1HNMR, 13CNMR and mass spectral data. The novel pyrazolines were screened for in vitro antitubercular activity by almar blue dye method against M. tuberculosis H37Rv. All the compounds exhibited excellent activity that could be due to the presence of 3,4-methylenedioxybenzene frame work in the molecules. Some of the compounds also showed in vitro cytotoxicity on EAC cell lines in tryphan blue exclusion assay suggesting their safety.

No MeSH data available.


Related in: MedlinePlus

Synthesis of title compounds 2a-g and 3a-g
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Figure 3: Synthesis of title compounds 2a-g and 3a-g

Mentions: Despite numerous reported methods for the preparation of 2-pyrazolines, the Fischer and Knoevenagel method of reacting α,β-unsaturated aldehydes and ketones with phenyl hydrazine in acetic acid is still the most popular one[28]. Chalcones are 1,3-diaryl-2-propen-1-ones and serve as important intermediates for the construction of corresponding 2-pyrazolines. Since piperonal is an aldehyde with 3,4-methylenedioxy benzene moiety, it was aptly used as a precursor for the development of 3,4-methylenedioxy benzene incorporated 2-pyrazolines. A series of chalcones (1a-g) was synthesized according to Claisen-Schmidt reaction[29] by condensing various substituted acetophenones with piperonal in presence of 50% sodium hydroxide solution at 10-15° in good to excellent yields. The cyclocondensation of chalcones 1a-g with hydrazine or phenylhydrazine in acetic acid yielded 1-acetyl-3,5-disubstituted-2-pyrazolines 2a-g or 1-phenyl-3,5-disubstituted 2-pyrazolines 3a-g, respectively in moderate to good yields[30]. However, 2,4-dinitrophenylhydrazine did not afford the corresponding 2-pyrazolines under similar conditions probably due to its poor solubility in the reaction medium. The synthetic approach of title compounds 2a-g and 3a-g is illustrated in Scheme 1. The structure of the synthesized compounds was assigned on the basis of UV, IR, 1H NMR, 13C NMR and Mass spectral analysis.


Novel 3,4-Methylenedioxybenzene Scaffold Incorporated 1,3,5-Trisubstituted-2-pyrazolines: Synthesis, Characterization and Evaluation for Chemotherapeutic Activity.

Deshpande SR, Nagrale SN, Patil MV, Chavan PS - Indian J Pharm Sci (2015 Jan-Feb)

Synthesis of title compounds 2a-g and 3a-g
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4355879&req=5

Figure 3: Synthesis of title compounds 2a-g and 3a-g
Mentions: Despite numerous reported methods for the preparation of 2-pyrazolines, the Fischer and Knoevenagel method of reacting α,β-unsaturated aldehydes and ketones with phenyl hydrazine in acetic acid is still the most popular one[28]. Chalcones are 1,3-diaryl-2-propen-1-ones and serve as important intermediates for the construction of corresponding 2-pyrazolines. Since piperonal is an aldehyde with 3,4-methylenedioxy benzene moiety, it was aptly used as a precursor for the development of 3,4-methylenedioxy benzene incorporated 2-pyrazolines. A series of chalcones (1a-g) was synthesized according to Claisen-Schmidt reaction[29] by condensing various substituted acetophenones with piperonal in presence of 50% sodium hydroxide solution at 10-15° in good to excellent yields. The cyclocondensation of chalcones 1a-g with hydrazine or phenylhydrazine in acetic acid yielded 1-acetyl-3,5-disubstituted-2-pyrazolines 2a-g or 1-phenyl-3,5-disubstituted 2-pyrazolines 3a-g, respectively in moderate to good yields[30]. However, 2,4-dinitrophenylhydrazine did not afford the corresponding 2-pyrazolines under similar conditions probably due to its poor solubility in the reaction medium. The synthetic approach of title compounds 2a-g and 3a-g is illustrated in Scheme 1. The structure of the synthesized compounds was assigned on the basis of UV, IR, 1H NMR, 13C NMR and Mass spectral analysis.

Bottom Line: A series of novel 3, 4-methylenedioxybenzene scaffold incorporated 1,3,5-trisubstituted-2-pyrazoline derivatives was synthesised as potent antitubercular agents via chalcone intermediates by reaction with hydrazines.The structures of the compounds were confirmed by IR, 1HNMR, 13CNMR and mass spectral data.All the compounds exhibited excellent activity that could be due to the presence of 3,4-methylenedioxybenzene frame work in the molecules.

View Article: PubMed Central - PubMed

Affiliation: Department of Medicinal and Pharmaceutical Chemistry, H. S. K. College of Pharmacy, BVVS Campus, Bagalkote-587 101, India.

ABSTRACT
A series of novel 3, 4-methylenedioxybenzene scaffold incorporated 1,3,5-trisubstituted-2-pyrazoline derivatives was synthesised as potent antitubercular agents via chalcone intermediates by reaction with hydrazines. The structures of the compounds were confirmed by IR, 1HNMR, 13CNMR and mass spectral data. The novel pyrazolines were screened for in vitro antitubercular activity by almar blue dye method against M. tuberculosis H37Rv. All the compounds exhibited excellent activity that could be due to the presence of 3,4-methylenedioxybenzene frame work in the molecules. Some of the compounds also showed in vitro cytotoxicity on EAC cell lines in tryphan blue exclusion assay suggesting their safety.

No MeSH data available.


Related in: MedlinePlus