A study on identification of nutraceutical value of new imidazolone schiff base analogues

Subbulakshmi N. Karanth, Badiadka Narayana, Balladka K. Sarojini, Saleemulla Khan, Shashidhara S. Kenkere

Research output: Contribution to journalArticle

Abstract

Background: Imidazolones as well as Schiff base are extensively used as building blocks for the synthesis of various pharmaceutically active agents. The use of synthetic antioxidant for use in the diet and therapy demands a great deal of research attention for synthetic antioxidants. It was observed that the π-excessive ring systems are responsible for antioxidant activity of the compounds. Objective: The primary objective of this study was to develop a new method to synthesize imidazalone derivatives which are evaluated for in vitro antioxidant activity in order to check their nutraceutical value. Methods: Novel method for the synthesis of imidazalone derivatives is developed starting from simple easily accessible glycine, thiophene aldehyde and benzoyl chloride. The synthesis of target molecules is achieved in four steps via formation of an intermediate oxazolone which undergoes ring opening on reaction with hydrazine hydrate and subsequent cyclization with aldehydes in presence of acid catalyst. Results: All Imidazolone compounds were evaluated for their in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. Almost all the tested imidazalone compounds showed moderate to excellent activity, the substitution on arylidene group substantially influenced their overall activity. The compound 3-{[(E)-(4-chlorophenyl)methylidene]amino}-2-phenyl-5- (thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one (9) showed very high radical scavenging capacity with IC50 value 2.886 µg/ml in comparison with the standard ascorbic acid (1.439 µg/ml). The antioxidant activities of the synthesized compounds appeared in the following order 6 >5> 13> 8>7>20>11>12>10>19>15>14>18>16 and 17. Further in silico studies complement the in vitro antioxidant studies. Conclusion: Compound, 3-{(4-chlorophenyl)methylidene]amino}-2-phenyl-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one (9) displayed best antioxidant activity due to the presence of active chloro group. Compounds bearing hydroxyl group at para and ortho position (16 and 18) showed very low activity. This anomalous result could be explained on the basis of intramolecular hydrogen bonding. These results were complement the in silico antioxidant studies.

Original languageEnglish
Pages (from-to)1358-1370
Number of pages13
JournalLetters in Drug Design and Discovery
Volume14
Issue number12
DOIs
Publication statusPublished - 01-12-2017

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Schiff Bases
Dietary Supplements
Antioxidants
hydrazine
Aldehydes
Computer Simulation
Oxazolone
Diet Therapy
imidazolone
Thiophenes
Cyclization
Hydrogen Bonding
Hydroxyl Radical
Glycine
Ascorbic Acid
Inhibitory Concentration 50
Acids

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery

Cite this

Karanth, Subbulakshmi N. ; Narayana, Badiadka ; Sarojini, Balladka K. ; Khan, Saleemulla ; Kenkere, Shashidhara S. / A study on identification of nutraceutical value of new imidazolone schiff base analogues. In: Letters in Drug Design and Discovery. 2017 ; Vol. 14, No. 12. pp. 1358-1370.
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A study on identification of nutraceutical value of new imidazolone schiff base analogues. / Karanth, Subbulakshmi N.; Narayana, Badiadka; Sarojini, Balladka K.; Khan, Saleemulla; Kenkere, Shashidhara S.

In: Letters in Drug Design and Discovery, Vol. 14, No. 12, 01.12.2017, p. 1358-1370.

Research output: Contribution to journalArticle

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T1 - A study on identification of nutraceutical value of new imidazolone schiff base analogues

AU - Karanth, Subbulakshmi N.

AU - Narayana, Badiadka

AU - Sarojini, Balladka K.

AU - Khan, Saleemulla

AU - Kenkere, Shashidhara S.

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N2 - Background: Imidazolones as well as Schiff base are extensively used as building blocks for the synthesis of various pharmaceutically active agents. The use of synthetic antioxidant for use in the diet and therapy demands a great deal of research attention for synthetic antioxidants. It was observed that the π-excessive ring systems are responsible for antioxidant activity of the compounds. Objective: The primary objective of this study was to develop a new method to synthesize imidazalone derivatives which are evaluated for in vitro antioxidant activity in order to check their nutraceutical value. Methods: Novel method for the synthesis of imidazalone derivatives is developed starting from simple easily accessible glycine, thiophene aldehyde and benzoyl chloride. The synthesis of target molecules is achieved in four steps via formation of an intermediate oxazolone which undergoes ring opening on reaction with hydrazine hydrate and subsequent cyclization with aldehydes in presence of acid catalyst. Results: All Imidazolone compounds were evaluated for their in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. Almost all the tested imidazalone compounds showed moderate to excellent activity, the substitution on arylidene group substantially influenced their overall activity. The compound 3-{[(E)-(4-chlorophenyl)methylidene]amino}-2-phenyl-5- (thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one (9) showed very high radical scavenging capacity with IC50 value 2.886 µg/ml in comparison with the standard ascorbic acid (1.439 µg/ml). The antioxidant activities of the synthesized compounds appeared in the following order 6 >5> 13> 8>7>20>11>12>10>19>15>14>18>16 and 17. Further in silico studies complement the in vitro antioxidant studies. Conclusion: Compound, 3-{(4-chlorophenyl)methylidene]amino}-2-phenyl-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one (9) displayed best antioxidant activity due to the presence of active chloro group. Compounds bearing hydroxyl group at para and ortho position (16 and 18) showed very low activity. This anomalous result could be explained on the basis of intramolecular hydrogen bonding. These results were complement the in silico antioxidant studies.

AB - Background: Imidazolones as well as Schiff base are extensively used as building blocks for the synthesis of various pharmaceutically active agents. The use of synthetic antioxidant for use in the diet and therapy demands a great deal of research attention for synthetic antioxidants. It was observed that the π-excessive ring systems are responsible for antioxidant activity of the compounds. Objective: The primary objective of this study was to develop a new method to synthesize imidazalone derivatives which are evaluated for in vitro antioxidant activity in order to check their nutraceutical value. Methods: Novel method for the synthesis of imidazalone derivatives is developed starting from simple easily accessible glycine, thiophene aldehyde and benzoyl chloride. The synthesis of target molecules is achieved in four steps via formation of an intermediate oxazolone which undergoes ring opening on reaction with hydrazine hydrate and subsequent cyclization with aldehydes in presence of acid catalyst. Results: All Imidazolone compounds were evaluated for their in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. Almost all the tested imidazalone compounds showed moderate to excellent activity, the substitution on arylidene group substantially influenced their overall activity. The compound 3-{[(E)-(4-chlorophenyl)methylidene]amino}-2-phenyl-5- (thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one (9) showed very high radical scavenging capacity with IC50 value 2.886 µg/ml in comparison with the standard ascorbic acid (1.439 µg/ml). The antioxidant activities of the synthesized compounds appeared in the following order 6 >5> 13> 8>7>20>11>12>10>19>15>14>18>16 and 17. Further in silico studies complement the in vitro antioxidant studies. Conclusion: Compound, 3-{(4-chlorophenyl)methylidene]amino}-2-phenyl-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one (9) displayed best antioxidant activity due to the presence of active chloro group. Compounds bearing hydroxyl group at para and ortho position (16 and 18) showed very low activity. This anomalous result could be explained on the basis of intramolecular hydrogen bonding. These results were complement the in silico antioxidant studies.

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