European Journal of Chemistry 2011, 2(3), 388-393. doi:10.5155/eurjchem.2.3.388-393.184

Synthesis and antimicrobial activity of novel oxime derivatives of phenothiazine


Ashutosh Barve (1,*) , Malleshappa Noolvi (2) , Niharika Subhedar (3) , Vishnu Dev Gupta (4) , Gaurav Bhatia (5)

(1) Department of Pharmaceutical Chemistry, Bhanwar Nahata College of Pharmacy, Mandsaur, 458001, India
(2) Department of Pharmaceutical Chemistry, Amar Shaheed Baba Ajit Singh Jujhar Singh Memorial College of Pharmacy, Bela, 140111, India
(3) Department of Pharmaceutical Chemistry, Bhanwar Nahata College of Pharmacy, Mandsaur, 458001, India
(4) Department of Pharmaceutical Chemistry, Bhanwar Nahata College of Pharmacy, Mandsaur, 458001, India
(5) Department of Pharmacognosy, Smriti College of Pharmaceutical Education, Indore, 452001, India
(*) Corresponding Author

Received: 25 Jun 2010, Accepted: 04 Nov 2010, Published: 30 Sep 2011

Abstract


A series of 4-methyl-2-oxo-pyranyl-phenothiazines (IIIa-j) followed by 4-methylpyrano-(2, 3-β)-phenothiazine-2(11H)-one oxime (IVa-j) were synthesized by using 7-hydroxy-4-methylcoumarin (I). Further reaction of (I) was carried out with substituted aromatic amines (a-j) to convert into 7-arylamino-4-methyl-coumarin (IIa-j). Additionally (IIa-j) was treated with sulphur in presence of iodine to obtain a series of novel 4-methyl-2-oxo-pyranyl-phenothiazine (IIIa-j) derivatives, which on treatment with hydroxylamine hydrochloride afforded the title compounds i.e. 4-methylpyrano-(2,3-β)-phenothiazine-2(11H)-one oxime (IVa-j). The structures of these compounds were confirmed by IR, NMR and Mass spectral analysis. The newly synthesized compounds were evaluated for antibacterial and antifungal activity. The results show that compound IIIa, IIIe, IIIh, IIIj, IVa, IVi and IVj exhibited moderate to good antibacterial and antifungal activity at 5-100 mcg/mL.

2_3_388_393_800


Keywords


Coumarin; Oxime; Phenothiazine; Antimicrobial activity; Anti-bacterial activity; Anti-fungal activity

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DOI: 10.5155/eurjchem.2.3.388-393.184

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How to cite


Barve, A.; Noolvi, M.; Subhedar, N.; Gupta, V.; Bhatia, G. Eur. J. Chem. 2011, 2(3), 388-393. doi:10.5155/eurjchem.2.3.388-393.184
Barve, A.; Noolvi, M.; Subhedar, N.; Gupta, V.; Bhatia, G. Synthesis and antimicrobial activity of novel oxime derivatives of phenothiazine. Eur. J. Chem. 2011, 2(3), 388-393. doi:10.5155/eurjchem.2.3.388-393.184
Barve, A., Noolvi, M., Subhedar, N., Gupta, V., & Bhatia, G. (2011). Synthesis and antimicrobial activity of novel oxime derivatives of phenothiazine. European Journal of Chemistry, 2(3), 388-393. doi:10.5155/eurjchem.2.3.388-393.184
Barve, Ashutosh, Malleshappa Noolvi, Niharika Subhedar, Vishnu Dev Gupta, & Gaurav Bhatia. "Synthesis and antimicrobial activity of novel oxime derivatives of phenothiazine." European Journal of Chemistry [Online], 2.3 (2011): 388-393. Web. 23 Oct. 2019
Barve, Ashutosh, Noolvi, Malleshappa, Subhedar, Niharika, Gupta, Vishnu, AND Bhatia, Gaurav. "Synthesis and antimicrobial activity of novel oxime derivatives of phenothiazine" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.3.388-393.184

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