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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 | Revised: 27 Oct 2010 | Accepted: 04 Nov 2010 | Published: 30 Sep 2011 | Issue Date: September 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.
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DOI: 10.5155/eurjchem.2.3.388-393.184
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Bhanwar Nahata College of Pharmacy, Mandsaur (Madhya Pradesh), India
Citations
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