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A facile synthesis, characterization and biological evaluation of novel spiro-thiazolidinone and quinazolinone-thiazolidine derivatives

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Title A facile synthesis, characterization and biological evaluation of novel spiro-thiazolidinone and quinazolinone-thiazolidine derivatives
 
Creator Srivastava, Krishna
Srivastava, Abhishek
Tiwari, Ram Prakash
Tripathi, Amit
Peta, Sreenivasulu
Verma, Manoj
 
Subject Spiro-indoline
Thiazolidine
Acetophenone
Thiourea
Isatin
Thioglycolic acid
Antimicrobial activity
Antifungal activity
 
Description 770-779
The present work aims to synthesize and to perform antibacterial and antifungal screening of some novel spirothiazolidinone
and quinazolinone-thiazolidine derivatives. The targeted derivatives have been synthesized in four
steps. In the first step benzoyl chloride and anthranilic acid react together to form phenyl-4H-benzo[d][1,3]oxazin-4-
one (1). Step 2 involves the reaction of 1 with thiourea and thiosemicarbazide to produce 4-oxo-2-phenylquinazoline-
3(4H)-carbothioamide (2) and 1-(4-oxo-2-henylquinazolin-3(4H)-yl) thiourea (3) respectively. The reaction of
synthesized compounds 2 and 3 with substituted isatin and substituted acetophenone yields imine derivatives 4a-c,
5a-c, 6a-c, and 7a-c respectively in the third step. The cyclization of imine derivatives with thioglycolic acid in the
presence of zinc chloride yields the targeted spiro-thiazolidinone (8a-c, and 10a-c) and quinazolinone-thiazolidine
(9a-c, and 11a-c) derivatives. Elemental analysis, FTIR, 1H NMR, and mass spectral studies have been used for the
characterization of the synthesized compounds. 8b (MIC 12.5 μg/mL) has been found to be the most effective
derivative against B. subtilis. Compounds 9c and 11b, both with MICs of 12.5 μg/mL, are extremely effective against
gram-negative bacterial strains of P. pneumonia, whereas compounds 9a and 11a have strong antibacterial activity
against E. coli (MICs 12.5 μg/mL). With an average MIC value of 12.5 μg/mL in each case, compounds 8c, 9a, 10a,
and 11a demonstrate good antifungal activity against A. niger, and C. albicans. The antifungal activity of compound
11b is highest against C. albican with MIC value of 6.25 μg/mL. The synthesized compounds exhibit strong
antibacterial and antifungal activity against distinct pathogens.
 
Date 2023-07-20T07:22:08Z
2023-07-20T07:22:08Z
2023-07
 
Type Article
 
Identifier 2583-1321 (Online); 0019-5103 (Print)
http://nopr.niscpr.res.in/handle/123456789/62310
https://doi.org/10.56042/ijc.v62i7.3830
 
Language en
 
Publisher NIScPR-CSIR,India
 
Source IJC Vol.62(07) [July 2023]