Synthesis and biological evaluation of novel methylene‐bisthiazolidinone derivatives as potential nematicidal agents

Srinivas, A.; Nagaraj, A.; Reddy, Ch. Sanjeeva

doi:10.1002/jhet.5570450409

Cited by 30 publications

(13 citation statements)

References 14 publications

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“…). Recent representative studies of 1 include the following: (i) 2‐phenyl‐5‐methyl derivative as mycelial growth inhibitor , (ii) 2‐aryl‐5‐(amide methylene) derivatives as C–C chemokine receptor type 4 (CCR4) antagonists , (iii) 2‐aryl‐5‐(amide methylene) derivatives as follicle‐stimulating hormone receptor antagonists , (iv) 2‐aryl‐5‐(carbonyl methylene) derivatives as bacterial and fungal growth inhibitors , and (v) 2‐aryl‐5‐carboxymethyl derivatives as nematicidal agents against Bacillus subtilis, Staphlococcus aureus, and Escherichia coli .…”

Section: Introductionmentioning

confidence: 99%

Stereocomplementary Synthesis of cis‐ and trans‐2‐(p‐Bromophenyl)‐5‐methylthiazolidin‐4‐ones: Useful Umpolung‐type Suzuki–Miyaura Cross‐coupling Partner and Donor

Sasaki

Nakatsuji

Tanabe

2018

Journal of Heterocyclic Chem

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Novel cis‐ and trans‐2‐(p‐bromophenyl)‐5‐methylthiazolidin‐4‐ones, S,N‐containing heterocyclic compounds, were provided in a cis‐stereocomplementary and trans‐stereocomplementary synthetic manner. cis‐Selective cyclo‐condensation proceeded between 2‐sulfanylpropanoic acid (thiolactic acid) and an imine derived from 4‐bromobenzaldehyde and methylamine, whereas Ti(OiPr)4 and Ti(OiBu)4‐promoted trans‐selective cyclo‐condensation proceeded between benzyl 2‐sulfanylpropanoate and the imine. The obtained cis‐ and trans‐2‐(p‐bromophenyl)‐5‐methylthiazolidin‐4‐ones were successfully converted to 2‐(3‐furyl)phenyl derivatives and bis(pinacolato)diborane derivatives utilizing Suzuki–Miyaura and Miyaura–Ishiyama cross‐coupling reactions, respectively, in an umpolung manner.

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Section: Introductionmentioning

confidence: 99%

Stereocomplementary Synthesis of cis‐ and trans‐2‐(p‐Bromophenyl)‐5‐methylthiazolidin‐4‐ones: Useful Umpolung‐type Suzuki–Miyaura Cross‐coupling Partner and Donor

Sasaki

Nakatsuji

Tanabe

2018

Journal of Heterocyclic Chem

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“…11 Thiazolidine-4-ones are known to exhibit diverse bioactivities, such as antiplatelet activating factor, 12 antihistaminic, 13 COX inhibitory, 14 Ca +2 channel blocking, 15 PAF antagonist, 16 cardioprotective, 17 anti-ischemic 18 and nematicidal activities. 19 Moreover, pyrazoles and their derivatives could be considered as possible antimicrobial agents. 20 The other derivatives display antidepressant, 21 antiarthritic 22 and cerebroprotecting 23 properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics

Srinivas

Sunitha²,

Karthik³

et al. 2017

ACSi

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“…Thiazolidinones possess antibacterial [7], antiinflammatory [8], antitubercular [9], anticancer [10], antitumor [11], anti HIV [12], antifungal [13], anesthetic [14], anti-viral [15], anticonvulsant [16], diuretic [17], nematicidal [18], and antihistaminic [19] activity.…”

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confidence: 99%

Synthesis and antimicrobial activity of 2-phenyl-3-{1-cyclopropyl-6-fluoro-7-[4-methylpiperazin-1-yl]-4-quinolone}carboxamido-3-thiazolidin-4-ones

Patel

2009

Pharm Chem J

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The title compounds VIa -j have been prepared from the lead molecule 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid I. The lead molecule was converted to hydrazide III via acid chloride II, which on reaction with different substituted aromatic aldehydes a -j afforded Schiff base, and on further structural variation of the Schiff base furnished the final compounds VIa -j (Scheme I).The synthesized compounds were tested for their antibacterial and antifungal activity (MIC) in vitro against two Gram-positive bacteria, S. aureus and S. pyogenes, and two Gram-negative bacteria E. coli and P. aeruginosa, and fungi C. albicans, A. niger, and A. clavatus, taking gentamycin, ampicillin, chloramphenicol, ciprofloxacin, norfloxacin, nystatin, and griseofulvin as standard drugs. All the synthesized compounds have been established by elemental analysis amd IR and NMR spectral data. Quinolones are extensively investigated as broad spectrum antibacterial [1, 2], antidiabetic [3], anticancer [4], antiviral [5], and anti-HIV [6] agents. Thiazolidinones possess antibacterial [7], antiinflammatory [8], antitubercular [9], anticancer [10], antitumor [11], anti HIV [12], antifungal [13], anesthetic [14], anti-viral [15], anticonvulsant [16], diuretic [17], nematicidal [18], and antihistaminic [19] activity.We have also synthesized some amide derivatives [20 -22] of quinolones and tested their activity. We observed that some of the compounds were potent and hence we initiated this work with a Schiff base and tried to synthesize more potent antimicrobial agents in addition to thiazolidinone with priority at C-3 and N-methylpiperazine at C-7.The 1 H NMR spectra of the lead molecule contained signals from the -OH of carboxylic acid at 13.59, a multiplet signal from N-CH proton at 3.77 -3.87, a multiplet signal from the cylcopropane proton at 0.85 -1.42, and peaks for three protons of the quinolone ring at 7.98 -8.84. These signals remained similar during further structural variation at C-3 and C-7 of the quinolone ring, with disappearance of the carboxylic acid group peak. The 1 H NMR of the hydrazide contained two singlet for NH at 8.64 and NH 2 at 5.72. The Schiff base contained signals for the -CH-proton at 5.13 -7.73 and a singlet for CONH similar to hydrazide. A multiplet at 2.77 -3.20 for the piperazin-1-yl group and a singlet for >N-CH 3 at 1.87 -1.95 were also observed; a singlet at 3.27 -4.07 for -CH 2 -and 5.67 -6.20 for the proton at C-2 of the cyclized thiazolidinone containing the aromatic ring at 7.67 for -OH was also observed.The IR spectra of the lead molecule contained absorption bands for >C=O of the quinolone ring at 1747 cm -1 , for carboxylic acid at 1725 cm -1 , and 2856 -2960 cm -1 for the cyclopropyl group. A band for the amide of the hydrazide at 1622 cm -1 and for the Schiff base for >N=CH-at 1615 cm -1 band were observed. In addition to the piperazine-1-yl group, an absorption band was observed at 1031 -1047 cm -1 for N-CH; for the thiazolidinone derivatives, the absorption ban...

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Synthesis and biological evaluation of novel methylene‐bisthiazolidinone derivatives as potential nematicidal agents

Cited by 30 publications

References 14 publications

Stereocomplementary Synthesis of cis‐ and trans‐2‐(p‐Bromophenyl)‐5‐methylthiazolidin‐4‐ones: Useful Umpolung‐type Suzuki–Miyaura Cross‐coupling Partner and Donor

Stereocomplementary Synthesis of cis‐ and trans‐2‐(p‐Bromophenyl)‐5‐methylthiazolidin‐4‐ones: Useful Umpolung‐type Suzuki–Miyaura Cross‐coupling Partner and Donor

Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics

Synthesis and antimicrobial activity of 2-phenyl-3-{1-cyclopropyl-6-fluoro-7-[4-methylpiperazin-1-yl]-4-quinolone}carboxamido-3-thiazolidin-4-ones

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