Facile synthesis of 3-(1-(4'-(3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-yl)biphenyl-4-yl)-5-oxo-2-phenyl-1H-imidazol-4(5H)-ylidene)indolin-2-ones: β-Lactam derivatives as antimicrobes

Bishnoi, Abha; Srivastava, Krishna; Singh, Suruchi

doi:10.5155/eurjchem.2.3.359-364.439

Cited by 3 publications

(4 citation statements)

References 20 publications

(18 reference statements)

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“…The reaction of compounds 1a-h with thioglycolic acid results in cyclization to yield 2a-h. The FTIR spectra of synthesized compounds 2a-h show a new absorption band of C=O in the range of 1650-1698 cm -1 [25,26]. In the 1 H NMR spectrum of compounds 2a-h, the signal of the two protons (O=C-CH2-S) appeared as a singlet at δ 2.81-2.94 ppm, the one proton singlet which was present at δ 8.89-8.97 ppm due to -N=CH-C-(1a-h) has been shifted to δ 3.32-3.45 ppm (due to -N-CH-S-).…”

Section: Resultsmentioning

confidence: 99%

“…In the 1 H NMR spectrum of compounds 2a-h, the signal of the two protons (O=C-CH2-S) appeared as a singlet at δ 2.81-2.94 ppm, the one proton singlet which was present at δ 8.89-8.97 ppm due to -N=CH-C-(1a-h) has been shifted to δ 3.32-3.45 ppm (due to -N-CH-S-). The IR and NMR data suggest the formation of 5 membered lactam ring in which the -CH2 and -CH groups are not attached directly [25,26]. The novel 3a-h was synthesized via cyclization of 1a-h with CH2COCl2.…”

Section: Resultsmentioning

confidence: 99%

“…Based on analytical and spectral data (FTIR and 1 H NMR) the molecular structure of the novel synthesized series was characterized. The characteristic FTIR spectrum of the synthesized compounds exhibits new absorption bands of C=O, and C-Cl at ~1660 and 770 cm -1 respectively [25,26]. Proton NMR spectra suggest that the compounds 3a-h contain two new doublets at δ 3.11-3.21 and 4.17-4.31 ppm due to -C-CH-Cl and -N-CH-of lactam ring respectively, while a singlet of 1a-h at δ 8.89-8.97 ppm due to -N=CH-C-was absent in 3a-h [25,26].…”

Section: Resultsmentioning

confidence: 99%

“…The characteristic FTIR spectrum of the synthesized compounds exhibits new absorption bands of C=O, and C-Cl at ~1660 and 770 cm -1 respectively [25,26]. Proton NMR spectra suggest that the compounds 3a-h contain two new doublets at δ 3.11-3.21 and 4.17-4.31 ppm due to -C-CH-Cl and -N-CH-of lactam ring respectively, while a singlet of 1a-h at δ 8.89-8.97 ppm due to -N=CH-C-was absent in 3a-h [25,26]. The mass fragmentation pattern of compounds 2a and 3a has been represented in table 1.…”

Section: Resultsmentioning

confidence: 99%

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Design and synthesis of novel lactam/thiazole derivatives having five membered thiazolyl ring and their antimicrobial activity

SRIVASTAVA¹,

TIWARI²,

SINGH³

et al. 2023

jrp

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In the present communication, we conceived a new synthetic approach for the preparation of novel thiazolyl-lactam/thiazole analogs. The reaction was started through cyclization of ketone with thiourea along with substituted aryl aldehydes to culminate imine derivatives which subsequently cyclized with thioglycolic acid/chloroacetyl chloride to produce final compounds. The structural elucidation of newly synthesized compounds was performed through elemental detections, FT-IR, 1 HNMR, and Mass spectrometric techniques. Antimicrobial studies were performed for all synthesized molecules by serial dilution method by tacking the positive (K. pneumonia, S. aureus, B. subtills) and negative (P. aeruginosa and E. coli.) bacterial strains. The in vitro antimicrobial screening results show that the compounds 2e, 3c, and 3d containing o-hydroxy, p-chloro, and p-nitro substituent respectively exhibit exceptional activity against S. aureus while compounds 2d and 3f bearing p-nitro and o-chloro substituent respectively were deemed to be the most competent against B. subtilis. Compounds 2d (p-nitro) and 2f (o-chloro) were found to be most potent against E. coli. In gram-negative bacterial strains, compounds 2c (p-chloro), 2g (4-OH,-OCH3), 3b (phydroxy), and 3e (o-hydroxy) were extremely potent against P. aeruginosa while compound 2e containing o-hydroxy group shows excellent activity against E.coli.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%