Synthesis and in vitro Study of Novel Methylenebis(phenyl-1,5-benzothiazepine)s (III) and Methylenebis(benzofuryl-1,5-benzothiazepine)s (V) as AntimicrobialAgents. -All compounds are tested for their antimicrobial and antifungal effects. Among them, derivatives (IIIf), (Ve) and (Vf) are found to be the most active ones against all the microorganisms. -(SANJEEVA REDDY*, C.; PURNACHANDRA REDDY, G.; NAGARAJ, A.; Chin.
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Multicomponent reactions O 0359An Efficient One-Pot Synthesis of β-Amino/β-Acetamido Carbonyl Compounds via ZrCl 4 -Catalyzed Mannich-Type Reaction. -ZrCl 4 is an efficient catalyst for the three-component reaction of carbonyl compounds (I), aromatic aldehydes (II), and aromatic primary amine (III) and for the four-component reaction of, aromatic aldehydes (V), acetyl chloride, and acetonitrile (VI). -(SANJEEVA REDDY*, C.; PURNACHANDRA REDDY, G.; Chin.
A series of methylenebis(phenyl-1,5-benzothiazepine)s 4 and methylenebis(benzofuryl-1,5-benzothiazepine)s 5 were prepared by the reaction of methylene-bis-chalcones 3 with 2-aminothiophenol for 4 and followed by the condensation with chloroacetone for 5. The structures of the synthesized compounds have been confirmed by their IR, 1 H NMR, 13 C NMR, MS and elemental analyses. All the synthesized compounds were tested for their antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. To elucidate the essential structural requirements for the antimicrobial activity, the preliminary structure-activity relationship has been described. Among the compounds tested, the dimeric compounds 4f, 4g, 5f and 5g were found to be most active against Bacillus subtilis, Bacillus sphaericus, Staphylococcus aureus, Klebsiella aerogenes and Chromobacterium violaceum. Similarly these dimeric compounds showed potent antifungal activity against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes. It is interesting to note that the dimeric compounds with substituents of heterocyclic ring at the 4th position of benzothiazepine system displayed notable antibacterial activity equal to that of streptomycin and penicillin. Further, the activity of all the dimeric compounds was compared with that of their monomeric compounds, and it is interesting to note that almost all the dimeric compounds showed enhanced activity than their monomeric compounds.
Experimental
Apparatus and reagentsMelting points were determined on a Fisher-Johns melting point apparatus and are uncorrected. The purities of the compounds were checked using precoated TLC plates. IR spectra were recorded on a Perkin-Elmer FTIR 5000 spectrometer, using KBr pellets. 1 H, 13 C NMR spectra in DMSO-d 6 were recorded on a Varian Gemini 300 MHz spectrometer and the chemical shifts (δ) were reported using TMS as an internal standard. Mass spectra were obtained on a VG micromass 7070H spectrometer. Elemental analyses were performed on a Perkin-Elmer CHN elemental analyzer. All the solvents and chemicals were purchased from Sigma-Aldrich chemical company and used without further purification.General procedure for the synthesis of methylenebis(chalcone)s (3a-3g)
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