150073-63-5Relevant academic research and scientific papers
Syntheses of 1,5-benzothiazepines: Part XXXIII- syntheses and antimicrobial studies of 10-substituted-6-(4-methoxyphenyl)-6H-6a,7-dihydro-7-(4- methoxyphenyl/3,4-dimethoxyphenyl)[1]benzopyrano-[3,4-c][1,5]benzothiazepines
Pant, Seema,Sharma, Priyanka,Sharma,Pant, Umesh C
, p. 1537 - 1544 (2008/09/19)
Two flavindogenides, 2-(4-methoxyphenyl)-3-(4-methoxybenzylidene)- flavanone, 8a and 2-(4-methoxyphenyl)-3-(3,4-dimethoxybenzylidene)-flavanone 8b, are reacted with 5-substituted-2-aminobenzenethiols 3a-f (the substituents being halogens, fluoro, chloro or bromo, methyl and alkoxyls, methoxyl or ethoxyl), to give respective 12 new compounds, 10-substituted-6-(4- methoxyphenyl)-6H-6a, 7-dihydro-7-(4-methoxyphenyl/3,4-dimethoxyphenyl)[l] benzopyrano[3,4-c]-[l,5]benzofhiazepines 10a-l in 55-67% yields. The products are characterized on the basis of analytical and spectral data. The synthesized compounds are screened for antimicrobial activity against the bacteria Staphylococcus aureus, Pseudomo-nas aeruginosa, and the fungus Candida albicans. All the methoxy-substituted benzopyranobenzothiazepines have showed moderate to comparable activity (using gatifloxin, natilmicin as reference standard) against the gram-positive bacteria S. aureus and the gram-negative bacteria P. aeruginosa. They have also showed significant antifungal activity (compared to fluconazole) against C. albicans, the maximum activity being that of the compound 10k having maximum methoxyl groups, while the fluoro compounds 10a and 10g are completely inactive.
NMR spectral studies of several series of E-3-arylideneflavanones: Realisation of some steric and electronic interactions
Mallik, Uttam K,Saha, Murari M,Mallik, Asok K
, p. 753 - 758 (2007/10/02)
H-2 of E-3-arylideneflavanones differing only in the β-phenyl group is found to experience a reverse substituent chemical shift (s.c.s.) effect.An unfavourable steric interaction between this proton and the ortho-protons of β-phenyl group has been related to this observation.An interesting feature in the 1H NMR spectra of the heterocyclic analogs 5a-c is the significant deshielding of H-2 and shielding of H-β in the case of 5a.Intramolecular hydrogen bond formation between H-2 and the furano oxygen of 5a is probably responsible for this observation.From a studyof the 1H and 13C NMR spectral features of 8a-e which differ only in the 4'-substituent, it may be concluded that a 4'-substituent can polarise the C3-C-β and C=O ?-bonds as well as the ?-system of ring-A.The results of dual substituent parameter analysis of s.c.s. values of C-3, C-β, C-4, C-8a and C-6 for the series 8 have also been presented.
