Nuclear magnetic resonance spectra of derivatives of various substituted indanones and tetralones

Imbach, J.‐L.; Pohland, Albert E; Weiler, Ernest D.; Cromwell, Norman H.

doi:10.1016/s0040-4020(01)97903-7

Cited by 20 publications

(5 citation statements)

References 24 publications

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“…All derivatives of 1 which have two free orthopositions in the benzylidene ring show in the low field an absorption corresponding to two h Y d r 0 g en at 0 m s and all mono-orthosubstituted benzylidene derivatives a multiplet corresponding to 0 n e h y d r 0 g en at 0 m , whilst in 2-(2, 6-dichlorobenzylidene)-l,3-indandione the absorption in the low field is absent (its NMR spectrum: 7.38 ppm (t, J = 4.5 cps, 3H); 7.73-8.09 ppm (m, 4H); 7.78 ppm (s, IH). A similar effect has been observed recently by Imbach and co-workers for those geometrical isomers of 2benzylidene-l-indanone in which the are cis to each other [3]. The absorption data in the low field for compounds of type I can best be explained by the diamagnetic anisotropy of the carbonyl group cis to the benzylidene ring.…”

Section: Nmr Spectrasupporting

confidence: 86%

Fulvenes and Thermochromic Ethylenes. Part 52 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their NMR and Infrared Spectra

Agranat¹,

Loewenstein²,

Bergmann³

1969

Israel Journal of Chemistry

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Section: Nmr Spectrasupporting

confidence: 86%

Fulvenes and Thermochromic Ethylenes. Part 52 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their NMR and Infrared Spectra

Agranat¹,

Loewenstein²,

Bergmann³

1969

Israel Journal of Chemistry

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“…For this reason, the methine protons are shifted downfield and frequently overlapped with the complex multiplet arising from the aromatic protons. Previous studies revealed that the methine absorptions of the E and Z isomers of 2-(phenylmethylene)-3,3-dimethyl-1-indanone were 7.65 and 6.80 ppm 10,11 and the relevant data for 2-(phenylmethylene)-4,4-dimethyl-1-tetralone were 7.71 and 6.63 ppm, respectively. 11 In the case of the 2-arylidene-1benzosuberones 3a-l,n, the methine protons and those of the condensed benzene ring in the peri position to the carbonyl group are overlapped in the region of 7.65-7.95 ppm.…”

Section: Chemistrymentioning

confidence: 95%

Conformational and Quantitative Structure−Activity Relationship Study of Cytotoxic 2-Arylidenebenzocycloalkanones

Dimmock

et al. 1999

J. Med. Chem.

116

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Various 2-arylideneindanones 1, 2-arylidenetetralones 2, and 2-arylidenebenzosuberones 3 were synthesized with the aim of determining the relative orientations of the two aryl rings which favored cytotoxicity. Molecular modeling of the unsubstituted compound in each series revealed differences in the spatial arrangements of the two aryl rings, and evaluation of these compounds against P388, L1210, Molt 4/C8, and CEM cells as well as a panel of human tumor cell lines indicated that in general the order of cytotoxicity was 3 > 2 > 1. In particular 2-(4-methoxyphenylmethylene)-1-benzosuberone (3k) had the greatest cytotoxicity, possessing 11 times the potency of the reference drug melphalan when all five screens were considered. Series 3 was considered in further detail. First, excision of the aryl ring fused to the cycloheptanone moiety in series 3 led to some 2-arylidene-1-cycloheptanones 4 which had approximately one-third of the bioactivity of the analogues 3. Second, in some screens cytotoxicity was correlated negatively with the sigma values and positively with the MR constants of the substituents in the arylidene aryl ring of 3. Third, X-ray crystallography of five representative compounds (3i,k-n) revealed differences in the locations of the aryl rings which may have contributed to the variations in cytotoxicity. Finally three members of series 3 inhibited RNA and protein syntheses and induced apoptosis in human Jurkat T cells. This study has revealed that 2-arylidene-1-benzosuberones are a group of useful cytotoxic agents, and in particular 3k serves as a prototypic molecule for subsequent structural modifications.

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“…The 4-chromanones 1a-l were synthesized from 2,3-dihydro-1-benzopyran-4-one and the appropriate aryl aldehyde as indicated in Scheme 1. In the case of the enones in series 2-4 and related compounds, 1 H NMR spectroscopy revealed that the olefinic hydrogen atoms of the E isomers absorb in the range of 7.2-8.0 ppm [8][9][10][11][12] while X-ray crystallography of representative molecules in series 2-4 confirmed the E stereochemistry [8,9]. In the case of 1a-l, 1 H NMR spectroscopy indicated that the compounds are isomerically pure and the olefinic protons absorb in the region of 7.8-8.0 ppm, confirming that these compounds are the E isomers.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells

Perjési

Das

Clercq

et al. 2008

European Journal of Medicinal Chemistry

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A series of 3-benzylidene-4-chromanones 1a-l were prepared and their cytotoxicity towards human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 lymphoid leukemia cells were compared to the previously generated biodata in these three assays for the isosteric 2-benzylidene-1-tetralones 2a-l. Over 40% of the compounds in series 1 were more potent than their counterparts in series 2, while equipotency was noted in one-third of the comparisons made. In general the IC(50) values of 1a-l towards the human T-lymphocytes were in the low micromolar range. Molecular modelling revealed differences in shapes of representative molecules in series 1 and 2 which may contribute to the variation in cytotoxic potencies. Most of the compounds in series 1 displayed greater potencies towards HSC-2, HSC-3, HSC-4 and HL-60 neoplasms than HGF, HPC, and HPLF normal cells and were well tolerated in mice.

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Nuclear magnetic resonance spectra of derivatives of various substituted indanones and tetralones

Cited by 20 publications

References 24 publications

Fulvenes and Thermochromic Ethylenes. Part 52 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their NMR and Infrared Spectra

Fulvenes and Thermochromic Ethylenes. Part 52 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their NMR and Infrared Spectra

Conformational and Quantitative Structure−Activity Relationship Study of Cytotoxic 2-Arylidenebenzocycloalkanones

Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells

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