E-2-benzylidenebenzocyclanones. II. IR and mass spectrometric investigations

Structural analysis of 2‐arylidene‐1‐indanone derivatives by electrospray ionization tandem mass spectrometry

“…Further, in the case of compound 10 , the B ring is devoid of aromatic protons; hence the justification that this may be the only pathway for loss of 20 Da (HF) in this molecule is fortified. Similar loss of the ortho substituent to form a stable cyclic ring was proposed to occur for benzylidenecyclanones under EI‐MS conditions . This type of loss to afford a stable six‐membered benzopyrylium ion has been observed in analogous 2‐benzylidenecyclohexanones and 2,6‐bis‐benzylidenecyclohexanones containing a halogen atom as ortho substituent in the aromatic ring under EI‐MS conditions .…”

“…; 1c–6c , Scheme ) was observed in the MS/MS spectra of compounds 1–6 in 4–20% RA (Table ). An interesting benzopyrylium product ion ( 5d and 6d ) at m/z 145 was seen in the case of compounds 5 and 6 by (1,8)(3,9)B + fragmentation with loss of respective substituents (H 2 O in 5 and HCN in 6 ; 8% RA; see Supplementary Figs. SF3 and SF4, Supporting Information).…”

“…The characteristic loss of the NO 2 radical and HNO 2 , along with the combined losses of 61 ( • NO 2 + • CH 3 ; 27% RA), 62 (HNO 2 + • CH 3 ; 22% RA) and 63 Da (HNO 2 + CH 4 ; 12% RA) were observed for compound 7 (R 3 = NO 2 ; see Supplementary Fig. SF5, Supporting Information).…”

“…While gas chromatography coupled with mass spectrometry (MS) and 1 H NMR analysis was also used to study the in‐solution and on‐plate light‐catalyzed E / Z isomerization of 2‐benzylidene‐1‐indanones, studies using electrospray ionization (ESI)‐MS have not been performed so far. Several E ‐2‐benzylideneindanones, tetralones and ‐benzosuberones with OCH 3 , NO 2 and F substituents in ortho , meta or para position have also been investigated by IR and EI‐mass spectrometry …”

Study on the interaction of some (E)-2-benzylidenebenzosuberone derivatives with serum albumin by UV-Vis method, inhibitory effect on topoisomerase

“…The wide range of biological activities of both naturally occurring and synthetic analogs, among others cytotoxic, antitumor, anti-inflammatory, and chemopreventive properties, are well documented in the literature [1][2][3][4][5][6][7] . To study the structure-activity relationship of chalcones, cyclic analogs were synthesized, and their molecular structure, chemical reactivity, and biological activity were investigated [8][9][10][11][12] .…”