Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

Abstract

1 H and 13 C NMR chemical shifts have been determined and assigned based on PFG 1 H, 13 C HMQC, and HMBC experiments for 3-(4 0 -X-benzyl)-4-chromenones (Ia, X = CN and Ib, X = NO 2 ), 3-(4 0 -X-benzyl)-4-thiochromenones (IIa, X = Cl and IIb, X = Br), (E)-3-(4 0 -Xbenzylidene)-4-chromanones (IIIa-IIIe, X = OCH 3 , CH 3 , Cl, N(CH 3 ) 2 , Br), (Z)-3-(4 0 -X-benzylidene)4-thiochromanones (IVa-IVd, X = Cl, Br, F, OCH 3 ), 2-benzyl-1,2,3, 4-tetrahydro-1-naphthol (V), 2-benzyl-and (E)-2-benzylidene-1-tetralones (VI and VII), and (E)-2-benzylidene-1-benzosuberol (VIII). The crystal structures have been determined for the following seven compounds: derivatives of 4-chromanones (IIIa-IIId), 1-tetrahydronaphtol (V), and 1-tetralones (VI and VII). The molecular features and intermolecular interactions in crystal state have been discussed.

3-Benzylidene-4-chromanones: a novel cluster of anti-tubercular agents

“…These molecules were shown by 1 H-NMR spectroscopy and in several cases by X-ray crystallography to adopt the E stereochemistry 13,14,16 . The choice of aryl substituents was made on the basis of their differing electronic, hydrophobic and steric properties.…”

The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

“…The relationship between cytotoxic activity (given as log 1 IC 50 ) and the percentage contribution to the Hirshfeld surface covered by CÁ Á ÁC contacts against cell line WM115. 2019) or from the Cambridge Structural Database [Version 5.41, last update November 2019;Groom et al, 2016;FAVVIH (Katrusiak et al, 1987), NAMXIK, NAMXOQ, NAMXUW,-NAMYEH, NAMYOR, NAMYUX, NAMZEI, NAMZOS, NAMZUY and NANBAH (Cheng et al, 2011), NANDOB (Valkonen et al, 2012), SECBAF (Gopaul et al, 2012a), YAWLEP (Gopaul et al, 2012b) and YEJPIO (Gopaul & Koorbanally, 2012)]. The scheme used for the search is presented in Fig.…”

3-(3-Nitrobenzyl)-4H-chromen-4-one

“…For the preparation, see: Valkonen et al (2012). For related structures, see: Sievä nen et al (2010); Gopaul et al (2012); Valkonen et al (2012).…”

“…For the preparation, see: Valkonen et al (2012). For related structures, see: Sievä nen et al (2010); Gopaul et al (2012); Valkonen et al (2012). For general background to homoisoflavoinoids, see: Shaikh et al (2011); du Toit et al (2010).…”