3,3,6,6-Tetramethyl-9-(2-nitrophenyl)-3,4,5,6,9,10-hexahydroacridine-1,8(2H,7H)-dione

Abstract

(Received 7 May 1996; accepted 25 June 1996) This work was funded by the Deutsche Forschungsgemeinschaft. SAAS thanks the Alexander von HumboldtStiftung for a postdoctoral fellowship. PL thanks the European Community for a postdoctoral grant (BBW 94.0162 CHBG CT 940731). AbstractThe title compound, C23H26N204, consists of a partially hydrogenated acridine moiety with one 2-nitrophenyl substituent on the central ring. The acridine nucleus suf-

The Crystal and Molecular Structure of 1,8-Dioxo-9- (o-nitrophenyl)-1,2,3,4,5,6,7,8-octahydroxanthene

“…The best plane passing through the ring A [except the atom C2] and ring C [except the atom C7] is 14.8°. The carbonyl groups C5 = O1 and C4 = O2 have bond lengths 1.223(3) c and 1.224(4) c , respectively and this is in agreement with an existing literature (BRITO-ARIAS et al, 1996). Bond angle C8A -O10 -C1A [ = 118.3(1)°] shows the sp 2 -hybridized behaviour of O10.…”

“…The octahydro xanthene core values obtained are compared with a 9-spiro octahydroxanthene derivative (DECLERCQ et al, 1981) and the values are given in square brackets. The grand mean of the bond lengths involving the C9 atom is 1.514 (5) The planar phenyl ring of the 2-nitrophenyl substitutent is almost perpendicular to the central ring with the dihedral angle between their least squares planes being 103.5(1)° and the mean C -C bond length within this ring is 1.377(4) c. These values are comparable to the values found in literature (MIAO et al, 1996 andBRITO-ARIAS et al, 1996). The O3 -N -O4 plane and the phenyl ring are tilted to one another by an angle of 123.1(1) °.…”

“…The central ring angles, C4A -C9 -C5A and C1A -O10 -C8A are 109.5(2)° [105.4°] and 118.3(2)°[ 117.4°], respectively]. The exocyclic angles around C9 atom, C4A -C9 -C15 and C5A -C9 -C15 are 114.6(2)° and 113.0(2)° , respectively, and in a similar acridine derivative, [where the central ring adopts a distorted boat conformation] the corresponding values are 110.69(11) ° and 108.73(9)° (BRITO-ARIAS et al, 1996).…”

Synthesis, α-Glucosidase Enzymatic Inhibition and Docking Studies of some Fused Heterocycles

“…The synthesis of hydroacridinone 4 was carried out according to scheme I consisting in the reaction between 2-nitrobenzaldehyde 1 with 2 equivalents of dimedone 2 under basic condition to yield heterocycle 4 (Figure 2). The synthesis of heterocycle 5 was carried out from intermediate 3 [16] which under reducing condition afforded the acridinone 5, and its structure confirmed by X ray diffraction analysis [17]. The hydro xanthone 6 was prepared also from intermediate 3 which was submitted to base treatment with sodium methoxide under refluxing conditions as described in scheme II.…”