PubMed · 5802373
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W Wiegrebe, H Reinhart, H Budzikiewicz, U Krüger. 1969. [Indanylisoquinoline].. https://doi.org/10.1016/0040-4020(69)80032-3
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Novel indeno[1,2-c]isoquinolinone derivatives were synthesized and evaluated as inhibitors of the nuclear enzyme poly(ADP-ribose) polymerase-1 (PARP-1). These potent nonmutagenic PARP-1 inhibitors possess an additional five-membered ring between the B and C rings of 6(5H)-phenanthridinone. The most potent PARP-1 inhibitors were obtained from the substitution of the D ring at the C-9 position, in particular sulfonamide and N-acyl analogues (6 and 11). The 9-sulfonamide analogues 11a and 12a exhibited IC(50) values of 1 and 10 nM, respectively.
Multiple-quantum proton NMR spectra of the 8-spin system of indene partially oriented in a nematic mesophase were acquired using a magnetic field gradient (MFG) method. Six-, seven- and eight-quantum spectra were solved to yield all intramolecular dipolar couplings (D(ij)) which were used to determine the molecular shape. The spectral widths of multiple-quantum spectra are dependent on molecular orientation and geometry and a novel method was developed to estimate the Saupe order parameters from the observed spectral widths of the high-order multiple-quantum spectra.
[formula: see text] This paper describes a new tandem reaction sequence leading to angularly fused polyquinanes from squaric acid-derived bicyclo[6.3.0]-undecadienediones. Such compounds undergo a dual Michael addition. The enolate form in the first intermolecular addition undergoes the second intramolecular transannular addition to give the angular polyquinanes. A particularly interesting example is a catalytic transformation of cis-13-methylyricyclo[10.3.0.0]pentadeca-4(5),12(13)-diene-3 ,14-dione to (3R*,3aS*,5aR*,9aR*,11aR*)-3-methyl-1,2,3,5,5a,6 ,7,10,11,11a-decahydro-4H- pentaleno[6a,1-c]indene-2,10-dione, a compound having the tetracyclic ring system found in the natural product waihoensene. The mechanism and synthetic scope of these reactions are discussed.