RESUMEN
Herein, a straightforward facile synthesis of indolo[2,3-c]quinoline analogues was reported from 2-arylamino(phenylsulfonyl)methylindoles involving PIDA/BF3·OEt2-mediated intramolecular dehydrogenative coupling (IDC) as a key step. Even though isomeric 3-arylamino(phenylsulfonyl)methylindoles, upon interaction with PIDA/BF3·OEt2, led to complications, synthesis of the indolo[3,2-c]quinoline framework could be easily achieved from N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamide by employing a Pd(0)-mediated intramolecular cyclization reaction. Under identical conditions, synthesis of indolo[2,3-c]quinolines was also accomplished from the respective N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamides. The SRB assay of fluorine-bound indoloquinolines displayed nanomolar-level cytotoxicity against a nonsmall lung cancer cell line, NCI-H460.
RESUMEN
Two new [1-(phenyl-sulfon-yl)-1H-indol-2-yl]methanamine derivatives, namely, N-(3-meth-oxy-phen-yl)-N-{[1-(phenyl-sulfon-yl)-1H-indol-2-yl]meth-yl}acetamide, C24H22N2O4S, (I), and N-(2,5-di-meth-oxy-phen-yl)-N-{[1-(phenyl-sulfon-yl)-1H-indol-2-yl]meth-yl}benzene-sulfonamide, C29H26N2O6S2, (II), reveal a nearly orthogonal orientation of their indole ring systems and sulfonyl-bound phenyl rings. The sulfonyl moieties adopt the anti-periplanar conformation. For both compounds, the crystal packing is dominated by C-Hâ¯O bonding [Câ¯O = 3.312â (4)-3.788â (8)â Å], with the structure of II exhibiting a larger number, but weaker bonds of this type. Slipped π-π inter-actions of anti-parallel indole systems are specific for I, whereas the structure of II delivers two kinds of C-Hâ¯π inter-actions at both axial sides of the indole moiety. These findings agree with the results of Hirshfeld surface analysis. The primary contributions to the surface areas are associated with the contacts involving H atoms. Although II manifests a larger fraction of the Oâ¯H/Hâ¯O contacts (25.8 versus 22.4%), most of them are relatively distal and agree with the corresponding van der Waals separations.
RESUMEN
An intramolecular Diels-Alder reaction of positionally isomeric indole-2/3-phenylvinyl-N-alkynylated (N-phenylsulfonyl)amines has been successfully exploited for the synthesis of quino[4,3-b]carbazole and its analogues. This reaction proceeds through a [4 + 2] cycloaddition followed by elimination and deprotection of phenylsulfonyl units to afford the quinocarbazoles in moderate to good yields. The reaction features a broad substrate scope and remarkable functional group forbearance. A preliminary in vitro cytotoxicity evaluation of representative quino[4,3-b]carbazoles was performed against NCI-H460 human cancer cell culture. Among the quino[4,3-b]carbazoles evaluated, five of the fluorine-containing quinocarbazoles displayed nano molar range (0.8-2.0 nm) GI50 values. The UV-vis and fluorescence spectral studies of representative quinocarbazoles were also performed. Like ellipticine, four of the quinocarbazoles displayed dual emissions confirming the existence of p-quinonoid like tautomeric forms in a polar protic solvent.
RESUMEN
In the title compounds, C22H16FNO2S2 (I) and C26H20FNO2S2 (II), the benzo-thio-phene rings are essentially planar with maximum deviations of 0.009â (1) and 0.001â (1)â Å for the carbon and sulfur atom in compounds I and II, respectively. In I, the thio-phene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, with a dihedral angle of 77.7â (1)°. In compound I, the mol-ecular structure is stabilized by weak C-Hâ¯O intra-molecular inter-actions formed by the sulfone oxygen atoms, which generate two S(5) ring motifs. In the crystal of I, N-Hâ¯O hydrogen bonds link the mol-ecules into R 2 2(8) rings, which are connected into a C(10) chain via C-Hâ¯F hydrogen bonds. Inter-molecular C-Hâ¯π inter-actions are also observed. In compound II, the mol-ecules are linked via C-Hâ¯O and C-Hâ¯F hydrogen bonding, generating infinite C(11) and C(13) chains running parallel to [010].
RESUMEN
In both of the title compounds, C26H19NO2S2, (I), and C25H19NO2S2, (II), the benzo-thio-phene rings are essentially planar with maximum deviations of 0.026â (1) and -0.016â (1)â Å for the carbon and sulfur atoms in compounds (I) and (II), respectively. In (I), the thio-phene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, subtending a dihedral angle of 88.1â (1)°, and the di-hydro-pyridine ring adopts a screw-boat conformation. In both compounds, the mol-ecular structure is consolidated by weak C-Hâ¯O intra-molecular inter-actions formed by the sulfone oxygen atoms, which generate S(5) ring motifs. In the crystal of II, mol-ecules are linked via C-Hâ¯O hydrogen bonds, generating C(7) chains running along the [100] direction. No significant inter-molecular inter-actions are observed in I.
RESUMEN
Heteroarylmethylenephosphorus ylides underwent Michael addition with alkynediones and alkynediesters, followed by intramolecular cyclization and elimination of triphenylphosphine oxide to afford 1,2-diaroylbenzenes and 1,2-alkoxycarbonylcarbo- and heterocycles. The analogous (4 + 2) cycloaddition led to the formation of 2,3-diaroylquinolines.
RESUMEN
One-pot synthesis of 3,4-benzo[c]-ß-carbolines was achieved from 2-aryl(tosylamino)methyl-3-bromoindoles via 10 mol % Pd(OAc)2/PPh3-mediated intramolecular Heck coupling using K2CO3 as a base in DMF at 110 °C with concomitant aromatization through an elimination of tosylsulfinic acid. Under identical conditions, the isomeric 3-aryl(tosylamino)methyl-2-bromoindoles upon intramolecular Heck reaction furnished benzo[4,5]isothiazolo[2,3-a]indole 5,5-dioxides instead of the expected γ-carbolines. However, synthesis of the expected γ-carboline framework, 3-tosyl-6,9-dihydro-1,2-benzo[a]-γ-carbolines, could be achieved from 3-aryl(tosylamino)methyl-2-bromoindoles containing a mesitylene sulfonyl unit as a protecting group on the indole nitrogen.
