1485-19-4Relevant academic research and scientific papers
Intramolecular Ritter reactions of 2-(2-cyanoethyl)tetrahydrocyclopenta-[b] indole and -carbazole derivatives
Maertens, Faye,Van Den Bogaert, An,Compernolle, Frans,Hoornaert, Georges J.
, p. 4648 - 4656 (2004)
Intramolecular Ritter reactions of 2-(2-cyanoethyl)tetrahydrocyclopenta[b] indole and -carbazole derivatives, prepared by a sequence of two different α-substitutions and Grignard reactions of the indole-based ketones 4-methyl-1,4-dihydrocyclopenta[b]indol-3(2H)-one and 9-methyl-2,3,4,9- tetrahydro-1H-carbazol-1-one, were used as key steps in the construction of various tetracyclic lactam compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Synthesis and In-vitro antitumor activities of some mannich bases of 9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones
Chen, Jing,Lou, Jianshu,Liu, Tao,Wu, Ru,Dong, Xiaowu,He, Qiaojun,Yang, Bo,Hu, Yongzhou
, p. 165 - 172 (2009)
A novel series of 2-substituted aminomethyl-9-alkyl-1,2,3,4- tetrahydrocarbazole-1-ones 5a-q was synthesized via aminomethylation of 9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones 4a-e with hydrochlorides of the respective amines 6a-m. The structures of these newly synthesized compounds were characterized by 1H-NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non-small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi-drug resistant subline (KB- VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2-diethyl-aminomethyl-9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 5c, exhibited a potential inhibitory effect against microtubule. 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine
Leclair, Alexandre,Wang, Qian,Zhu, Jieping
, p. 1209 - 1215 (2022/01/19)
A single-electron transfer (SET) oxidation of indole or benzo[b]thiophene to a radical cation reverses the intrinsic polarity of these π-excessive bicyclic heteroarenes. Here we report an oxidative two-carbon homologation of cyclobutanols to cyclohexenones under a visible-light photoredox catalysis. 1-(Indol-2-yl)cyclobutan-1-ols are converted to 2,3,4,9-tetrahydro-1H-carbazol-1-ones, important structural motifs found in alkaloids and pharmaceuticals, with a broad substrate scope. A mechanistic study suggests that the reaction is initiated by an SET from an indole to an excited acridinium salt to generate the radical cation, which is followed by two consecutive 1,2-alkyl migrations and a rearomatization. Benzo[b]thiophene-substituted cyclobutanols are similarly converted to 2,3-dihydrodibenzo[b,d]thiophen-4(1H)-ones. A total synthesis of (±)-uleine featuring this ring-expansion process is documented.
N-methylation of aromatic amines and N-heterocycles under acidic conditions with the TTT (1,3,5-trioxane-triethylsilane-trifluoroacetic acid) system
Popp, Tobias A.,Bracher, Franz
, p. 3333 - 3338 (2016/11/29)
A novel reductive N-methylation protocol under acidic conditions with the TTT (1,3,5-trioxane-triethylsilane-trifluoroacetic acid) system is disclosed. This method is highly specific for aromatic amines and several N-heterocycles (indoles and annulated analogues, phenoxazine, phenothiazine), insensitive to steric hindrance, and compatible with a wide range of functional groups. Further the N-methylation step can be combined with an in situ N-Boc deprotection. Compounds in which the nucleophilicity of the NH group is eliminated by protonation under the reaction conditions (aliphatic amines, azaarenes of noteworthy basicity) are inert. In several examples, it was demonstrated that the TTT system is complementary to other N-methylation protocols.
A novel necroptosis inhibitor - Necrostatin-21 and its SAR study
Wu, Zhijie,Li, Ying,Cai, Yu,Yuan, Junying,Yuan, Chengye
supporting information, p. 4903 - 4906 (2013/09/02)
An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM.
Design, synthesis and antiproliferative activity of indole analogues of indanocine
Tunbridge, Gemma A.,Oram, Joseph,Caggiano, Lorenzo
supporting information, p. 1452 - 1456 (2013/11/19)
The design and synthesis of a novel series of indole-analogues of indanocine is reported, together with their antiproliferative activity in the NCI's panel of cancer cell lines. Indanocine displays potent activity against a wide range of cancer cell lines
Tetracyclic compounds from tetrahydrocarbazolones. Part 1. Synthesis from 2,3,4,9-tetrahydrocarbazol-1-ones
Joseph, Delphine,Martarello, Laurent,Kirsch, Gilbert
, p. 2001 - 2014 (2007/10/03)
Reaction of several 2,3,4,9-tetrahydrocarbazol-1-ones 1 was used to synthesise new thieno, furo and selenadiazolo annelated carbazoles.
Nucleophilic-Type Radical Cyclizations of Indoles: Conversion of 2-Cyano 3-Substituted Indoles to Spiro-Annelated Indolines and Tetrahydrocarbazolones
Yang, Chau-Chen,Chang, Han-Ting,Fang, Jim-Min
, p. 3100 - 3105 (2007/10/02)
Oxidative photocyclizations of appropiate 2-anilino alkenenitriles (6) afforded a series of indole-2-carbonitriles (7) having bromoalkyl substituents at the C-3 positions.Upon treatment with Bu3SnH, these indolecarbonitriles underwent intramolecular cycli
REACTIVITE PHOTOCHIMIQUE DES α-AMINOENONES: REACTIONS DE CYCLISATION ET NOUVEAU TYPE DE REACTION DANS LES α-SULFONAMIDOCYCLOHEXENONES
Arnould, J.C.,Cossy, J.,Pete, J.P.
, p. 1585 - 1592 (2007/10/02)
The photochemical behaviour of 2-alkylamino 2-cyclohexenones is very sensitive to the nitrogen substituents. α-Ketoazetidines are produced by irradiation of 2-methanesulfonamido-2-cyclohexenones; however a desulfonation and aryl migration process can complete in the case of 2-arenesulfonamido-2-cyclohexenones.Furthermore divinylamine and photo-Fries rearrangements are the main reactions with 2-anilino 2-cyclohexenone and 2-benzoylamido 2-cyclohexenone respectively.
