- An entry to 2-(cyclobut-1-en-1-yl)-1: H -indoles through a cyclobutenylation/deprotection cascade
-
A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles. Preliminary experimental and density functional theory calculations suggest that a Boc-group transfer is involved in the underlying mechanism.
- Natho, Philipp,Yang, Zeyu,Allen, Lewis A. T.,Rey, Juliette,White, Andrew J. P.,Parsons, Philip J.
-
supporting information
p. 4048 - 4053
(2021/05/19)
-
- Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- And C3-Borylated Indolines
-
Indole dearomatization is an important strategy to access indolines: a motif present in a variety of natural products and biologically active molecules. Herein, a method for transition-metal catalyzed regioselective dearomative arylboration of indoles to
- Brown, M. Kevin,Crook, Phillip F.,Kuniyil, Rositha,Liu, Peng,Trammel, Grace L.
-
supporting information
p. 16502 - 16511
(2021/10/20)
-
- Synthesis and antiproliferative activity of substituted 3[2-(1h-indol-3-yl)- 1,3-thiazol-4-yl]-1h-pyrrolo[3,2-b]pyridines, marine alkaloid nortopsentin analogues
-
A large number of indolyl-4-azaindolyl thiazoles, nortopsentin analogues, were conveniently synthesized. The antiproliferative activity of the new derivatives was examined against four human tumor cell lines with different histologic origin. Seven derivatives consistently reduced the growth of the experimental models independently of TP53 gene status and exhibited the highest activity against the malignant peritoneal mesothelioma (STO) cell line. The most active compound of this series acts as a CDK1 inhibitor, and was found to cause cell cycle arrest at G2/M phase, to induce apoptosis by preventing the phosphorylation of survivin in Thr34 and to increase the cytotoxic activity of paclitaxel in STO cells.
- Carbone,Pennati,Barraja,Montalbano,Parrino,Spanò,Lopergolo,Sbarra,Doldi,Zaffaroni,Cirrincione,Diana
-
p. 1654 - 1666
(2014/05/20)
-
- SUBSTITUTED BENZOFURAN COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
-
The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.
- -
-
Page/Page column 89; 90
(2013/03/26)
-
- Novel 1H-pyrrolo[2,3-b]pyridine derivative nortopsentin analogues: Synthesis and antitumor activity in peritoneal mesothelioma experimental models
-
In this study, we describe the synthesis of new nortopsentin analogues, 1H-pyrrolo[2,3-b]pyridine derivatives and their biological effects in experimental models of diffuse malignant peritoneal mesothelioma (DMPM), a rare and rapidly fatal disease, poorly responsive to conventional therapies. The three most active compounds, 1f (3-[2-(5-fluoro-1-methyl-1H-indol-3-yl)-1,3- thiazol-4-yl]-1H-pyrrolo[2,3-b]pyridine), 3f (3-[2-(1H-indol-3-yl)-1,3-thiazol- 4-yl]-1-methyl-1H-pyrrolo[2,3-b]pyridine), and 1l (3-[2-(5-fluoro-1-methyl-1H- indol-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrolo[2,3-b] pyridine), which were shown to act as cyclin-dependent kinase 1 inhibitors, consistently reduced DMPM cell proliferation and induced a caspase-dependent apoptotic response, with a concomitant reduction of the expression of the active Thr34- phosphorylated form of the antiapoptotic protein survivin. Moreover, the combined treatment of DMPM cells with 3f derivative and paclitaxel produced a synergistic cytotoxic effect, which was paralleled by an enhanced apoptotic response. In the mouse model, i.p. administration of 1f, 3f, and 1l derivatives was effective, resulting in a significant tumor volume inhibition of DMPM xenografts (range, 58-75%) at well-tolerated doses, and two complete responses were observed in each treatment group.
- Carbone, Anna,Pennati, Marzia,Parrino, Barbara,Lopergolo, Alessia,Barraja, Paola,Montalbano, Alessandra,Spanò, Virginia,Sbarra, Stefania,Doldi, Valentina,De Cesare, Michelandrea,Cirrincione, Girolamo,Diana, Patrizia,Zaffaroni, Nadia
-
p. 7060 - 7072
(2013/10/01)
-
- Palladium catalyzed tandem alkenyl- and aryl-C-N bond formation: A cascade N-annulation route to 4-, 5-, 6- and 7-chloroindoles
-
A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the N-nucleophile.
- Henderson, Luke C.,Lindon, Matthew J.,Willis, Michael C.
-
experimental part
p. 6632 - 6638
(2010/10/03)
-
- SUBSTITUTED PYRAZOLES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE
-
The present invention relates to substituted pyrazoles, compositions containing such compounds and methods of treatment. The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes
- -
-
Page/Page column 33-34
(2008/06/13)
-
- A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols
-
2-Indolyl borates are prepared via addition of LDA to a mixture of N-Bo-indole and triisopropyl borate at 0-5 °C. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).
- Vazquez, Enrique,Davies, Ian W.,Payack, Joseph F.
-
p. 7551 - 7552
(2007/10/03)
-
- Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines
-
Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).
- Clark,Muchowski,Fisher,Flippin,Repke,Souchet
-
p. 871 - 878
(2007/10/02)
-
