59050-53-2Relevant academic research and scientific papers
Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction
Arion, Vladimir B.,Bacher, Felix,Chuang, Hsiang-Yu,Kuznetcova, Irina,Vegh, Daniel
, p. 143 - 151 (2022/02/05)
Paullone isomers are known as inhibitors of tubulin polymerase and cyclin dependent kinases (Cdks), which are potential targets for cancer chemotherapy. Herein we report an efficient and clean pathway to the fourth isomer, which remained elusive so far, namely 7,8-dihydroindolo[2,3-d][1]benzazepin-6(5H)-one. Moreover, we demonstrate the generality of our pathway by synthesizing two closely related analogues, one containing a bromo substituent and the other one incorporating an 8-membered instead of a 7-mem-bered ring. The key transformation in this four-step synthesis, with an overall yield of 29%, is the Fischer indole reaction of 2-nitro-phenylacetyl acetoacetate with 1-benzyl-1-phenylhydrazine in acetic acid that delivers methyl 2-(1-benzyl-3-(2-nitrophenyl)-1H-indol-2-yl)acetate in 55% yield.
Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties
Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto
supporting information, p. 13613 - 13623 (2021/08/23)
A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.
Novel convenient one-pot method for the synthesis of indoloquinolines
Aksenov,Gasanova,Abakarov,Aksenova,Aksenov
, p. 836 - 840 (2019/06/03)
A novel one-pot method based on the sequence of the Fisher reaction between nitroacetophenone and phenylhydrazines, the reduction with metallic tin directly in polyphosphoric acid, and acylation has been developed for the synthesis of indoloquinolines. Th
Access to 2-Arylindoles via Decarboxylative C?C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts
Arun, Velladurai,Pilania, Meenakshi,Kumar, Dalip
supporting information, p. 3345 - 3349 (2016/12/14)
Easily accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2-arylindoles and heteroaryl carboxylates in a regioselective fashion. C2-arylated indoles were produced using a Pd-catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base-free conditions. This protocol was successfully utilized to synthesize Paullone, a cyclin-dependent kinase (CDK) inhibitor.
Activity of 2-aryl-2-(3-indolyl)acetohydroxamates against drug-resistant cancer cells
Aksenov, Alexander V.,Smirnov, Alexander N.,Magedov, Igor V.,Reisenauer, Mary R.,Aksenov, Nicolai A.,Aksenova, Inna V.,Pendleton, Alexander L.,Nguyen, Gina,Johnston, Robert K.,Rubin, Michael,De Carvalho, Annelise,Kiss, Robert,Mathieu, Véronique,Lefranc, Florence,Correa, Jaime,Cavazos, David A.,Brenner, Andrew J.,Bryan, Brad A.,Rogelj, Snezna,Kornienko, Alexander,Frolova, Liliya V.
, p. 2206 - 2220 (2015/03/30)
Many types of tumor, including glioma, melanoma, non-small cell lung, esophageal, and head and neck cancer, among others, are intrinsically resistant to apoptosis induction and poorly responsive to current therapies with proapoptotic agents. In addition, tumors often develop multidrug resistance based on the cellular efflux of chemotherapeutic agents. Thus, novel anticancer agents capable of overcoming these intrinsic or developed tumor resistance mechanisms are urgently needed. We describe a series of 2-aryl-2-(3-indolyl)acetohydroxamic acids that are active against apoptosis-and multidrug-resistant cancer cells as well as glioblastoma neurosphere stemlike cell cultures derived from patients. Thus, the described compounds serve as a novel chemical scaffold for the development of potentially highly effective clinical cancer drugs.
Synthesis of 2-Substituted Indoles through Visible Light-Induced Photocatalytic Cyclizations of Styryl Azides
Xia, Xu-Dong,Xuan, Jun,Wang, Qiang,Lu, Liang-Qiu,Chen, Jia-Rong,Xiao, Wen-Jing
, p. 2807 - 2812 (2016/02/18)
A visible light-induced photocatalytic intramolecular cyclization of styryl azides has been developed in the presence of the ruthenium complex Ru(bpy)3Cl2 (0.5 mol%) as photocatalyst at room temperature. The present photocatalytic strategy features operational simplicity as well as high functional group tolerance, and provides a facile access to various 2-substituted N-free indoles in good to excellent yields. Importantly, the present process can employ sunlight as the light source to afford the corresponding products without loss of reaction efficiency.
Concise synthesis and CDK/GSK inhibitory activity of the missing 9-azapaullones
Power, David P.,Lozach, Olivier,Meijer, Laurent,Grayson, David H.,Connon, Stephen J.
body text, p. 4940 - 4944 (2010/10/04)
A remarkably concise, chromatography-free route to the parent compound of the paullone family of cyclin-dependent kinase (CDK) inhibitors is reported. A similar strategy allowed the synthesis of the hitherto missing 9-azapaullone and its protonated, N-oxidised and N-alkylated derivatives. Screening studies identified an active and strongly selective inhibitor of CDK9/cyclin T.
A flexible synthesis of indoles from ortho -substituted anilines: A direct synthesis of isocryptolepine
Kraus, George A.,Guo, Haitao,Kumar, Ganesh,Pollock Iii, Gerald,Carruthers, Heather,Chaudhary, Divya,Beasley, Jonathan
experimental part, p. 1386 - 1393 (2010/07/16)
The reaction of anilines bearing a benzylic activating group in the ortho position with aromatic aldehydes or α,β-unsaturated aldehydes results in an efficient synthetic route to substituted indoles. Georg Thieme Verlag Stuttgart · New York.
Synthesis of new fused and substituted benzo and pyrido carbazoles via C-2 (het)arylindoles
Bourderioux, Aurélie,Kassis, Paméla,Mérour, Jean-Yves,Routier, Sylvain
experimental part, p. 11012 - 11019 (2009/04/11)
In the course of a program aimed at designing new antitumor agents, we were interested in the synthesis of new substituted benzo and pyrido carbazoles. The synthesis was performed through an efficient four-step sequence from a 2-trimethylstannylindole derivative and via C-2 (het)arylindoles. The synthetic sequence was developed using two palladium mediated reactions including, at the end of the synthesis, a direct (het)arylannulation, which led to the desired heterocycles.
Structure-activity relationships of antimalarial indoloquinolines
Werbel, L. M.,Kesten, S. J.,Turner, W. R.
, p. 837 - 852 (2007/10/02)
Structure-activity relationships have been ascertained and chemical metodology developed for a series of antimalarial 3-chloroindoloquinoline-5-oxides.The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3.Substitution at positions 7,8,9,10 in not essential, although the most potent analog in our studies was the 8-nitro compound 4vv. indoloquinolines / antimalarial agents
