19017-00-6Relevant academic research and scientific papers
Copper-Catalyzed Oxidative Cyclization of Alkynes with Sulfonylhydrazides Leading to 2-Sulfonated 9H-pyrrolo[1,2-a]indol-9-ones
Zhu, Xin-Yu,Li, Ming,Han, Ya-Ping,Chen, Si,Li, Xue-Song,Liang, Yong-Min
, p. 8761 - 8768 (2017)
A copper-catalyzed oxidative cyclization procedure has been developed for the production of 2-sulfonated 9H-pyrrolo[1,2-a]indol-9-ones via the direct sulfonylation of N-propargyl-substituted indoles with sulfonylhydrazides and tert-butyl hydroperoxide (TBHP). This novel protocol, which tolerates a broad range of functional groups, offers a simple, efficient, and atom-economical route to a series of fluorazones in good yields under mild conditions.
A tunable copper-catalyzed multicomponent reaction towards alkaloid-inspired indole/lactam polycycles
Mardjan,Perie,Parrain,Commeiras
, p. 3304 - 3309 (2017)
A versatile copper(i)-catalyzed cascade multicomponent reaction strategy between readily available (Z)-3-iodoacrylic acids, terminal alkynes, and primary amines is reported, leading to a great diversity of complex heterocyclic backbones based on biorelevant indole/lactam scaffolds.
[1,3]-Dipolar cycloaddition of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)-1H-indole
Dürüst, Ya?ar,Sa?irli, Akin,Kariuki, Benson M.,Knight, David W.
, p. 6012 - 6019 (2014)
[1,3]-Dipolar cycloadditions of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)indole gave fused pyrazole derivatives when carried out in refluxing toluene. While the first two dipolarophiles gave single regi
Amalgamating Isatin/Indole/Nitroimidazole with 7-chloroquinolines via azide-alkyne cycloaddition: Synthesis, anti-plasmodial, and cytotoxic evaluation
Kumar, Sumit,Saini, Anu,Legac, Jenny,Rosenthal, Philip J.,Raj, Raghu,Kumar, Vipan
, p. 1355 - 1361 (2020)
The present paper describes the synthesis, anti-plasmodial, and cytotoxic evaluation of 7-chloroquinoline-based conjugates with isatins/indoles/ nitroimidazoles, obtained via Cu-promoted 1,3-dipolar cycloadditions. On contemplating SAR of the synthesized series, the inclusion of indole and nitroimidazole-core improved the anti-plasmodial activities while the isatin seemed to have a lesser effect. The conjugate with a nitroimidazole-core and hexyl chain length as a spacer between the two pharmacophores was found to be most potent among the synthesized series and displayed an IC50 of 0.12?μM and a selectivity index of 1748.
“Click” reaction mediated synthesis of costunolide and dehydrocostuslactone derivatives and evaluation of their cytotoxic activity
Pavan Kumar, Ch.,Devi,Ashok Yadav,Rao Vadaparthi,Shankaraiah,Sowjanya,Jain, Nishant,Suresh Babu
, p. 1063 - 1078 (2016)
As part of pharmacological–phytochemical integrated studies on medicinal plants from Indian flora, costunolide (1) and dehydrocostus lactone (2), were isolated as major phytochemicals from Saussurea lappa, a plant traditionally used in different Asian systems of medicine. A series of 1,4-disubstituted-1,2,3-triazoles conjugates were synthesized through diastereo selective Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reactions. All these triazolyl derivatives (5a–5j) & (7a–7j) were well characterized using modern spectroscopic techniques and evaluated for their anticancer activity against a panel of five human cancerous celllines. The results indicated that all the analogs displayed moderate cytotoxic activity.
Tandem Carbenoid C-H Functionalization/Conia-ene Cyclization of N-Propargyl Indoles Generates Pyrroloindoles under Cooperative Rh(II)/Zn(II) Catalysis
Bhat, Aabid H.,Alavi, Sima,Grover, Huck K.
supporting information, p. 224 - 229 (2020/02/20)
The decomposition of diazodicarbonyl compounds in the presence of various metal catalysts has become a reliable method for the functionalization of indoles via carbenoid intermediates. Exploiting the nucleophilic reactivity of the in situ generated malonic ester product formed, we herein report a tandem C-H functionalization/Conia-ene cyclization of N-alkyne tethered indoles. This double functionalization of diazodicarbonyls generates a range of pyrrolo[1,2-a]-, pyrido[1,2-a]-, and azepino[1,2-a]indole products with good synthetic efficiency.
Purine and purine isostere derivatives of ferrocene: An evaluation of ADME, antitumor and electrochemical properties
?imek, Helena,Grb?i?, Petra,Jadre?ko, Dijana,Markovi?, Vesna Gabelica,Mi?eti?, Petra,Padovan, Jasna,Paveli?, Kre?imir,Paveli?, Sandra Kraljevi?,Pi?kor, Martina,Rai?-Mali?, Silvana,Rep, Valentina
, (2020/04/10)
Novel purine and purine isosteres containing a ferrocene motif and 4,1-disubstituted (11a?11c, 12a?12c, 13a?13c, 14a?14c, 15a?15c, 16a, 23a?23c, 24a?24c, 25a?25c) and 1,4-disubstituted (34a?34c and 35a?35c) 1,2,3-triazole rings were synthesized. The most
Catalytic Tandem Friedel-Crafts Alkylation/C4-C3 Ring-Contraction Reaction: An Efficient Route for the Synthesis of Indolyl Cyclopropanecarbaldehydes and Ketones
Turnu, Francesca,Luridiana, Alberto,Cocco, Andrea,Porcu, Stefania,Frongia, Angelo,Sarais, Giorgia,Secci, Francesco
supporting information, p. 7329 - 7332 (2019/10/02)
A general strategy for the synthesis of indolyl cyclopropanecarbaldehydes and ketones via a Br?nsted acid-catalyzed indole nucleophilic addition/ring-contraction reaction sequence has been exploited. The procedure leads to a wide panel of cyclopropyl carbonyl compounds in generally high yields with a broad substrate scope.
Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors
Fu, Dong-Jun,Li, Ping,Wu, Bo-Wen,Cui, Xin-Xin,Zhao, Cheng-Bin,Zhang, Sai-Yang
, p. 309 - 322 (2019/01/30)
Structurally diverse trimethoxyphenyl-1,2,3-triazole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three cancer cell lines (PC3, MGC803 and HepG2). Among them, trimethoxyphenyl-1,2,3-triazole containing the
Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis
Rochette, étienne,Desrosiers, Vincent,Soltani, Yashar,Fontaine, Frédéric-Georges
supporting information, p. 12305 - 12311 (2019/08/20)
The potential advantages of using arylboronic esters as boron sources in C-H borylation are discussed. The concept is showcased using commercially available 2-mercaptopyridine as a metal-free catalyst for the transfer borylation of heteroarenes using arylboronates as borylation agents. The catalysis shows a unique functional group tolerance among C-H borylation reactions, tolerating notably terminal alkene and alkyne functional groups. The mechanistic investigation is also described.
