- Copper-Catalyzed Oxidative Cyclization of Alkynes with Sulfonylhydrazides Leading to 2-Sulfonated 9H-pyrrolo[1,2-a]indol-9-ones
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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.
- Zhu, Xin-Yu,Li, Ming,Han, Ya-Ping,Chen, Si,Li, Xue-Song,Liang, Yong-Min
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- A tunable copper-catalyzed multicomponent reaction towards alkaloid-inspired indole/lactam polycycles
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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.
- Mardjan,Perie,Parrain,Commeiras
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- [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
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[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
- Dürüst, Ya?ar,Sa?irli, Akin,Kariuki, Benson M.,Knight, David W.
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- Amalgamating Isatin/Indole/Nitroimidazole with 7-chloroquinolines via azide-alkyne cycloaddition: Synthesis, anti-plasmodial, and cytotoxic evaluation
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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.
- Kumar, Sumit,Saini, Anu,Legac, Jenny,Rosenthal, Philip J.,Raj, Raghu,Kumar, Vipan
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- “Click” reaction mediated synthesis of costunolide and dehydrocostuslactone derivatives and evaluation of their cytotoxic activity
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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.
- Pavan Kumar, Ch.,Devi,Ashok Yadav,Rao Vadaparthi,Shankaraiah,Sowjanya,Jain, Nishant,Suresh Babu
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- Tandem Carbenoid C-H Functionalization/Conia-ene Cyclization of N-Propargyl Indoles Generates Pyrroloindoles under Cooperative Rh(II)/Zn(II) Catalysis
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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.
- Bhat, Aabid H.,Alavi, Sima,Grover, Huck K.
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supporting information
p. 224 - 229
(2020/02/20)
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- Purine and purine isostere derivatives of ferrocene: An evaluation of ADME, antitumor and electrochemical properties
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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
- ?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
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- Catalytic Tandem Friedel-Crafts Alkylation/C4-C3 Ring-Contraction Reaction: An Efficient Route for the Synthesis of Indolyl Cyclopropanecarbaldehydes and Ketones
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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.
- Turnu, Francesca,Luridiana, Alberto,Cocco, Andrea,Porcu, Stefania,Frongia, Angelo,Sarais, Giorgia,Secci, Francesco
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supporting information
p. 7329 - 7332
(2019/10/02)
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- Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors
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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
- Fu, Dong-Jun,Li, Ping,Wu, Bo-Wen,Cui, Xin-Xin,Zhao, Cheng-Bin,Zhang, Sai-Yang
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p. 309 - 322
(2019/01/30)
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- Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis
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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.
- Rochette, étienne,Desrosiers, Vincent,Soltani, Yashar,Fontaine, Frédéric-Georges
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supporting information
p. 12305 - 12311
(2019/08/20)
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- Design and synthesis of multipotent 3-aminomethylindoles and 7-azaindoles with enhanced protein phosphatase 2A-activating profile and neuroprotection
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We report the synthesis and pharmacological evaluation of new 3-aminomethylindoles derivatives with neuroprotective properties designed to present multi-target activity centered on reducing the neuronal Ca2+ overload and preventing phosphatase
- Lajarín-Cuesta, Rocío,Arribas, Raquel L.,Nanclares, Carmen,García-Frutos, Eva M.,Gandía, Luis,de los Ríos, Cristóbal
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p. 294 - 309
(2018/08/17)
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- Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source
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The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.
- Zhang, Xingjie,Xie, Xin,Liu, Yuanhong
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supporting information
p. 7385 - 7389
(2018/06/11)
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- Bodipy-squaraine triads: Preparation and study of the intramolecular energy transfer, charge separation and intersystem crossing
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Two triads (BDP-SQ and Styryl-BDP-SQ) were prepared with Bodipy, styrylBodipy and Squaraine (SQ) units. SQ shows unexpected efficient intersystem crossing (ISC. ΦT = 50%), which is attributed to S1→T1 transition. In the two triads, the F?rster Resonance Energy Transfer (FRET) direction, as well as the spatial localization of the T1 state, was judiciously tuned. The cascade photophysical properties of the triads were studied with steady-state and time-resolved optical spectroscopies, as well as with electrochemical characterization and theoretical computations. We show that triplet state was produced in triad BDP-SQ upon photoexcitation, but in Styryl-BDP-SQ the fast FRET and the charge separation (CS) processes compete with the ISC of the SQ unit, and no triplet state was formed upon photoexcitation. The singlet energy transfer kinetics were found to be 1.6 and 0.6 ps, respectively and are solvent polarity dependent. Charge transfer was confirmed with ultrafast transient absorption spectroscopy.
- Dong, Yu,Iagatti, Alessandro,Foggi, Paolo,Zhao, Jianzhang,Mazzone, Gloria,Xu, Kejing,Ji, Wei,Di Donato, Mariangela,Russo, Nino
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p. 560 - 572
(2017/09/08)
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- Design, synthesis and antifungal activity of novel indole derivatives linked with the 1,2,3-triazole moiety via the CuAAC click reaction
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A series of novel indole derivatives linked with the 1,2,3-triazole moiety was designed, synthesised by the CuCl2/Zn-catalysed Huisgen cycloaddition and characterised. The antifungal activity of all the prepared compounds against Colletotrichum capsici and cotton Physalospora pathogens was evaluated and the results indicated that these compounds showed inhibitory effect for fungi and the inhibition ratio of the best was up to 83.3%. The preliminary structure-activity relationship is also discussed in this paper.
- Xu, Guiqing,Zhao, Jinglin,Jiang, Yuqin,Zhang, Peng,Li, Wei
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p. 269 - 272
(2016/07/06)
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- Electrophilic Cyclization of Aryl Propargylic Alcohols: Synthesis of Dihalogenated 6,9-Dihydropyrido[1,2-a]indoles via a Cascade Iodocyclization
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A strategy for the synthesis of 6,9-dihydropyrido[1,2-a]indoles through a cascade iodocyclization of 4-(3-methyl-1H-indol-1-yl)-1,1-diphenylbut-2-yn-1-ol derivatives is presented. This reaction was conducted under very mild conditions and in a short time. The reactions are metal-free, are environmentally friendly and give up to 94% yield. Moreover, the obtained halides allow functional group diversification by palladium-catalyzed coupling reactions, which could act as potential intermediates for the synthesis of valuable compounds.
- Wang, Jia,Zhu, Hai-Tao,Chen, Si,Xia, Yu,Jin, Dong-Po,Qiu, Yi-Feng,Li, Ying-Xiu,Liang, Yong-Min
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supporting information
p. 10975 - 10986
(2016/11/28)
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- HETEROARYL COMPOUNDS FOR KINASE INHIBITION
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Compounds and pharmaceutical compositions that modulate kinase activity, including mutant EGFR and mutant HER2 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including mutant EGFRand mutant HER2 activity, are described herein.
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Paragraph 00404
(2016/12/01)
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- Synthesis and evaluation of N-heteroarylsubstituted triazolosulfonamides as carbonic anhydrase inhibitors
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A new series of N-heteroarylsubstituted triazolosulfonamide compounds were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase (hCA) I and II were evaluated. Compounds (3 a-k) were prepared by propargylation of N-heteroaryl compounds. Compound 5 was obtained from sulfanilamide and sodium nitrite followed by addition of sodium azide. The products (6 a-k) were synthesized from compounds 3 and 5. The results showed that all the synthesized compounds were inhibited the CA isoenzymes activity. Figure 6a (IC50 = 0.52 μM for hCA I and 0.34 μM for hCA II) has the most inhibitory effect among the synthesized compounds.
- Balci, Ahmet,Arslan, Mustafa,Nixha, Arleta Rifati,Bilen, Cigdem,Ergun, Adem,Gen?er, Nahit
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p. 377 - 382
(2015/07/27)
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- An eco-friendly synthesis of novel 3,5-disubstituted-1,2-isoxazoles in PEG-400, employing the Et3N-promoted hydroamination of symmetric and unsymmetric 1,3-diyne-indole derivatives
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A facile, efficient and atom-economic synthesis of 3,5-disubstituted 1,2-isoxazoles bearing indole moieties, is reported. The synthesis of these isoxazoles was carried out by the triethylamine-promoted reaction of symmetric and unsymmetric 1,3-diyne indole derivatives with hydroxylamine in PEG-400, as an eco-friendly solvent, under relatively mild conditions. The synthesis of the starting 1,3-diyne indole derivatives was performed by the aerobic self-coupling of diversely functionalized N-propargyl indoles and N-propargyl carbazole under copper catalysis, or by the reaction of the propargyl derivatives with phenyl- or p-tolyl-acetylene under combined nickel and copper catalysis. The isoxazolation reaction was optimized, its scope and limitations were studied and a detailed reaction mechanism was proposed.
- Bassaco, Mariana M.,Fortes, Margiani P.,Back, Davi F.,Kaufman, Teodoro S.,Silveira, Claudio C.
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p. 60785 - 60797
(2015/02/19)
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- Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation: C-H versus C-C cleavage in TMEDA
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Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation reactions have been achieved under facile and mild conditions. TMEDA coupled with various terminal alkynes via C-H bond cleavage in good yields using atmospheric oxygen as an oxidant. Switching from air to TBHP afforded aminomethylation products of terminal alkynes through C-C bond cleavage of TMEDA. The protocol provided a novel strategy to prepare bi/tridentate N-ligand.
- Shen, Qi,Zhang, Lei,Zhou, Yu-Ren,Li, Jian-Xin
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supporting information
p. 6725 - 6728
(2013/11/19)
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- Platinum-catalysed bisindolylation of allenes: A complementary alternative to gold catalysis
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Pt versus Au: Platinum-catalysed addition of nucleophiles to allenes follows a distinctly different pathway to the process catalysed by gold(I) complexes; the platinum catalyst leads to different products with indoles involving a bisindolylation reaction, whereas gold(I) gives allyl indoles from a single addition (see scheme).
- Munoz, Maria Paz,De La Torre, Maria C.,Sierra, Miguel Angel
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supporting information; experimental part
p. 4499 - 4504
(2012/05/05)
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- Gold-catalyzed annulations of 1-(2,3-butadienyl)-1H-indole derivatives
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Gold-ringing! Modification of the substitution at C2 drives an entirely different cyclization of N-tethered allenylindoles. An efficient cycloisomerization takes place for the case of R being hydrogen, that is, compatible with additional functional groups. A methyl at C2 precludes this possibility and launches a stepwise process that can be tuned to yield macrocyclic trimers.
- Barluenga, Jose,Piedrafita, Maria,Ballesteros, Alfredo,Suarez-Sobrino, Angel L.,Gonzalez, Jose M.
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supporting information; experimental part
p. 11827 - 11831
(2011/01/04)
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- Regioselective synthesis and biological evaluation of bis(indolyl)methane derivatized 1,4-disubstituted 1,2,3-bistriazoles as anti-infective agents
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The regioselective synthesis of 1,4-disubstituted 1,2,3-bistriazoles from a variety of N-propargyl bis(indolyl)methanes with sodium azide using CuI as the catalyst in polyethyleneglycol-400 is reported. This process is of considerable synthetic advantages
- Damodiran,Muralidharan,Perumal, Paramasivan T.
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experimental part
p. 3611 - 3614
(2010/03/31)
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- SYNTHESIS OF SOME DERIVATIVES OF INDOLE AND INDOLOINDOLES UNDER CONDITIONS OF INTERPHASE CATALYSIS
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The preparation of N-alkyl and N,N-dialkyl derivatives of indole, 3H,8H-indolo-, 3H,8H-indolo-, and 1H,6H-indoloindole under conditions of interphase catalysis is studied.In the case of indole, it is found possible to form 1,3-dipropa
- Samsoniya, Sh. A.,Esakiya, N. A.,Suvorov, N. N.
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p. 366 - 369
(2007/10/02)
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- 1,3-Dipolar Cycloadditions to Nitrogen-substituted Allenes
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A series of nitrogen-substituted allenes (2a-h) was treated with 3,5-dichloro-2,4,6-trimethylbenzonitrile oxide (4) in boiling tetrachloromethane.The reaction occured predominantly (or exclusively) at the α,β double bond.Regardless of the site of cycloaddition, the carbon of the nitrile oxide bonded selectively to the central carbon of the allene. 4-Methylene-4,5-dihydroisoxazole monoadducts (5) reacted further to form spiro-diadducts.The stereochemistry of one diadduct was determined by X-ray diffraction analysis.
- Broggini, Gianluigi,Bruche, Luca,Zecchi, Gaetano,Pilati, Tullio
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p. 533 - 539
(2007/10/02)
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- Selective N-Prop-2-ynylation of Heterocycles induced by Solid-Liquid Phase Transfer Catalysis without Solvent and Use of Solid Inorganic Supports
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Complementary processes promote the N-prop-2-ynylation of heterocycles: solid-liquid phase transfer catalysis without added solvent in the presence or absence of alumina or titanium dioxide and alkylation on 'basic' alumina in 'dry media'.
- Galons, Herve,Bergerat, Isabelle,Combet-Farnoux, Claude,Miocque, Marcel,Decodts, Guy,Bram, Georges
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p. 1730 - 1731
(2007/10/02)
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