16800-68-3Relevant articles and documents
Construction of Oxepino[3,2-b]indoles via [4+3] Annulation of 2-Ylideneoxindoles with Crotonate-Derived Sulfur Ylides
Fei, Xing-Hai,Guan, Xiang,He, Bin,Li, Zong-Qin,Wang, Da-Peng,Yang, Fen-Fen,Yang, Yuan-Yong,Zhao, Yong-Long,Zhou, Meng
, p. 3018 - 3024 (2021/06/26)
A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed. A series of oxepino[3,2-b]indoles were prepared in moderate to excellent yields (62-93%) under mild conditions. Moreover, the synthetic oxepino[3,2-b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF-7 cells, and its IC50 values for these two kinds of tumor cells up to 5.40±0.88 μM and 18.41±0.50 μM, respectively. (Figure presented.).
Phenylimino Indolinone: A Green-Light-Responsive T-Type Photoswitch Exhibiting Negative Photochromism
Buma, Wybren Jan,Crespi, Stefano,Di Donato, Mariangela,Doria, Sandra,Feringa, Ben L.,Hilbers, Michiel F.,Kiss, Ferdinand L.,Simeth, Nadja A.,Stindt, Charlotte N.,Szymański, Wiktor,Toyoda, Ryojun,Wesseling, Sammo
, p. 25290 - 25295 (2021/10/25)
Imines are photoaddressable motifs useful in the development of new generations of molecular switches, but their operation with low-energy photons and control over isomer stability remain challenging. Based on a computational design, we developed phenylimino indolinone (PIO), a green-light-addressable T-type photoswitch showing negative photochromism. The isomerization behavior of this photoactuator of the iminothioindoxyl (ITI) class was studied using time-resolved spectroscopies on time scales from femtoseconds to the steady state and by quantum-chemical analyses. The understanding of the isomerization properties and substituent effects governing these photoswitches opens new avenues for the development of novel T-type visible-light-addressable photoactuators based on C=N bonds.
Azaaurones as Potent Antimycobacterial Agents Active against MDR- and XDR-TB
Campani?o, André,Carrasco, Marta P.,Njoroge, Mathew,Seldon, Ronnett,Chibale, Kelly,Perdig?o, Jo?o,Portugal, Isabel,Warner, Digby F.,Moreira, Rui,Lopes, Francisca
, p. 1537 - 1546 (2019/08/02)
Herein we report the screening of a small library of aurones and their isosteric counterparts, azaaurones and N-acetylazaaurones, against Mycobacterium tuberculosis. Aurones were found to be inactive at 20 μm, whereas azaaurones and N-acetylazaaurones emerged as the most potent compounds, with nine derivatives displaying MIC99 values ranging from 0.4 to 2.0 μm. In addition, several N-acetylazaaurones were found to be active against multidrug-resistant (MDR) and extensively drug-resistant (XDR) clinical M. tuberculosis isolates. The antimycobacterial mechanism of action of these compounds remains to be determined; however, a preliminary mechanistic study confirmed that they do not inhibit the mycobacterial cytochrome bc1 complex. Additionally, microsomal metabolic stability and metabolite identification studies revealed that N-acetylazaaurones are deacetylated to their azaaurone counterparts. Overall, these results demonstrate that azaaurones and their N-acetyl counterparts represent a new entry in the toolbox of chemotypes capable of inhibiting M. tuberculosis growth.
Potent Inhibitors of Plasmodial Serine Hydroxymethyltransferase (SHMT) Featuring a Spirocyclic Scaffold
Schwertz, Geoffrey,Witschel, Matthias C.,Rottmann, Matthias,Leartsakulpanich, Ubolsree,Chitnumsub, Penchit,Jaruwat, Aritsara,Amornwatcharapong, Watcharee,Ittarat, Wanwipa,Sch?fer, Anja,Aponte, Raphael A.,Trapp, Nils,Chaiyen, Pimchai,Diederich, Fran?ois
, p. 931 - 943 (2018/04/20)
With the discovery that serine hydroxymethyltransferase (SHMT) is a druggable target for antimalarials, the aim of this study was to design novel inhibitors of this key enzyme in the folate biosynthesis cycle. Herein, 19 novel spirocyclic ligands based on
Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites
Carrasco, Marta P.,Machado, Marta,Gon?alves, Lídia,Sharma, Moni,Gut, Jiri,Lukens, Amanda K.,Wirth, Dyann F.,André, Vania,Duarte, Maria Teresa,Guedes, Rita C.,dos Santos, Daniel J. V. A.,Rosenthal, Philip J.,Mazitschek, Ralph,Prudêncio, Miguel,Moreira, Rui
, p. 2194 - 2204 (2016/10/19)
The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.
N-heterocyclic carbene-catalyzed enantioselective annulation of indolin-3-ones with bromoenals
Ni, Qijian,Song, Xiaoxiao,Raabe, Gerhard,Enders, Dieter
, p. 1535 - 1538 (2014/06/09)
N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented. More NHC-organocatalysis: N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented.
Identification, design and biological evaluation of heterocyclic quinolones targeting plasmodium falciparum Type II NADH:Quinone oxidoreductase (PfNDH2)
Leung, Suet C.,Gibbons, Peter,Amewu, Richard,Nixon, Gemma L.,Pidathala, Chandrakala,Hong, W. David,Pacorel, Bénédicte,Berry, Neil G.,Sharma, Raman,Stocks, Paul A.,Srivastava, Abhishek,Shone, Alison E.,Charoensutthivarakul, Sitthivut,Taylor, Lee,Berger, Olivier,Mbekeani, Alison,Hill, Alasdair,Fisher, Nicholas E.,Warman, Ashley J.,Biagini, Giancarlo A.,Ward, Stephen A.,O'Neill, Paul M.
, p. 1844 - 1857 (2012/05/05)
Following a program undertaken to identify hit compounds against NADH:ubiquinone oxidoreductase (PfNDH2), a novel enzyme target within the malaria parasite Plasmodium falciparum, hit to lead optimization led to identification of CK-2-68, a molecule suitab
Design, synthesis and pharmacological evaluation of conformationally restricted N-arylsulfonyl-3-aminoalkoxy indoles as a potential 5-HT6 receptor ligands
Nirogia, Ramakrishna V.S.,Kambhampati, Ramasastri,Daulatabad, Anand V.,Gudla, Parandhama,Shaikh, Mohammad,Achanta, Pramod Kumar,Shinde, Anil K.,Dubey, Pramod Kumar
, p. 341 - 349 (2012/01/06)
A series of novel conformationally restricted N1-arylsulfonyl-3-aminoalkoxy indoles were designed and synthesized as 5-HT6 receptor (5-HT6R) ligands. Many of the synthesized compounds have moderate in vitro-binding affinities at 5-HT6R. The lead compound 8b (% inhibition=97.2 at 1 μM) from this series has good pharmacokinetic profile in male Wister rats and is active in animal model of cognition like Morris water maze. The details of chemistry, SAR, pharmacokinetics and pharmacological data constitute the subject matter of this report.
Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists
Nirogi, Ramakrishna V.S.,Deshpande, Amol D.,Kambhampati, Ramasastri,Badange, Rajesh Kumar,Kota, Laxman,Daulatabad, Anand V.,Shinde, Anil K.,Ahmad, Ishtiyaque,Kandikere, Vishwottam,Jayarajan, Pradeep,Dubey
scheme or table, p. 346 - 349 (2011/02/28)
N1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (Ki = 3.4 nM, functional assay IC 50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter.
Synthesis and physical properties of various organic dyes derived from a single core skeleton, 1,2-dihydroindol-3-one
Matsumoto, Shoji,Samata, Daisuke,Akazome, Motohiro,Ogura, Katsuyuki
supporting information; body text, p. 111 - 114 (2009/04/14)
Various organic dyes were synthesized from 1,2-dihydroindol-3-one analogue via Robinson ring annulation, which proceeded efficiently using DBU as a base to give the π-expanded compounds. These compounds exhibited longer Stokes shifts (over 100 nm) than the 1,2-dihydroindol-3-ones (50-80 nm). Emission peaks of the obtained materials covered the 440-640 nm range.
