- Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source
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A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.
- Cheng, Didi,Li, Jingyi,Li, Yujin,Ling, Fei,Liu, Lei,Liu, Tao,Zhong, Weihui
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supporting information
p. 4107 - 4113
(2021/06/17)
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- Spirocyclization reactions and antiproliferative activity of indole phytoalexins 1-methoxybrassinin and its 1-substituted derivatives
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The effect of the reaction temperature and the solvent on the diastereoselectivity of the spirocyclization of 1-methoxybrassinin leading to 1-methoxyspirobrassinol methyl ether was studied. 1-Acyl derivatives of 1-methoxyspirobrassinol and 1-methoxyspirobrassinol methyl ether were prepared by the bromine-mediated spirocyclization reactions of derivatives of brassinin bearing an acyl group on the indole nitrogen with water or methanol as nucleophilic agents. The cyclization of 1-acyl derivatives of brassinin afforded the trans-diastereoisomer as the major product, whereas using 1-methoxybrassinin afforded the cis- and trans-isomers in a ratio near to 1:1. Bromospirocyclization of brassinin and 1-methylbrassinin in the presence of methanol resulted in the formation of spirobrassinin and 1-methylspirobrassinin. The newly synthesized analogues of indole phytoalexins exhibited more significant antiproliferative activity against human leukemia cell lines than the natural phytoalexins.
- Budovská, Mariana,Pilátová, Martina Bago,Tischlerová, Viera,Moj?i?, Ján
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p. 198 - 234
(2018/05/09)
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- Spirocyclization reactions and antiproliferative activity of indole phytoalexins 1-methoxybrassinin and its 1-substituted derivatives
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The effect of the reaction temperature and the solvent on the diastereoselectivity of the spirocyclization of 1-methoxybrassinin leading to 1-methoxyspirobrassinol methyl ether was studied. 1-Acyl derivatives of 1-methoxyspirobrassinol and 1-methoxyspirobrassinol methyl ether were prepared by the bromine-mediated spirocyclization reactions of derivatives of brassinin bearing an acyl group on the indole nitrogen with water or methanol as nucleophilic agents. The cyclization of 1-Acyl derivatives of brassinin afforded the trans-diastereoisomer as the major product, whereas using 1-methoxybrassinin afforded the cis-And trans-isomers in a ratio near to 1:1. Bromospirocyclization of brassinin and 1-methylbrassinin in the presence of methanol resulted in the formation of spirobrassinin and 1-methylspirobrassinin. The newly synthesized analogues of indole phytoalexins exhibited more significant antiproliferative activity against human leukemia cell lines than the natural phytoalexins.
- Budovská, Mariana,Pilátová, Martina Bago,Tischlerová, Viera,Moj?i?, Ján
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p. 198 - 234
(2017/09/25)
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- COMPOSITIONS AND METHODS FOR TARGETING RECEPTORS EXPRESSED IN THE GUT
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The invention relates to novel compounds and pharmaceutical preparations thereof, as well as methods of making and using these compounds. The invention further relates to methods of treating or preventing disease using the novel compounds of the invention
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Page/Page column 39; 40
(2016/02/09)
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- POLYMERASE, ENDONUCLEASE, AND HELICASE INHIBITORS AND METHODS OF USING THEREOF
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Inhibitors of DNA damage polymerases, endonucleases, and helicases are provided. In particular, compounds comprising Formula (I) are described.
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Paragraph 0169
(2014/11/13)
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- NBu4NI-catalyzed C3-formylation of indoles with N-methylaniline
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nBu4NI-catalyzed C3-selective formylation of N-H and N-substituted indoles by using N-methylaniline as a formylating reagent was first successfully demonstrated.
- Li, Lan-Tao,Huang, Juan,Li, Hong-Ying,Wen, Li-Juan,Wang, Peng,Wang, Bin
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supporting information; experimental part
p. 5187 - 5189
(2012/06/01)
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- Synthesis and biological evaluation of curcumin analogues having a piperidone core as potential antioxidant agents
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A series of new unsymmetrical curcumin derivatives were designed and synthesised to which the indole fragment was introduced according to the principle of association. These compounds were characterised by 1H NMR, IR, ESIMS and elemental analys
- Wang, Jian,Sun, Gangchun,Li, Zhicheng,Mai, Wenpeng,Xie, Jingxi
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experimental part
p. 63 - 65
(2012/05/19)
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- N-1 and C-3 substituted indole Schiff bases as selective COX-2 inhibitors: Synthesis and biological evaluation
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A group of N-1 and C-3 disubstituted-indole Schiff bases bearing an indole N-1 (R′ = H, CH2Ph, COPh) substituent in conjunction with a C-3 -CHN-C6H4-4-X (X = F, Me, CF3, Cl) substituent were synthesized and eval
- Kaur, Jatinder,Bhardwaj, Atul,Huang, Zhangjian,Knaus, Edward E.
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experimental part
p. 2154 - 2159
(2012/04/18)
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- Synthesis and evaluation of indole, pyrazole, chromone and pyrimidine based conjugates for tumor growth inhibitory activities - Development of highly efficacious cytotoxic agents
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Based upon the lead compounds 10 and 11, a number of conjugates were synthesized by the combination of chromone-pyrimidine, chromone-indolinone, chromone-pyrazole, indole-pyrimidine, indole-indolinone and indole-pyrazole moieties. Evaluation of these compounds for tumor growth inhibitory activities over 60 human tumor cell lines provided highly efficacious compounds 15, 41, 43, 66, 69, and 72 with an average GI50 over all the 60 human tumor cell lines as 3.2 μM, 3.1 μM, 1.7 μM, 2.6 μM, 50.1 μM and 2.0 μM, respectively.
- Singh, Palwinder,Kaur, Matinder,Holzer, Wolfgang
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experimental part
p. 4968 - 4982
(2010/11/20)
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- A catalytic antibody programmed for torsional activation of amide bond hydrolysis
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Amidase antibody 312d6, obtained against the sulfonamide hapten 4a that mimics the transition state for hydrolysis of a distorted amide, accelerates the hydrolysis of the corresponding amides 1a-3a by a factor of 103 at pH 8. The mechanisms of
- Aggarwal, Ranjana,Benedetti, Fabio,Berti, Federico,Buchini, Sabrina,Colombatti, Alfonso,Dinon, Francesca,Galasso, Vinicio,Norbedo, Stefano
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p. 3132 - 3142
(2007/10/03)
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- A new synthesis of aplysinopsin, a marine alkaloid and its analogues and their biological activities
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Aplysinopsin (1) and its analogues (3a-3d, 6a-6e and 7d) have been synthesised and evaluated for their broad biological activities.Of the compounds tested, compound 3a, 4b, 5b and 7a show high order of in vitro antileishmanial activity.Compound 3a also shows moderate antiviral activity against Ranikhet disease virus (RDV) and compounds 4d, 4e, 5a, 5b, 6c, and 7d show moderate antimicrobial activity.
- Gulati, Deepa,Chauhan, P. M. S.,Pratap, Ram,Bhakuni, D. S.
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- Synthesis of 1,3-substituted indoles, 2,4,6-substituted-s-triazines and 4,5-substituted pyrazoles as possible antifilarial agents
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The synthesis of a series of 1,3-substituted indoles (6-11), 2,4,6-substituted s-triazines (12-18) and 4,5-substituted pyrazoles (21-27) has been carried out.These compounds (6-11, 12-18 and 21-27) have been tested for their antifilarial activity against L. carinii and B. malayi at a dose of 30 mg/kg * 5 days.The compounds 16 and 17 show 75percent and 70percent microfilaricidal activity respectively against L. carinii while the latter exhibits 85percent microfilaricidal and 50percent adulticidal action against B. malayi in Mastomys at 200mg/kg p.o. * 5 days.
- Chauhan, P. M. S.,Chatterjee, R. K.
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- Bioactive Marine Alkaloids
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The chemistry and biology of bioactive alkaloids isolated during the last ten years have been reviewed.Syntheses of bioactive marine indole alkaloids, aplysinopsins, bromoaplysinopsins, their relative and their biological activities are reported.
- Bhakuni, D. S.
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p. 329 - 340
(2007/10/02)
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- Regio- and Stereo-chemical Aspects of Photocycloaddition Between 1-Benzoylindoles and Olefins
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The regio- and stereo-selectivities in the photocycloaddition of a series of 1-benzoylindoles with vinyl acetate and methyl acrylate have been investigated.With some exceptions, the 1-benzoylindoles gave exclusively or predominatly the corresponding 1-acetoxy-3-benzoyl and 3-benzoyl-1-methoxycarbonyl-1,2,2a,7b-tetrahydro-3H-cyclobutindoles as mixtures of stereoisomers.
- Ikeda, Masazumi,Ohno, Kazunori,Mohri, Shin-ichiro,Takahashi, Masami,Tamura, Yasumitsu
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p. 405 - 412
(2007/10/02)
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- PREPARATION AND REACTIONS OF 3-(AMINOMETHYLENE)-3H-INDOLES
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A series of 3-(aminomethylene)-3H-indoles (1a-e and 6a-8a) was prepared by the condensation of 3-indolecarbaldehydes (2-5) with secondary amines.Among them, 3-(1-pyrrolidinylmethylene)-3H-indoles (1a and 6a-8a) were obtained as stable colorless prisms, while 3-(piperidinomethylene)-3H-indole (1b) and 3-(morpholinomethylene)-3H-indole (1c) readily polymerized in refluxing benzene.Reaction of 1 with electrophiles, such as alkyl and acyl halides, gave 1-substituted 3-aminomethylene-3H-indolium salts, which were converted to the corresponding 1-substituted 3-indolecarbaldehydes by hydrolysis.Reaction of 1 with active methylene compounds proceeded under mild reaction conditions to afford the corresponding condensation products in good yields.Successive reaction of 1 with electrophiles and nucleophiles provided a convenient route to 1,3-disubstituted indole derivatives.Keywords-conjugated enamine; 3-indolecarbaldehyde; 3-(aminomethylene)-3H-indole; 3-(aminomethylene)-3H-indolium salt; active methylene compounds; 3-(substituted vinyl)indole; gramine; electrophilic reaction; condensation
- Moriya, Tamon,Hagio, Katsuaki,Yoneda, Naoto
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p. 1711 - 1721
(2007/10/02)
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