cas 202807-44-1, 6-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE

Articles about 202807-44-1Total 16 be found

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Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles
Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.
Ackermann, Lutz,Jacob, Nicolas,Oliveira, Jo?o C. A.,Wencel-Delord, Joanna,Zaid, Yassir
supporting information
p. 798 - 806
(2022/02/03)

Enantioselective Propargylation of Oxonium Ylide with α-Propargylic-3-Indolymethanol: Access to Chiral Propargylic Indoles
An enantioselective three-component reaction of α-propargylic-3-indolymethanol with diazoindolinone and alcohol under cocatalysis of Rh(II) and chiral phosphoric acid (CPA) has been reported. It proceeds through the regio-and enantiospecific addition of the in situ formed oxonium ylide to the α-propargylic indole iminium ion that is generated from 3-indolyl propargylic alcohol with CPA. This work features an asymmetric counteranion-directed propargylation of oxonium ylide, and provides an efficient access to chiral propargylic indole derivatives with high yields and enantioselectivities.
Liu, Xiangrong,Tian, Xue,Huang, Jiawu,Qian, Yu,Xu, Xinfang,Kang, Zhenghui,Hu, Wenhao
supporting information
p. 1027 - 1032
(2022/02/05)

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source
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
supporting information
p. 4107 - 4113
(2021/06/17)

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3
A variety of structurally novel polycyclic sulfonyl indolines have been synthesized via FeCl2-catalyzed or UV-driven intramolecular formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methyl)propiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.
Lu, Lin,Luo, Chenguang,Peng, Hui,Jiang, Huanfeng,Lei, Ming,Yin, Biaolin
supporting information
p. 2602 - 2605
(2019/04/30)

Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers
Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions, and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature. Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.
Zhang, Weijie,Tang, Juntao,Yu, Wenguang,Huang, Qiao,Fu, Yu,Kuang, Guichao,Pan, Chunyue,Yu, Guipeng
p. 8084 - 8091
(2018/07/30)

Synthesis and evaluation of selenium-containing indole chalcone and diarylketone derivatives as tubulin polymerization inhibition agents
Sixteen new selenium-containing indole chalcone and diarylketone derivatives were synthesized and evaluated as tubulin polymerization inhibitors. Among them, compound 25b exhibited the most potent antiproliferative activities against six human cancer cell lines with IC50 values of 0.004-0.022 μM. A microtubule dynamics assay and an immunofluorescence assay confirmed that 25b could effectively inhibit tubulin polymerization (IC50 = 2.1 ± 0.27 μM). Further cellular mechanism studies revealed that 25b induced G2/M phase arrest, which was further evidenced by the decrease in the mitochondrial membrane potential (MMP).
Zhang, Shun,An, Baijiao,Li, Jiayan,Hu, Jinhui,Huang, Ling,Li, Xingshu,Chan, Albert S. C.
p. 7404 - 7410
(2017/09/25)

Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction
An investigation of the mechanism of benzoic acid/thiourea co-catalysis in the asymmetric Pictet-Spengler reaction is reported. Kinetic, computational, and structure-activity relationship studies provide evidence that rearomatization via deprotonation of
Klausen, Rebekka S.,Kennedy, C. Rose,Hyde, Alan M.,Jacobsen, Eric N.
p. 12299 - 12309
(2017/09/12)

Synthesis, Evaluation, and Mechanism Study of Novel Indole-Chalcone Derivatives Exerting Effective Antitumor Activity Through Microtubule Destabilization in Vitro and in Vivo
Twenty-nine novel indole-chalcone derivatives were synthesized and evaluated for antiproliferative activity. Among them, 14k exhibited most potent activity, with IC50 values of 3-9 nM against six cancer cells, which displayed a 3.8-8.7-fold increase in activity when compare with compound 2. Further investigation revealed 14k was a novel tubulin polymerization inhibitor binding to the colchicine site. Its low cytotoxicity toward normal human cells and nearly equally potent activity against drug-resistant cells revealed the possibility for cancer therapy. Cellular mechanism studies elucidated 14k arrests cell cycle at G2/M phase and induces apoptosis along with the decrease of mitochondrial membrane potential. Furthermore, good metabolic stability of 14k was observed in mouse liver microsomes. Importantly, 14k and its phosphate salt 14k-P inhibited tumor growth in xenograft models in vivo without apparent toxicity, which was better than the reference compound CA-4P and 2. In summary, 14k deserves consideration for cancer therapy.
Yan, Jun,Chen, Jie,Zhang, Shun,Hu, Jinhui,Huang, Ling,Li, Xingshu
p. 5264 - 5283
(2016/07/06)

Synthesis, biological evaluation and mechanism study of chalcone analogues as novel anti-cancer agents
A series of novel chalcone analogues were designed, synthesized and evaluated as anticancer agents. The results of antiproliferative activity tests showed that most of the analogues exhibited moderate to very good antiproliferative activities with GI50 values in the micromol to sub-micromol range. Especially compound 10a gave 0.026 μM to 0.035 μM GI50 for five cancer cell lines. The mechanistic studies including tubulin polymerization inhibition, disruption of microtubule dynamics and cell cycle arrest assay demonstrated that compound 10a could effectively inhibit in vitro cellular tubulin polymerization, interfere with the mitosis, resulting in a prolonged G2/M cell cycle arrest and ultimately lead to cell apoptosis of cancer cells. Taken together, these results suggested that 10a may became a promising lead compound for development of new anticancer drugs.
Chen, Jie,Yan, Jun,Hu, Jinhui,Pang, Yanqing,Huang, Ling,Li, Xingshu
p. 68128 - 68135
(2015/08/24)

Aerobic transition-metal-free visible-light photoredox indole C-3 formylation reaction
An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.
Li, Xiang,Gu, Xiangyong,Li, Yongjuan,Li, Pixu
p. 1897 - 1900
(2014/06/24)

PPh3-catalyzed knoevenagel condensation: A facile synthesis of 5-(1H-indol-3-yl)meth-ylene)-2, 2-dimethyl-1, 3-dioxane-4, 6-dione, and their N-alkyl derivatives by using peg-600 as the reaction medium
Triphenylphosphine (TPP) has been utilized as a novel and efficient catalyst for the Knoevenagel condensation of indole-3-carboxaldehydes 1(a-e), 1-methyl-1H-indole-3-carboxaldehydes 4(a-e), and 1-ethyl-1H-indole-3- carboxaldehydes 6(a-e) with the active methylene compound, that is, meldrum's acid (2), to afford substituted derivatives 5-((1H-indol-3-yl) methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 3(a-e), 2,2-dimethyl-5-((1-methyl- 1H-indol-3-yl)methylene)-1,3-dioxane-4,6-dione 5(a-e), and 2,2-dimethyl-5-((1- ethyl-1H-indol-3-yl)methylene)-1,3-dioxane-4,6-dione 7(a-e), respectively, in ethanol medium at RT just within 1 h in excellent yields. The products 3(a-e) were reacted independently with alkylating agents, that is, DMS and DES in the presence of PEG-600 as an efficient and green solvent, to afford the corresponding N-substituted methyl and ethyl derivatives 5(a-e) and 7(a-e), respectively.
Venkatanarayana, Muvvala,Kumar Dubey, Pramod
scheme or table
p. 41 - 48
(2012/04/04)

L-Proline-catalyzed Knoevenagel condensation: A facile, green synthesis of (E)-ethyl 2-cyano-3-(1H-indol-3-yl)acrylates and (E)-3-(1H-indol-3-yl) acrylonitriles
L-Proline has been utilized as a novel and ecofriendly catalyst in ethanol medium for the Knoevenagel condensation of indole-3-carboxyaldehydes and their N-methyl derivatives 1(a-e) and 4(a-e) with the active methylene compound, ethyl cyanoacetate (2) to afford substituted (E)-ethyl 2-cyano-3-(1H-indol-3-yl) acrylates 3(a-e) and 5(a-e) respectively. These products were reacted with dimethyl sulfate in the presence of PEG-600 as an efficient and green solvent to afford the corresponding N-mthylated derivatives 5(a-e). These Knoevenagel products react with 5% NaOH, yielding (E)-3-(1H-indol-3-yl)acrylonitriles 6(a-e) and 7(a-e). Copyright Taylor & Francis Group, LLC.
Venkatanarayana,Dubey
scheme or table
p. 1746 - 1759
(2012/05/04)

Simple and efficient Knoevenagel synthesis of (E)-2-((1H-indol-3-yl) methylene)-3-oxoindolylnitrile catalysed by PPh3
Triphenylphosphine (TPP) is found to be an efficient catalyst for the Knoevenagel condensation of indole-3-carboxyaldehydes 1(a-e) and their N-substituted derivatives 4(a-e) with the active methylene compound, i.e., 3-cyanoacetylindole (2), affording novel substituted olefins 3(a-e) and 5(a-e) respectively. The latter products reacted with DMS in the presence of PEG-600 to afford the corresponding N, Nl dimethylated derivatives 6(a-e). Indian Academy of Sciences.
Venkatanarayana,Dubey
scheme or table
p. 609 - 614
(2012/06/29)

Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids
A concise 11-step total synthesis of (-)- and ent-(+)-vindoline (3) is detailed based on a unique tandem intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole inspired by the natural product structure, in which three rings and four C-C bonds are formed central to the characteristic pentacyclic ring system setting all six stereocenters and introducing essentially all the functionality found in the natural product in a single step. As key elements of the scope and stereochemical features of the reaction were defined, a series of related natural products of increasing complexity were prepared by total synthesis including both enantiomers of minovine (4), 4-desacetoxy-6,7-dihydrovindorosine (5), 4-desacetoxyvindorosine (6), and vindorosine (7) as well as /V-methylaspidospermidine (11). Subsequent extensions of the approach provided both enantiomers of 6,7-dihydrovindoline (8), 4-desacetoxyvindoline (9), and 4-desacetoxy-6,7-dihydrovindoline (10).
Ishikawa, Hayato,Elliott, Gregory I.,Velcicky, Juraj,Choi, Younggi,Boger, Dale L.
p. 10596 - 10612
(2007/10/03)

Total synthesis of (-)- and ent-(+)-vindoline
(Chemical Equation Presented) Two exceptionally concise total syntheses of (-)- and ent-(+)-vindoline are detailed enlisting a diastereoselective tandem [4 + 2]/[3 + 2] cycloaddition of a 1,3,4-oxadiazole. The unique reaction cascade assembles the fully functionalized pentacyclic ring system of vindoline in a single step that forms four C-C bonds and three rings while introducing all requisite functionality and setting all six stereocenters within the central ring including three contiguous and four total quaternary centers.
Choi, Younggi,Ishikawa, Hayato,Velcicky, Juraj,Elliott, Gregory I.,Miller, Michael M.,Boger, Dale L.
p. 4539 - 4542
(2007/10/03)

Substituted pyrroles
Compounds of the formula wherein R1and R1′are independently alkyl, aryl, alkenyl or alkynyl; R2and R2′are independently hydrogen, alkyl, aralkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, acylaminoalkyl, alkylsulphonylaminoalkyl, arylsulphonyl-aminoalkyl, mercaptoalkyl, alkylthioalkyl, carboxyalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylthio or alkylsulphinyl; R4, R5, R6, R7, R4′, R5′, R6′, and R7′each independently are hydrogen, CO2R9, CH2OR10, CHO, CH2NR11R12, CON(R13)2, halogen, cyano, aryl, alkyl, hydroxy, alkoxy, aryloxy, haloalkyl, nitro, amino, aralkyloxy, acylamino, monoalkylamino, dialkylamino, thio, alkyl, alkylsulphinyl, alkylsulphonyl, arylsulphinyl, azide, phosphate or phosphonate provided that at least one of R4, R5, R6and R7and at least one of R4′, R5′, R6′, and R7′are other than hydrogen, with the proviso that when R6is methoxy, R5or R5′ are not methoxy; R8is alkyl or aryl; R9is alkyl or aryl; R10is hydrogen, alkyl or aryl; R11and R12are independently hydrogen, alkyl, aryl, aralkyl or acyl; R13is hydrogen, alkyl, aryl or aralkyl; and one of X and Y signifies O and the other signifies O, S, (H,OH) or (H,H); as well as pharmaceutically acceptable prodrugs or pharmaceutically acceptable salts of acidic compounds of formula I with bases and or basic compounds of formula I with acids are antiproliferative agents useful in the treatment of cancer.
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(2008/06/13)