18735-98-3Relevant academic research and scientific papers
Access to Indole-Fused Polyheterocycles via Pd-Catalyzed Base-Free Intramolecular Cross Dehydrogenative Coupling
Cheng, Chao,Chen, Wen-Wen,Xu, Bin,Xu, Ming-Hua
, p. 11501 - 11507 (2016)
A base-free process to access indole-fused polyheterocycles via a highly efficient and atom-economic palladium-catalyzed intramolecular cross dehydrogenetive coupling (CDC) reaction of 4-aniline substituted coumarins, quinolinones, and pyrones has been developed. A wide range of indolo[3,2-c]coumarins, indolo[3,2-c]quinolinones, and indolo[3,2-c]pyrones can be facilely afforded in good to excellent yields (up to 99%).
Macrocyclic bis(ureas) as ligands for anion complexation
Kretschmer, Claudia,Dittmann, Gertrud,Beck, Johannes
, p. 1834 - 1839 (2014)
Two macrocyclic bis(ureas) 1 and 2, both based on diphenylurea, have been synthesized. Compound 1 represents the smaller ring with two ethynylene groups as linkers and 2 the larger ring with two butadiynylene groups. On thermal treatment to 130 °C molecule 1 splits up into two dihydroindoloquinolinone (3) molecules. Both compounds 1 and 2 form adducts with polar molecules such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) and act as complexing agents towards a series of anions (Cl-, Br-, I-, NO3 -, HSO4-). The crystal structures of 3, 2.2DMSO, 2.2DMF, and of the complex NEt4[Br.2] have been determined. Quantitative investigations of the complexation equilibria were performed via 1H NMR titrations. While 1 is a rather weak complexing agent, the large ring of 2 binds anions with association constants up to log K = 7.93 for chloride ions.
Copper(I)-Catalyzed Nitrile-Addition/ N-Arylation Ring-Closure Cascade: Synthesis of 5,11-Dihydro-6 H-indolo[3,2- c]quinolin-6-ones as Potent Topoisomerase-I Inhibitors
Hsueh, Wen-Yun,Lee, Ying-Shuan E.,Huang, Min-Sian,Lai, Chin-Hung,Gao, Yu-Sheng,Lin, Jo-Chu,Chen, Yu-Fen,Chang, Chih-Lin,Chou, Shan-Yen,Chen, Shyh-Fong,Lu, Yann-Yu,Chang, Lien-Hsiang,Lin, Shu Fu,Lin, Yu-Hsiang,Hsu, Pi-Chen,Wei, Win-Yin,Huang, Ya-Chi,Kao, Yi-Feng,Teng, Li-Wei,Liu, Hung-Huang,Chen, Ying-Chou,Yuan, Ta-Tung,Chan, Ya-Wen,Huang, Po-Hsun,Chao, Yu-Ting,Huang, Shin-Yi,Jian, Bo-Han,Huang, Hsin-Yi,Yang, Sheng-Chuan,Lo, Tzu-Hao,Huang, Guan-Ru,Wang, Shao-Yun,Lin, Her-Sheng,Chuang, Shih-Hsien,Huang, Jiann-Jyh
, p. 1435 - 1453 (2021)
In this paper, we present a copper(I)-catalyzed nitrile-addition/N-arylation ring-closure cascade for the synthesis of 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones from 2-(2-bromophenyl)-N-(2-cyanophenyl)acetamides. Using CuBr and t-BuONa in dimethylformamide (DMF) as the optimal reaction conditions, the cascade reaction gave the target products, in high yields, with a good substrate scope. Application of the cascade reaction was demonstrated on the concise total syntheses of alkaloid isocryptolepine. Further optimization of the products from the cascade reaction led to 3-chloro-5,12-bis[2-(dimethylamino)ethyl]-5,12-dihydro-6H-[1,3]dioxolo[4′,5′:5,6]indolo[3,2-c]quinolin-6-one (2k), which exhibited the characteristic DNA topoisomerase-I inhibitory mechanism of action with potent in vitro anticancer activity. Compound 2k actively inhibited ARC-111- and SN-38-resistant HCT-116 cells and showed in vivo activity in mice bearing human HCT-116 and SJCRH30 xenografts. The interaction of 2k with the Top-DNA cleavable complex was revealed by docking simulations to guide the future optimization of 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones as topoisomerase-I inhibitors.
Ruthenium-and osmium-arene complexes of 2-substituted indolo[3,2- c ]quinolines: Synthesis, structure, spectroscopic properties, and antiproliferative activity
Filak, Lukas K.,Muehlgassner, Gerhard,Bacher, Felix,Roller, Alexander,Galanski, Markus,Jakupec, Michael A.,Keppler, Bernhard K.,Arion, Vladimir B.
, p. 273 - 283 (2011)
The synthesis of new modified indolo[3,2-c]quinoline ligands L 1-L8 with metal-binding sites is reported. By coordination to ruthenium-and osmium-arene moieties 16 complexes of the type [(η6-p-cymene)M(L)Cl]Cl (1a,b-8a,b), where M is RuII or OsII and L is L1-L8, have been prepared. All compounds were comprehensively characterized by elemental analysis, electrospray ionization mass spectrometry, IR, UV-vis, and NMR spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction (2a, 4a, 4b, 5a, 7a, and 7b). The complexes were tested for antiproliferative activity in vitro in three human cancer cell lines, namely, CH1 (ovarian carcinoma), SW480 (colon adenocarcinoma), and A549 (non-small-cell lung cancer), yielding IC 50 values in the submicromolar or low micromolar range.
Double Palladium Catalyzed Reductive Cyclizations. Synthesis of 2,2′-, 2,3′-, and 3,3′-Bi-1H-indoles, Indolo[3,2-b]indoles, and Indolo[2,3-b]indoles
Ansari, Nurul H.,Dacko, Christopher A.,Akhmedov, Novruz G.,S?derberg, Bj?rn C. G.
, p. 9337 - 9349 (2016/10/14)
A palladium catalyzed, carbon monoxide mediated, double reductive cyclization of 1,4-, 1,3-, and 2,3-bis(2-nitroaryl)-1,3-butadienes to afford 2,2′-, 2,3′-, and 3,3′-biindoles, respectively, was developed. In contrast, reductive cyclizations of 1,2-bis(2-nitroaryl)ethenes were nonselective, affording mixtures of monocyclized indoles, indolo[3,2-b]indole, indolo[1,2-c]quinazolin-6(5H)-ones, and 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones. Nonselective product formation was also observed from reductive cyclization of 1,1-bis(2-nitroaryl)ethenes, producing indolo[2,3-b]indoles and indolo[2,3-c]quinolin-6-ones. Carbon monoxide insertion to give the carbonyl containing products was the major or sole reaction path starting from 1,1- or 1,2-bis(2-nitroaryl)ethenes.
Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation
Mahajan, Pankaj S.,Humne, Vivek T.,Tanpure, Subhash D.,Mhaske, Santosh B.
supporting information, p. 3450 - 3453 (2016/07/26)
The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and 18O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C-H activation were used as key steps in the formal total synthesis of antimalarial natural product isocryptolepine.
INDOLO[3, 2-C]QUINOLINE DERIVATIVE, METHOD FOR PRODUCING THE DERIVATIVE, AND ANTIMALARIAL AGENT AND ANTICANCER AGENT COMPRISING THE DERIVATIVE
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Paragraph 0135; 0136, (2016/10/10)
PROBLEM TO BE SOLVED: To provide an antimalarial agent having high antimalarial activity (especially, effective even against chloroquine-resistant malaria parasites) and high safety, and an anticancer agent having high antitumor activity and low toxicity for non-tumor cells. SOLUTION: Provided are an antimalarial agent and an anticancer agent comprising an indolo [3,2-c] quinoline derivative (A) represented by the following formula (A) or a pharmaceutically acceptable salt thereof as an active ingredient. In the formula (A), R1 represents a prescribed substituent such as a halogen atom or the like; R2 represents a prescribed substituent such as an aminoalkylamino group or the like; R3 represents an alkyl group; R4 represents a prescribed substituent such as a halogen atom or the like; n represents an integer of 1 to 4; and m represents an integer of 0 to 4. COPYRIGHT: (C)2015,JPO&INPIT
Synthesis and in vitro cytotoxic effect of 6-amino-substituted 11H- and 11Me-indolo[3,2-c]quinolines
Wang, Ning,?witalska, Marta,Wu, Ming-Yu,Imai, Kento,Ngoc, Tran Anh,Pang, Cui-Qing,Wang, Li,Wietrzyk, Joanna,Inokuchi, Tsutomu
, p. 314 - 323 (2014/04/17)
A series of 6-amino-11H- indolo[3,2-c]quinoline derivatives with various substituents on the quinoline ring were synthesized. A methyl group introduced to N-11 of the intermediate 4 to elaborate novel analog 7. The cytotoxic effect of these 6-amino-substituted 11H- and 11-methyl-indolo[3,2-c]quinoline derivatives in vitro were tested against MV4-11 (human leukemia), A549 (non-small cell lung cancer) and HCT116 (colon cancer) and BALB/3T3 (normal murine fibroblasts). All the N-11 methylated compounds significantly increased the cytotoxicity. Compound 7p was most active with the IC50 value of 0.052 μM against the MV4-11 cell line, and also exhibited a selective activity against A549, HCT116 and BALB/3T3 cell line, with the respective IC50 values of 0.112, 0.007 and 0.083 μM, which were higher or comparable to those of the anticancer drug doxorubicin HCl. The binding constants of 5g and 7h to salmon fish sperm DNA were also evaluated using UV-vis absorption spectroscopy, indicating intercalation binding with constants of 1.05 × 106 L/mol and 4.84 × 106 L/mol.
Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11
Wang, Ning,Wicht, Kathryn J.,Imai, Kento,Wang, Ming-Qi,Anh Ngoc, Tran,Kiguchi, Ryo,Kaiser, Marcel,Egan, Timothy J.,Inokuchi, Tsutomu
, p. 2629 - 2642 (2014/05/06)
A series of indolo[3,2-c]quinolines were synthesized by modifying the side chains of the ω-aminoalkylamines at the C6 position and introducing substituents at the C2 position, such as F, Cl, Br, Me, MeO and NO2, and a methyl group at the N11 po
Synthesis of diversely substituted indoloquinolinones via Pd(II)/Cu(II)-mediated oxidative C-C bond formation and I(III)-mediated C-N bond formation
Zhang, Xiang,Zhang-Negrerie, Daisy,Deng, Jun,Du, Yunfei,Zhao, Kang
, p. 12750 - 12759 (2014/01/17)
A series of indoloquinolinones bearing different aromatic substitutents were readily synthesized starting from an aryl amine, a methyl 3-oxo-3-phenylpropanoate derivative, and methoxylamine through a series of reactions of coupling/enamination, oxidative
