18735-98-3Relevant articles and documents
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%).
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.
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
