Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions

被引:10
|
作者
Zhang, Zhenguo [1 ]
Liu, Xiaoxiao [1 ]
Zong, Xinlong [1 ]
Yuan, Yalin [1 ]
Liu, Shuanglei [1 ]
Zhang, Ting [1 ]
Wu, Zishang [1 ]
Yang, Jingying [1 ]
Jia, Zhenhua [1 ]
机构
[1] Nanjing Tech Univ, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Peoples R China
关键词
transition-metal-free; 3,3'-bisindolylmethane; biological activity; diversity; FRIEDEL-CRAFTS ALKYLATION; TRIS-INDOLE ALKALOIDS; ENANTIOSELECTIVE SYNTHESIS; DEEP-WATER; BIS(INDOLYL)METHANES; DIM; 3,3'-BISINDOLYLMETHANES; ACTIVATION; DISCOVERY; EFFICIENT;
D O I
10.6023/cjoc202008003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3,3'-Bisindolylmethanes (3,3'-BIMs) compounds are important indole alkyloads and their units are widely found in various natural products, functional materials and synthetic pharmaceutical compounds. Due to diverse biological activities and functionalities, for instance, antioxidant, anti-inflammatory, antiangiogenic, anti-bacterial and anti-cancer etc., the construction of 3,3'-BIMs is raised considerable concerns. Conventional methods especially focused on symmetrical 3,3'-BIMs were the condensition of indoles with carbonyl compounds via Friedel-Crafts pathway in the presence of Bronsted acids or Lewis acids. However, the utilization of transtion metals led the residue into the products and environmental contamination. The recent advance on the synthesis of 3,3'-BIMs since 2010, mainly concerned on the approaches and corresponding mechanism to prepare symmetrical and unsymmetrical 3,3'-BIMs under transition-metal-free conditions is summarized and discussed, aiming to provide important theoretical evidence and techinical support for further biological evaluations on desired compounds.
引用
收藏
页码:52 / 64
页数:13
相关论文
共 69 条
  • [1] One-Pot Construction of 3,3′-Bisindolylmethanes through Bartoli Indole Synthesis
    Abe, Takumi
    Nakamura, Shuuhei
    Yanada, Reiko
    Choshi, Tominari
    Hibino, Satoshi
    Ishikura, Minoru
    [J]. ORGANIC LETTERS, 2013, 15 (14) : 3622 - 3625
  • [2] [Anonymous], 2008, RJK TAYLOR
  • [3] [Anonymous], 1886, CHEM BER
  • [4] FgaPT2, a biocatalytic tool for alkyl-diversification of indole natural products
    Bandari, Chandrasekhar
    Scull, Erin M.
    Bavineni, Tejaswi
    Nimmo, Susan L.
    Gardner, Eric D.
    Bensen, Ryan C.
    Burgett, Anthony W.
    Singh, Shanteri
    [J]. MEDCHEMCOMM, 2019, 10 (08) : 1465 - 1475
  • [5] Benabadji SH, 2004, ACTA PHARMACOL SIN, V25, P666
  • [6] Discovery of 3,3′-diindolylmethanes as potent antileishmanial agents
    Bharate, Sandip B.
    Bharate, Jaideep B.
    Khan, Shabana I.
    Tekwani, Babu L.
    Jacob, Melissa R.
    Mudududdla, Ramesh
    Yadav, Rammohan R.
    Singh, Baljinder
    Sharma, P. R.
    Maity, Sudip
    Singh, Baldev
    Khan, Ikhlas A.
    Vishwakarma, Ram A.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 : 435 - 443
  • [7] (+/-)-GELLIUSINE-A AND (+/-)-GELLIUSINE-B, 2 DIASTEREOMERIC BROMINATED TRIS-INDOLE ALKALOIDS FROM A DEEP-WATER NEW CALEDONIAN MARINE SPONGE (GELLIUS OR ORINA SP)
    BIFULCO, G
    BRUNO, I
    MINALE, L
    RICCIO, R
    CALIGNANO, A
    DEBITUS, C
    [J]. JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09): : 1294 - 1299
  • [8] FURTHER BROMINATED BIS-INDOLE AND TRIS-INDOLE ALKALOIDS FROM THE DEEP-WATER NEW-CALEDONIAN MARINE SPONGE ORINA SP
    BIFULCO, G
    BRUNO, I
    RICCIO, R
    LAVAYRE, J
    BOURDY, G
    [J]. JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (08): : 1254 - 1260
  • [9] Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions
    Chen, Shanping
    Li, Yuxia
    Ni, Penghui
    Huang, Huawen
    Deng, Guo-Jun
    [J]. ORGANIC LETTERS, 2016, 18 (20) : 5384 - 5387
  • [10] 3,3′-diindolylmethane suppresses the inflammatory response to lipopolysaccharide in murine macrophages
    Cho, Han Jin
    Seon, Mi Ra
    Lee, Yeo Myeong
    Kim, Jaebong
    Kim, Jin-Kyung
    Kim, Sang Geon
    Park, Jung Han Yoon
    [J]. JOURNAL OF NUTRITION, 2008, 138 (01): : 17 - 23