104831-79-0Relevant academic research and scientific papers
Catalytic Enantioselective Diels-Alder Reactions of Benzoquinones and Vinylindoles with Chiral Magnesium Phosphate Complexes
Bai, Yujia,Yuan, Jinping,Hu, Xiaoyue,Antilla, Jon C.
supporting information, p. 4549 - 4553 (2019/06/27)
Tetrahydrocarbazole and its derivatives have received much attention due to the prevalence of this scaffold in natural products and their use in organic synthesis. We have developed a Diels-Alder reaction of benzoquinones and 3-vinylindoles catalyzed by c
Synthesis and biological evaluation of novel podophyllotoxin analogs as antitumor agents
Zhang, Zhong-Heng,Zhang, Li-Ming,Luo, Gang,Zhang, Shi,Chen, Hong,Zhou, Jing
, p. 527 - 534 (2014/06/09)
A series of 4β N-indole-substituted podophyllotoxin derivatives were synthesized. Nine target compounds were evaluated against human cancer cell lines (HeLa, K562, and K562/A02) using MTT assay including three imine derivatives 8, 9, and 10in vitro. The result showed that the three compounds had higher antitumor activity than their reduced forms. Among them, compounds 8, 9, 11, and 16 were superior to the positive control VP-16.
Regioselective synthesis of 4-substituted indoles via C-H activation: A ruthenium catalyzed novel directing group strategy
Lanke, Veeranjaneyulu,Ramaiah Prabhu, Kandikere
, p. 6262 - 6265 (2014/01/17)
A highly regioselective functionalization of indole at the C-4 position by employing an aldehyde functional group as a directing group, and Ru as a catalyst, under mild reaction conditions (open flask) has been uncovered. This strategy to synthesize 4-substituted indoles is important, as this class of privileged molecules serves as a precursor for ergot alkaloids and related heterocyclic compounds.
Total synthesis of (±)-hyrtiazepine
Ito, Fumihiro,Shudo, Koichi,Yamaguchi, Kentaro
experimental part, p. 1805 - 1811 (2011/04/16)
The total synthesis of the azepinoindole alkaloid, (±)-hyrtiazepine, was achieved. Construction of the azepinoindole core structure was carried out by C-4 selective α-hydroxyalkylation of 5-hydroxyindole, introduction of serine at C-3 of the indole moiety, and intramolecular imination.
Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines
Penthala, Narsimha Reddy,Yerramreddy, Thirupathi Reddy,Crooks, Peter A.
scheme or table, p. 591 - 593 (2010/04/05)
The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. The analogs 3a, 3b, 3d-3g, 3k and 3l were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC50 values a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization.
Novel substituted (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents
Reddy, Y. Thirupathi,Sekhar, Konjeti R.,Sasi, Nidhish,Reddy, P. Narsimha,Freeman, Michael L.,Crooks, Peter A.
scheme or table, p. 600 - 602 (2010/04/26)
A series of (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-dione (9a-9m) and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione (10a-10i) derivatives that incorporate a variety of aromatic substituents in both the indole and N-benzyl moieties have been synthesized. These analogs were evaluated for their radiosensitization activity against the HT-29 cell line. Three analogs, 10a, 10b, and 10c were identified as the most potent radiosensitizing agents.
Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones
Thirupathi Reddy,Narsimha Reddy,Koduru, Srinivas,Damodaran, Chendil,Crooks, Peter A.
scheme or table, p. 3570 - 3574 (2010/07/17)
A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione (3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC50 values of 4.4 and 5.2 μM, respectively, compared to 5-fluorouracil (IC50 = 15.2 μM) against MCF-7 cells.
