1-Phenyl-1H-indole derivatives as a new class of Bcl-2/Mcl-1 dual inhibitors: Design, synthesis, and preliminary biological evaluation

Xu, Guangsen; T, Liu; Zhou, Yi; Xia, Yang; Fang, Hao

doi:10.1016/j.bmc.2017.08.024

Cited by 25 publications

(11 citation statements)

References 26 publications

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“…Both B-cell lymphoma (Bcl-2) and myeloid cell leukemia sequence 1 (Mcl-1) are proteins that help with the development and survival of multiple tumor types. Therefore, Fang [ 174 ] focused on studying the properties of indole derivatives with a phenyl substituent at position 1 as compounds that exhibit potent inhibitory activity against Bcl-2. The introduction of the aryl substituents was again catalyzed by cuprous oxide, although the reactions were performed in refluxing DMF.…”

Section: N -Arylated Indoles As Biologically Active Substancesmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.

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Section: N -Arylated Indoles As Biologically Active Substancesmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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“…In our previous studies, a series of indole-based compounds were found to show Bcl-2 inhibitory activities [17]. Some of them showed potent inhibitory activities against Bcl-2 and Mcl-1 proteins, however, they showed poor antiproliferative activities.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and anticancer activity studies of novel indole derivatives as Bcl-2/Mcl-1 dual inhibitors

Liu

Zhou

et al. 2022

Med Chem Res

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A series of novel indole derivatives were designed, synthesized and evaluated for the binding a nity of Bcl-2 family proteins and antiproliferative activity against three selected cancer cell lines (PC-3, Jurkat, and MDA-MB-231). The preliminary structure-activity relationship (SAR) for this indole scaffold was summarized. Among all the compounds, compound 9k showed the best inhibitory activity against Bcl-2 and Mcl-1 proteins with IC 50 values of 7.63 µM and 1.53 µM, respectively, which is comparable to the positive control AT-101. The docking study of it with Bcl-2 and Mcl-1 proteins indicated that it could bind to the active pocket of them through Van der Waals forces, hydrogen bond, etc. However, the three compounds with good binding a nity of Bcl-2 protein exhibited weaker antitumor activity compared to AT-101, which need further modi cation.

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“…The B‐cell lymphoma 2 (Bcl‐2) is a family of proteins, which plays a vital role in the regulation of programmed cell death and cell survival 21,22 . They are located predominantly in the walls of the mitochondria.…”

Section: Introductionmentioning

confidence: 99%

“…[16][17][18][19][20] The B-cell lymphoma 2 (Bcl-2) is a family of proteins, which plays a vital role in the regulation of programmed cell death and cell survival. 21,22 They are located predominantly in the walls of the mitochondria. Regulation of the Bcl-2 family occurs through transcriptional, translational and phosphorylation mechanisms.…”

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confidence: 99%

Spectroscopic characterization, DFT studies, molecular docking and cytotoxic evaluation of 4‐nitro‐indole‐3‐carboxaldehyde: A potent lung cancer agent

Jeyaseelan¹,

Benial²

2020

J of Molecular Recognition

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The 4-nitro-1H-indole-carboxaldehyde (NICA) molecule was characterized experimentally using FT-IR, FT-Raman and UV-Vis spectra, and it was studied theoretically using DFT calculations. The optimized structure of the NICA molecule was determined by DFT calculations using B3LYP functional with cc-pVTZ basis set. The electron localization function (ELF) and local orbital localizer (LOL) studies were performed to visualize the electron delocalization in the molecule. The experimental and theoretical wavenumbers of the title molecule were assigned using VEDA 4.0 program. The charge delocalization and stability of the title molecule were investigated using natural bond orbital (NBO) analysis. Frontier molecular orbitals (FMOs) and related molecular properties were calculated. UV-Vis spectrum was calculated theoretically and validated experimentally. The reactive sites of the molecule were studied from the MEP surface and Fukui function analysis. The molecular docking analysis reveals that the NICA ligand shows better inhibitory activity against RAS, which causes lung cancer. The in vitro cytotoxic activity of the molecule against human lung cancer cell lines (A549) was determined by MTT assay. Thus, the NICA molecule can be used as a potential candidate for the development of the drug against lung cancer.

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1-Phenyl-1H-indole derivatives as a new class of Bcl-2/Mcl-1 dual inhibitors: Design, synthesis, and preliminary biological evaluation

Cited by 25 publications

References 26 publications

Recent Progress Concerning the N-Arylation of Indoles

Recent Progress Concerning the N-Arylation of Indoles

Design, synthesis and anticancer activity studies of novel indole derivatives as Bcl-2/Mcl-1 dual inhibitors

Spectroscopic characterization, DFT studies, molecular docking and cytotoxic evaluation of 4‐nitro‐indole‐3‐carboxaldehyde: A potent lung cancer agent

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