[(2-Phenylindol-3-yl)methylene]propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G2/M phase and apoptosis

Pojarová, Michaela; Kaufmann, Doris; Gastpar, Robert; Nishino, Tsuyuki; Reszka, Przemysław; Bednarski, Patrick J.; Angerer, Erwin von

doi:10.1016/j.bmc.2007.07.046

Cited by 51 publications

(21 citation statements)

References 26 publications

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“…Indole derivatives are an important class of therapeutic agents in medicinal chemistry [9,10]. The various activities associated with them include analgesic [5] antiallergic [11], antibacterial [9], antitumor [10], anti HIV [12], antioxidant [13], and antirheumatoid activities [10]. Some of the indole analogues also inhibit development of bladder cancer, cell carcinoma, lung cancer, colon cancer, mammary tumors, prostate cancer, and breast tumor cells [14,15].…”

Section: Introductionmentioning

confidence: 99%

Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity

et al. 2017

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Two new compounds, 1H-indole-7-amine (1) and N-(1H-indol-7-yl)-2-methylbenzamide (2)were synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound 2 was further elucidated by single-crystal X-ray diffraction technique. Moreover, the crystal packing of compound 2 is analyzed in terms of non-covalent N-H···O, C-H···π, and parallel displaced π···π interactions. Hirshfeld surface analysis and decomposed fingerprint plots of the compound 2 were performed to visualize the presence of strong hydrogen bond N-H···O and C-H···π stacking interactions. Hirshfeld surface analysis and decomposed fingerprint plots show that the structure of compound 2 is stabilized by H···H, N-H···O, C-H···π and π···π intermolecular interactions and these interactions contribute mostly to molecular self-assembly in the crystal. In addition, compound 2 was evaluated for both their in-vitro antibacterial and antifungal activity. The obtained results have been reported, explained and compared with fluconazole and ampicillin used as reference drugs. KEYWORDSAntimicrobial activity Single crystal structure Molecular self-assembly Hirshfeld surface analysis Deformation electron density Indole-based benzamide derivative Cite this: Eur.

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Section: Introductionmentioning

confidence: 99%

Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity

et al. 2017

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“…A series of 2-phenylindole derivatives with well-expressed cytotoxicity against human breast cancer cell line MDA-MB 231 [13][14][15], were selected to perform the present study. The structural formula of the studied compounds is shown in Fig.…”

Section: The Studied Compounds and Their Biological Activity Datamentioning

confidence: 99%

“…For example, compounds 4, 9, 25, 33, and 42, which contain higher electronegative group -OCH 3 or halogen as substituent R 1 , have higher activity than compounds 2, 8, 26, 20 and 43, which contain lower electronegative H atom. For another example, compounds 3, 6,9,12,13,14, and 17-19 with relatively lower electronegative C atom as the first atom of substituent X also show lower activity than compounds 20, 22, 25, 28, 31, 32, and 39-41 with relatively higher electronegative O atom. One bigger blue contour is found around the substituent R 2 , indicating that negatively charged substituent in the area is unfavorable.…”

Section: Main Factors Affecting the Activity Based On A Combined Comfmentioning

confidence: 99%

“…In addition to its potent cytotoxicity, CA-4 is one of the few tubulin targeting agents reported to have selective vascular-disrupting activity [11,12]. Recently, von Angerer and coworkers have synthesized a series of 2-phenylindole derivatives and assessed their anticancer activities in human breast cancer cell lines [13][14][15]. They found that these compounds prevent the polymerization of the a/b-tubulin dimers to functional microtubules by binding to the colchicine-binding site and all have pronounced cytotoxicity, demonstrating the great potential of developing 2-phenylindole derivatives as a new class of anticancer drug.…”

Section: Introductionmentioning

confidence: 99%

“…In this work, CoMFA and docking studies of 43 tubulin inhibitors, 2-phenylindole derivatives with anticancer activity against human breast cancer cell line MDA-MB 231 [13][14][15], were carried out. The purpose of this article focuses to establish an optimal 3D-QSAR model for these compounds by using the CoMFA method and explore the inhibition mechanism via docking analysis combined with 3D-QSAR.…”

Section: Introductionmentioning

confidence: 99%

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CoMFA and docking studies of 2-phenylindole derivatives with anticancer activity

Liao

Miao

et al. 2009

European Journal of Medicinal Chemistry

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First Report on 3‐(3‐oxoaryl) Indole Derivatives as Anticancer Agents: Microwave Assisted Synthesis, In Vitro Screening and Molecular Docking Studies

et al. 2019

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In this study ZrCl4 was identified as an efficient Lewis acid catalyst for the synthesis of 3‐(3‐oxoaryl) indole derivatives via microwave assisted Michael addition of 2‐phenylindole with chalcones under solvent‐free condition. The reaction proceeds smoothly with high efficiency under green reaction condition to afford a range of 3‐(3‐oxoaryl) indole derivatives exclusively within a short period of time in excellent yields. The synthesized compounds have shown promising in vitro anticancer activity against murine melanoma (B16F10) and human breast cancer (MCF7) cell lines. Molecular docking analysis showed that this type of indole derivatives may act as anticancer agents through the inhibition of tubulin polymerization.

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[(2-Phenylindol-3-yl)methylene]propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G2/M phase and apoptosis

Cited by 51 publications

References 26 publications

Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity

Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity

CoMFA and docking studies of 2-phenylindole derivatives with anticancer activity

First Report on 3‐(3‐oxoaryl) Indole Derivatives as Anticancer Agents: Microwave Assisted Synthesis, In Vitro Screening and Molecular Docking Studies

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