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Chemical Structure| 128796-39-4 Chemical Structure| 128796-39-4
Chemical Structure| 128796-39-4

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Synonyms: 4-Trifluoromethylphenylboronic acid

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Wen Ren ; Yuling Deng ; Jacob D. Ward ; Rebecca Vairin ; Ruoli Bai b ; Hashini I. Wanniarachchi , et al.

Abstract: The synthesis and evaluation of small-molecule inhibitors of tubulin polymerization remains a promising approach for the development of new therapeutic agents for cancer treatment. The natural products colchicine and combretastatin A-4 (CA4) inspired significant drug discovery campaigns targeting the colchicine site located on the beta-subunit of the tubulin heterodimer, but so far these efforts have not yielded an approved drug for cancer treatment in human patients. Interest in the colchicine site was enhanced by the discovery that a subset of colchicine site agents demonstrated dual functionality as both potent antiproliferative agents and effective vascular disrupting agents (VDAs). Our previous studies led to the discovery and development of a 2-aryl-3-aroyl-indole analogue (OXi8006) that inhibited tubulin polymerization and demonstrated low nM IC50 values against a variety of human cancer cell lines. A water-soluble phosphate prodrug salt (OXi8007), synthesized from OXi8006, displayed promising vascular disrupting activity in mouse models of cancer. To further extend structure-activity relationship correlations, a series of 6-aryl-3-aroyl-indole analogues was synthesized and evaluated for their inhibition of tubulin polymerization and cytotoxicity against human cancer cell lines. Several structurally diverse molecules in this small library were strong inhibitors of tubulin polymerization and of MCF-7 and MDA-MB-231 human breast cancer cells. One of the most promising analogues (KGP591) caused significant G2/M arrest of MDA-MB-231 cells, disrupted microtubule structure and cell morphology in MDA-MB-231 cells, and demonstrated significant inhibition of MDA-MB-231 cell migration in a wound healing (scratch) assay. A phosphate prodrug salt, KGP618, synthesized from its parent phenolic precursor, KGP591, demonstrated significant reduction in bioluminescence signal when evaluated in vivo against an orthotopic model of kidney cancer (RENCA-luc) in BALB/c mice, indicative of efficacy. The most active compounds from this series offer promise as anticancer therapeutic agents.

Keywords: Inhibitors of tubulin polymerization ; Vascular disrupting agents ; synthesis ; Molecular docking ; Antiproliferative agents ; Inhibitors of cell migration

Purchased from AmBeed: ; ; ; ; ; 64-86-8 ; ; ; ; ; ; ; ; 4521-61-3 ; 4521-61-3 ; 87199-18-6 ; 64-86-8 ; 64-86-8 ; 128796-39-4 ; 5720-05-8 ; 64-86-8

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon ; Swager, Timothy M. ;

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki−Miyaura coupling reaction ; size-selective reaction ; catalyst processing

Alternative Products

Product Details of 4-(Trifluoromethyl)phenylboronic acid

CAS No. :128796-39-4
Formula : C7H6BF3O2
M.W : 189.93
SMILES Code : FC(C1=CC=C(B(O)O)C=C1)(F)F
Synonyms :
4-Trifluoromethylphenylboronic acid
MDL No. :MFCD00151855
InChI Key :ALMFIOZYDASRRC-UHFFFAOYSA-N
Pubchem ID :2734389

Safety of 4-(Trifluoromethyl)phenylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of 4-(Trifluoromethyl)phenylboronic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 128796-39-4 ]
  • Downstream synthetic route of [ 128796-39-4 ]

[ 128796-39-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 3132-99-8 ]
  • [ 128796-39-4 ]
  • [ 343604-24-0 ]
References: [1] Patent: WO2005/118542, 2005, A1, . Location in patent: Page/Page column 45-46.
[2] ChemMedChem, 2016, p. 2194 - 2204.
[3] Archiv der Pharmazie, 2005, vol. 338, # 1, p. 9 - 17.
[4] Pharmazie, 2003, vol. 58, # 12, p. 854 - 856.
[5] Organic Letters, 2011, vol. 13, # 5, p. 952 - 955.
[6] Angewandte Chemie - International Edition, 2018, vol. 57, # 17, p. 4622 - 4626[7] Angew. Chem., 2018, vol. 130, # 17, p. 4712 - 4716,5.
 

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