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Chemistry
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Organoboron
methoxyphenylboronic acid
3-Methoxybenzeneboronic acid
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methoxyphenylboronic acid
methoxyphenylboronic-acid methoxyphenylboronic

[ CAS No. 10365-98-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 10365-98-7
Chemical Structure| 10365-98-7
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Quality Control of [ 10365-98-7 ]

COA NMR CNMR HPLC LC-MS

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Product Citations

Product Citations      Expand+

Wen Ren ; Yuling Deng ; Jacob D. Ward , et al. DOI:

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 , et al. DOI:

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

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 128796-39-4 ; ; ; ;

Product Details of [ 10365-98-7 ]

CAS No. :10365-98-7 MDL No. :MFCD00161359
Formula : C7H9BO3 Boiling Point : -
Linear Structure Formula :(HO)2BC6H4OCH3 InChI Key :NLLGFYPSWCMUIV-UHFFFAOYSA-N
M.W : 151.96 Pubchem ID :2734370
Synonyms :
Chemical Name :3-Methoxyphenylboronic acid

Calculated chemistry of [ 10365-98-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.76
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : -0.63
Log Po/w (MLOGP) : 0.0
Log Po/w (SILICOS-IT) : -0.76
Consensus Log Po/w : -0.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.56
Solubility : 4.21 mg/ml ; 0.0277 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 5.71 mg/ml ; 0.0376 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.4
Solubility : 6.08 mg/ml ; 0.04 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 10365-98-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10365-98-7 ]

* 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.

  • Downstream synthetic route of [ 10365-98-7 ]

[ 10365-98-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 29976-20-3 ]
  • [ 10365-98-7 ]
  • C21H21NO2 [ No CAS ]
Reference： [1]Synthesis,2006,p. 2855 - 2864
  • 2
  • [ 10365-98-7 ]
  • [ 4983-28-2 ]
  • [ 1350660-11-5 ]
YieldReaction ConditionsOperation in experiment
25% With copper diacetate; triethylamine; In dichloromethane; Intermediate 25: 2-Chloro-5-(3-methoxyphenoxy)pyrimidine A mixture of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> (l .Og, 7.66mmol), 3-methoxyphenyl boronic acid (1.16g, 7.66mmol), copper (II) acetate (1.39g, 7.66mmol), triethylamine(5.34mL, 7.66mmol) and powdered 4A molecular sieves in dichloromethane (30mL) was stirred under air for 3 days. A calcium chloride guard tube was used to protect the reaction from moisture. The reaction mixture was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgS04), the solvent removed under reduced pressure and the crude product was purified by flash chromatography, using 0-15percent ethyl acetate:hexane as eluent, to provide 2-chloro-5- (3-methoxyphenoxy)-pyrimidine (0.448g, 25percent) as yellow oil.Mass: (ES+) 237 (M+H)+ NMR: deltaEta (CDC13) 3.82 (3H, s), 6.63 (2H, m), 6.81 (IH, br d), 7.33 (IH, t) and 8.39 (2H, s).
Reference： [1]Patent: WO2011/144578,2011,A1 .Location in patent: Page/Page column 40
  • 3
  • [ 10365-98-7 ]
  • [ 33332-28-4 ]
  • [ 1159821-17-6 ]
YieldReaction ConditionsOperation in experiment
44.15% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; toluene; at 120℃; for 0.25h;Microwave irradiation; 6-(3-methoxy-phenyl)-pyrazin-2ylamine To a solution of <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (0.5 g, 3.85 mmol) in a mixture of toluene/ethanol (4:1 , 10 ml), 3-methoxyphenylboronic acid (0.64 g, 4.24 mmol), tetrakis(triphenylphosphino)palladium(0) (0.13 g, 0.11 mmol) and cesium carbonate (2.51 g, 7.71 mmol) are added, degassed briefly and irradiated in microwave at 120°C for 15 minutes. The reaction mixture is passed through celite, washed with dichloromethane, the filterate is concentrated and purified by column using silica gel (60-120) mesh to get the product as yellow solid (0.34 g, 44.15 percent); TLC: Pet ether/Ethylacetate(7/3) Rf - 0.2; 1H NMR: 400 MHz, DMSO-d6: delta [ppm] 8.27 (s, 1 H), 7.83 (s, 1H), 7.57-7.52 (m, 2H), 7.37 (t, J = 7.88 Hz, 1 H), 7.00-6.97 (m, 1 H), 6.51 (br s, 2H), 3.80 (s, 3H); LCMS: Mass found (M+, 202.3) Method: A-0.1 percent TFA in H20, B-0.1 percent TFA in ACN: Flow - 2.0ml/min. Column: XBridge C8 (50 X 4.6 mm, 3.5 pm), +ve mode Rt (min): 2.48 area percent -98.79 (Max), 99.35 (254 nm).
Reference： [1]Patent: WO2013/131609,2013,A1 .Location in patent: Page/Page column 103; 104
  • 4
  • [ 10365-98-7 ]
  • [ 118289-17-1 ]
  • 2-(3-methoxyphenyl)isonicotinaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A suspension of 3-bromobenzaldehyde (200 mg; commercial) and (3-cyanophenyl)boronic acid neopentyl glycol ester (325 mg; commercial) in toluene/EtOH (2.3 mL; 1 : 1) was treated with sat. aq. Na2C03 (2.3 mL) and degassed by bubbling with nitrogen for 5 min. The suspension was treated with Pd(PPh3)4 (28 mg) and refluxed overnight in a sealed tube. The reaction mixture was allowed to reach rt and diluted with water and EA. The aq. layer was extracted with EA and the combined org. layers were washed with brine, dried over MgS04, filtered and evaporated under reduced pressure. After purification by CC (Hept/EA 2: 1 to 1 : 1), the title compound was obtained as an off-white solid (325 mg; quantitative yield). Starting from 3-methoxyphenylboronic acid (50 mg), 2-bromoisonicotinaldehyde (61 mg), tetrakis-(triphenylphosphine)-palladium (15 mg) and K2C03 (136 mg), and proceeding in analogy to Preparation A, 2-(3-methoxyphenyl)isonicotinaldehyde was obtained. The latter was reacted without purification with (R)-5-(2-aminoethyl)-3-(3-oxo-3,4-dihydro- 2H-benzo[£][l,4]thiazin-6-yl)oxazolidin-2-one (77 mg; prepared according to WO 2009/104147), in analogy to Example 1, affording after purification by prep-HPLC (Method 1), the title compound as a colourless powder (39 mg; 24percent yield).
Reference： [1]Patent: WO2014/170821,2014,A1 .Location in patent: Page/Page column 87; 88; 131
  • 5
  • [ 10365-98-7 ]
  • [ 89694-46-2 ]
Reference： [1]Organic Letters,2015,vol. 17,p. 1042 - 1045
  • 6
  • [ 17285-36-8 ]
  • [ 10365-98-7 ]
  • 5-chloro-6-(3-methoxyphenyl)pyridazin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
360 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; at 85.0℃; for 16.0h;Inert atmosphere; A. 5-Chloro-6-(3-methoxyphenyl)pyridazin-3(2H)-one. To a 50-mL round-bottom flask was placed a solution of <strong>[17285-36-8]5,6-dichloro-2,3-dihydropyridazin-3-one</strong> (990 mg, 6.00 mmol) and (3- methoxyphenyl)boronic acid (900 mg, 5.91 mmol) in EtOH (45 mL) and water (9 mL) then Na2C03 (1062 mg, 10.02 mmol) and Pd(PPh3)4 (288 mg, 0.24 mmol) were added under nitrogen. The reaction was stirred for 16 h at 85°C, cooled to rt, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtO Ac/petroleum ether (2: 1) affording 360 mg of the title compound as a white solid. Mass Spectrum (LCMS, ESI pos): Calcd. for CiiH10ClN2O2+: 237.0 (M+H); Found: 237.0.
Reference： [1]Patent: WO2018/81377,2018,A1 .Location in patent: Paragraph 0138
  • 7
  • [ 10365-98-7 ]
  • [ 5350-41-4 ]
  • [ 23450-27-3 ]
Reference： [1]RSC Advances,2019,vol. 9,p. 5738 - 5741

Tags: 10365-98-7 synthesis path| 10365-98-7 SDS| 10365-98-7 COA| 10365-98-7 purity| 10365-98-7 application| 10365-98-7 NMR| 10365-98-7 COA| 10365-98-7 structure

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Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Nomenclature of Ethers • Preparation of Alkylbenzene • Preparation of Ethers • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Vilsmeier-Haack Reaction
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