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[ CAS No. 13331-27-6 ] {[proInfo.proName]}

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Chemical Structure| 13331-27-6
Chemical Structure| 13331-27-6
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Product Citations

Product Citations

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

Product Details of [ 13331-27-6 ]

CAS No. :13331-27-6 MDL No. :MFCD00007193
Formula : C6H6BNO4 Boiling Point : No data available
Linear Structure Formula :O2N(C6H4)B(OH)2 InChI Key :ZNRGSYUVFVNSAW-UHFFFAOYSA-N
M.W : 166.93 Pubchem ID :1677
Synonyms :

Calculated chemistry of [ 13331-27-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.09
TPSA : 86.28 ?2

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) : -6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.65
Log Po/w (WLOGP) : -0.73
Log Po/w (MLOGP) : -0.84
Log Po/w (SILICOS-IT) : -2.85
Consensus Log Po/w : -0.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.52
Solubility : 5.01 mg/ml ; 0.03 mol/l
Class : Very soluble
Log S (Ali) : -2.04
Solubility : 1.53 mg/ml ; 0.00917 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.66
Solubility : 36.4 mg/ml ; 0.218 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 13331-27-6 ]

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

Application In Synthesis of [ 13331-27-6 ]

* 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 [ 13331-27-6 ]

[ 13331-27-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1920-66-7 ]
  • [ 13331-27-6 ]
  • 4-amino-5-nitro-2-(3-nitrophenyl)pyrimidine [ No CAS ]
  • 2
  • [ 29022-11-5 ]
  • [ 13331-27-6 ]
  • [ 210282-31-8 ]
  • 2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • [(5S,10bR)-8-(3-Nitro-phenyl)-3-oxo-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline-5-carbonyl]-amino}-acetic acid [ No CAS ]
  • 3
  • [ 29022-11-5 ]
  • [ 13331-27-6 ]
  • [ 210282-31-8 ]
  • 2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 2-{2-[1-(carboxymethyl-carbamoyl)-2-(3'-nitro-biphenyl-3-yl)-ethylcarbamoyl]-ethyl}-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 4
  • [ 2401-21-0 ]
  • [ 13331-27-6 ]
  • [ 847406-42-2 ]
YieldReaction ConditionsOperation in experiment
39% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 24h; A solution of 2,3-dichloro-iodobenzene (6.00 G, 22. 0 mmol) in 60 mL toluene and 20 mL eth- anol was treated with 3-nitro-phenylboron. ic acid (4. 22 G, 25. 3 mmol) and NA2CO3 (2 N in H20, 30. 0 ML). Then mixture was purged with N2 for 5 min and Pd- (PPH3) (1. 02 G, 0. 879 mmol) was added. The mixture was heated to 90°C for 24 h and cooled to ambient temperature and concentrated in vacuo. The residual oil was partitioned with Et2O (80 M. L) and washed with dilute brine solution (3x50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The resulting white solid was recrystallized from hexane and to give the title compound (2.30 g, 39percent) as a fluffy white SOLID. 1H NMR (CDC13,400 MHz) 5 8.29 (m, 2H), 7.76 (m, 1H), 7.63 (t, J=7. 61 Hz, 1H), 7. 55 (m, 1H), 7. 31 (t, J=7.81 HZ, 1H), 7.26 (m, 1H.)
  • 5
  • [ 74137-36-3 ]
  • [ 13331-27-6 ]
  • [ 1155890-29-1 ]
  • 6
  • [ 1445-39-2 ]
  • [ 13331-27-6 ]
  • [ 1111104-92-7 ]
  • 7
  • [ 13331-27-6 ]
  • [ 145691-59-4 ]
  • [ 1397270-97-1 ]
  • 8
  • [ 3199-50-6 ]
  • [ 13331-27-6 ]
  • [ 56656-35-0 ]
YieldReaction ConditionsOperation in experiment
32.5% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; In water; at 70℃; for 3.33h;Inert atmosphere; General procedure: Mixtures of the aryl bromides 24 or 30 (2.65mmol), the boronic acids 23a or 23b (2.23mmol), tetrabutylammonium bromide (796mg, 2.47mmol), and K2CO3 (2.9g, 21mmol) were suspended in distilled water (10mL) under argon for 20min. Then Pd(OAc)2 (9.2mg, 0.04mmol) was added, and the resulting suspensions were heated to 70C and stirred under argon for 3h. After cooling down, the solutions were diluted with distilled water (10mL) and extracted with CH2Cl2 (3×15mL). The combined organic layers were dried over Na2SO4 and the solvents were evaporated. The crude residues were further purified by silica gel column chromatography, eluting with hexane-ethyl acetate 8:2, to provide the products 25a-b or 25d.
  • 9
  • [ 13331-27-6 ]
  • [ 34259-99-9 ]
  • 4‐(3‐nitrophenyl)‐1,3‐thiazole [ No CAS ]
  • 10
  • [ 1885-32-1 ]
  • [ 13331-27-6 ]
  • 8-methyl-2-(3-nitrophenyl)-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one [ No CAS ]
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