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[ CAS No. 141776-91-2 ] {[proInfo.proName]}

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Chemical Structure| 141776-91-2
Chemical Structure| 141776-91-2
Structure of 141776-91-2 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Dube, Phelelisiwe S. ; Angula, Klaudia T. ; Legoabe, Lesetja J. , et al. DOI: PubMed ID:

Abstract: Herein, we describe 39 novel quinolone compounds bearing a hydrophilic amine chain and varied substituted benzyloxy units. These compounds demonstrate broad-spectrum activities against acid-fast bacterium, Gram-pos. and -neg. bacteria, fungi, and leishmania parasite. Compound 30 maintained antitubercular activity against moxifloxacin-, isoniazid-, and rifampicin-resistant Mycobacterium tuberculosis, while 37 exhibited low micromolar activities (<1 μg/mL) against World Health Organization (WHO) critical pathogens: Cryptococcus neoformans, Acinetobacter baumannii, and Pseudomonas aeruginosa. Compounds in this study are metabolically robust, demonstrating % remnant of >98% after 30 min in the presence of human, rat, and mouse liver microsomes. Several compounds thus reported here are promising leads for the treatment of diseases caused by infectious agents.

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Product Details of [ 141776-91-2 ]

CAS No. :141776-91-2 MDL No. :MFCD00010304
Formula : C7H5BrF2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :KVSVNRFSKRFPIL-UHFFFAOYSA-N
M.W : 207.02 Pubchem ID :518896
Synonyms :

Calculated chemistry of [ 141776-91-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.19
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 2.68
Log Po/w (WLOGP) : 3.55
Log Po/w (MLOGP) : 3.95
Log Po/w (SILICOS-IT) : 3.67
Consensus Log Po/w : 3.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.19
Solubility : 0.134 mg/ml ; 0.000646 mol/l
Class : Soluble
Log S (Ali) : -2.33
Solubility : 0.963 mg/ml ; 0.00465 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.22
Solubility : 0.0125 mg/ml ; 0.0000604 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 141776-91-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P390-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 UN#:3265
Hazard Statements:H314-H290 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 141776-91-2 ]

* 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 [ 141776-91-2 ]

[ 141776-91-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 141776-91-2 ]
  • [ 22916-47-8 ]
  • 3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1-(3,5-difluoro-benzyl)-3<i>H</i>-imidazol-1-ium; bromide [ No CAS ]
  • 2
  • [ 50820-65-0 ]
  • [ 141776-91-2 ]
  • [ 691399-51-6 ]
YieldReaction ConditionsOperation in experiment
84% Under a nitrogen atmosphere: to a solution of LH-INDOLE-6-CARBOXYLIC acid methyl ester (367 mg, 2.09 mmol) in DMF (10 mL) was added NaH (60% in oil, 101 mg, 2.52 mmol) at room temperature. After stirring for 15 min 1-BROMOMETHYL-3, 5-difluoro- benzene (325 PL, 2.51 mmol) was added and the mixture was stirred at room temperature for 4 h. The reaction was quenched with 3% aqueous citric acid (10 ML) and ethyl acetate (30 mL) was added. The mixture was washed with 3% aqueous citric acid (3X20 mL) and brine (20 mL). The organic phase was dried (MGS04) and concentrated in vacuo to give a pale yellow oil (702 mg). The crude product was purified over a 20 g silica SPE cartridge (ethyl acetate/heptane 1: 9) to give the title compound as a colourless oil, which slowly crystallised on standing (530 mg, yield = 84%). LCMS: 4.08 min (99%, MH+= 302) ; 1H NMR (CDC13) : 8 3.92 (3,3H, CO2CH3), 5.37 (s, 2H, NCH2Ar), 6.54-6. 60 (m, 2H), 6.64 (d, 1H, J = 3.1 Hz), 6.67-6. 74 (m, 1H), 7.27 (d, IH, J = 3.1 Hz), 7.68 (d, 1H, J = 8.6 Hz), 7.83 (d, LH, J = 8. 6 Hz), 8.01 (s, 1H).
  • 3
  • [ 53241-92-2 ]
  • [ 141776-91-2 ]
  • [ 1345869-53-5 ]
  • 4
  • [ 141776-91-2 ]
  • [ 1201597-22-9 ]
  • 5
  • [ 110-15-6 ]
  • [ 141776-91-2 ]
  • [ 436-77-1 ]
  • C58H54F6N2O6(2+)*C4H4O4(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.25g Weighing 6.10g of <strong>[436-77-1]fangchinoline</strong>,3.50 g of 3,5-difluorobenzyl bromide and 0.50 g of potassium carbonate dissolved in DMSO 200 mLIn a 500 mL three-necked flask, the mixture was heated and stirred to boiling, and stirred and reacted for 6 hours.The whole reaction of the <strong>[436-77-1]fangchinoline</strong>base was detected by HPLC, the solvent was distilled off under reduced pressure, and the temperature was lowered to room temperature.Add 40% 1,4-succinic acid (to solution pH = 7.5) and stir to boiling for 6 h.Cool to room temperature, add 80 mL of water and extract 3 times with chloroform (300 mL × 3).HPLC separates the separation and purification process of the reaction and the product,The extract was dried over anhydrous Na 2 SO 4 for 8 h, and the chloroform was recovered. The solid was dried at 60 C for 4 h.That is, 6.25 g of a product as a pale yellow powder. The melting point of the desired product: 223.1-224.6 C, TOF-HRMS: M / e (1105.1214), molecular formula: C62H58O10N2F6, that is, Table 2Compound III169.
  • 6
  • [ 110-15-6 ]
  • [ 141776-91-2 ]
  • [ 436-77-1 ]
  • C44H44F2N2O6*C4H6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.95 g Weigh 6.10g of <strong>[436-77-1]fangchinoline</strong>, 2.10g of 3,5-difluorobenzyl bromide and 1.40g of potassium carbonate dissolved in DMSO 200mLIn a 500 mL three-necked flask, the mixture was heated and stirred to boiling, and stirred and reacted for 6 hours.TLC detection of all reactions of <strong>[436-77-1]fangchinoline</strong>, decompressionEvaporate the solvent and cool to room temperature.20%1,4-succinic acidNeutralize to pH=7.0, add 50 mL of water and extract 3 times with chloroform (150 mL)×3), TLC traces the reaction and the separation and purification process of the product. The extract is dried with anhydrous Na2SO4 for 8 h to recover chloroform.Dry at 60 C for 4 h,That is, 5.95 g of a product as a pale yellow powder.
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