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[ CAS No. 5809-23-4 ] {[proInfo.proName]}

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Chemical Structure| 5809-23-4
Chemical Structure| 5809-23-4
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Product Citations

Product Citations

Anita Marfavi ; Liam D. Adair ; Elizabeth J. New , et al. DOI:

Abstract: Two novel chromenylium-based probes were developed by functionalisation of the 5-position of the xanthene core with either a para-N-methyldiaminoacetic acid (MIDA) boronate ester (CRpMD) or closo?1,7-carborane (CRmCB). CRpMD revealed near-infrared emission at 655 nm, demonstrating a bathochromic shift compared to the analogous phenyl derivative (CRPh). Both boron-containing probes were found to be sensitive to changes in acidic pH, with CRpMD also displaying a dual fluorescence response at alkaline pH (pKa1 = 2.40 and pKa2 = 9.16). CRmCB showed a ca. 3-fold increase in fluorescence intensity at 638 nm from pH 7.01 to 2.00, with a pKa = 2.08. Moreover, CRpMD and CRmCB were successfully taken up by A549 lung cancer cells to assess their intracellular biodistributions, thereby showcasing the future potential of these probes for time-resolved pH measurements using confocal microscopy.

Keywords: Near-infrared ; Fluorescence microscopy ; Fluorescent probes ; BoronpH sensor

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Product Details of [ 5809-23-4 ]

CAS No. :5809-23-4 MDL No. :MFCD00134669
Formula : C18H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :FQNKTJPBXAZUGC-UHFFFAOYSA-N
M.W : 313.35 Pubchem ID :79878
Synonyms :

Calculated chemistry of [ 5809-23-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.22
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 89.12
TPSA : 77.84 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 3.84
Log Po/w (WLOGP) : 3.17
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.19
Solubility : 0.0201 mg/ml ; 0.0000643 mol/l
Class : Moderately soluble
Log S (Ali) : -5.17
Solubility : 0.00212 mg/ml ; 0.00000675 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.57
Solubility : 0.00853 mg/ml ; 0.0000272 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.48

Safety of [ 5809-23-4 ]

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

Application In Synthesis of [ 5809-23-4 ]

* 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 [ 5809-23-4 ]

[ 5809-23-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 58196-33-1 ]
  • [ 5809-23-4 ]
  • 6-(2-carboxyphenyl)-9-(diethylamino)-3,4-dihydro-2H-chromeno[3,2-g]quinoline [ No CAS ]
  • 2
  • [ 58196-33-1 ]
  • [ 5809-23-4 ]
  • 9-(diethylamino)-1,2,3,4-tetrahydro-3'H-spiro[chromeno[3,2-g]quinoline-6,1'-isobenzofuran]-3'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With sulfuric acid; at 90℃; for 8h; Compound b (1.05 g, 3.35 mmol) was placed in a 75 ml pressurized bottle, 10 ml of concentrated sulfuric acid was added, and Compound 5a (500 mg, 3.35 mmol) was added portionwise to the reaction solution. 90 C reaction 8h. After cooling to room temperature, the reaction solution was poured into 300 ml of ice and neutralized with saturated sodium hydroxide solution until neutral. A solid precipitated out, was filtered, washed with water, the cake was dried and purified by column chromatography. Obtained red solid 1.30g, yield 91%
91% With sulfuric acid; for 24h;Sealed tube; Heating; Compound 1 (1.05 g, 3.35 mmol) and 2 (0.50 g, 3.35 mmol) were dissolvedin concentrated H2SO4 in pressure tube and stirred at 90oC for 24 h. After the completion ofthe reaction, the reaction mixture was poured into ice and neutralized with NaOH aqueoussolution, then extracted with dichloromethane 3 times and dried over Na2SO4. Evaporation ofthe solvent resulted in a red solid. The crude material was purified by flash columnchromatography to yield the product as a red solid (1.30 g) in a 91% yield.
  • 3
  • [ 58196-33-1 ]
  • [ 5809-23-4 ]
  • 9-(diethylamino)-1-nitroso-1,2,3,4-tetrahydro-3'H-spiro[chromeno[3,2-g]quinoline-6',1'-isobenzofuran]-3'-one [ No CAS ]
  • 4
  • [ 3839-35-8 ]
  • [ 5809-23-4 ]
  • [ 302776-68-7 ]
YieldReaction ConditionsOperation in experiment
47.6% With potassium carbonate; In N,N-dimethyl-formamide; at 100 - 110℃; for 4h;Large scale; 2- (4-N, N-diethylamino-2-hydroxybenzoyl) benzoic acid (1.1 kg, 3.51 mol) synthesized in Preparation Example 1,Hexyl 4-methylbenzenesulfonate (1.1 kg, 4.22 mol), K2CO3 (0.9 kg, 7.02 mol) synthesized in Preparation Example 2-4 was stirred with 1.65 L of DMF.After raising the internal temperature to 100 ~ 110 and stirred for 4 hours, cooled and extracted with 3.5 L of ethyl acetate and 3.5 L of purified water.The separated organic layer was concentrated under reduced pressure after decolorizing for 1 hour using 5% charcoal at an internal temperature of 30-50 C.The concentrated residue was crystallized by the crystallization method of Example 3 to obtain the title compound (0.66 kg, 47.6%) in the form of crystalline particles.
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