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[ CAS No. 4408-64-4 ] {[proInfo.proName]}

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Chemical Structure| 4408-64-4
Chemical Structure| 4408-64-4
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Quality Control of [ 4408-64-4 ]

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Product Citations

Product Citations      Expand+

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

Purchased from AmBeed: ; ;

Andrew R. Mahoney ; Kelly M. Storek ; William M. Wuest DOI: PubMed ID:

Abstract: The search for antibiotics that function through novel mechanisms of action is ongoing, and recent progress in our lab identified the tricarboxylic acid cycle as a viable option. Promysalin is a secondary metabolite capable of species-specific inhibition of Pseudomonas aeruginosa, a common opportunistic pathogen. Promysalin disrupts primary metabolism in this bacterium by competitively inhibiting succinate dehydrogenase at the ubiquinone binding site. However, the activity of promysalin in cellulo is marred potentially by its chemical instability and/or propensity for efflux. To assess the success of these novel analogues, a novel strain of P. aeruginosa harboring gene deletions of eight efflux pumps and porins was developed and implemented. Herein, we disclose the synthesis and biological investigation of six promysalin analogues to overcome these liabilities and demonstrate that efflux likely plays a significant role in tolerating the effect of the inhibitor.

Purchased from AmBeed: ; 24850-33-7 ; 58479-61-1 ; ; 67843-74-7 ; ; 37342-97-5 ; 18162-48-6 ; 34164-50-6 ; ; 1310-73-2 ; 814-68-6 ; 111-71-7 ; 693-25-4

Product Details of [ 4408-64-4 ]

CAS No. :4408-64-4 MDL No. :MFCD00004284
Formula : C5H9NO4 Boiling Point : -
Linear Structure Formula :(HOCOCH2)2NCH3 InChI Key :XWSGEVNYFYKXCP-UHFFFAOYSA-N
M.W : 147.13 Pubchem ID :20441
Synonyms :
Chemical Name :2,2'-(Methylazanediyl)diacetic acid

Calculated chemistry of [ 4408-64-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.6
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 32.59
TPSA : 77.84 ?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) : -9.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.79
Log Po/w (XLOGP3) : -3.32
Log Po/w (WLOGP) : -0.91
Log Po/w (MLOGP) : -0.96
Log Po/w (SILICOS-IT) : -1.39
Consensus Log Po/w : -1.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : 1.6
Solubility : 5900.0 mg/ml ; 40.1 mol/l
Class : Highly soluble
Log S (Ali) : 2.26
Solubility : 26700.0 mg/ml ; 182.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.86
Solubility : 1070.0 mg/ml ; 7.24 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.3

Safety of [ 4408-64-4 ]

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 [ 4408-64-4 ]

* 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 [ 4408-64-4 ]

[ 4408-64-4 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 4408-64-4 ]
  • [ 87199-17-5 ]
  • [ 1072960-66-7 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃;Molecular sieve; Inert atmosphere; 0.4 mmol of 4-formylphenylboronic acid, 0.5 mmol of N-methyliminodiacetic acid, 4? molecular sieve (40 mg)After dissolving in N, N-dimethylformamide,Under an argon atmosphereStir at 130 C.The amount of 4-formyl phenyl bromic acid consumed was checked to complete the reaction, and the mixture was cooled to 80 C to produce a compound represented by formula (32).
In N,N-dimethyl-formamide; at 130℃;Molecular sieve; Inert atmosphere; Formyl phenylboronic acid (0.5 mmol), N-methyliminodiacetic acid (1.5 mmol) and 4A molycularis (200 mg) were dissolved in 4 mL of N, N-dimethylformamide (DMF).The reaction mixture was stirred in an argon atmosphereThe reaction mixture was heated to 130 C and stirred.Respectively. After completion of the reaction, the reaction mixture was cooled to room temperature.[0228](I). Without filtration or separation, (a) into the cooled mixtureA mixture of 1,2-phenylenediamine (1, 0.55 mmol; 1.1 eq) and a catalytic amount of KI (0.1 mmol, 0.2 eq)And the inner wall was washed with 1 mL of DMFAnd the mixture was stirred in an atmosphere exposed to air at 80 C.When the mixture prepared in (A) was exhausted, the reaction was terminated and the reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. The mixtureAnd purified by solid column chromatography to prepare a benzimidazole derivative substituted with a boronic acid.
  • 2
  • [ 4408-64-4 ]
  • [ 191162-40-0 ]
  • [ 1219720-20-3 ]
YieldReaction ConditionsOperation in experiment
93% In dimethyl sulfoxide; benzene; for 3h;Inert atmosphere; Reflux; To form protected organoboronic acid 2j, the general procedure was followed using N-methylindole-2-boronic acid (3.00 g, 17.1 mmol), N-methyliminodiacetic acid (2.77 g, 18.9 mmol), benzene (60 mL) and DMSO (30 mL). The mixture was refluxed for 3 h. The product was eluted with Et2θ:MeCN 2:1 to afford the boronate ester 2j as a colorless crystalline solid (4.55 g, 93%). TLC (EtOAc) Rf = 0.39, visualized by UV (254 nm) and KMnO4. 1H-NMR (500 MHz, CD3CN) δ 7.57 (app dt, / = 8.0, 1.0 Hz, 1 H), 7.39 (dd, / = 8.0, 1.0 Hz, 1 H), 7.20 (ddd, / = 8.0, 7.0, 1.0 Hz, 1 H), 7.04 (ddd, / = 8.0, 7.0, 1.0 Hz, 1 H), 6.66 (d, / = 1.0 Hz, 1 H), 4.07 (d, / = 1 7 Hz, 2H), 3.92 (d, / = 1 7 Hz, 2H), 3.82 (s, 3H), 2.56 (s, 3H). 13C-NMR (125 MHz, CD3CN) δ 169.4, 141.3, 129.0, 122.9, 121.5, 120.0, 1 1 1.4, 1 10.6, 62.3, 47.8, 32.8. 11 B-NMR (96 MHz, CD3CN) δ 10.8. HRMS (EI +) Calculated for C14H15BN2O4 (M) + : 286.1 125, Found: 286.1 127. IR (thin film, cm -1) 3000, 2948, 1765, 1653, 1617, 1508, 1456, 1509, 1456, 1360, 1332, 1276, 1236, 1 161 , 1037, 998, 962, 897, 859.
  • 3
  • [ 4408-64-4 ]
  • [ 148493-34-9 ]
  • [ 1404227-30-0 ]
  • 4
  • [ 4408-64-4 ]
  • [ 148493-34-9 ]
  • [ 1404227-06-0 ]
  • 5
  • [ 4408-64-4 ]
  • [ 115377-93-0 ]
  • [ 1613586-42-7 ]
  • 6
  • [ 3153-26-2 ]
  • [ 17217-57-1 ]
  • [ 4408-64-4 ]
  • [ 7732-18-5 ]
  • [VO(mIDA)(4,4'-dimethoxy-2,2'-dipyridyl)]*1.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 70℃; for 0.416667h; General procedure: The solutions contained 1) VO(acac)2 (5.3 g, 20.0 mmol), H2IDA (2.66 g, 20.0 mmol) and dmbipy (3.68 g, 17.0 mmol) in water (100 mL) and 2) VO(acac)2 (5.3 g, 20.0 mmol), mH2IDA (2.94 g,20.0 mmol) and dmbipy (3.68 g, 17.0 mmol) in water (100 mL) were heated about 25 min at 70°C in a heating mantle. Then, after several days, dark green crystals of [VO(mIDA)(dmbipy)*]1.5H2O and the grey-green powder of [VO(IDA)(dmbipy)]*2H2O were obtained. The composition of the studied compounds was established on the basis of the elemental analysis of carbon, hydrogen and nitrogen (CARBO ERBA type CHNS e O 1108). Anal. Calcd for [VO(mIDA)(dmbipy)]*1.5H2O (percent): C, 42.20, H, 4.84, N, 9.23. Found:C, 42.54, H, 4.94, N, 9.03.
  • 7
  • [ 4408-64-4 ]
  • [ 72824-04-5 ]
  • [ 1422023-40-2 ]
  • 8
  • [ 4408-64-4 ]
  • [ 1072960-66-7 ]
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