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[ CAS No. 179324-69-7 ] {[proInfo.proName]}

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Chemical Structure| 179324-69-7
Chemical Structure| 179324-69-7
Structure of 179324-69-7 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Brett H. Pogostin ; Samuel X. Wu ; Michael J. Swierczynski , et al. DOI:

Abstract: Maintaining safe and potent pharmaceutical drug levels is often challenging. Multidomain peptides (MDPs) assemble into supramolecular hydrogels with a well-defined, highly porous nanostructure that makes them attractive for drug delivery, yet their ability to extend release is typically limited by rapid drug diffusion. To overcome this challenge, we developed self-assembling boronate ester release (SABER) MDPs capable of engaging in dynamic covalent bonding with payloads containing boronic acids (BAs). As examples, we demonstrate that SABER hydrogels can prolong the release of five BA-containing small-molecule drugs as well as BA-modified insulin and antibodies. Pharmacokinetic studies revealed that SABER hydrogels extended the therapeutic effect of ganfeborole from days to weeks, preventing Mycobacterium tuberculosis growth better than repeated oral administration in an infection model. Similarly, SABER hydrogels extended insulin activity, maintaining normoglycemia for six days in diabetic mice after a single injection. These results suggest that SABER hydrogels present broad potential for clinical translation.

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Product Details of [ 179324-69-7 ]

CAS No. :179324-69-7 MDL No. :MFCD09056737
Formula : C19H25BN4O4 Boiling Point : -
Linear Structure Formula :(CH3)2CHCH2CH(B(OH)2)NHCOCH(CH2C6H5)NHCOC4H3N2 InChI Key :GXJABQQUPOEUTA-RDJZCZTQSA-N
M.W : 384.24 Pubchem ID :387447
Synonyms :
PS-341;LDP-341;MLN 341. US brand name: VELCADE.;MLN341;MG-341;NSC 681239
Chemical Name :((R)-3-Methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronic acid

Calculated chemistry of [ 179324-69-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.37
Num. rotatable bonds : 11
Num. H-bond acceptors : 6.0
Num. H-bond donors : 4.0
Molar Refractivity : 105.3
TPSA : 124.44 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 0.36
Log Po/w (MLOGP) : -0.8
Log Po/w (SILICOS-IT) : 0.12
Consensus Log Po/w : 0.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.71
Solubility : 0.753 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (Ali) : -3.64
Solubility : 0.0884 mg/ml ; 0.00023 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.73
Solubility : 0.00722 mg/ml ; 0.0000188 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.61

Safety of [ 179324-69-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P301+P310-P304+P340-P320-P330-P361-P405-P501 UN#:3249
Hazard Statements:H300-H310-H330-H372 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 179324-69-7 ]

* 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 [ 179324-69-7 ]

[ 179324-69-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 179324-69-7 ]
  • [ 130-85-8 ]
  • (bortezomib)2-pamoic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 20℃; for 2h; A 25 mL flask was charged with 0.85 grams of 4-[(3-Carboxy-2- hydroxynaphthalen-1 -yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid (pamoic acid) and 1 .7 grams of Bortezomib. Ten grams of dimethylformamide was added and the mixture was stirred at room temperature. The reaction mixture clarified over time, and was complete in 2 hours by TLC. The reaction mixture was filtered using a 0.45 m PVDF syringe filter and added dropwise to 250 mL ethyl ether under vigorous stirring resulting in the formation of a white precipitate. The solid was collected by vacuum filtration, transferred to a tared vial, and dried extensively under high vacuum to afford 2 grams of pure compound. TLC: 70:30 Acetone: Heptane Rf 0.5 on silica gel 60 F254 plates
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