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[ CAS No. 934-32-7 ] {[proInfo.proName]}

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Chemical Structure| 934-32-7
Chemical Structure| 934-32-7
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Product Citations

Product Citations      Expand+

Ryan M. Hacker ; Daniela M. Grimard ; Katie A. Morgan , et al. DOI: PubMed ID:

Abstract: With the recent clinical success of anti-amyloid-β (Aβ) monoclonal antibodies, there is a renewed interest in agents which target the Aβ peptide of Alzheimer's disease (AD). Metal complexes are particularly well-suited for this development, given their structural versatility and ability to form stabile interactions with soluble Aβ. In this report, a small series of ruthenium–arene complexes were evaluated for their respective ability to modulate both the aggregation and cytotoxicity of Aβ. First, the stability of the complexes was evaluated in a variety of aqueous media where the complexes demonstrated exceptional stability. Next, the ability to coordinate and modulate the Aβ peptide was evaluated using several spectroscopic methods, including thioflavin T (ThT) fluorescence, dynamic light scattering (DLS), and transmission electron microscopy (TEM). Overall, the complex RuBO consistently gave the greatest inhibitory action towards Aβ aggregation, which correlated with its ability to coordinate to Aβ in solution. Furthermore, RuBO also had the lowest affinity for serum albumin, which is a key consideration for a neurotherapeutic, as this protein does not cross the blood brain barrier. Lastly, RuBO also displayed promising neuroprotective properties, as it had the greatest inhibition of Aβ-inducted cytotoxicity.

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Walczak, Juliusz Maksymilian ; Iwaszkiewicz-Grzes, Dorota ; Ziomkowska, Michalina , et al. DOI: PubMed ID:

Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5′-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (A2) revealed the most promising activity. Subsequently, an observed structure-activity relationship was discussed.

Keywords: Mycophenolic acid ; amide derivatives ; heterocycles ; benzoxazole ; IMPDH inhibition

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Product Details of [ 934-32-7 ]

CAS No. :934-32-7 MDL No. :MFCD00005596
Formula : C7H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :JWYUFVNJZUSCSM-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :13624
Synonyms :
2-Iminobenzimidazoline;1H-Benzimidazol-2-ylamine
Chemical Name :1H-Benzo[d]imidazol-2-amine

Calculated chemistry of [ 934-32-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.5
TPSA : 54.7 ?2

Pharmacokinetics

GI absorption : High
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) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.62
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : 1.15
Log Po/w (MLOGP) : 0.78
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 0.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.9
Solubility : 1.66 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.02 mg/ml ; 0.0227 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.404 mg/ml ; 0.00303 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 934-32-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 934-32-7 ]

* 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 [ 934-32-7 ]

[ 934-32-7 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 934-32-7 ]
  • [ 6628-68-8 ]
  • 4-hydroxy-3-(2'-phenylethyl)pyrimido-<1,2-a> benzimidazole-2-one [ No CAS ]
  • 2
  • [ 934-32-7 ]
  • [ 5432-53-1 ]
  • Dimethyl-[4-(2-methyl-1,4-dihydro-benzo[4,5]imidazo[1,2-a]pyrimidin-4-yl)-phenyl]-amine [ No CAS ]
  • 3
  • [ 934-32-7 ]
  • [ 17823-69-7 ]
  • 3-(1H-benzimidazol-2-ylamino)-2-cyano-3-methylsulfanylacrylamide [ No CAS ]
  • 4
  • [ 934-32-7 ]
  • [ 17823-69-7 ]
  • [ 183998-92-7 ]
  • 5
  • [ 934-32-7 ]
  • [ 26673-30-3 ]
  • C17H14ClN3 [ No CAS ]
  • 6
  • [ 934-32-7 ]
  • [ 19832-98-5 ]
  • C18H17N3 [ No CAS ]
  • 7
  • [ 934-32-7 ]
  • [ 2012-74-0 ]
  • [ 851110-98-0 ]
  • 8
  • [ 1184-90-3 ]
  • [ 95-54-5 ]
  • [ 934-32-7 ]
  • 9
  • [ 934-32-7 ]
  • [ 28710-97-6 ]
  • 4-[(1H-benzo[d]imidazol-2-yl)diazenyl]-3-amino-1-phenyl-1H-pyrazol-5-one [ No CAS ]
  • 10
  • [ 934-32-7 ]
  • [ 5424-47-5 ]
  • 2-(thiophen-2-yl)-3,4-dihydro-pyrimido[1,2-a]benzimidazole [ No CAS ]
  • 11
  • [ 934-32-7 ]
  • [ 146137-78-2 ]
  • [ 1613287-72-1 ]
  • 12
  • [ 934-32-7 ]
  • [ 105763-77-7 ]
  • N2,N4-di(1H-benzo[d]imidazol-2-yl)-6-methoxyquinazoline-2,4-diamine [ No CAS ]
  • 13
  • [ 934-32-7 ]
  • [ 871125-82-5 ]
  • N-(4-((4-fluorobenzyl)oxy)phenyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 14
  • [ 934-32-7 ]
  • [ 41602-56-6 ]
  • (E)-2-(((1H-benzo[d]imidazol-2-yl)imino)methyl)-5-(dimethylamino)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.2% In ethanol; for 4h;Reflux; 2-Aminobenzimidazole (0.80 g,6 mmol) and compound 1 (0.99 g, 6 mmol) were dissolved in25 mL ethanol. The resulting solution was heated at reflux for4 h. The solvent was removed by a rotary evaporator at reducedpressure. The crude product was purified by silica gel columnchromatography (ethyl acetate/n-hexane 1:3) and recrystallizedwith ethanol to yield yellow solid. Yield: 1.03 g (61.2%);1H NMR (400 MHz, DMSO-d6) delta 3.05 (s, 6H, CH3), 6.16-7.53(m, 7H, Ar-H), 9.34 (s, 1H, CH=N), 12.41 (s, 1H, NH), 12.85(s, 1H, OH); ESIMS: 280.1408 (M + H+).
  • 15
  • [ 40263-57-8 ]
  • [ 934-32-7 ]
  • 2-(2-amino-1H-benzo[d]imidazole-1-yl)pyridin-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With copper(l) iodide; 8-quinolinol; caesium carbonate; In tert-butyl alcohol; at 90℃; for 16h;Sealed tube; General procedure: To a 2-5mL microwave vial was added 2-aminobenzimidazole (150mg, 1.13mmol), Cs2CO3 (918mg, 2.82mmol, 2.5 eq.), CuI (21mg, 0.11mmol, 0.1 eq.), 8-hydroxyquinoline (25mg, 0.17mmol, 0.15 eq.) and the appropriately substituted bromo or iodobenzene (1.24mmol, 1.1 eq.) were suspended in t-BuOH (2mL). The vial was sealed and heated at 110C (for bromobenzenes) or 90C (for iodobenzenes) for 16h. The cooled mixture was poured into EtOAc/MeOH (20:1) (30mL), filtered through Celite and evaporated under reduced pressure. The residue was purified by column chromatography using DCM/MeOH/NH4OH (89:10:1) to give typically colourless amorphous solids. This method produced compounds 2a-2l, 3a-3r, 4a, 4b, 5a, 5b, 6a-6d, 7, 8a-8c, 10.
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