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[ CAS No. 123-11-5 ] {[proInfo.proName]}

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Chemical Structure| 123-11-5
Chemical Structure| 123-11-5
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Product Citations

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Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier , et al. DOI: PubMed ID:

Abstract: PBRM1 is a subunit of the PBAF chromatin remodeling complex that uniquely contains six bromodomains. PBRM1 can operate as a tumor suppressor or tumor promoter. PBRM1 is a tumor promoter in prostate cancer, contributing to migratory and immunosuppressive phenotypes. Selective chemical probes targeting PBRM1 bromodomains are desired to elucidate the association between aberrant PBRM1 chromatin binding and cancer pathogenesis and the contributions of PBRM1 to immunotherapy. Previous PBRM1 inhibitors unselectively bind SMARCA2 and SMARCA4 bromodomains with nanomolar potency. We used our protein-detected NMR screening pipeline to screen 1968 fragments against the second PBRM1 bromodomain, identifying 17 hits with Kd values from 45 μM to >2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 100-52-7 ; 123-11-5 ; 1711-06-4 ; 454-89-7 ; ; ; ; ; ; ; ; ; ; ; ; ; 118-92-3 ; 22458-07-7 ; ; ; ; ; 97-96-1 ; ; 89-98-5

Nkomba, Gaofenngwe ;

Abstract: Despite the availability of various classes of antiepileptic drugs (AEDs), about one third of epileptic patients do not experience satisfactory seizure control with present treatments. This has been an important drive in the search for alternative epilepsy treatment. The endogenous nucleoside adenosine is a known anticonvulsant through activation of adenosine A1 receptors. The development of adenosine derivatives such as N6-cyclohexyladenosine (CHA) as anticonvulsants had limitations which include pronounced peripheral side effects, mainly cardiovascular effects. Over the years, non-nucleoside agonists have been investigated as an alternative set of compounds which are highly potent and selective to specific adenosine receptor (AR) subtypes. The aim of this study was to investigate the use of amino-3,5-dicyanopyridine and thieno[2,3- b]pyridine derivatives as potential A1 AR agonists. A total of 23 test compounds were synthesised (6a–s and 7a–d) and 7 of these were novel (6d and 6k–p), while 4 compounds (7a–d) have been synthesised before but have never been tested for AR affinity. The effect of intramolecular cyclisation that occurs during synthesis of thieno[2,3-b]pyridines from the intermediate compounds, amino-3,5-dicyanopyridines, in relation to AR binding was evaluated. Overall, amino-3,5-dicyanopyridine displayed superior activity towards rA1 ARs compared to thieno[2,3]pyridines. The general poor activity of thieno[2,3-b]pyridines suggest that the intramolecular cyclisation results in molecular stiffening or rigidity which negatively affects binding to the receptors, perhaps, due to steric hindrance. For instance, compound 6f (open ring) had a six-fold better inhibition constant (Ki) value of 48 nM for the A1 subtype compared to its closed ring counterpart compound 7d (rA1Ki = 305 nM). Generally, most amino-3,5- dicyanopyridines exhibited greater affinity toward the rA1 AR (Ki

Keywords: Epilepsy ; Antiepileptic drugs ; Adenosine A1/A2A receptor agonists ; Amino-3 ; 5- dicyanopyridine derivatives ; Thieno[2 ; 3-b]pyridine derivatives ; Intramolecular cyclisation

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Product Details of [ 123-11-5 ]

CAS No. :123-11-5 MDL No. :MFCD00003385
Formula : C8H8O2 Boiling Point : -
Linear Structure Formula :C6H4(COH)(OCH3) InChI Key :ZRSNZINYAWTAHE-UHFFFAOYSA-N
M.W : 136.15 Pubchem ID :31244
Synonyms :
p-Anisaldehyde;Anisaldehyde;4-Anisaldehyde;P-Methoxybenzaldehyde;Anisic aldehyde

Calculated chemistry of [ 123-11-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.32
TPSA : 26.3 Ų

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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 1.51
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.07 mg/ml ; 0.00785 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 1.6 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.492 mg/ml ; 0.00361 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 123-11-5 ]

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 [ 123-11-5 ]

* 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.

  • Upstream synthesis route of [ 123-11-5 ]
  • Downstream synthetic route of [ 123-11-5 ]

[ 123-11-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 123-11-5 ]
  • [ 92409-15-9 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 16, p. 3761 - 3771
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