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[ CAS No. 3731-51-9 ] {[proInfo.proName]}

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Chemical Structure| 3731-51-9
Chemical Structure| 3731-51-9
Structure of 3731-51-9 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations      Expand+

Ingraham, Charles H. IV ; Stalinska, Joanna ; Carson, Sean C. , et al. DOI: PubMed ID:

Abstract: Glioblastomas are highly aggressive brain tumors for which therapeutic options are very limited. In a quest for new anti-glioblastoma drugs, we focused on specific structural modifications to the benzoyl-phenoxy-acetamide (BPA) structure present in a common lipid-lowering drug, fenofibrate, and in our first prototype glioblastoma drug, PP1. Here, we propose extensive computational analyses to improve the selection of the most effective glioblastoma drug candidates. Initially, over 100 structural BPA variations were analyzed and their physicochemical properties, such as water solubility (- logS), calculated partition coefficient (ClogP), probability for BBB crossing (BBB_SCORE), probability for CNS penetration (CNS-MPO) and calculated cardiotoxicity (hERG), were evaluated. This integrated approach allowed us to select pyridine variants of BPA that show improved BBB penetration, water solubility, and low cardiotoxicity. Herein the top 24 compounds were synthesized and analyzed in cell culture. Six of them demonstrated glioblastoma toxicity with IC50 ranging from 0.59 to 3.24 μM. Importantly, one of the compounds, HR68, accumulated in the brain tumor tissue at 3.7 ± 0.5 μM, which exceeds its glioblastoma IC50 (1.17 μM) by over threefold.

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Robert Kaw?cki ; DOI: PubMed ID:

Abstract: N-Sulfenylimines (sulfenimines, thiooximes, N-alkylidenesulfenamides) were efficiently synthesized through the reaction of primary amines and disulfides with NBS or bromine. This reaction can be carried out in an open flask at room temperature without the need for any transition-metal-containing additives. The use of thiols instead of disulfides gave similar results. A wide range of amines were reacted with aryl and alkyldisulfides, resulting in the formation of sulfenimines in a yield of 44–99%.

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Giri R. Gnawali ; Koichi Okumura ; Karolina Perez , et al. DOI: PubMed ID:

Abstract: Compound VBT-5445 was identified as an inhibitor to block the association of Pim and the protein Enhancer of Decapping 3 (EDC3), a Pim substrate, which normally functions to enhance the decapping of messenger RNA (mRNA). It was also shown to inhibit both the Pim and mTORC protein kinases. The activity of this compound class can be fine-tuned by structural modification. A series of VBT analogs were designed, synthesized, and evaluated. These compounds decrease the growth of multiple cancer types, including pancreas, prostate, breast, lung, and leukemia. Notably, 6-methyl (GRG-1-31, 6d), 4-chloro (GRG-1-34, 6e), 4-Bromo (GRG-1-35, 6f), and phenylthio substituted (GRG-1-104, 6n) derivatives are highly potent at inhibiting tumor growth. The ability of these compounds to block cancer growth in vitro is highly correlated with their activity as mTORC inhibitors. The toxicity of GRG 1–34 is low in mice treated with twice-daily gavage for 30 days and did not induce weight loss. Pharmacokinetics of a single oral dose demonstrated a peak concentration at 0.5?h after gavage. In summary, further development of this compound class has the potential to inhibit important signaling pathways and impact cancer treatment.

Keywords: Quinoline derivatives ; Pim kinase ; Antitumor activity ; mTORC

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Product Details of [ 3731-51-9 ]

CAS No. :3731-51-9 MDL No. :MFCD00006360
Formula : C6H8N2 Boiling Point : No data available
Linear Structure Formula :C5H4N(CH2)NH2 InChI Key :WOXFMYVTSLAQMO-UHFFFAOYSA-N
M.W : 108.14 Pubchem ID :19509
Synonyms :
Chemical Name :Pyridin-2-ylmethanamine

Calculated chemistry of [ 3731-51-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.91
TPSA : 38.91 ?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) : -7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : -0.21
Log Po/w (WLOGP) : 0.39
Log Po/w (MLOGP) : -0.14
Log Po/w (SILICOS-IT) : 1.01
Consensus Log Po/w : 0.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.87
Solubility : 14.7 mg/ml ; 0.136 mol/l
Class : Very soluble
Log S (Ali) : -0.15
Solubility : 76.5 mg/ml ; 0.707 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.0
Solubility : 1.07 mg/ml ; 0.00991 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 3731-51-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 3731-51-9 ]

* 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 [ 3731-51-9 ]
  • Downstream synthetic route of [ 3731-51-9 ]

[ 3731-51-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 3731-51-9 ]
  • [ 141774-61-0 ]
Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2928 - 2931
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