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Chemical Structure| 330792-70-6 Chemical Structure| 330792-70-6

Structure of 330792-70-6

Chemical Structure| 330792-70-6

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Product Details of [ 330792-70-6 ]

CAS No. :330792-70-6
Formula : C16H12N4O
M.W : 276.29
SMILES Code : N#CC1=C(N)NN=C1C2=CC=C(OC3=CC=CC=C3)C=C2
MDL No. :MFCD20270361
InChI Key :HNIMEQCLCNSCGH-UHFFFAOYSA-N
Pubchem ID :22346784

Safety of [ 330792-70-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 330792-70-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 17
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 79.66
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

87.72 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.92
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.33
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.33
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.72
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.63

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.05
Solubility 0.0245 mg/ml ; 0.0000887 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.85
Solubility 0.00391 mg/ml ; 0.0000142 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-5.74
Solubility 0.000507 mg/ml ; 0.00000184 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.62 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<0.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.55

Application In Synthesis of [ 330792-70-6 ]

* 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 [ 330792-70-6 ]

[ 330792-70-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 330792-70-6 ]
  • [ 188869-05-8 ]
  • 3-cyano-2-(4-phenoxyphenyl)-5,6-dihydro-4H-pyrazolo[5',1':2,3]imidazo [4,5-c]pyridine-7(8H)-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% [0427] A mixture of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (1.5 g, 5.4mmol) and K2C03 (2.24 g, 16.3 mmol) in 50 mL of DMF at 80 DC was stirred under N2 for 45min before tert-butyl3-bromo-4-oxopiperidine-1-carboxylate (4.5 g, 16.3 mmol) was added inone portion. Then the mixture was stirred at 80 DC for 1 hr. After cooling down toRT, 150 mLof water and 150 mL of EA was added. Aqueous phase was further extracted with EA (1 00 mL x 3). The combined organic layers were washed with brine, dried over Na2S04 and concentratedto get crude product which was chromatographed on I5 g of silica gel using DCM/MeOH (40011to 20011) as eluant to afford 850 mg (35%) oftert-butyl3-cyano-2-(4-phenoxyphenyl)-5,6-dihydro -4H -pyrazolo[5', I' :2,3 ]imidazo[ 4,5-c ]pyridine-? (8H)-carboxylate as an off-white solid.MS (ESI) m/e [M+ It 455.9.
35% 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (1.5 g, 5.4 mmol)And a mixture of K2CO3 (2.24 g, 16.3 mmol) in DMF (50 mL),Stir for 45 minutes under nitrogen at 80C.Then, <strong>[188869-05-8]tert-butyl 3-bromo-4-oxopiperidine-1-carboxylate</strong> (4.5 g, 16.3 mmol) was added in one portion.The reaction mixture was stirred at 80 C for 1 h.It was then cooled to room temperature and water (150 mL) and EA (150 mL) were added.The aqueous phase was further extracted with EA (100 mL x 3) and the combined organic phases were washed with saturated brine, dried over Na2SO4, concentrated, and purified on a tannin extract column (15 g of silica gel, DCM/MeOH = 400/1 to 200/1).An off-white solid product 3-cyano-2-(4-phenoxyphenyl)-5,6-dihydro-4H-pyrazolo[5',1':2,3]imidazo[4, 5-c]tert-Butyl pyridine-7(8H)-carboxylate (850 mg, 35%).
  • 2
  • [ 330792-70-6 ]
  • [ 188869-05-8 ]
  • 2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5',1':2,3]imidazo[4,5-c]pyridine-3-carboxamide trifluoroacetate [ No CAS ]
  • 3
  • [ 80370-42-9 ]
  • [ 330792-70-6 ]
  • ethyl 3‐cyano‐2‐(4‐phenoxyphenyl)pyrazolo[1,5‐a]pyrimidine‐6‐carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid; In ethanol; at 20℃; for 16h; [0565] To a solution of 5-amino-3-(4-phenoxyphenyl)-IH-pyrazole-4-carbonitrile (276 mg, 1.0mmol) in EtOH (10 mL) was added ethyl2-formyl-3-oxopropanoate (144 mg, 1.0 mmol) andHOAc (5 drops). After stirring at RT for 16 hr, the mixture was filtered. The cake was washedwith H20 (10 mL x 2) and dried to afford 250 mg (65percent) of ethyl3-cyano-2-(4-phenoxyphenyl)pyrazolo[l,5-a]pyrimidine-6-carboxylate as a yellow solid. MS (ESI) m/e[M+ It 384.9.
 

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