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Chemical Structure| 2227-98-7 Chemical Structure| 2227-98-7

Structure of 2227-98-7

Chemical Structure| 2227-98-7

4-Aminopyrrolo[3,2-d]pyrimidine

CAS No.: 2227-98-7

4.5 *For Research Use Only !

Cat. No.: A172095 Purity: 98%

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Product Details of [ 2227-98-7 ]

CAS No. :2227-98-7
Formula : C6H6N4
M.W : 134.14
SMILES Code : NC1=C2C(NC=N1)=CC=N2
MDL No. :MFCD11520862
InChI Key :YRVFQPBPZCRUDX-UHFFFAOYSA-N
Pubchem ID :5287565

Safety of [ 2227-98-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2227-98-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 38.29
TPSA ?

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

67.59 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.42
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

-0.3
Log Po/w (WLOGP)?

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

0.55
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.

-0.43
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

0.89
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.23

Water Solubility

Log S (ESOL):?

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

-1.15
Solubility 9.53 mg/ml ; 0.071 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.66
Solubility 29.4 mg/ml ; 0.219 mol/l
Class?

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

Very 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

-2.15
Solubility 0.958 mg/ml ; 0.00714 mol/l
Class?

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

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

No
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

No
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

No
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

No
Log Kp (skin permeation)?

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

-7.33 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

1.0
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<1.0
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)

1.66

Application In Synthesis of [ 2227-98-7 ]

* 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 [ 2227-98-7 ]

[ 2227-98-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 50-00-0 ]
  • [ 24629-25-2 ]
  • [ 2227-98-7 ]
  • (2S,3S)-2-[({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3-methylpentan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% In water; tert-butyl alcohol; at 70℃; for 16h;Inert atmosphere; [0051] Example I. Synthesis of (2S,3S)-2-[({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7- yl}methyl)amino]-3-methylpentan-l-ol (11). (0085) (0086) [0052] (2S,3S)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3- methylpentan-l-ol (1.1). (2S,35)-2-Amino-3-methylpentan-l-ol (0.120 g, 1.02 mmol), 9- deazaadenine (0.137 g, 1.02 mmol), and aq. formaldehyde solution (37percent, 0.092 mL, 1.22 mmol) were heated and stirred in tert-butanol (3 mL) at 70 °C for 16 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue purified by chromatography on silica gel (CHC13-7M NH3/MeOH, 92:8 then 89: 11 then 85: 15) to afford LI as a colourless waxy solid (0.120 g, 45percent). NMR (500 MHz, CD3OD): delta 8.16 (s, 1H), 7.47 (s, 1H), 3.98 (s, 2H), 3.69 (dd, J = 11.3, 4.3 Hz, 1H), 3.51 (dd, J = 11.3, 7.1 Hz, 1H), 2.62 (ddd, J = 7.0. 4.4, 4.4 Hz, 1H), 1.67 (m, 1H), 1.46 (m, 1H), 1.17 (m, 1H), 0.89-0.85 (m, 6H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.1 (C), 150.8 (CH), 146.7 (C), 129.0 (CH), 1 15.4 (C), 114.9 (C), 63.1 (CH), 62.1 (CH2), 41.8 (CH2), 36.7 (CH), 27.2 (CH2), 15.0 (CH3), 12.3 (CH3). ESI-HRMS calcd for Ci3H22N50+, (M+H)+, 264.1819, found 264.1820.
 

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