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Chemical Structure| 57103-21-6 Chemical Structure| 57103-21-6

Structure of 57103-21-6

Chemical Structure| 57103-21-6

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Product Details of [ 57103-21-6 ]

CAS No. :57103-21-6
Formula : C18H11I2N
M.W : 495.10
SMILES Code : IC1=CC2=C(N(C3=CC=CC=C3)C4=C2C=C(I)C=C4)C=C1
MDL No. :MFCD11521285
InChI Key :AWGAUYXFWGUFNE-UHFFFAOYSA-N
Pubchem ID :13407347

Safety of [ 57103-21-6 ]

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

Computational Chemistry of [ 57103-21-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 19
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 106.21
TPSA ?

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

4.93 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.65
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

6.3
Log Po/w (WLOGP)?

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

5.99
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.

5.83
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

5.96
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.55

Water Solubility

Log S (ESOL):?

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

-7.48
Solubility 0.0000163 mg/ml ; 0.000000033 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-6.19
Solubility 0.000318 mg/ml ; 0.000000642 mol/l
Class?

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

Poorly 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

-8.38
Solubility 0.00000208 mg/ml ; 0.0000000042 mol/l
Class?

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

Poorly soluble

Pharmacokinetics

GI absorption?

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

Low
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

Yes
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

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.

-4.85 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

1.0
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

1.0
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

2.0
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

1.0 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<2.0
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)

2.2

Application In Synthesis of [ 57103-21-6 ]

* 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 [ 57103-21-6 ]

[ 57103-21-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 57103-20-5 ]
  • [ 57103-21-6 ]
YieldReaction ConditionsOperation in experiment
85% With N-iodo-succinimide; acetic acid; at 20℃; [0102] 24.3 g (100 mmol) N-phenyl-<strong>[57103-20-5]3,6-dibromocarbazole</strong> in a glacial acetic acid (500 mL) solution was added with 44.9 g (200 mmol) of N-iodine succinimide to be stirred overnight at room temperature. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture until the liquid properties became neutral. The mixture was filtrated and the obtained solid was washed with water and dried to give N-phenyl-3,6-diiodinecarbazole (hereinafter, shown as PhI2Cz) with a yield of 85percent. [0103] By using the obtained PhI2Cz, a coupling reaction was performed with carbazole in the similar manner as described in the synthesis of N-ethyl-3,6-di(N-carbazolyl)carbazole to give the compound in the title, N-phenyl-3,6-di(N-carbazolyl)carbazole as a beige solid (yield: 85percent). NMR data are shown in FIG. 15 (1H NMR) and FIG. 16 (13C NMR). [0104] 1H NMR(300 MHz, CDCl3) delta 7.20-7.80(m, 21H), 8.15(d, J=7.8 Hz, 4H), 8.27(s, 2H). [0105] 13C NMR(75.5 MHz, CDCl3) delta 109.7, 111.3, 119.7, 120.3, 123.2, 123.9, 125.9, 126.3, 127.2, 128.2, 130.2, 130.4, 137.1, 140.7, 141.8. [0106] It had the melting point at 283° C and showed the sublimation point at 410° C under normal pressure. Formation of a uniform film over a substrate by a vacuum evaporation method was confirmed. Absorption maximum was at 341 nm in methanol and 344 nm for the evaporated film. It was fluorescent, showing the maximum of fluorescence at 435 nm in methanol and 409 nm for the evaporated film. The HOMO level was at -5.64 eV, and the LUMO level was at -2.33 eV. The absorption spectra for the methanol solution and evaporated film are shown in FIG. 10. The respective fluorescent spectrum and excitation spectrum are shown in FIG. 11.
 

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