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Chemical Structure| 17573-94-3 Chemical Structure| 17573-94-3

Structure of 17573-94-3

Chemical Structure| 17573-94-3

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Product Citations

Product Citations

Rajapaksha, Ishanka N. ; Wang, Jing ; Leszczynski, Jerzy ; Scott, Colleen N. ;

Abstract: NIR dyes have become popular for many applications, including biosensing and imaging. For this reason, the mol. switch mechanism of the xanthene dyes makes them useful for in vivo detection and imaging of bioanalytes. Our group has been designing NIR xanthene-based dyes by the donor-acceptor-donor approach; however, the equilibrium between their opened and closed forms varies depending on the donors and spacer. We synthesized donor-acceptor-donor NIR xanthene-based dyes with an alkyne spacer via the Sonogashira coupling reaction to investigate the effects of the alkyne spacer and the donors on the maximum absorption wavelength and the mol. switching (ring opening) process of the dyes. We evaluated the strength and nature of the donors and the presence and absence of the alkyne spacer on the properties of the dyes. It was shown that the alkyne spacer extended the conjugation of the dyes, leading to absorption wavelengths of longer values compared with the dyes without the alkyne group. In addition, strong charge transfer donors shifted the absorption wavelength towards the NIR region, while donors with strong π-donation resulted in xanthene dyes with a smaller equilibrium constant DFT/TDDFT calculations corroborated the exptl. data in most of the cases. Dye 2 containing the N,N-dimethylaniline group gave contrary results and is being further investigated.

Keywords: donor-acceptor-donor ; NIR dyes ; xanthene dyes ; amine donors ; alkyne spacers

Alternative Products

Product Details of [ 17573-94-3 ]

CAS No. :17573-94-3
Formula : C10H11N
M.W : 145.20
SMILES Code : CN(C)C1=CC=C(C#C)C=C1
MDL No. :MFCD00168816
InChI Key :ZWMAYLMVFSCMMS-UHFFFAOYSA-N
Pubchem ID :5191884

Safety of [ 17573-94-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H317-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 17573-94-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 48.58
TPSA ?

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

3.24 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.31
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

2.69
Log Po/w (WLOGP)?

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

1.81
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.

2.67
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

2.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.3

Water Solubility

Log S (ESOL):?

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

-2.77
Solubility 0.245 mg/ml ; 0.00169 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.41
Solubility 0.564 mg/ml ; 0.00388 mol/l
Class?

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

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

-2.57
Solubility 0.393 mg/ml ; 0.0027 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

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

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.

-5.28 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

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<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)

1.45

Application In Synthesis of [ 17573-94-3 ]

* 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 [ 17573-94-3 ]

[ 17573-94-3 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 13195-50-1 ]
  • [ 17573-94-3 ]
  • (4-(2-(5-nitrothien-2-yl)ethynyl)phenyl)dimethylamine [ No CAS ]
  • 3
  • [ 17573-94-3 ]
  • [ 3974-16-1 ]
  • [ 926008-65-3 ]
  • 4
  • [ 146533-41-7 ]
  • [ 17573-94-3 ]
  • [ 926008-69-7 ]
  • 5
  • [ 4181-20-8 ]
  • [ 17573-94-3 ]
  • [ 137832-78-1 ]
  • 6
  • [ 121554-10-7 ]
  • [ 17573-94-3 ]
  • [ 1310330-63-2 ]
  • 7
  • [ 22034-13-5 ]
  • [ 17573-94-3 ]
  • [ 1242469-75-5 ]
  • 8
  • [ 4181-20-8 ]
  • [ 17573-94-3 ]
  • C38H32IN3 [ No CAS ]
  • 9
  • [ 4038-15-7 ]
  • [ 17573-94-3 ]
  • 1-(2,4-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-1-(4-methoxyphenyl)prop-2-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% n-BuLi (2.5 M in hexanes) (11.80mL, 29.4 mmol) was added portionwise via syringe to a cold (-70 C)stirred solution of 4-ethynyl-N,N-dimethylaniline (4.27 g, 29.4 mmol) inanhydrous THF (30 mL) under N2. The cold solution was stirred for 30min and then <strong>[4038-15-7](2,4-dimethoxyphenyl)(4-methoxyphenyl)methanone</strong>(4.00 g, 14.7 mmol) was added in a single portion. The cooling bath wasremoved and the mixture stirred for 20 h at room temperature under N2.The reaction mixture was diluted with water (150 mL) and extractedwith EtOAc (3 × 75 mL). The combined organic extracts were washedwith water (150 mL), dried with anhydrous sodium sulfate and evaporatedto afford a brown oil. Elution from silica with 20% EtOAc/petroleumether afforded the title compound as an orange powder (0.87 g,85%); m.p. = 49-50 C; νmax (neat) 3506, 2932, 2834, 2217, 1605,1503, 1245, 1206, 1156, 1028, 816, 586 and 523 cm 1; 1H NMR (400MHz, CDCl3) δH 2.95 (6H, s, NMe2), 3.78 (3H, s, OMe), 3.80 (3H, s,OMe), 3.81 (3H, s, OMe), 4.77 (1H, s, OH), 6.44 (1H, dd, J = 8.6, 2.4 Hz,Ar-H), 6.51 (1H, d, J = 2.4 Hz, Ar-H), 6.58-6.62 (2H, m, Ar-H),6.84-6.88 (2H, m, Ar-H), 7.30-7.35 (3H, m, Ar-H), 7.49-7.53 (2H, m,Ar-H); 13C{1H} NMR (100 MHz, CDCl3) δC 40.24, 55.27, 55.41, 55.93,74.27, 87.39, 89.35, 100.16, 103.97, 109.97, 111.69, 113.17, 126.25,127.71, 129.22, 132.82, 137.45, 150.12, 157.94, 158.78, 160.58; HRMS(ESI) found [M+H]+ = 418.2002. C26H27NO4 requires [M+H]+ =418.2018.
 

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Technical Information

Categories

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