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Chemical Structure| 80-48-8 Chemical Structure| 80-48-8

Structure of 80-48-8

Chemical Structure| 80-48-8

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Product Citations

Product Citations

Tyler J. Adams ; Naz F. Tumpa ; Maithili Acharya ; Quy H. Nguyen ; Nuren Shuchi ; Mia Baliukonis , et al.

Abstract: Water-soluble dipyridinium thiazolo[5,4-d]thiazole (TTz) compounds are incorporated into inexpensive poly(vinyl alcohol) (PVA)/borax films and exhibit fast (<1 s), high-contrast photochromism, photofluorochromism, and oxygen sensing. Under illumination, the films change from clear/yellow TTz2+ to purple TTz•+ and then blue TTz0. The contrast and speed of the photochromism are dependent on the polymer matrix redox properties and the concentration of TTz2+. The photoreduced films exhibit strong, near-infrared light (1000–1500 nm) absorbances in addition to visible color changes. Spectroscopic ellipsometry was used to establish the complex dielectric function for the TTz2+ and TTz0 states. Incorporating non-photochromic dyes yields yellow-to-green and pink-to-purple photochromism. Additionally, when illuminated, reversible photoactuation occurs, causing mechanical contraction in the TTz-embedded films. The blue film returns to its colorless state via exposure to O2, making the films able to sense oxygen and leak direction for smart packaging. These films show potential for use in self-tinting smart windows, eyeglasses, displays, erasable memory devices, fiber optic communication, and oxygen sensing.

Keywords: photochromic ; photofluorochromic ; photoactuator ; thiazolothiazole ; oxygen sensor ; sensing ; green chemistry

Purchased from AmBeed: ; ; ;

Alternative Products

Product Details of [ 80-48-8 ]

CAS No. :80-48-8
Formula : C8H10O3S
M.W : 186.23
SMILES Code : CC1=CC=C(S(=O)(OC)=O)C=C1
MDL No. :MFCD00008417
InChI Key :VUQUOGPMUUJORT-UHFFFAOYSA-N
Pubchem ID :6645

Safety of [ 80-48-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314-H317-H401
Precautionary Statements:P260-P264-P270-P272-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P333+P313-P362+P364-P405-P501
Class:8
UN#:3265
Packing Group:

Computational Chemistry of [ 80-48-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 45.59
TPSA ?

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

51.75 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.9
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

1.54
Log Po/w (WLOGP)?

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

2.41
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.

1.78
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

1.11
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.75

Water Solubility

Log S (ESOL):?

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

-2.2
Solubility 1.17 mg/ml ; 0.00627 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.

-2.24
Solubility 1.08 mg/ml ; 0.00581 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

-2.84
Solubility 0.27 mg/ml ; 0.00145 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

Yes
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.

-6.34 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

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)

2.02

Application In Synthesis of [ 80-48-8 ]

* 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 [ 80-48-8 ]
  • Downstream synthetic route of [ 80-48-8 ]

[ 80-48-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 80-48-8 ]
  • [ 400827-68-1 ]
  • [ 400827-64-7 ]
YieldReaction ConditionsOperation in experiment
74.3%
Stage #1: for 12 h; Reflux
Stage #2: With pyridine; phosphorus pentachloride In dichloromethane at -10 - -5℃; for 2 h;
Stage #3: With hydrogenchloride In dichloromethane; 2-methyl-propan-1-ol; acetone at 25 - 30℃;
A glass round bottom flask was charged with 35g (51,7 mmol) of 5-Thia-1-azabicyclo[4.2.0]oct- 2-ene-2-carboxylic acid, 8-oxo-7-[(2-phenylacetyl)amino]-3-[[4-(4-pyridinyl)-2-thiazolyl]thio]-, diphenylmethyl ester, (6R,7R) and 75 mE of dichloromethane, at 25°C. To the obtained solution were added 48 mE (258,5 mmol) of methyl paratoluenesulphonate and the mixture was heated to reflux and maintained for 12 hours under reflux, then cooled to room temperature. In glass lined reactor were charged 32,3 g (155,1 mmol) of phosphorous pentachloride and 75 mE of dichloromethane. The obtained suspension was cooled to -5÷0°C and 12.3 g (155,1 mmol)of pyridine were added dropwise by maintaining the temperature at -5÷0°C, then the mixture was maintained under stifling for 15 minutes at the same temperature. To the mixture, cooled to -1 0÷-5°C, was carefully added the solution prepared in the round bottom flask, keeping the temperature between -1 0÷-5°C; the mixture thus obtained was maintained under stifling for 2 hours at the same temperature. 105 mE of isobutanol were carefully added, in about 30 minutes, by maintaining the temperature at -5°C0°C; the obtained mixture was heated at 28÷30°C and left to react at the same temperature for 3.5 hours. The mixture was concentrated under vacuum to 1/3 of its volume, diluted with 200 mE of acetone and maintained under stifling for 1 hour at 25÷30°C. 70 mE of 32percent hydrochloric acid were added, keeping the temperature in the range of 25÷30°C, and themixture was maintained under stirring overnight. The obtained suspension was filtered, the cake was washed with acetone (2 x 35 ml). The wet solid was dried under vacuum at 40°C overnight yielding 18.4 g (38,4 mmol) of 4-[2- [[(6R,7R)-7-amino-2-carboxy-8-oxo-5-thia- 1- azabicyclo [4.2.01 oct-2-en-3-yl]thio] -4-thiazolyl] -1 -methyl pyridinium, chloride, hydrochloride (1:1:1) as a crystalline solid. Yield 74,3percent.
References: [1] Patent: WO2016/128580, 2016, A1, . Location in patent: Page/Page column 21.
 

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