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Chemical Structure| 1046864-83-8 Chemical Structure| 1046864-83-8

Structure of 1046864-83-8

Chemical Structure| 1046864-83-8

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Product Details of [ 1046864-83-8 ]

CAS No. :1046864-83-8
Formula : C24H24N2O6S2
M.W : 500.59
SMILES Code : O=C(N1C(C(C2=C1C3=CC=CS3)=C(C4=CC=CS4)N(C(OC(C)(C)C)=O)C2=O)=O)OC(C)(C)C
MDL No. :MFCD28098465
InChI Key :JWVNTGQABFZACQ-UHFFFAOYSA-N
Pubchem ID :59629049

Safety of [ 1046864-83-8 ]

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

Computational Chemistry of [ 1046864-83-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 34
Num. arom. heavy atoms 18
Fraction Csp3 0.33
Num. rotatable bonds 8
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 133.8
TPSA ?

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

153.08 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.91
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

3.96
Log Po/w (WLOGP)?

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

5.58
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.

2.64
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

5.81
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.38

Water Solubility

Log S (ESOL):?

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

-5.3
Solubility 0.0025 mg/ml ; 0.00000499 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.

-6.88
Solubility 0.0000667 mg/ml ; 0.000000133 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

-5.84
Solubility 0.000719 mg/ml ; 0.00000144 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

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

No
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

Yes
Log Kp (skin permeation)?

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

-6.54 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

1.0
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

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<3.0
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)

4.2

Application In Synthesis of [ 1046864-83-8 ]

* 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.

  • Downstream synthetic route of [ 1046864-83-8 ]

[ 1046864-83-8 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 1046864-83-8 ]
  • [ 1046864-84-9 ]
YieldReaction ConditionsOperation in experiment
50% With N-Bromosuccinimide; at 20.0℃; for 40h;Darkness; T-Boc TPP (2.36 g, 4.71 mmol) was added to CF in a 2-neck round bottom flask and stirred at room temperature.After light protection using an aluminum foil, NBS (2.09 g, 2.5 eq.) Was added and stirred for 40 hours or more.The reaction was monitored by TLC. When the reaction proceeded, the crude mixture was immediately evaporated and the CF / EtOHTo obtain a dark needle-like compound (Yield: 50%).
50% With N-Bromosuccinimide; at 20.0℃;Darkness; The t-l3oc TPP (2.36 g, 4.71 mmol) was added to CF in a 2-neck round bottom flask, and the mixture was stirred at room temperature. Light protection was performed by using an aluminum foil, and then N135 (2.09 g, 2.5 eq.) was added thereto and the mixture was stirred for 40 hours or more. It was confirmed through TLC whether the reaction proceeded, and if the reaction proceeded, the crude mixture was immediately evaporated and recrystallization was performed by using CF/EtOH, thereby obtaining 1.6 g (yield:50%) of Compound 2 having a dark brown needle shape. The NMR result of Compound 2 is illustrated in the following FIG. 4, and the MS data thereof are illustrated in the following FIG. 5.
With N-Bromosuccinimide; In chloroform; for 12h;Darkness; 3.0 g (6.0 mmol) of the compound represented by the chemical formula (1-1), 2.5 g (13.8 mmol) of N-bromosuccinimide and 200 mL of chloroform were placed in a 500 mL eggplant flask and shielded from light C for 12 hours. Next, after distilling off the solvent under reduced pressure, 100 mL of MeOH was added. Further, the precipitate was collected by filtration to obtain 3.1 g (yield: 78.8%) of a compound represented by the chemical formula (1-4) which is a dark green powder. The compound represented by the chemical formula (1-4) had m / z of 658.9, 656.9, and 660.9 ([M+H] +)
  • 2
  • [ 1046864-83-8 ]
  • [ 1046864-84-9 ]
  • [ 1383956-04-4 ]
  • 3
  • 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]
  • [ 34619-03-9 ]
  • [ 1046864-83-8 ]
  • 4
  • [ 1046864-83-8 ]
  • di-tert-butyl 3,6-bis(5-ethynylthiophen-2-yl)-1,4-dioxopyrrolo-[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate [ No CAS ]
  • 5
  • [ 1046864-83-8 ]
  • di-tert-butyl 3,6-bis[5-(1-octyl-1H-1,2,3-triazol-4-yl)thiophen-2-yl]-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate [ No CAS ]
  • 6
  • [ 1046864-83-8 ]
  • di-tert-butyl 1,4-dioxo-3,6-bis{5-[(trimethylsilyl)ethynyl]thiophen-2-yl}pyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate [ No CAS ]
  • 7
  • 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]
  • [ 24424-99-5 ]
  • [ 1046864-83-8 ]
YieldReaction ConditionsOperation in experiment
60% 2 spherical round bottom flaskTPP (4.0 g, 13.3 mmol) was added to a 2-neck round bottom flaskDimethylaminopyridine was added to the catalyst, and the mixture was stirred for about one hour.Then, di- (t-butyl) -dicarbonate (7.26 g, 33.2 mmol) was dissolved in anhydrous THF under nitrogen atmosphere using a syringe and stirred at RT for 12 hours .After the reaction was confirmed by TLC, the THF was reduced in pressure. After silica packing with hexane + Et3N as an eluent and loading the reaction mixture, the impurities were removed by flowing Hx: EA = 4: 1, and chloroform was added thereto. Respectively.After completion of the column, the solvent was removed by decompression, followed by washing with hexane and drying well in a vacuum oven to obtain 4.0 g (yield: 60%) of a dark brown solid compound t-Boc TPP.
60% TPP (4.0 g, 13.3 mmol) was dissolved in an anhydride THF in a 2-neck round bottom flask, and then, dimethylamonopyridine as a catalyst was added thereto, and the resulting mixture was stirred for about 1 hour. And then, di-(t-butyl)-dicarbonate (7.26 g, 33.2 mmol) was dissolved well in the anhydride THF, the solution was added to the flask under a nitrogen condition by using a syringe, and the resulting mixture was stirred at R.T. for 12 hours. The reaction was confirmed by TLC, and after the reaction was terminated, the THF was placed under reduced pressure. Silica packing was achieved by using hexane +Et3N as an eluent, and the reaction mixture was loaded, and then flowed at Hx:EA=4: 1 to remove impurities, and chloroform was flowed. Afier the column chromatography, pressure was reduced to remove the solvent, and the residue was washed with hexane and dried well in a vacuum oven, thereby obtaining 4.0 g of a dark brown solid compound t-Boc TPP (yield: 60%). The NMR result of Compound 1 is illustrated in the following FIG. 2, and the MS data thereof are illustrated in the following FIG. 3.
54.1% With dmap; In tetrahydrofuran; at 20.0℃; for 15h; 4.0 g (13.3 mmol) of the compound represented by the chemical formula (2-1), 12.0 g (54.9 mmol) of Di-tertbutyl dicarbonate, 200 mL of dry THF and 3.3 g (26.7 mmol) of dimethylaminopyridine (DMAP) , Placed in a 500 mL recovery flask, and then stirred at room temperature for 15 hours. Next, after distilling off the solvent under reduced pressure, 100 mL of MeOH was added. Further, the precipitate was collected by filtration and then purified using silica gel column chromatography (solvent: dichloromethane) to obtain 3.6 g (yield: 54.1) of the compound represented by the chemical formula (1-1) which is a red powder %) Was obtained. The compound represented by the chemical formula (1-1) had m / z of 501.01 ([M + H] +)
  • 8
  • [ 1046864-83-8 ]
  • C40H32N2O6S4 [ No CAS ]
  • 9
  • [ 1003-31-2 ]
  • [ 1046864-83-8 ]
  • 10
  • [ 1046864-83-8 ]
  • C44H52N2O6S4 [ No CAS ]
  • 11
  • [ 1046864-83-8 ]
  • C52H56N2O6S6 [ No CAS ]
  • 12
  • [ 1046864-83-8 ]
  • 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% at 250.0℃;Inert atmosphere; 50 mg (0.10 mmol) of the compound represented by the chemical formula (1-1) was placed in an Al pan and then heated in a nitrogen atmosphere at 20 C./min using a thermal analyzer EXSTRA 6200 (manufactured by Seiko Instruments Inc.) at 250 C. And the weight change (TG) was measured to obtain 29 mg (yield quant.) Of the compound represented by the chemical formula (2-1) which is a dark purple solid. The compound represented by the chemical formula (2-1) had m / z of 300.1 ([M + H] +)
  • 13
  • [ 1046864-83-8 ]
  • tetra-tert-butyl 6,6’-([2,2’-bithiophene]-5,5’-diyl)bis(1,4dioxo-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate) [ No CAS ]
  • 14
  • [ 1046864-83-8 ]
  • 6,6’-([2,2’-bithiophene]-5,5’-diyl)bis(3-(thiophen-2-yl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione) [ No CAS ]
 

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