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Chemical Structure| 7605-28-9 Chemical Structure| 7605-28-9

Structure of 7605-28-9

Chemical Structure| 7605-28-9

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Product Details of [ 7605-28-9 ]

CAS No. :7605-28-9
Formula : C8H7NO2S
M.W : 181.21
SMILES Code : N#CCS(=O)(C1=CC=CC=C1)=O
MDL No. :MFCD00007550
InChI Key :ZFCFFNGBCVAUDE-UHFFFAOYSA-N
Pubchem ID :82077

Safety of [ 7605-28-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331
Precautionary Statements:P261-P280-P301+P310-P311
Class:6.1
UN#:3439
Packing Group:

Computational Chemistry of [ 7605-28-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 44.09
TPSA ?

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

66.31 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.76
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

0.95
Log Po/w (WLOGP)?

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

2.06
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.

0.88
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

0.96
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.12

Water Solubility

Log S (ESOL):?

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

-1.8
Solubility 2.87 mg/ml ; 0.0158 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.

-1.93
Solubility 2.13 mg/ml ; 0.0118 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

-2.81
Solubility 0.279 mg/ml ; 0.00154 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.

-6.73 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)

2.15

Application In Synthesis of [ 7605-28-9 ]

* 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 [ 7605-28-9 ]

[ 7605-28-9 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 34259-99-9 ]
  • [ 7605-28-9 ]
  • [ 143031-99-6 ]
  • 2
  • [ 5460-32-2 ]
  • [ 7605-28-9 ]
  • [ 112520-84-0 ]
  • 3
  • [ 25365-71-3 ]
  • [ 7605-28-9 ]
  • [ 1519005-31-2 ]
YieldReaction ConditionsOperation in experiment
33% With triethylamine; In N,N-dimethyl-formamide; at 80 - 90℃; for 0.75h; General procedure: To a suspension of the iminium salt prepared as above from the proper indole, a solution of suitable active methylene reagent (11mmol) and triethylamine (1.21g, 12mmol) in dry DMF (8mL), pre-warmed to 80C, was added in one portion. The reaction mixture was stirred for 45min at 90C (for 13b: 1.5h at 105C). After cooling to rt, Et3N·HCl precipitated and the resulting suspension was treated with water (50mL). Then, work-ups 1-4 were carried out, as follows: (0038) Work-up 1 (for 9a, i, j, n, o; 10j; 12a, i; 13a-d, f, i-k, m, o; 14a, j; 15a, j; 16a, j): the suspension was allowed to stand for 2h. The precipitate obtained was filtered off, air dried and purified by crystallization. (0039) Work-up 2 (for 12n; 13e): the precipitate was filtered off and dissolved in CH2Cl2. The organic layer was washed with water (3×20mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the solvent, the crude product was purified by crystallization from ethanol. (0040) Work-up 3 (for 12j; 13h): the precipitate was filtered off, air dried, purified by chromatography (eluents: petroleum ether/ethyl acetate) and then crystallized from CHCl3 and diethyl ether (12j) or ethyl acetate mixture (13h). (0041) Work-up 4 (for 9g; 10i; 11j; 13l, n): the reaction mixture was extracted with ethyl acetate (9g; 10i; 11j) or CH2Cl2 (13l, n) (3×35mL). The combined organic extracts were washed with water (5×30mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the filtrate, the crude products 10i and 13l were crystallized from the proper solvent(s). Conversely, the crude products 9g and 13n were purified by chromatography (eluent: petroleum ether/ethyl acetate) and then crystallized from the proper solvent mix. For 11j, the filtrate was extracted with 1N HCl (10mL×2), the organic layer (CH2Cl2) was separated and discarded, while the acid aqueous phase was made alkaline with 1N NaOH (25mL) and extracted with dichloromethane. The combined organic extracts were washed with water (2×20mL), dried over anhydrous Na2SO4 and evaporated in vacuo: the residue was crystallized from acetonitrile.
  • 4
  • [ 26260-02-6 ]
  • [ 19591-17-4 ]
  • [ 7605-28-9 ]
  • 7-(phenylsulfonyl)indolo[1,2-a]quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% General procedure: A dry sealed tube was charged with a magnetic stirrer, substituted<strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100 mg for each example,0.38 mmol), malononitrile or 2-sulfonylacetonitriles(0.46 mmol, 1.2 equiv), CuI (0.038 mmol, 0.1 equiv), L-proline(0.076 mmol, 0.2 equiv), and K2CO3 (0.76 mmol, 2 equiv) in0.77 mL of DMSO. The tube was evacuated and backfilled withargon and the process was repeated three times. The mixturewas stirred at 80 C for 12 h under an argon atmosphere.After the starting material was consumed completely,2-iodobenzaldehyde (0.4 mmol, 1.05 equiv) with 0.77 mL ofDMSO was charged successively to the tube via syringe,and then the resulting mixture was stirred at 80 C foranother 12 h under an argon atmosphere. After thereaction was complete, the reaction mixture was cooledto room temperature and the reaction mixture was partitionedbetween ethyl acetate or dichloromethane and water. Theorganic layer was separated and the aqueous layer was extractedwith ethyl acetate or dichloromethane for three times. Thecombined organic solution was washed with water, brine, driedover anhydrous Na2SO4, and concentrated under reducedpressure to give the crude product. Purification by chromatographyon silica gel using petroleum ether/ethyl acetate ordichloromethane/ethyl acetate as eluent provided the desiredproduct.
  • 5
  • [ 606-83-7 ]
  • [ 7605-28-9 ]
  • [ 2286-54-6 ]
  • [ 3112-85-4 ]
YieldReaction ConditionsOperation in experiment
62% With aluminum (III) chloride; at 200℃; for 3h;Inert atmosphere; General procedure: In a 10 mL round-bottomed flask, (phenylsulfonyl)acetonitrile (544mg, 3.0 mmol, 1.0 equiv) was added to a mixture of acid 1(3.0mmol) and AlCl3(8 mg, 0.06 mmol, 0.02 equiv). The mixture was then stirred under argon at 200 C for 3 h. After completion of the reaction, the crude mixture was diluted with CH2Cl2(5 mL + 5 mL),silica gel (3 g) was then added to make a solid deposit after evaporation of the solvent. A silica gel column chromatography (eluent:PE-EtOAc, 95:5) finally afforded the pure nitrile together with methyl phenyl sulfone.
  • 6
  • [ 2215-77-2 ]
  • [ 7605-28-9 ]
  • [ 3112-85-4 ]
  • [ 3096-81-9 ]
YieldReaction ConditionsOperation in experiment
53% With aluminum (III) chloride; at 200℃; for 3h;Inert atmosphere; General procedure: In a 10 mL round-bottomed flask, (phenylsulfonyl)acetonitrile (544mg, 3.0 mmol, 1.0 equiv) was added to a mixture of acid 1(3.0mmol) and AlCl3(8 mg, 0.06 mmol, 0.02 equiv). The mixture was then stirred under argon at 200 C for 3 h. After completion of the reaction, the crude mixture was diluted with CH2Cl2(5 mL + 5 mL),silica gel (3 g) was then added to make a solid deposit after evaporation of the solvent. A silica gel column chromatography (eluent:PE-EtOAc, 95:5) finally afforded the pure nitrile together with methyl phenyl sulfone.
 

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