74124-92-8|2-ACetamido-2,3-dihydro-1h-indene-5-sulfonyl chloride| Ambeed

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Quality Control of [ 74124-92-8 ] Purity: 95% SDS Specification

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Product Details of [ 74124-92-8 ]

CAS No. :	74124-92-8
Formula :	C₁₁H₁₂ClNO₃S
M.W :	273.74
SMILES Code :	CC(NC1CC2=C(C=C(S(Cl)(=O)=O)C=C2)C1)=O
MDL No. :	MFCD27500981
InChI Key :	XNVZUBLWWSTORI-UHFFFAOYSA-N
Pubchem ID :	20347856

Safety of [ 74124-92-8 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H314-H331
Precautionary Statements:	P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P405-P501
Class:	8(6.1)
UN#:	2923
Packing Group:	Ⅲ

Computational Chemistry of [ 74124-92-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	64.77
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.62 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.89
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.62
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.3
Log P_o/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.	1.24
Log P_o/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	1.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.62
Solubility	0.655 mg/ml ; 0.00239 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.	-2.74
Solubility	0.502 mg/ml ; 0.00184 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	-3.92
Solubility	0.0325 mg/ml ; 0.000119 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	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	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.	-6.82 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	0.0
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<0.0
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)	2.51

Application In Synthesis of [ 74124-92-8 ]

* 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 [ 74124-92-8 ]

[ 74124-92-8 ] Synthesis Path-Downstream 1~16

1
[ 13935-80-3 ]
[ 74124-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorosulfonic acid; In acetone; acetonitrile; at 3 - 80℃; for 21.0h;	EXAMPLE 2 2-Acetylamino-indan-5-sulfonyl chloride To a 2 L 3-necked glass reaction flask equipped with stirrer, condenser, thermocouple, 500 mL addition funnel and nitrogen inlet was added N-acetyl-2-aminoindan (0.96 mol, 167.70 g) and acetonitrile (490 mL). The reaction mixture was stirred and cooled in an ice-bath to about 3-5 C. and ClSO3H (3.83 mol, 440 g) was added slowly. The first 30% of the reagent was added over 30 minutes while maintaining the reaction temperature below 15 C. The ice-bath was then removed and the reaction mixture was warmed to room temperature. The remaining 70% of the reagent was added over 30 minutes and the temperature of the reaction solution rose to 80 C. at the end of the addition. The yellow reaction solution was stirred at 50 C. for about 20 hours. The reaction solution was cooled to 30 C. and slowly poured into a vigorously stirred mixture of ice (1620 g), water (945 mL), and acetonitrile (135 mL) in an ice-bath over about 10-15 minutes. The temperature of the quenching mixture dropped from 5 C. to -6 C. A white solid precipitated and the mixture was stirred at about 0-5 C. for 30 minutes. The solid was collected by vacuum filtration and slurried 4 times with a cold mixture of water (4*300 mL). The pH of the last slurry was around 2-3. The solid was then slurried with cold acetone (300 mL) (5-7 C.), collected by filtration, and finally rinsed with of cold acetone (200 mL). The solid product was air-dried for 4 hours, followed by drying in a vacuum oven at room temperature for 48 hours. The product was obtained as a white solid. mp 158-160 C. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (br s, 1H), 7.45 (s, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.15 (d, J=7.8 Hz, 1H), 4.45 (br m, 1H), 3.15 (m, 2H), 2.77 (dd, J=16.2, 5.7 Hz, 2H), 1.85 (s, 3H). 13C NMR (300 MHz, DMSO-d6) δ 169.6, 145.3, 142.3, 140.9, 123.9, 123.7, 121.6, 50.2, 38.6, 38.4, 22.2. MS (ESI): m/z 274.0 (MH+)

References: [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 5416 - 5431.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5781 - 5786.
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 2743 - 2749.
[4]Patent: US2005/240049,2005,A1 .Location in patent: Page/Page column 28-29.

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