Home Cart Sign in  
Chemical Structure| 582-33-2 Chemical Structure| 582-33-2

Structure of 582-33-2

Chemical Structure| 582-33-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Ganga Reddy Velma ; Megan S. Laham ; Cutler Lewandowski ; Ana C. Valencia-Olvera ; Deebika Balu ; Annabelle Moore , et al.

Abstract: Therapeutics enhancing apolipoprotein (APOE) positive function are a priority, because APOE4 is the major genetic risk factor for Alzheimer’s disease (AD). The function of APOE, the key constituent of lipoprotein particles that transport cholesterol and lipids in the brain, is dependent on lipidation by ABCA1, a cell_x005f_x0002_membrane cholesterol transporter. ABCA1 transcription is regulated by liver X receptors (LXR): agonists have been shown to increase ABCA1, often accompanied by unwanted lipogenesis and elevated triglycerides (TG). Therefore, nonlipogenic ABCA1-inducers (NLAI) are needed. Two rounds of optimization of an HTS hit, derived from a phenotypic screen, gave lead compound 39 that was validated and tested in E3/4FAD mice that express human APOE3/4 and five mutant APP and PSEN1 human transgenes. Treatment with 39 increased ABCA1 expression, enhanced APOE lipidation, and reversed multiple AD phenotypes, without increasing TG. This NLAI/LXR-agonist study is the first in a human APOE-expressing model with hallmark pathology.

Purchased from AmBeed: ; ; ;

Alternative Products

Product Details of [ 582-33-2 ]

CAS No. :582-33-2
Formula : C9H11NO2
M.W : 165.19
SMILES Code : CCOC(=O)C1=CC(N)=CC=C1
MDL No. :MFCD00007794
InChI Key :ZMCBYSBVJIMENC-UHFFFAOYSA-N
Pubchem ID :11400

Safety of [ 582-33-2 ]

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

Computational Chemistry of [ 582-33-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 46.93
TPSA ?

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

52.32 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.87
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

2.14
Log Po/w (WLOGP)?

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

1.45
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.

1.64
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

1.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.68

Water Solubility

Log S (ESOL):?

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

-2.38
Solubility 0.682 mg/ml ; 0.00413 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.

-2.87
Solubility 0.223 mg/ml ; 0.00135 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

-2.51
Solubility 0.509 mg/ml ; 0.00308 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

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.

-5.79 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)

1.34

Application In Synthesis of [ 582-33-2 ]

* 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 [ 582-33-2 ]

[ 582-33-2 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 582-33-2 ]
  • [ 3101-60-8 ]
  • [ 60377-65-3 ]
  • 3
  • [ 582-33-2 ]
  • [ 494769-34-5 ]
  • [ 79-46-9 ]
  • [ 494769-35-6 ]
YieldReaction ConditionsOperation in experiment
90.5% With acetic acid; In ethanol; dichloromethane; Step 3 Synthesis of N-isopropyl-alpha-[2-N-(1,1-dimethylethoxycarbonyl)aminothiazol-4-yl] nitrone (24) 2.22 9 (9.72 mmol) of compound 22, 3.47g (33.65 mmol) of 2-nitropropane (4), and 2.54 g (38.84 mmol) of zinc were placed in a round-bottomed flask along with 95% ethanol (50 mL) and cooled to 0 C. 4.67 g (77.77 mmol) of acetic acid was added slowly with stirring. The solution was allowed to come to room temperature, stirred for 6 hours. CH2Cl2 was added to the reaction mixture and it was filtered through a Celite pad and concentrated under reduced pressure. The residue was purified by short flash column chromatography (silica, Hex:EtOAc=1:1) to give 2.51 g (8.80 mmol) of compound 24 in 90.5% yield. 1H NMR (CDCl3): 8.71 (s, 1H), 7.63 (S, 1H), 4.21 (septet, J=6.6 Hz, 1H), 1.55 (s, 9H), 1.49 (d, J=6.6 Hz, 6H)
  • 4
  • [ 582-33-2 ]
  • [ 17823-69-7 ]
  • [ 1456732-62-9 ]
YieldReaction ConditionsOperation in experiment
Dissolved 0.500 g <strong>[17823-69-7]2-cyano-3,3-bis(methylthio)acrylamide</strong> in 15 mL EtOH and added Ethyl 3-aminobenzoate (1.0 eq.) . Stirred reaction at 75 C until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75 C until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain ethyl 3-((5-amino-4-carbamoyl-lH-pyrazol-3-yl)amino)benzoate as a yellow powder. Product was allowed to dry under vacuum for 1 hr. ethyl 3-((5-amino-4-carbamoyl- lH-pyrazol-3-yl)amino)benzoate
  • 5
  • [ 582-33-2 ]
  • [ 30131-16-9 ]
  • ethyl 3-(4-(4-phenylbutoxy)benzamido)benzoate [ No CAS ]
  • 6
  • [ 582-33-2 ]
  • [ 30131-16-9 ]
  • 3-(4-(4-phenylbutoxy)benzamido)benzoic acid [ No CAS ]
  • 7
  • [ 582-33-2 ]
  • [ 383134-85-8 ]
  • ethyl 3-[[2-(5-fluoro-2-methoxyphenyl)acetyl]amino]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In 1,4-dioxane; ethyl acetate; at 20℃; for 2h; A mixture of ethyl 3-aminobenzoate (300 mg, 1.82 mmol) and 2-(5-fluoro-2-methoxy- phenyl)acetic acid (334 mg, 1.82 mmol) in 1,4-dioxane (5 mL) was treated with 50% T3P solution in EtOAc (2.31 mL, 1.82 mmol) and TEA (634 muL, 3.63 mmol). After stirring at room temperature for 2 hours, the mixture was partitioned between water (20 mL) and EtOAc (20 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. Purification of the crude residue by chromatography on silica eluting with EtOAc in heptane afforded the titled compound as a white solid.1H NMR (500 MHz, DMSO-d6) delta 10.31 (s, 1H), 8.26 (t, J = 1.8 Hz, 1H), 7.86- 7.82 (m, 1H , 7.63 dt, J = 7.79, 1.2 Hz, 1H , 7.45 t, J = 7.9 Hz, 1H), 7.11 (dd, J = 9.2, 3.1 Hz, 1H),Hz, 1H), 4.31 (q, J = 7.1 Hz, 2H), 3.75 [M+H]+ (100% 215nm)
  • 8
  • [ 582-33-2 ]
  • [ 940875-99-0 ]
YieldReaction ConditionsOperation in experiment
100% To a solution of m-amino benzoic acid ethyl ester (1.65 g, 10.0 mmol) in concentrated HCl (10 mL) was added an aqueous solution (2.5 mL) of NaNO2 (690 mg, 1.0.0 mmol) at 0 C. the reaction mixture was stirred for 1 h. A solution of SnCl2.2H2O (4.52 g, 20 mmol) in concentrated HCl (1 mL) was then added at 0 C. The reaction solution was stirred for 2 h at room temperature. The precipitate was filtered and washed with ethanol and ether to yield ethyl 3-hydrazinobenzoate hydrogen chloride (2.1 g, yield 100%) as a white solid, which was used for the next reaction without further purification. 1H NMR (400 MHz, DMSO-d6): δ 9.09 (s, 1H), 7.68 (dd, J = 13.9, 8.2 Hz, 2H), 7.27 (d, J = 31.6 Hz, 2H), 4.97 (s, 3H), 3.92 (d, J = 5.5 Hz, 1H), 3.35 (s, 5H), 2.36 (s, 3H), 1.23 (s, 3H) ppm. MS: (M+H)+: m/z = 181.1.
100% To a solution of m-amino benzoic acid ethyl ester (1.65 g, 10.0 mmol) in concentrated HCl (10 mL) was added an aqueous solution (2.5 mL) of NaNO2 (690 mg, 1.0.0 mmol) at 0 C. the reaction mixture was stirred for 1 h. A solution of SnCl2.2H2O (4.52 g, 20 mmol) in concentrated HCl (1 mL) was then added at 0 C. The reaction solution was stirred for 2 h at room temperature. The precipitate was filtered and washed with ethanol and ether to yield ethyl 3-hydrazinobenzoate hydrogen chloride (2.1 g, yield 100%) as a white solid, which was used for the next reaction without further purification. 1H NMR (400 MHz, DMSO-d6): δ 9.09 (s, 1H), 7.68 (dd, J = 13.9, 8.2 Hz, 2H), 7.27 (d, J = 31.6 Hz, 2H), 4.97 (s, 3H), 3.92 (d, J = 5.5 Hz, 1H), 3.35 (s, 5H), 2.36 (s, 3H), 1.23 (s, 3H) ppm. MS: (M+H)+: m/z = 181.1.
 

Historical Records

Technical Information

Categories