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Chemical Structure| 2510-27-2 Chemical Structure| 2510-27-2
Chemical Structure| 2510-27-2

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2-(3,5-Dimethylisoxazol-4-yl)acetic acid

CAS No.: 2510-27-2

4.5 *For Research Use Only !

Cat. No.: A226330 Purity: 98%

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Product Details of [ 2510-27-2 ]

CAS No. :2510-27-2
Formula : C7H9NO3
M.W : 155.15
SMILES Code : O=C(O)CC1=C(C)ON=C1C
MDL No. :MFCD05864546
InChI Key :ZEONKMXUCHNYRN-UHFFFAOYSA-N
Pubchem ID :2063338

Safety of [ 2510-27-2 ]

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

Calculated chemistry of [ 2510-27-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 5
Fraction Csp3 0.43
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 37.98
TPSA ?

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

63.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.22
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

0.63
Log Po/w (WLOGP)?

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

0.92
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.

0.06
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

1.37
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.84

Water Solubility

Log S (ESOL):?

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

-1.4
Solubility 6.13 mg/ml ; 0.0395 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.

-1.53
Solubility 4.53 mg/ml ; 0.0292 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

-1.78
Solubility 2.59 mg/ml ; 0.0167 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.

-6.8 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.

0.56

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)

2.75

Application In Synthesis [ 2510-27-2 ]

* 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 [ 2510-27-2 ]

[ 2510-27-2 ] Synthesis Path-Downstream   1~20

  • 2
  • [ 6066-82-6 ]
  • [ 2510-27-2 ]
  • N-<(3,5-dimethylisoxazol-4-yl)-acetoxy>-succinimide [ No CAS ]
  • 3
  • [ 2510-27-2 ]
  • [ 37059-79-3 ]
  • diphenylmethyl 7β-(3,5-dimethylisoxazol-4-yl-acetamido)-3-<(2-methylthiadiazol-5-yl)-thiomethyl>-ceph-3-em-4-carboxylate [ No CAS ]
  • 4
  • [ 2510-27-2 ]
  • [ 53090-86-1 ]
  • diphenylmethyl 7β-(3,5-dimethylisoxazol-4-yl-acetamido)-3-<(1-methyltetrazol-5-yl)-thiomethyl>-ceph-3-em-4-carboxylate [ No CAS ]
  • 5
  • [ 2510-27-2 ]
  • [ 144102-13-6 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride;N,N-dimethyl-formamide; In 1,2-dichloro-ethane; at 20℃; for 1.0h; Example 9 2-(1-{4-[2-(3,5-Dimethyl-isoxazol-4-yl)-acetylamino]-2-fluoro-phenyl}-piperidin-4-yl)-N,N-diethyl-2-phenyl-acetamide; A mixture of <strong>[2510-27-2](3,5-dimethyl-isoxazol-4-yl)-acetic acid</strong> (1.0 mmol) and DMF (0.050 mL) in DCE (10 mL) was treated with (COCl)2 (10 mmol), dropwise. The mixture was stirred at rt for 1 h and was concentrated.
  • 6
  • [ 2510-27-2 ]
  • [ 15205-11-5 ]
  • N-[(2-chloro-4-fluorophenyl)methyl]-2-(3,5-dimethyl-4-isoxazolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 22℃; for 18.0h; Example 1 lambda/-[(2-Chloro-4-fluorophenyl)methyl]-2-(3,5-dimethyl-4- isoxazolyl)acetamide (E1 ); (3,5-Dimethyl-4-isoxazolyl)acetic acid (0.100 g, 0.64 mmol, purchased from commercial sources) was dissolved in anhydrous dimethylformamide (3 ml) and to this was added water soluble carbodiimide (0.148 g, 0.773 mmol), 1- hydroxybenzotriazole (0.104 g, 0.77 mmol), N-ethyl morpholine (0.246 ml, 1.93 mmol), and [(2-chloro-4-fluorophenyl)methyl]amine (0.1 17 g). The mixture was stirred at room temperature (22C) for 18 hrs and then evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give pure lambda/-[(2-chloro-4-fluorophenyl)methyl]-2-(3,5-dimethyl-4-isoxazolyl)acetamide (0.135 g) as a white solid. LC/MS [M+H]+ = 297, retention time = 2.46 minutes.
  • 7
  • 1-(2-bromo-4-fluorophenyl)methan-1-amine [ No CAS ]
  • [ 2510-27-2 ]
  • N-[(2-bromo-4-fluorophenyl)methyl]-2-(3,5-dimethyl-4-isoxazolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 5.0h; Example 2 lambda/-[(2-Bromo-4-fluorophenyl)methyl]-2-(3,5-dimethyl-4- isoxazolyl)acetamide (E2); (3,5-Dimethyl-4-isoxazolyl)acetic acid (0.051 g, 0.33 mmol) was dissolved in dichloromethane (4 ml) and to this was added water soluble carbodiimide (0.059 g, 0.31 mmol), 1-hydroxybenzotriazole (0.041 g, 0.31 mmol), N-ethyl morpholine (0.156 ml, 1.24 mmol), and [(2-bromo-4-fluorophenyl)methyl]amine (0.075 g, 0.31 mmol). The mixture was stirred at room temperature for 5 hrs and then the mixture was washed sequentially with saturated aqueous sodium hydrogen carbonate and 2N aqueous hydrogen chloride. The organic layer was filtered through a hydrophobic frit and evaporated to give the crude product. The crude material was purified by mass- directed automated HPLC to give pure lambda/-[(2-bromo-4-fluorophenyl)methyl]-2-(3,5- <n="18"/>dimethyl-4-isoxazolyl)acetamide (0.061 g) as a white solid. LC/MS [M+H]+ = 341 , retention time = 2.57 minutes.
  • 9
  • [ 2510-27-2 ]
  • 7β-(3,5-dimethylisoxazol-4-yl-acetamido)-3-<(2-methylthiadiazol-5-yl)-thiomethyl>-ceph-3-em-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With hydrazine hydrate; In methanol; at 20℃; for 3.0h; General procedure: Ester Hydrolysis To a solution of the ester (1.0 eq.) in methanol (1.4 mL mmol"1) was added hydrazine monohydrate (1.5 eq.) and the reaction stirred at room temperature for 3 h. Reaction mixture was concentrated under reduced pressure, yielding carboxylic acid without further purification.
  • 12
  • [ 2510-27-2 ]
  • [ 1443209-30-0 ]
  • [ 1443209-37-7 ]
  • 13
  • [ 18835-02-4 ]
  • [ 2510-27-2 ]
  • 14
  • [ 2510-27-2 ]
  • C26H30N4O5S [ No CAS ]
  • 15
  • [ 2510-27-2 ]
  • [ 1443208-91-0 ]
  • 16
  • [ 13984-53-7 ]
  • [ 2510-27-2 ]
  • 17
  • [ 154928-90-2 ]
  • [ 2510-27-2 ]
  • 18
  • [ 2510-27-2 ]
  • C9H17N3O2 [ No CAS ]
  • C16H24N4O4 [ No CAS ]
  • 19
  • [ 2510-27-2 ]
  • 3-[1-(azetidin-3-ylsulfonyl)-4-piperidyl]furo[3,2-b]pyridine hydrochloride [ No CAS ]
  • 2-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[3-(4-furo[3,2-b]pyridin-3-ylpiperidin-1-yl)sulfonylazetidin-1-yl]ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
15 mg With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 1.0h; To the solution of 3-[l -(azetidin-3 -yl sulfonyl)-4-piperidyl] furo [3 ,2-b]pyridinehydrochloride salt (35.8 mg, 1 equiv.) and <strong>[2510-27-2]2-(3,5-dimethylisoxazol-4-yl)acetic acid</strong> (17.1 mg, 1.1 equiv.) in DMF (1.0 mL) DIPEA (57.4 1iL, 3.3 equiv.) was added, followed by HATU (41.8 mg, 1.1 equiv.), and the resulting solution was stirred at RT. After one hour, reaction mixture was diluted with EtOAc (10 mL), transferred to a separatory funnelcontaining distilled water and extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4, filtered, and solvent was removed in vacuo. The crude product was purified by preparative TLC eluting with 10% MeOHIEtOAc to afford the expected product (15 mg). LCMS: MW (calcd): 458.53; MS (ES, m/z): 459.7 [M+H].
  • 20
  • [ 2510-27-2 ]
  • [ 40217-17-2 ]
  • (R)-4-benzyl-3-(2-(3,5-dimethylisoxazol-4-yl)acetyl)oxazolidin-2-one [ No CAS ]
 

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