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[ CAS No. 1821-12-1 ] {[proInfo.proName]}

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Chemical Structure| 1821-12-1
Chemical Structure| 1821-12-1
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Product Citations

Griffin, Matthew E. ; Tsukidate, Taku ; Hang, Howard C. DOI: PubMed ID:

Abstract: The characterization of microbiota mechanisms in health and disease has reinvigorated pattern recognition receptors as prominent targets for immunotherapy. Notably, our recent studies on Enterococcus species revealed peptidoglycan remodeling and activation of NOD2 as key mechanisms for microbiota enhancement of immune checkpoint inhibitor therapy. Inspired by this work and other studies of NOD2 activation, we performed in silico ligand screening and developed N-arylpyrazole dipeptides as novel NOD2 agonists. Importantly, our N-arylpyrazole NOD2 agonist is enantiomer-specific and effective at promoting immune checkpoint inhibitor therapy and requires NOD2 for activity in vivo. Given the significant functions of NOD2 in innate and adaptive immunity, these next-generation agonists afford new therapeutic leads and adjuvants for a variety of NOD2-responsive diseases.

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Product Details of [ 1821-12-1 ]

CAS No. :1821-12-1 MDL No. :MFCD00004403
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :HOOCCH2CH2CH2C6H5 InChI Key :OBKXEAXTFZPCHS-UHFFFAOYSA-N
M.W : 164.20 Pubchem ID :4775
Synonyms :
4-PBA;Benzenebutyric acid
Chemical Name :4-Phenylbutanoic acid

Calculated chemistry of [ 1821-12-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.6
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 2.09
Log Po/w (MLOGP) : 2.29
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.533 mg/ml ; 0.00325 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.234 mg/ml ; 0.00143 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.174 mg/ml ; 0.00106 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 1821-12-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1821-12-1 ]

* 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.

  • Upstream synthesis route of [ 1821-12-1 ]
  • Downstream synthetic route of [ 1821-12-1 ]

[ 1821-12-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1821-12-1 ]
  • [ 1370290-52-0 ]
  • [ 4521-22-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3285 - 3306
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3285 - 3306
  • 2
  • [ 1821-12-1 ]
  • [ 583-53-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 15, p. 5431 - 5435
  • 3
  • [ 1821-12-1 ]
  • [ 40353-34-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 4
  • [ 1821-12-1 ]
  • [ 16503-46-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 21, p. 2765 - 2770
  • 5
  • [ 1821-12-1 ]
  • [ 26673-32-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 6
  • [ 6340-79-0 ]
  • [ 35656-89-4 ]
  • [ 1821-12-1 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 170,174
  • 7
  • [ 1821-12-1 ]
  • [ 15118-60-2 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 779
[2] Journal of the American Chemical Society, 1934, vol. 56, p. 744
[3] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,219
  • 8
  • [ 1821-12-1 ]
  • [ 27913-58-2 ]
YieldReaction ConditionsOperation in experiment
42% With sulfuric acid; iodine; acetic acid; periodic acid In water at 70℃; for 19 h; A mixture of 4-phenylbutanoic acid (20.0 g, 121.8 mmol), H5IO6 (5.56 g, 24.4 mmol), iodine (13.30 g, 52.4 mmol), 10 M H2SO4 (5.0 mL), water (36 mL) and acetic acid (166 mL) was heated at 70° C. for 19 h.
The reaction mixture was cooled and evaporated to dryness.
The residue was dissolved in EtOAc (300 mL) and washed with aqueous Na2S2O3 (2*200 mL), brine (2*200 mL), dried over Na2SO4, filtered, and evaporated to leave a yellow solid.
The crude product was precipitated from EtOAc/hexane at 0° C. to afford product as light yellow solid (15.0 g, 42percent).
1H NMR (400 MHz, CDCl3) δ 11.0 (brs, 1H), 7.61 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.0 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 2.38 (t, J=7.6 Hz, 2H).
Reference: [1] Mendeleev Communications, 2015, vol. 25, # 2, p. 111 - 113
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5919 - 5924
[3] Patent: US2018/66298, 2018, A1, . Location in patent: Paragraph 0172; 0173; 0174
[4] Journal of the American Chemical Society, 1943, vol. 65, p. 1273,1274
[5] Patent: US2348231, 1940, ,
[6] Patent: US2348231, 1940, ,
  • 9
  • [ 1821-12-1 ]
  • [ 27913-58-2 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 32, p. 6945 - 6958
[2] Phytochemistry, 2013, vol. 96, p. 223 - 234
  • 10
  • [ 1821-12-1 ]
  • [ 22009-40-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 11
  • [ 1821-12-1 ]
  • [ 1716-12-7 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide In water 0.40 g (2.436 mmol) of 4-phenylbutyric acid are suspended in 30 ml of H2O, and then 0.097 g (2.436 mmol) of sodium hydroxide is added. After the acid has been dissolved, the solution is concentrated by rotary evaporation and twice dewatered azeotropically with toluene. This gives 0.44 g (96.0percent) of sodium 4-phenylbutyrate in solid form.
88.2% With sodium hydroxide In ethanol for 4 h; Industrial scale As shown in Fig. 5, 6000 ml of anhydrous ethanol and 243.6 g of sodium hydroxide were successively charged into 10 L of a four-necked reaction flask. After heating and stirring, 1000 g of phenylbutyric acid prepared in Example 3 was added thereto, stirred and heated to dissolve, (TLC developing solvent: methanol: dichloromethane = 1: 2, Rf = 0.2 for phenylbutyric acid, Rf = 0.1 for sodium phenylbutyrate), and the reaction was terminated for about 4 hours. Add 30g of activated carbon reflux 10 minutes, slightly cold, filter to remove activated carbon. Collect the liquid at 50 ° C. Distillation to remove most of the solvent. A large amount of white solid precipitated. After cooling the residue to 15 ° C, the solid was collected by filtration and washed with 100 ml of absolute ethanol. The solid was dried at 40 ° C for 4 hours and then dried at 60 ° C for 12 hours to give 1000 g of white sodium phenylbutyrate in 88.2percent yield, HPLC purity of 99.77percent (octadecyl silane bonded silica as stationary phase, Glacial acetic acid-methanol-water (1:49:50) as the mobile phase; detection wavelength of 245nm), high-performance liquid chromatography shown in Figure 5, the results shown in Table 8, we can see that a single impurity control Within 0.1percent.
Reference: [1] Patent: US2012/77677, 2012, A1, . Location in patent: Page/Page column 3
[2] Patent: CN105924345, 2016, A, . Location in patent: Paragraph 0084; 0089
[3] Patent: US2007/4805, 2007, A1, . Location in patent: Page/Page column 5
[4] Patent: US2008/171792, 2008, A1, . Location in patent: Page/Page column 7
[5] Crystal Growth and Design, 2010, vol. 10, # 4, p. 1990 - 2003
[6] Langmuir, 2012, vol. 28, # 25, p. 9332 - 9340
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