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[ CAS No. 168824-94-0 ] {[proInfo.proName]}

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Chemical Structure| 168824-94-0
Chemical Structure| 168824-94-0
Structure of 168824-94-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 168824-94-0 ]

CAS No. :168824-94-0 MDL No. :MFCD09029520
Formula : C16H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GFJCZDJPSXKGSF-UHFFFAOYSA-N
M.W : 272.34 Pubchem ID :18377349
Synonyms :

Calculated chemistry of [ 168824-94-0 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.44
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 83.48
TPSA : 45.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.82
Log Po/w (XLOGP3) : 2.8
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 3.03
Consensus Log Po/w : 2.77

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.43
Solubility : 0.102 mg/ml ; 0.000374 mol/l
Class : Soluble
Log S (Ali) : -3.41
Solubility : 0.106 mg/ml ; 0.00039 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.35
Solubility : 0.0122 mg/ml ; 0.0000448 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.47

Safety of [ 168824-94-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 168824-94-0 ]

* 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 [ 168824-94-0 ]
  • Downstream synthetic route of [ 168824-94-0 ]

[ 168824-94-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 16502-01-5 ]
  • [ 24424-99-5 ]
  • [ 168824-94-0 ]
YieldReaction ConditionsOperation in experiment
81% for 9 h; 516 mg of intermediate A was dissolved in CH2C12, di-tert-butyl dicarbonate ((Boc) 20) was added,After the reaction was stirred at room temperature for 9 h. After the reaction was monitored, the reaction system was diluted with CH2C12 (20 mL) and extracted with pure waterThree times, and finally washed with saturated brine once, the extracted organic phase collected dry, spin dry, under the silica gel column chromatography665 mg of intermediate B3 was isolated and the eluent in column chromatography was PE / EtOAc = 4: 1 with a reaction yield of 81percent; product
2.5 g With triethylamine In dichloromethane at 0 - 20℃; for 2 h; Inert atmosphere To a stirred solution of 2,3 ,4,9-tetrahydro-1 Η-β-carboline (2.3 g, 13.364 mmol) and triethylamine (2.80 ml, 20.046 mmol) in dichloromethane (45 ml) was added boc anhydride (3.50 g, 16.037 mmol) at 0°C under N2 atmosphere and the resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane (50 ml) and washed with water (2 x 20 ml). The combined organic phase was dried over Na2SC>4, filtered and concentrated under reduced pressure yielding crude fe/f-butyl 1 ,3,4,9-tetrahydro- 2H-β-3-carboline-2-carboxylate (2.50 g, 9.186 mmol), which was used further synthesis without further purification. LCMS: Method B: 2.422 min. MS: ES 217.3 (M-56).
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 11, p. 2197 - 2206
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 639 - 651
[3] Patent: CN106883230, 2017, A, . Location in patent: Paragraph 0037
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 47, p. 14968 - 14972[5] Angew. Chem., 2017, vol. 129, # 47, p. 15164 - 15168,5
[6] Angewandte Chemie - International Edition, 2017, vol. 56, # 21, p. 5760 - 5764[7] Angew. Chem., 2017, vol. 129, p. 5854 - 5858,5
[8] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4780 - 4785
[9] Patent: US5563147, 1996, A,
[10] Patent: WO2006/55752, 2006, A2, . Location in patent: Page/Page column 24
[11] Patent: WO2009/3003, 2008, A2, . Location in patent: Page/Page column 56
[12] Patent: US2005/288317, 2005, A1, . Location in patent: Page/Page column 23
[13] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5964 - 5969
[14] Chemistry - A European Journal, 2018, vol. 24, # 9, p. 2065 - 2069
[15] Patent: WO2018/167276, 2018, A1, . Location in patent: Paragraph 00176; 00178
[16] Patent: CN108623585, 2018, A, . Location in patent: Paragraph 0114; 0115; 0116; 0117
  • 2
  • [ 1579291-49-8 ]
  • [ 168824-94-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2781 - 2791
  • 3
  • [ 61-54-1 ]
  • [ 168824-94-0 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5964 - 5969
[2] Patent: CN106883230, 2017, A,
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 47, p. 14968 - 14972[4] Angew. Chem., 2017, vol. 129, # 47, p. 15164 - 15168,5
[5] Chemistry - A European Journal, 2018, vol. 24, # 9, p. 2065 - 2069
[6] Patent: WO2018/167276, 2018, A1,
[7] Patent: CN108623585, 2018, A,
  • 4
  • [ 191171-55-8 ]
  • [ 168824-94-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2781 - 2791
  • 5
  • [ 615-36-1 ]
  • [ 168824-94-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2781 - 2791
  • 6
  • [ 79099-07-3 ]
  • [ 168824-94-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2781 - 2791
  • 7
  • [ 159503-90-9 ]
  • [ 168824-94-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2781 - 2791
  • 8
  • [ 120-72-9 ]
  • [ 168824-94-0 ]
Reference: [1] Patent: CN108623585, 2018, A,
  • 9
  • [ 487-89-8 ]
  • [ 168824-94-0 ]
Reference: [1] Patent: CN108623585, 2018, A,
  • 10
  • [ 3156-51-2 ]
  • [ 168824-94-0 ]
Reference: [1] Patent: CN108623585, 2018, A,
  • 11
  • [ 4894-26-2 ]
  • [ 24424-99-5 ]
  • [ 168824-94-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1103 - 1106
  • 12
  • [ 1579291-74-9 ]
  • [ 138647-49-1 ]
  • [ 168824-94-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2781 - 2791
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