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[ CAS No. 1124-11-4 ] {[proInfo.proName]}

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Chemical Structure| 1124-11-4
Chemical Structure| 1124-11-4
Structure of 1124-11-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1124-11-4 ]

CAS No. :1124-11-4 MDL No. :MFCD00006146
Formula : C8H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :FINHMKGKINIASC-UHFFFAOYSA-N
M.W : 136.19 Pubchem ID :14296
Synonyms :
Ligustrazine;Chuanxiongzine;TMP;NSC 46451;NSC 36080;Chuanxingzine;2,3,5,6-Tetramethylpyrazine

Calculated chemistry of [ 1124-11-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.9
TPSA : 25.78 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 1.71
Log Po/w (MLOGP) : 0.55
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 1.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.93
Solubility : 1.58 mg/ml ; 0.0116 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 5.17 mg/ml ; 0.0379 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.17
Solubility : 0.0921 mg/ml ; 0.000676 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 1124-11-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1124-11-4 ]

* 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 [ 1124-11-4 ]
  • Downstream synthetic route of [ 1124-11-4 ]

[ 1124-11-4 ] Synthesis Path-Upstream   1~8

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Reference: [1] Journal of Agricultural and Food Chemistry, 1997, vol. 45, # 5, p. 1878 - 1882
  • 2
  • [ 513-86-0 ]
  • [ 13623-11-5 ]
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  • [ 84310-28-1 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 1, p. 245 - 248
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  • [ 108-50-9 ]
  • [ 14667-55-1 ]
  • [ 80935-98-4 ]
  • [ 13925-07-0 ]
  • [ 15707-34-3 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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  • [ 13925-07-0 ]
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
  • 7
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YieldReaction ConditionsOperation in experiment
65%
Stage #1: With dihydrogen peroxide; acetic acid In water at 70℃; for 8 h;
Stage #2: at 125℃; for 3 h;
Stage #3: at 20℃; for 5 h;
In a 500 ml round-bottom flask TMP (13.6 g 100 mmol) was added and dissolved in glacial acetic acid (15 mL) 30 hydrogen peroxide (8 mL 75 mmol) was added and reaced for 4 hours at 70 and 30 hydrogen peroxide (8 mL 75 mmol) was added and then further reacted for 4 hours and monitored by TLC until the reaction product was no longer generated. The resulting material was allowed to return to room temperature then placed in an ice bath adjusted to pH 10 with a solution of 10 sodium hydroxide extracted with chloroform dried over anhydrous sodium sulfate and filtered and concentrated to give crude material of TMP nitric oxide. Without isolation the crude materil was added with acetic anhydride (14.3 mL 150 mmol) heated to 125 with reflux for 3 hours and monitored by TLC until the starting material completely comsumed and the excess acetic anhydride was removed by distillation to give TMP acetyl compound allowed to return to room temperature then placed in an ice bath a solution of 10 sodium hydroxide was added to adjust pH to 12 stirred for 5 hours at room temperature extracted with chloroform dried over anhydrous sodium sulfate filtered and concentrated and the resulting material as separated with column chromatography eluted with ethyl acetate /petroleum ether (11) to give the compound TMP-OH as a white solid (9.88 g 65) .
65% at 70℃; for 8 h; In a 500 ml round-bottom flask, TMP (13.6 g, 100 mmol) was added and dissolved in glacial acetic acid (15 mE), 30percent hydrogen peroxide (8 mE, 75 mmol) was added, and reaced for 4 hours at 70° C., and 30percent hydrogen peroxide (8 mE, 75 mmol) was added and then thrther reacted for 4 hours and monitored by TEC until the reaction product was no longer generated. The resulting material was allowed to return to room temperature then placed in an ice bath, adjusted to pH 10 with a solution of 10percent sodium hydroxide, extracted with chloroform, dried over anhydrous sodium sulfate, and filtered and concentrated to give crude material of TMP nitric oxide. Without isolation, the crude material was added with acetic anhydride (14.3 mE, 150 mmol), heated to 125° C. with reflux for 3 hours, and monitored by TEC until the starting material completely consumed, and the excess acetic anhydride was removed by distillation to give TMP acetyl compound, allowed to return to room temperature then placed in an ice bath, a solution of 10percent sodium hydroxide was added to adjust pH to 12, stirred for 5 hours at room temperature, extracted with chloroform, dried over anhydrous sodium sulfate, filtered and concentrated, and the resulting material as separated with colunm chromatography eluted with ethyl acetate/petroleum ether (1:1) to give the compound TMP-OH as a white solid (9.88 g, 65percent).
1.85 g at 90℃; for 6 h; 2.17 g (16 mmol) of ligustrazine was dissolved in 20 ml of glacial acetic acid. Add 1.8 ml (16 mmol) of 30percent hydrogen peroxide at 90 ° C for 4 h.Then, 1.8 ml (16 mmol) of 30percent hydrogen peroxide was added to continue the reaction for 2 h, and the reaction was completely monitored by TLC.Add an appropriate amount of sodium sulfite to neutralize excess hydrogen peroxide, filter the reaction solution, cool the filtrate to room temperature, and adjust the pH to 10 with 50percent sodium hydroxide.The mixture was extracted with methylene chloride. The organic layer was collected, dried over anhydrous sodium sulfate and dried over anhydrous sodium sulfate. This crude product was added to 1.51 ml (16 mmol) of acetic anhydride, and the mixture was heated to reflux at 550 ° C for 2.5 hr.This black slurry was placed in a solution of 20 ml (THF: MeOH: H 2 O = 3:1:1), 1.92 g (48 mmol) of sodium hydroxide was added portionwise, and the reaction was stirred for 2 h.The organic layer was extracted with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate and filtered.Recovering the solvent under reduced pressureThe crude hydroxyxazine was recrystallized from n-hexane to give 1.85 g of yellow needle crystals.
Reference: [1] Patent: WO2015/109935, 2015, A1, . Location in patent: Page/Page column 17; 18
[2] Patent: US2016/326099, 2016, A1, . Location in patent: Paragraph 0108
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 10, p. 3315 - 3320
[4] Journal of Chemical Research, 2006, # 9, p. 577 - 579
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2123 - 2126
[6] Chemische Berichte, 1990, vol. 123, p. 523 - 533
[7] Chemische Berichte, 1990, vol. 123, p. 523 - 533
[8] Chemical Biology and Drug Design, 2012, vol. 79, # 5, p. 731 - 739
[9] Medicinal Chemistry, 2012, vol. 8, # 5, p. 928 - 933,6
[10] Journal of Natural Products, 2012, vol. 75, # 9, p. 1589 - 1594,6
[11] Medicinal Chemistry, 2014, vol. 10, # 1, p. 81 - 89
[12] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1747 - 1760
[13] Patent: CN105237487, 2016, A,
[14] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 1, p. 56 - 65
[15] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 26 - 38
[16] MedChemComm, 2017, vol. 8, # 3, p. 652 - 656
[17] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 34 - 48
[18] Patent: CN106518791, 2017, A,
[19] Chemistry of Natural Compounds, 2017, vol. 53, # 1, p. 114 - 117[20] Khim. Prir. Soedin., 2017, vol. 53, # 1, p. 96 - 98,3
[21] Patent: CN104774196, 2017, B,
[22] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 1821 - 1832
[23] Patent: CN108440512, 2018, A,
[24] Patent: CN108484511, 2018, A,
[25] Patent: CN108456179, 2018, A, . Location in patent: Paragraph 0068; 0069
[26] Patent: CN108456239, 2018, A,
[27] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1859 - 1866
[28] Molecules, 2018, vol. 23, # 10,
[29] Patent: US2018/346430, 2018, A1, . Location in patent: Paragraph 0038
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Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 647 - 649
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