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[ CAS No. 89226-50-6 ] {[proInfo.proName]}

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Chemical Structure| 89226-50-6
Chemical Structure| 89226-50-6
Structure of 89226-50-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 89226-50-6 ]

CAS No. :89226-50-6 MDL No. :MFCD00871291
Formula : C35H38N4O6 Boiling Point : -
Linear Structure Formula :- InChI Key :ANEBWFXPVPTEET-UHFFFAOYSA-N
M.W : 610.70 Pubchem ID :4008
Synonyms :
CV-4093;Franidipine;Manidipine 6300;(±)-Manidipine

Calculated chemistry of [ 89226-50-6 ]

Physicochemical Properties

Num. heavy atoms : 45
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.31
Num. rotatable bonds : 12
Num. H-bond acceptors : 8.0
Num. H-bond donors : 1.0
Molar Refractivity : 183.85
TPSA : 116.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.09
Log Po/w (XLOGP3) : 5.2
Log Po/w (WLOGP) : 3.49
Log Po/w (MLOGP) : 2.54
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 3.89

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.41
Solubility : 0.00024 mg/ml ; 0.000000392 mol/l
Class : Poorly soluble
Log S (Ali) : -7.4
Solubility : 0.0000242 mg/ml ; 0.0000000396 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.82
Solubility : 0.000000918 mg/ml ; 0.0000000015 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 5.38

Safety of [ 89226-50-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89226-50-6 ]

* 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 [ 89226-50-6 ]
  • Downstream synthetic route of [ 89226-50-6 ]

[ 89226-50-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 89226-50-6 ]
  • [ 89226-75-5 ]
YieldReaction ConditionsOperation in experiment
81.8% With hydrogenchloride In methanol; dichloromethane at 0 - 10℃; for 1 h; Large scale The manidipine alkali 2.25 kg added to the dichloromethane 6.75 L, methanol 4.5 L after dissolving cooling to 0 - 10 °C, drops of concentrated hydrochloric acid 1.07 L, after adding, thermal insulation stirring reaction 1 h, then adding methyl tert-butyl ether 13.5 L, then stirring 1 h, a large number of solid precipitation, filtering, washing the cake with a small amount of methyl tert-butyl ether, dichloromethane is used for the filter cake 22 L reflux beating 1 h, cooling to room temperature, filtering. A small amount of methyl tert-butyl ether cake washing, 40 - 50 °C blast drying, to obtain 2.05 kg yellow solid. The yield is 81.8percent, purity 99.8869percent, HPLC Atlas see Figure 2.
Reference: [1] Patent: CN108218765, 2018, A, . Location in patent: Paragraph 0046; 0047
[2] Patent: WO2011/23954, 2011, A2, . Location in patent: Page/Page column 18
[3] Patent: US2012/232091, 2012, A1, . Location in patent: Page/Page column 6
  • 2
  • [ 89226-75-5 ]
  • [ 89226-50-6 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide In waterCooling with ice Weigh 12g of sodium hydroxide, was added 18mL of water, to prepare a 40percent aqueous sodium hydroxide solution, while cooling on ice.Weigh manidipine hydrochloride (20.5 g of) was added and stirred mechanically assembled of three ice-bath cooled flask (a 500 mL), and then water (100mL).Open stirred, ice-cold 40percent sodium hydroxide solution is added dropwise to the previously prepared ice bath cooled three-necked flask.Ethyl acetate was added during the addition (90mL).After all the lye was added, stirring was stopped and rested stratification.Aqueous phase measured pH to 11 to 12, and liquid separation.The aqueous phase was extracted twice with ethyl acetate (30mL × 2), and the combined organic phase was washed with water (50 mL), saturated sodium chloride solution (50 mL) and washed once each.Then, the organic phase was dried over anhydrous sodium sulfate (15g) for 2 hours.Filter, 35 solvent was removed by evaporation under reduced pressure.As a yellow solid manidipine free base, yield 98percent
Reference: [1] Patent: CN105439942, 2016, A, . Location in patent: Paragraph 0040; 0041; 0042
  • 3
  • [ 39562-17-9 ]
  • [ 89226-50-6 ]
YieldReaction ConditionsOperation in experiment
91.43% at 40 - 75℃; for 6.5 h; (50 g, 0.132 mol) of β-aminocrotonic acid diphenylmethylpiperazine ethyl ester2- (3-nitrobenzylidene) acetoacetate (49.30 g, 0.198 mol)Was added to a reaction flask equipped with absolute ethanol (180 ml)The temperature in the reactor was raised to 40 ° C over 1 h,And insulation 1h;The temperature in the reactor was then raised to 75 ° C in 1 h,And insulation 0.5h,Continue to heat to reflux,Reflux 3h,After the reaction was complete, the crude of manilide was obtained,And then cooled to 0 ° C overnight,The resulting filter cake was recrystallized from 90 mL of methanol to give 73.62 g of a white solid,The yield was 91.43percent.
Reference: [1] Patent: CN106380442, 2017, A, . Location in patent: Paragraph 0018; 0020; 0022
  • 4
  • [ 10527-64-7 ]
  • [ 74936-72-4 ]
  • [ 89226-50-6 ]
Reference: [1] Patent: WO2011/23954, 2011, A2, . Location in patent: Page/Page column 18
[2] Patent: US2012/232091, 2012, A1, . Location in patent: Page/Page column 5-6
  • 5
  • [ 99-61-6 ]
  • [ 89226-49-3 ]
  • [ 14205-39-1 ]
  • [ 89226-50-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
  • 6
  • [ 10527-64-7 ]
  • [ 89226-50-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
  • 7
  • [ 841-77-0 ]
  • [ 89226-50-6 ]
Reference: [1] Patent: WO2011/23954, 2011, A2,
[2] Patent: US2012/232091, 2012, A1,
  • 8
  • [ 89226-49-3 ]
  • [ 89226-50-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
  • 9
  • [ 90120-00-6 ]
  • [ 14205-39-1 ]
  • [ 89226-50-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
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