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Flavopiridol HCl
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[ CAS No. 131740-09-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 131740-09-5
Chemical Structure| 131740-09-5
Structure of 131740-09-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 131740-09-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 131740-09-5 ]

SDS Specification
Alternatived Products of [ 131740-09-5 ]

Product Details of [ 131740-09-5 ]

CAS No. :131740-09-5 MDL No. :MFCD26792554
Formula : C21H21Cl2NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :LGMSNQNWOCSPIK-LWHGMNCYSA-N
M.W : 438.30 Pubchem ID :9910986
Synonyms :
HMR-1275 Hydrochloride;L86-8275 Hydrochloride;L-868,275;HL 275;Flavopiridol (hydrochloride);DSP-2033;HMR-1275;Alvocidib;NSC 649890;Alvocidib Hydrochloride;Flavopiridol Hydrochloride
Chemical Name :2-(2-Chlorophenyl)-5,7-dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-one hydrochloride

Calculated chemistry of [ 131740-09-5 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 118.8
TPSA : 94.14 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 4.05
Log Po/w (WLOGP) : 3.73
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 3.37
Consensus Log Po/w : 2.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.39
Solubility : 0.00181 mg/ml ; 0.00000412 mol/l
Class : Moderately soluble
Log S (Ali) : -5.73
Solubility : 0.000815 mg/ml ; 0.00000186 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.59
Solubility : 0.00113 mg/ml ; 0.00000257 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.29

Safety of [ 131740-09-5 ]

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 [ 131740-09-5 ]

* 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 [ 131740-09-5 ]

[ 131740-09-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 113225-21-1 ]
  • [ 131740-09-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium-t-butoxide / N,N-dimethyl-formamide / 1.5 h / 5 - 25 °C / Inert atmosphere 1.2: 6.5 h / 25 - 30 °C / Inert atmosphere 1.3: 50 °C / Inert atmosphere 2.1: BBr3 / methanol; chlorobenzene; lithium hydroxide monohydrate / 7 h / 25 - 75 °C / Inert atmosphere 2.2: 20 - 79 °C / Inert atmosphere 3.1: hydrogenchloride / ethanol / 35 - 74 °C / Inert atmosphere 3.2: 4 h / 80 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Pharma (in: Sumitomo Chemical); Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2022/220072, 2022, A1
  • 2
  • [ 7335-25-3 ]
  • [ 131740-09-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium-t-butoxide / N,N-dimethyl-formamide / 1.5 h / 5 - 25 °C / Inert atmosphere 1.2: 6.5 h / 25 - 30 °C / Inert atmosphere 1.3: 50 °C / Inert atmosphere 2.1: BBr3 / methanol; chlorobenzene; lithium hydroxide monohydrate / 7 h / 25 - 75 °C / Inert atmosphere 2.2: 20 - 79 °C / Inert atmosphere 3.1: hydrogenchloride / ethanol / 35 - 74 °C / Inert atmosphere 3.2: 4 h / 80 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Pharma (in: Sumitomo Chemical); Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2022/220072, 2022, A1
  • 3
  • [ 146426-40-6 ]
  • [ 131740-09-5 ]
YieldReaction ConditionsOperation in experiment
22.4 g Stage #1: 2-(2-chlorophenyl)-5,7-dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-one With hydrogenchloride In ethanol at 35 - 74℃; Inert atmosphere; Stage #2: In butanone at 80℃; for 4h; Inert atmosphere; 6 Reference Example 6: Manufacturing Method of Alvocidib Hydrochloride Ethanolate Under a nitrogen atmosphere, a crude alvocidib free form (20 g) was dissolved in ethanol (228 g). The mixture was warmed to 35° C. Concentrated hydrochloric acid (10.4 g) was added dropwise while maintaining an internal temperature of 35° C., and a dropping funnel was washed with ethanol (4.6 g). The mixture was warmed to 74° C. and hot-filtered. The filtration paper was washed with ethanol (23 g). The filtrate and washing solution were combined and concentrated under atmospheric pressure (distillation volume of 190 g). The mixture was cooled to 25° C. and incubated overnight. The mixture was cooled to -10° C. and incubated for 2 hours. The precipitate was filtered out, washed with cold ethanol (94 g), and dried to obtain alvocidib hydrochloride ethanolate (22.4 g, yield: 93%).1H-NMR (400 MHz, MeOH-d4) δ: 1.17 (t, J=7.2 Hz, 3H), 1.83-1.91 (m, 1H), 2.86 (s, 3H), 3.09-3.21 (m, 2H), 3.32-3.35 (m, 1H), 3.45 (ddd, J=12.6 Hz, 2.4 Hz, 2.4 Hz, 1H), 3.50-3.53 (m, 1H), 3.60 (q, J=7.1 Hz, 2H), 3.69-3.74 (m, 1H), 4.26 (s, 1H), 6.34 (s, 1H), 6.48 (s, 1H), 7.52 (ddd, J=7.3 Hz, 7.3 Hz, 1.3 Hz, 1H), 7.58 (ddd, J=7.6 Hz, 7.6 Hz, 1.9 Hz, 1H), 7.62 (dd, J=7.8 Hz, 1.4 Hz, 1H), 7.76 (dd, J=7.6 Hz, 1.6 Hz, 1H) Reference Example 7: Manufacturing Method of Alvocidib Hydrochloride Under a nitrogen atmosphere, alvocidib hydrochloride ethanolate (20 g) was dissolved in methyl ethyl ketone (297 g). The mixture was warmed to 80° C. and incubated for 4 hours. The mixture was cooled to 22° C. and incubated for 1 hour. The precipitate was filtered out, washed with methyl ethyl ketone (69 g), and dried to obtain alvocidib hydrochloride (17.7 g, yield: 98%, HPLC purity: 99.6 area %, optical purity: >99.9% ee).1H-NMR (400 MHz, MeOH-d4) δ: 1.83-1.91 (m, 1H), 2.85 (s, 3H), 3.10-3.22 (m, 2H), 3.34 (s, 1H), 3.42-3.46 (m, 1H), 3.49-3.53 (m, 1H), 3.69-3.73 (m, 1H), 4.26 (s, 1H), 6.34 (s, 1H), 6.48 (s, 1H), 7.52 (ddd, J=7.4 Hz, 7.4 Hz, 1.5 Hz, 1H), 7.58 (ddd, J=7.8 Hz, 7.8 Hz, 2.0 Hz, 1H), 7.63 (dd, J=7.8 Hz, 1.4 Hz, 1H), 7.75 (dd, J=7.4 Hz, 1.4 Hz, 1H)
Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Pharma (in: Sumitomo Chemical); Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2022/220072, 2022, A1 Location in patent: Paragraph 0152-0157

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[ 131740-09-5 ]

Chemical Structure| 146426-40-6

A172904[ 146426-40-6 ]

2-(2-Chlorophenyl)-5,7-dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-one

Reason: Free-salt