PF-05212384

Description

Product Name: PF-05212384
CAS No.: 1197160-78-3
Chemical Name: PF-05212384
Synonyms: CS-46;PKI587;PF-05212384;PKI 587 PF 05212384;GEDATOLISIB;PKI-587;PF-05212384 (PKI-587);PF-05212384 USP/EP/BP;GEDATOLISIB;PF-05212384;PKI-587 ( Gedatolisib );Gedatolisib (PF-05212384, PKI-587)
CBNumber: CB32500950
Molecular Formula: C32H41N9O4
Formula Weight: 615.73
MOL File: 1197160-78-3.mol

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PF-05212384 Property

Melting point:: 226-227°C
Density: 1.364
storage temp.: Refrigerator
solubility: DMSO
pka: 13.97±0.70(Predicted)
form: Solid
color: Off-White
InChIKey: DWZAEMINVBZMHQ-UHFFFAOYSA-N
SMILES: N(C1=CC=C(C(N2CCC(N(C)C)CC2)=O)C=C1)C(NC1=CC=C(C2=NC(N3CCOCC3)=NC(N3CCOCC3)=N2)C=C1)=O

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Safety

HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 14567
Product name: PF-05212384
Purity: ≥98%
Packaging: 1mg
Price: $37
Updated: 2024/03/01

Cayman Chemical

Product number: 14567
Product name: PF-05212384
Purity: ≥98%
Packaging: 5mg
Price: $161
Updated: 2024/03/01

Cayman Chemical

Product number: 14567
Product name: PF-05212384
Purity: ≥98%
Packaging: 10mg
Price: $283
Updated: 2024/03/01

Tocris

Product number: 4823
Product name: PF05212384
Purity: ≥98%(HPLC)
Packaging: 10
Price: $275
Updated: 2021/12/16

TRC

Product number: D461135
Product name: N-[4-[[4-(Dimethylamino)-1-piperidinyl]carbonyl]phenyl]-N''-[4-(4,6-di-4-morpholinyl-1,3,5-triazin-2-yl)phenyl]-urea
Packaging: 50mg
Price: $670
Updated: 2021/12/16

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PF-05212384 Chemical Properties,Usage,Production

Description

Gedatolisib (PF-05212384, PKI-587) is a highly potent dual inhibitor of PI3Kα, PI3Kγ and mTOR with IC50 of 0.4 nM, 5.4 nM and 1.6 nM in cell-free assays, respectively. Phase 2.

Chemical Properties

Off-White Solid

Uses

This compound shows inhibitory activity against PI3K-α, PI3K-γ and mTOR. Potent PI3K/mTOR Dual Inhibitor.

Biological Activity

pf-05212384 is an inhibitor of pi3k/mtor with ic50 values of 0.4nm, 6nm, 8nm, 6nm and 1.4nm for pi3kα, pi3kβ, pi3kγ, pi3kδ and mtor, respectively [1].pf-05212384 is a pan-pi3k/mtorinhibitor and shows to be highly selective for pi3k and mtor. besides the wt p13k, pf-05212384 can also inhibit mutant p13k with ic50 values of 0.6nm for both h1047r and e545k mutants. in cellular assay, pf-05212384 potently inhibits tumor growth in mda-361 and pc3-mm2 cell lines with ic50 values of 4nm and 13.1nm, respectively. meanwhile, pf-05212384 suppresses the phosphorylation of pi3k/mtor signaling pathway proteins in cells. it inhibits the phosphorylation of akt as well as the akt effector proteins including gsk3 kinase, enos and pras 40. moreover, pf-05212384 has potent anti-tumor activity in a variety of xenograft models including h1975, bt474, hct116, h1975 and u87mg [1, 2]

Synthesis

50533-97-6

1197160-66-9

1197160-78-3

The general procedure for the synthesis of 1-(4-(4-(dimethylamino)piperidine-1-carbonyl)phenyl)-3-(4-(4,6-dimorpholin-1,3,5-triazin-2-yl)phenyl)urea from 4-dimethylaminopiperidine and 4-(3-(4-(4,6-dimorpholin-1,3,5-triazin-2-yl)phenyl)urea was carried out in the following manner: first, at 50 °C, a mixture of 1-(4-(4-(dimethylamino)piperidin-1-carbonyl)phenyl)-3-(4-(4,6-dimorpholin-1,3,5-triazin-2-yl)phenyl)urea was added to 4-(3-(4-(4-(4,6-dimorpholin-1,3,5-triazin-2-yl)phenyl)ureido)benzoic acid (45.5 g, 0.09 mol) in a slurry of anhydrous THF (1.6 L) was added to N,N'-carbonyldiimidazole (28 g, 0.17 mol). The reaction mixture was heated for 2 h. 4-Dimethylaminopiperidine (23.5 g, 0.18 mol) was added and stirred for 16 h at 53°C. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filter cake was washed with 2-propanol and dried over air to give a white powder of 97% purity in 88% yield (49.2 g, 0.08 mol). Subsequently, the solid was dissolved in dimethylacetamide (DMAC, 165 ml) at 70 °C with stirring for 1 h. 2-Propanol (640 ml) was added and stirring was continued for 1 h at 65 °C. The resulting solid was filtered, washed with 2-propanol and finally dried in a vacuum oven at 70 °C for 16 h to obtain a crystalline white powder (45 g) of >99% purity. After the above post-treatment and crystallization process, the product had a Pd residue content of 20 ppm.

in vivo

Gedatolisib (PKI-587; administered i.v. at 20 mg/kg on days 1, 5, 9) exhibits potent antitumor efficacy against MDA-361 tumors in mice^[1].
Gedatolisib exhibits terminal elimination half-life (T_1/2 14.4 h) due to high plasma clearance (7 mL/min/kg) combined with large volumes of distribution (7.2 L/kg respectively) following i.v. administration (25 mg/kg) female nude mice^[1].

Animal Model:	Female nude mice bearing MDA-361 xenograft model^[1].
Dosage:	20 mg/kg
Administration:	Administered i.v. at 20 mg/kg on an intermittent regimen (days 1, 5, 9).
Result:	Caused regression of large staged (~900 mm³) tumors. The minimum efficacious dose (MED) was determined to be 3 mg/kg against MDA-361 tumors and maximum tolerated single dose (MTD) was determined to be 30 mg/kg.

Enzyme inhibitor

This dual PI3K/mTOR (phosphoinositide-3-kinase and mammalian target of rapamycin) signal-transduction pathway inhibitor and antineoplastic agent (F.Wt. = 615.73; CAS 1197160-78-3); Solubility (25°C): 2 mg/mL DMSO, <1 mg/mL Water), also known as PF-05212384 and systematically as 1-(4- (4-(dimethylamino)piperidine-1-carbonyl)phenyl)-3-(4-(4,6-dimorpholino- 1,3,5-triazin-2-yl)phenyl)urea, inhibits PI3K-α, PI3K-γ and mTOR with IC50 of 0.4 nM, 5.4 nM and 1.6 nM, respectively. PKI-587 also inhibits mutant forms of PI3Kα, including the PI3Kα-H1047R and PI3Kα-E545K with IC50 of 0.6 nM and 0.6 nM, respectively.

IC 50

PI3Kα: 0.4 nM (IC₅₀); PI3Kα-H1047R: 0.6 nM (IC₅₀); PI3Kα-E545K: 0.6 nM (IC₅₀); PI3Kγ: 5.4 nM (IC₅₀); PI3Kβ: 6 nM (IC₅₀); PI3Kδ: 6 nM (IC₅₀); mTOR: 1.6 nM (IC₅₀); mTORC1; mTORC2

References

[1] venkatesan a m, dehnhardt c m, delos santos e, et al. bis (morpholino-1, 3, 5-triazine) derivatives: potent adenosine 5′-triphosphate competitive phosphatidylinositol-3-kinase/mammalian target of rapamycin inhibitors: discovery of compound 26 (pki-587), a highly efficacious dual inhibitor. journal of medicinal chemistry, 2010, 53(6): 2636-2645.
[2] mallon r, feldberg l r, lucas j, et al. antitumor efficacy of pki-587, a highly potent dual pi3k/mtor kinase inhibitor. clinical cancer research, 2011, 17(10): 3193-3203.

PF-05212384 Preparation Products And Raw materials

Raw materials

Preparation Products

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PF-05212384 Suppliers

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View Lastest Price from PF-05212384 manufacturers

Wuhan Nutra Biotechnology Co.,Ltd

Product: Gedatolisib;PKI-587 1197160-78-3
Price: US $200.00-0.00/g
Min. Order: 1g
Purity: 98%+
Supply Ability: 100kgs
Release date: 2021-05-24

Career Henan Chemical Co

Product: PF-05212384 1197160-78-3
Price: US $2.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2018-12-24

1197160-78-3, PF-05212384Related Search:

PF-562271 Ketohexokinase inhibitor 1 PF-6274484 PF-9366 4-[(Diethylamino)methyl]-N-[2-(2-methoxyphenyl)ethyl]-N-(3R)-3-pyrrolidinylbenzamide 3-(5-fluoro-indol-3-yl)-pyrrolidine-2,5-dione PF06869206 N,N-DIMETHYLHYDROXYLAMINE HYDROCHLORIDE N,N'-Dimethyl-1,3-propanediamine N,N-Dimethylbenzylamine N,N-Dimethylbenzamide N,N-Dimethylpropionamide N-Methylpiperidine Selumetinib MK-2206 2HCl IPI 145 PD 0332991 HCl Rapamycin

PF-05212384

PKI587

CS-46

PKI 587 PF 05212384

PF-05212384; PKI587; PKI 587;PKI-587;PF-05212384;PF-05212384

GEDATOLISIB;PF-05212384

N-[4-[[4-(Dimethylamino)-1-piperidinyl]carbonyl]phenyl]-N'-[4-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]phenyl]urea

1-(4-(4-(dimethylamino)piperidine-1-carbonyl)phenyl)-3-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)phenyl)urea

Gedatolisib (PF-05212384, PKI-587)

N-[4-[[4-(Dimethylamino)-1-piperidinyl]carbonyl]phenyl]-N'-[4-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]phenyl]urea PF-05212384 (PKI-587)

PKI-587 N-[4-[[4-(Dimethylamino)-1-piperidinyl]carbonyl]phenyl]-N'-[4-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]phenyl]urea

PKI-587 ( Gedatolisib )

GEDATOLISIB;PKI-587

GEDATOLISIB (PF-05212384, PKI-587);PKI-587

1-(4-(4-(Dimethylamino)piperidine-1-carbonyl)phenyl)-3-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl

PF-05212384 (PKI-587)

[(2R)-3-BENZOYLOXY-4,4-DIFLUORO-5-OXOOXOLAN-2-YL]METHYL BENZOATE

1-[4-[4-(dimethylamino)piperidine-1-carbonyl]phenyl]-3-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]urea

Urea, N-[4-[[4-(dimethylamino)-1-piperidinyl]carbonyl]phenyl]-N'-[4-(4,6-di-4-morpholinyl-1,3,5-triazin-2-yl)phenyl]-

PF-05212384 USP/EP/BP

mTOR,Mammalian target of Rapamycin,Inhibitor,PI3K,PF 05212384,Gedatolisib,Phosphoinositide 3-kinase,PKI587,PKI 587,inhibit,PF05212384

N-[4-[[4-(Dimethylamino)-1-piperidinyl]carbonyl]phenyl]-N'-[4-(4,6-di-4-morpholinyl-1,3,5-triazin-2-yl)phenyl]-urea

1197160-78-3

C32H41N9O4

Akt

mTOR

PI3K

PI3K/Akt/mTOR

Inhibitors