9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one

Iupac Name：9-(6-aminopyridin-3-yl)-1-[3-(trifluoromethyl)phenyl]benzo[h][1,6]naphthyridin-2-one

Molecular Weight：432.406

Modify Date.: 2022-11-22 20:09

Introduction: Torin 2 is a potent and selective mTOR inhibitor with IC50 of 0.25 nM in p53?/? MEFs cell line; 800-fold greater selectivity for mTOR than PI3K and improved pharmacokinetic properties. Inhibition of ATM/ATR/DNA-PK with EC50 of 28 nM/35 nM/118 nM,in PC3 cell lines respectively. View more+

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1. Names and Identifiers

1.1 Name: 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one
1.2 Synonyms: 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one Torin 2 9-(6-AMino-pyridin-3-yl)-... 9-(6-AMino-pyridin-3-yl)-1-(3-trifluoroMethyl-phenyl)-1H-benzo[h][1,6]naphthyridin-2-one Torin 2 Torin 2 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one

1.3 CAS No.: 1223001-51-1

1.4 CID: 51358113

1.5 Molecular Formula: C24H15F3N4O (isomer)

1.6 Inchi: InChI=1S/C24H15F3N4O/c25-24(26,27)17-2-1-3-18(11-17)31-22(32)9-6-16-13-29-20-7-4-14(10-19(20)23(16)31)15-5-8-21(28)30-12-15/h1-13H,(H2,28,30)

1.7 InChkey: GUXXEUUYCAYESJ-UHFFFAOYSA-N

1.8 Canonical Smiles: C1=CC(=CC(=C1)N2C(=O)C=CC3=CN=C4C=CC(=CC4=C32)C5=CN=C(C=C5)N)C(F)(F)F

1.9 Isomers Smiles: C1=CC(=CC(=C1)N2C(=O)C=CC3=CN=C4C=CC(=CC4=C32)C5=CN=C(C=C5)N)C(F)(F)F

2. Properties

2.1 Density: 1.427

2.1 Boiling point: 623.66 °C at 760 mmHg

2.1 Refractive index: 1.676 (Predicted)

2.1 Flash Point: 330.978 °C

2.1 PSA: 73.80000

2.1 logP: 5.78310

2.1 Color/Form: white to beige

2.2 pKa: 5.66±0.26(Predicted)

3. Use and Manufacturing

3.1 Usage: Torin 2 is a potent, selective, and orally available mammalian target of rapamycin (mTOR) inhibitor for treatment of cancer. 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-oneSupplier

4. Safety and Handling

4.1 RIDADR: NONH for all modes of transport

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. Other Information

6.0 Mesh Entry Terms: 9-(6-aminopyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)benzo(h)(1,6)naphthyridin-2(1H)-one

6.1 体内研究: Torin 2 exhibits >95% pharmacodynamic response and half-time of 11.7 min in the mouse liver microsome stability study. Torin 2 exhibits the best bioavailability (51%), short half-life (0.72 hours) and low clearance(19.6 mL/min/kg) in male Swiss albino mice following intravenous and oral administration. Torin 2(20mg/kg) ablates MYCN tumors with reduction in MYCN protein levels and induction of apoptosis in Th-MYCN mice.

6.2 Description: Torin 2 is a potent and selective mTOR inhibitor with IC50 of 0.25 nM in p53?/? MEFs cell line; 800-fold greater selectivity for mTOR than PI3K and improved pharmacokinetic properties. Inhibition of ATM/ATR/DNA-PK with EC50 of 28 nM/35 nM/118 nM,in PC3 cell lines respectively.

6.3 In vitro: Torin 2 has the same binding mode as PI3Kγ, V882 serves as a hinge binding point and in the inner hydrophobic pocket Y867, D841 and D964 provide three more hydrogen bonds with aminopyridine side chain analogous to Y2225, D2195 and D2357 of mTOR. Torin 2 inhibits mTORC1, thus activates TFEB by promoting its nuclear translocation with EC50 of 1.666 mM. Torin 2(< 50 nM) causes a significant reduction in viability of both MZ-CRC-1 and TT cells. Torin 2 (100 nM) exerts a significant reduction of migration of both MZ-CRC-1 and TT cells.

6.4 In vivo: Torin 2 exhibits >95% pharmacodynamic response and half-time of 11.7 min in the mouse liver microsome stability study. Torin 2 exhibits the best bioavailability (51%), short half-life (0.72 hours) and low clearance(19.6 mL/min/kg) in male Swiss albino mice following intravenous and oral administration. Torin 2(20mg/kg) ablates MYCN tumors with reduction in MYCN protein levels and induction of apoptosis in Th-MYCN mice.

6.5 Uses: Torin 2 is a potent, selective, and orally available mammalian target of rapamycin (mTOR) inhibitor for treatment of cancer.

7. Computational chemical data

Molecular Weight: 432.406g/mol
Molecular Formula: C₂₄H₁₅F₃N₄O
Compound Is Canonicalized: True
XLogP3-AA: 4.4
Exact Mass: 432.11979560
Monoisotopic Mass: 432.11979560
Complexity: 729
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 72.1
Heavy Atom Count: 32
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB7oYAAAAAAAAAAAAAAAAAAAAAAAAA8eIECAAAAAACx/AAAHwAQAAAADAjBnhQ98PNIEACoAzd3dACCgCkxAiAI2CA4ZNiIIOLA0dGEJAhglALIyacQgMAOiAACQAACAAAQAASAAAQAAAAAAAAAAA==

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9. Realated Product Infomation

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