N-(1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-yl)-2-phenylacetamide

Base Information

• Chemical Name: N-(1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-yl)-2-phenylacetamide
• CAS No.: 365565-02-2
• Molecular Formula: C₂₆H₂₃N₃O
• Molecular Weight: 393.488
• Hs Code.: 3504009000
• UNII: M7JJR8HX5D
• ChEMBL ID: CHEMBL283047
• Mol file: 365565-02-2.mol

Synonyms:N-1-benzyl-2,3-dihydro-1H-pyrrolo(2,3-b)quinolin-4-yl-2-phenylacetamide;PGP 4008;PGP-4008;PGP4008

Chemical Property of N-(1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-yl)-2-phenylacetamide

Chemical Property:

• PSA: 48.72000
• LogP: 5.69320
• Storage Temp.: −20°C
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 393.184112366
• Heavy Atom Count: 30
• Complexity: 569

Purity/Quality:

≥95% ^*data from raw suppliers

PGP-4008 ≥95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-21/22-34-37-52/53
• Safety Statements: 22-24/25-61-45-36/37/39-26-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(C2=NC3=CC=CC=C3C(=C21)NC(=O)CC4=CC=CC=C4)CC5=CC=CC=C5
• Description: PGP-4008 is a selective inhibitor of P-glycoprotein (P-gp) that does not affect the activity of multidrug resistance-related protein 1 (MRP1). It is effective in vitro and, when delivered intraperitoneally, in vivo, inhibiting tumor growth when given with doxorubicin . PGP-4008 also enhances the ability of docetaxel to inhibit growth and drive apoptosis in ovarian cancer cells.

Technology Process of N-(1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-yl)-2-phenylacetamide

There total 4 articles about N-(1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-yl)-2-phenylacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

phenylacetyl chloride (103-80-0) + 1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine (135882-37-0) → PGP-4008 (365565-02-2)

Guidance literature:

1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

phenylacetyl chloride; In N,N-dimethyl-formamide; at -5 ℃; for 3h;

DOI:10.1021/jm0303204

Reference yield:

1-benzyl-2-pyrrolidone (5291-77-0) → PGP-4008 (365565-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: phosphorus oxychloride; SnCl₄ / CHCl₃; tetrahydrofuran / 1.5 h / 20 °C

1.2: 91 percent / CHCl₃; tetrahydrofuran / 5 h / 50 °C

2.1: 39 percent / lithium diisopropylamine / tetrahydrofuran; cyclohexane / -35 - -10 °C

3.1: NaH / dimethylformamide / 0.08 h / 0 °C

3.2: 52 percent / dimethylformamide / 3 h / -5 °C

With tin(IV) chloride; sodium hydride; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; chloroform; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1021/jm0303204

Reference yield:

anthranilic acid nitrile (1885-29-6) → PGP-4008 (365565-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: phosphorus oxychloride; SnCl₄ / CHCl₃; tetrahydrofuran / 1.5 h / 20 °C

1.2: 91 percent / CHCl₃; tetrahydrofuran / 5 h / 50 °C

2.1: 39 percent / lithium diisopropylamine / tetrahydrofuran; cyclohexane / -35 - -10 °C

3.1: NaH / dimethylformamide / 0.08 h / 0 °C

3.2: 52 percent / dimethylformamide / 3 h / -5 °C

With tin(IV) chloride; sodium hydride; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; chloroform; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1021/jm0303204

upstream raw materials:

phenylacetyl chloride

1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine

1-benzyl-2-pyrrolidone

anthranilic acid nitrile