SGI-1027

Base Information

• Chemical Name: SGI-1027
• CAS No.: 1020149-73-8
• Molecular Formula: C27H23N7O
• Molecular Weight: 461.526
• Mol file: 1020149-73-8.mol

Synonyms:SGI-1027;N-[4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)benzamide;DNA Methyltransferase Inhibitor II;Benzamide, N-[4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)-;N-[4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)benzamide SGI-1027;SGI-1027 N-[4-[(2-Amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)benzamide;N-[4-[(2-amino-6-methylpyrimidin-4-yl)amino]phenyl]-4-(quinolin-4-ylamino)benzamide

Chemical Property of SGI-1027

Chemical Property:

• Melting Point: >280℃
• PKA: 13.31±0.70(Predicted)
• PSA: 125.30000
• Density: 1.387±0.06 g/cm3(Predicted)
• LogP: 5.46390
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 35 mg/ml)

Purity/Quality:

98%,99%, ^*data from raw suppliers

SGI 1027 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: SGI-1027 is a DNMT inhibitor with IC50 of 6, 8, 7.5 μM for DNMT1, DNMT3A, and DNMT3B in cell-free assays, respectively. SGI-1027 (1020149-73-8) is a potent and selective inhibitor of DNA methyl transferase inhibiting DNMT1, DNMT3A and DNMT3B with comparable potency (IC50=12.5, 8.0 and 7.5 mM respectively).1? Treatment of various cancer cell lines with SGI-1027 results in selective degradation of DNMT1 (MG-132 sensitive) with minimal effect on DNMT3A and 3B at 2.5-5 mM.1 Prolonged treatment of RKO cells resulted in reexpression of silenced tumor suppressor genes.1 Synergizes with doxorubicin at growth inhibition in neuroblastoma cell lines.2 Disrupts the MKK3-MYC complex in cells and inhibits MYC transcriptional activity in colon and breast cancer cells.3
• Uses: SGI-1027 is a quinoline derivative and a potent inhibitor of DNA methyltransferase (DNMT). SGI-1027 can be used as a potential therapeutic agent for the treatment of cancer and other diseases and also as a research tool to investigate the role of DNMTs in epigenetic events.

Technology Process of SGI-1027

There total 9 articles about SGI-1027 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: 79.0%

N4-(4-aminophenyl)-6-methyl-2,4-diamino-pyrimidine (20719-43-1) + 4-(quinolin-4-ylamino)benzoic acid (133041-90-4) → N-[4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)benzamide (1020149-73-8)

Guidance literature:

4-(quinolin-4-ylamino)benzoic acid; With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

N⁴-(4-aminophenyl)-6-methyl-2,4-diamino-pyrimidine; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1021/jm4012627

Reference yield:

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) → N-[4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)benzamide (1020149-73-8)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium diacetate; potassium carbonate; XPhos / tert-butyl alcohol; water / 1.5 h / 110 °C / Sealed tube; Inert atmosphere

2: hydrogen / ethanol / 24 h / Inert atmosphere

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 65 °C / Inert atmosphere

With hydrogen; palladium diacetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; XPhos; In ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: |Buchwald-Hartwig Coupling;

DOI:10.1016/j.bmcl.2013.01.085

Reference yield:

4-nitro-aniline (100-01-6,104810-17-5) → N-[4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl]-4-(4-quinolinylamino)benzamide (1020149-73-8)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium diacetate; potassium carbonate; XPhos / tert-butyl alcohol; water / 1.5 h / 110 °C / Sealed tube; Inert atmosphere

2: hydrogen / ethanol / 24 h / Inert atmosphere

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 65 °C / Inert atmosphere

With hydrogen; palladium diacetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; XPhos; In ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: |Buchwald-Hartwig Coupling;

DOI:10.1016/j.bmcl.2013.01.085

upstream raw materials:

N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-nitrobenzamide

4-chloroquinoline

2-amino-6-methyl-4-chloropyrimidine

p-aminoethylbenzoate

Refernces

• 1、 García-Domínguez, Patricia,Dell'Aversana, Carmela,Alvarez, Rosana,Altucci, Lucia,De Lera, ángel R.. "Synthetic approaches to DNMT inhibitor SGI-1027 and effects on the U937 leukemia cell line". . p. 1631 - 1635. Retrieved 2013/04/10.