BI-97C1

Base Information

• Chemical Name: BI-97C1
• CAS No.: 1228108-65-3
• Molecular Formula: C₄₂H₄₀N₂O₈
• Molecular Weight: 700.788
• Mol file: 1228108-65-3.mol

Synonyms:1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide;1,1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-N5-((R)-2-PHENYLPROPYL)-N5'-((R)-2-PHENYLPROPYL)-2,2'-BINAPHTHYL-5,5'-DICARBOXAMIDE (ATROPISOMERIC MIX);Sabutoclax;UNII-39Y89ZRK34;

Chemical Property of BI-97C1

Chemical Property:

• Boiling Point: 905.9±65.0 °C(Predicted)
• PKA: 7.35±0.50(Predicted)
• PSA: 186.56000
• Density: 1.358±0.06 g/cm3(Predicted)
• LogP: 8.72700
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

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

Sabutoclax ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sabutoclax(BI-97C1) is a pan-Bcl-2 inhibitor, including Bcl-xL, Bcl-2, Mcl-1 and Bfl-1 with IC50 of 0.31 μM, 0.32 μM, 0.20 μM and 0.62 μM, respectively. Sabutoclax is a novel putative MCL-1 inhibitor that induces mitochondrial fragmentation either upstream of or independent of apoptosis.

Technology Process of BI-97C1

There total 5 articles about BI-97C1 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: 72.0%

1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide (1173895-39-0) → 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide (1173895-60-7,1228108-65-3,1228178-73-1,1228178-77-5,1228178-80-0)

Guidance literature:

1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide; With boron tribromide; In dichloromethane; at -78 - 20 ℃;

With hydrogenchloride; In dichloromethane; water; at 20 ℃; Cooling with ice;

DOI:10.1021/jm900472s

Reference yield:

(rac)-gossypol (303-45-7) → 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide (1173895-60-7,1228108-65-3,1228178-73-1,1228178-77-5,1228178-80-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydroxide / water / 3.5 h / 90 °C / Inert atmosphere; Darkness

2.1: potassium carbonate / acetone / 24 h / Inert atmosphere; Reflux

3.1: titanium tetrachloride / 20 °C

3.2: 20 °C

4.1: sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide / acetonitrile / 20 °C

4.2: 20 °C

5.1: boron tribromide / dichloromethane

With sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide; boron tribromide; titanium tetrachloride; potassium carbonate; sodium hydroxide; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jm100746q

Reference yield:

apogossypol (784206-41-3,475-56-9) → 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide (1173895-60-7,1228108-65-3,1228178-73-1,1228178-77-5,1228178-80-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetone / 24 h / Inert atmosphere; Reflux

2.1: titanium tetrachloride / 20 °C

2.2: 20 °C

3.1: sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide / acetonitrile / 20 °C

3.2: 20 °C

4.1: boron tribromide / dichloromethane

With sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide; boron tribromide; titanium tetrachloride; potassium carbonate; In dichloromethane; acetone; acetonitrile;

DOI:10.1021/jm100746q

upstream raw materials:

1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide

(rac)-gossypol

apogossypol

5,5'-diisopropyl-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene

Downstream raw materials:

6,6',7,7'-tetrahydroxy-3,3'-dimethyl-1,1',4,4'-tetraoxo-N₅,N₅'-bis(2-phenylpropyl)-1,1',4,4'-tetrahydro-2,2'-binaphthyl-5,5'-dicarboxamide

Refernces

• 1、 Wei, Jun,Kitada, Shinichi,Stebbins, John L.,Placzek, William,Zhai, Dayong,Wu, Bainan,Rega, Michele F.,Zhang, Ziming,Cellitti, Jason,Yang, Li,Dahl, Russell,Reed, John C.,Pellecchia, Maurizio. "Synthesis and biological evaluation of apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins". scheme or table. p. 8000 - 8011. Retrieved 2011/03/19.