Marinopyrrole A

Base Information

• Chemical Name: Marinopyrrole A
• CAS No.: 1227962-62-0
• Molecular Formula: C₂₂H₁₂Cl₄N₂O₄
• Molecular Weight: 510.16
• Mol file: 1227962-62-0.mol

Synonyms:

Chemical Property of Marinopyrrole A

Chemical Property:

• Melting Point: 205-207℃
• Boiling Point: 732.4±60.0 °C(Predicted)
• PKA: 6.87±0.30(Predicted)
• Density: 1.62±0.1 g/cm3(Predicted)
• Solubility.: Soluble in DMSO

Purity/Quality:

97% ^*data from raw suppliers

1,1''-(4,4'',5,5''-Tetrachloro[1,3''-bi-1H-pyrrole]-2,2''-diyl)bis[1-(2-hydroxyphenyl)methanone] ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1,1''-(4,4'',5,5''-Tetrachloro[1,3''-bi-1H-pyrrole]-2,2''-diyl)bis[1-(2-hydroxyphenyl)methanone] is a marine anticancer compound. Also, it possesses anti-bacterial properties against methicillin-resistant Staphylococcus aureus.

Technology Process of Marinopyrrole A

There total 8 articles about Marinopyrrole A 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: 95.0%

(4,4′,5,5′-tetrachloro-1′H-[1,3′-bipyrrole]-2,2′-diyl)bis((2-methoxyphenyl)methanone) (1227869-61-5,1306747-24-9,1306747-25-0) → [4,5-dichloro-1-[4,5-dichloro-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]pyrrol-2-yl]-(2-hydroxyphenyl)methanone (1010732-14-5,1227962-62-0,1306747-26-1)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; Inert atmosphere;

DOI:10.1021/cc100052j

Reference yield:

1'H-1,3'-bipyrrole-2,2'-diylbis[(2-methoxyphenyl)methanone] (1227869-59-1) → [4,5-dichloro-1-[4,5-dichloro-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]pyrrol-2-yl]-(2-hydroxyphenyl)methanone (1010732-14-5,1227962-62-0,1306747-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuryl dichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere

2: boron tribromide / dichloromethane / 1 h / 0 °C / Inert atmosphere

With sulfuryl dichloride; boron tribromide; In dichloromethane;

DOI:10.1016/j.tetlet.2010.09.059

Reference yield:

ethyl 1'H-1,3'-bipyrrole-2'-carboxylate (1305334-93-3) → [4,5-dichloro-1-[4,5-dichloro-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]pyrrol-2-yl]-(2-hydroxyphenyl)methanone (1010732-14-5,1227962-62-0,1306747-26-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: aluminum (III) chloride / dichloromethane / 0 - 25 °C / Inert atmosphere

3.1: sulfuryl dichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: boron tribromide / dichloromethane / 1 h / 0 °C / Inert atmosphere

With aluminum (III) chloride; n-butyllithium; sulfuryl dichloride; boron tribromide; In tetrahydrofuran; hexane; dichloromethane; 2.1: Friedel Crafts acylation;

DOI:10.1016/j.tetlet.2010.09.059

upstream raw materials:

(4,4′,5,5′-tetrachloro-1′H-[1,3′-bipyrrole]-2,2′-diyl)bis((2-methoxyphenyl)methanone)

1'H-1,3'-bipyrrole-2,2'-diylbis[(2-methoxyphenyl)methanone]

ethyl 1'H-1,3'-bipyrrole-2'-carboxylate

1'H-[1,3'-bipyrrol]-2'-yl(2-methoxyphenyl)methanone

Downstream raw materials:

C₃₇H₂₆Cl₄N₄O₈

(4,4',5,5'-tetrachloro-1'H-1,3'-bipyrrole-2,2'-diyl)bis((2-acetoxyphenyl)methanone)