Azuloxa

Base Information

• Chemical Name: Azuloxa
• CAS No.: 97683-31-3
• Molecular Formula: C15H17NaO3S
• Molecular Weight: 300.34845
• Hs Code.: 2904100000
• Mol file: 97683-31-3.mol

Synonyms:trisodium,3-ethyl-7-propan-2-ylazulene-1-sulfonate,hydrate;Egualen sodium hydrate (JAN),hydrate;

Chemical Property of Azuloxa

Chemical Property:

• Melting Point: 153 °C
• PSA: 205.97000
• LogP: 13.32200

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Egualen, formulated as a sodium salt, was marketed in Japan for the treatment of gastric ulcers and gastritis. It is a water-soluble sodium sulfonate analog of guaiazulene, a natural azulene with anti-ulcer activity. Egualen can be prepared from an 7- isopropyl azulen-2-yl carboxylate by successive 3-acetylation, reduction, decarboxylation and finally, sulfonylation in l-position. The mechanism of action is not well defined; egualen is a weak inhibitor of the enzyme system H+/K+ ATPase and a weak antagonist of prostanoid receptors; concomitantly, it was shown to possess some anti-inflammatory properties. In animal models of gastric ulcers induced with cortisone or acetic acid, oral treatment with egualen sodium promoted healing of ulcers and, at higher doses, mucosal regeneration. The data available from clinical studies for egualen are limited; in one trial, the combination of egualen sodium and cimetidine administered to patients with unhealing gastric ulcers produced an appreciable rate of healing without any adverse events.
• Uses: Egualen Sodium can be used in combination of anti-ulcer drugs and gastric acid secretion inhibitors to treat digestive tract diseases.

Technology Process of Azuloxa

There total 4 articles about Azuloxa 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: 57.0%

1-ethyl-5-isopropylazulene (99287-76-0) → sodium 3-ethyl-7-isopropyl-1-azulenesulfonate (97683-31-3)

Guidance literature:

1-ethyl-5-isopropylazulene; With sulfur trioxide pyridine complex; In benzene; at 80 ℃; for 3.5h;

With sodium hydroxide; In water; benzene; at 32.5 ℃; for 2h; Further stages.;

DOI:10.1021/ol0156897

Reference yield:

3-bromo-5-isopropyl-3,8a-dihydro-2H-azulen-1-one → sodium 3-ethyl-7-isopropyl-1-azulenesulfonate (97683-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DMAP / diethyl ether / 0.17 h / 20 °C

2.1: 0.083 g / palladium acetate; o-(dicyclohexylphosphino)biphenyl; potassium fluoride / tetrahydrofuran / 0.17 h / Heating

3.1: sulfur trioxide-pyridine complex / benzene / 3.5 h / 80 °C

3.2: 57 percent / NaOH / benzene; H₂O / 2 h / 32.5 °C

With dmap; potassium fluoride; O-(dicyclohexylphosphino)biphenyl; palladium diacetate; sulfur trioxide pyridine complex; In tetrahydrofuran; diethyl ether; benzene; 2.1: Suzuki coupling reaction;

DOI:10.1021/ol0156897

Reference yield:

trifluoro-methanesulfonic acid 5-isopropyl-azulen-1-yl ester (817623-99-7) → sodium 3-ethyl-7-isopropyl-1-azulenesulfonate (97683-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 0.083 g / palladium acetate; o-(dicyclohexylphosphino)biphenyl; potassium fluoride / tetrahydrofuran / 0.17 h / Heating

2.1: sulfur trioxide-pyridine complex / benzene / 3.5 h / 80 °C

2.2: 57 percent / NaOH / benzene; H₂O / 2 h / 32.5 °C

With potassium fluoride; O-(dicyclohexylphosphino)biphenyl; palladium diacetate; sulfur trioxide pyridine complex; In tetrahydrofuran; benzene; 1.1: Suzuki coupling reaction;

DOI:10.1021/ol0156897

upstream raw materials:

1-ethyl-5-isopropylazulene

trifluoro-methanesulfonic acid 5-isopropyl-azulen-1-yl ester

1-methoxycarbonyl-3-ethyl-7-isopropylazulene

Downstream raw materials:

{4-[2-(3-Ethyl-7-isopropyl-azulene-1-sulfonylamino)-ethyl]-phenoxy}-acetic acid methyl ester

Refernces

• 1、 Yanagisawa,Wakabayashi,Tomiyama,Yasunami,Takase. "Synthesis and anti-ulcer activities of sodium alkylazulene sulfonates". . p. 641 - 647. Retrieved 2007/10/02.