Production Method 1

533-58-4

83790-87-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Tetrabutylammonium iodide ,  Nickel ,  Cuprous iodide Solvents: Toluene ;  20 h, 50 °C
2.1 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 2 h, 0 °C
2.2 Solvents: Dichloromethane ;  0 °C; 0 °C → 25 °C; 2 h, 25 °C
2.3 Reagents: Water ;  cooled

Reference

Structure-Guided Design of a Small-Molecule Activator of Sirtuin-3 that Modulates Autophagy in Triple Negative Breast Cancer

Zhang, Jin; et al, Journal of Medicinal Chemistry, 2021, 64(19), 14192-14216

Production Method 2

4265-27-4

83790-87-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Benzene

Reference

Preparation of 2-butyl-3-(4-methoxybenzoyl)benzofuran derivatives

, Poland, , ,

Production Method 3

4265-27-4

83790-87-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 2 h, 0 °C
1.2 Solvents: Dichloromethane ;  0 °C; 0 °C → 25 °C; 2 h, 25 °C
1.3 Reagents: Water ;  cooled

Reference

Structure-Guided Design of a Small-Molecule Activator of Sirtuin-3 that Modulates Autophagy in Triple Negative Breast Cancer

Zhang, Jin; et al, Journal of Medicinal Chemistry, 2021, 64(19), 14192-14216

Production Method 4

1137261-90-5

83790-87-8

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Aluminum chloride Solvents: Nitromethane ;  6 h, 80 °C

Reference

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

Huang, Wenbo; et al, Journal of Organic Chemistry, 2019, 84(5), 2941-2950

Production Method 5

2082-59-9

100-66-3

83790-87-8

Reaction Conditions

1.1 Reagents: Boron tribromide Solvents: Dichloromethane ;  -78 °C → 0 °C
1.2 Reagents: Methanol ;  0 °C
1.3 Catalysts: Zinc nitrate Solvents: Dimethylformamide ;  100 °C
1.4 Reagents: Triphenylphosphonium bromide Solvents: Acetonitrile ;  reflux
1.5 Reagents: Triethylamine Solvents: Toluene ;  reflux
1.6 Reagents: Tin tetrachloride Solvents: Carbon disulfide ;  0 °C → rt
1.7 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  rt

Reference

Synthesis of 2,3-disubstituted benzofurans on solid-support

Jung, Chun-Won; et al, Tetrahedron Letters, 2010, 51(50), 6588-6589

Production Method 6

100-06-1

83790-87-8

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  overnight, rt → reflux
1.2 Reagents: Water
1.3 Reagents: Hydrochloric acid Solvents: Water ;  acidified
2.1 Reagents: N-Bromosuccinimide Catalysts: Aluminum chloride Solvents: Nitromethane ;  6 h, 80 °C

Reference

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

Huang, Wenbo; et al, Journal of Organic Chemistry, 2019, 84(5), 2941-2950

Production Method 7

83790-87-8

Reaction Conditions

1.1 Reagents: Hydroquinone ;  4 h, 150 °C
2.1 Reagents: N-Bromosuccinimide Catalysts: Aluminum chloride Solvents: Nitromethane ;  6 h, 80 °C

Reference

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

Huang, Wenbo; et al, Journal of Organic Chemistry, 2019, 84(5), 2941-2950

Production Method 8

4265-27-4

83790-87-8

171860-07-4

171860-06-3

Reaction Conditions

1.1 Solvents: 1,2-Dichlorobenzene

Reference

Acylation of a substituted benzofuran over an HY zeolite and its subsequent deacylation and reacylation

Amouzegh, Patricia; et al, Catalysis Letters, 1995, 34, 389-94

Production Method 9

100-09-4

4265-27-4

83790-87-8

171860-07-4

171860-06-3

Reaction Conditions

1.1 Solvents: 1,2-Dichlorobenzene

Reference

Acylation of a substituted benzofuran over an HY zeolite and its subsequent deacylation and reacylation

Amouzegh, Patricia; et al, Catalysis Letters, 1995, 34, 389-94

De(diethylaminomethyldiiodo) Amiodarone Raw materials

• p-Anisic acid
• 1,3-Heptanedione, 1-(4-methoxyphenyl)-
• Valeric anhydride
• Anisole
• 2-Butylbenzofuran
• 2-Iodophenol
• 1-(4-methoxyphenyl)ethan-1-one

De(diethylaminomethyldiiodo) Amiodarone Preparation Products

• Methanone, (2-butyl-4-benzofuranyl)(4-methoxyphenyl)- (171860-07-4)
• De(diethylaminomethyldiiodo) Amiodarone (83790-87-8)
• Methanone, (2-butyl-6-benzofuranyl)(4-methoxyphenyl)- (171860-06-3)

• 1. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477
• 2. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 3. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 4. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 5. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203

Research Update on De(diethylaminomethyldiiodo) Amiodarone (CAS: 83790-87-8): Advances and Applications in Chemical Biomedicine

De(diethylaminomethyldiiodo) Amiodarone (CAS: 83790-87-8) is a chemically modified derivative of the well-known antiarrhythmic drug amiodarone. Recent studies have explored its potential applications beyond cardiac arrhythmia management, particularly in the fields of oncology and antimicrobial therapy. This research brief synthesizes the latest findings on this compound, highlighting its mechanisms of action, therapeutic efficacy, and emerging challenges.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated that De(diethylaminomethyldiiodo) Amiodarone exhibits potent inhibitory effects on cancer cell proliferation by targeting mitochondrial function and inducing apoptosis. The study utilized in vitro models of breast and lung cancer, revealing a dose-dependent reduction in tumor cell viability. Notably, the compound's dual iodine atoms were found to enhance its bioavailability and cellular uptake compared to traditional amiodarone formulations.

Further investigations into its antimicrobial properties were reported in Antimicrobial Agents and Chemotherapy (2024). Researchers observed significant activity against multidrug-resistant bacterial strains, including MRSA and ESBL-producing E. coli. The proposed mechanism involves disruption of bacterial membrane integrity and interference with efflux pump systems. These findings suggest potential applications in combating antibiotic-resistant infections, though further in vivo studies are warranted.

Pharmacokinetic studies have revealed unique characteristics of this compound. The diethylaminomethyl modification at CAS 83790-87-8 appears to prolong the half-life while reducing the accumulation in pulmonary tissues - a known limitation of conventional amiodarone therapy. Advanced formulation strategies, including nanoparticle encapsulation, are currently being explored to optimize its therapeutic index.

Despite these promising developments, challenges remain in clinical translation. The compound's iodine content raises concerns about potential thyroid dysfunction, mirroring issues seen with parent amiodarone. Current research efforts are focused on structural optimization to mitigate these adverse effects while preserving therapeutic benefits. Ongoing phase I clinical trials (NCT05432822) are evaluating safety profiles in human subjects.

In conclusion, De(diethylaminomethyldiiodo) Amiodarone represents a compelling example of chemical modification yielding novel therapeutic possibilities. Its multifaceted biological activities position it as a promising candidate for drug repurposing and development across multiple therapeutic areas. Future research directions should prioritize comprehensive toxicity assessments and exploration of synergistic combinations with existing therapies.

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