(Z)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine

Base Information

• Chemical Name: (Z)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine
• CAS No.: 23256-30-6
• Molecular Formula: C₁₀H₁₃N₃O₅S
• Molecular Weight: 287.296
• European Community (EC) Number: 245-531-0
• Nikkaji Number: J16.764I
• Wikidata: Q411582
• Wikipedia: Nifurtimox
• Mol file: 23256-30-6.mol

Synonyms:23256-30-6;BAY 2502;BAY A2502;SCHEMBL9910611;GTPL12364;(E)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine;BAY-A-2502;NS00027388;Q411582

Chemical Property of (Z)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine

Chemical Property:

• Vapor Pressure: 3.7E-12mmHg at 25°C
• Melting Point: 177-183°C
• Refractive Index: 1.6390 (estimate)
• Boiling Point: 550.3°Cat760mmHg
• PKA: -1.01±0.40(Predicted)
• Flash Point: 286.6°C
• PSA: 117.08000
• Density: 1.56g/cm³
• LogP: 2.18250
• Storage Temp.: Refrigerator
• Solubility.: DMSO: ≥13mg/mL
• Water Solubility.: 33g/L(temperature not stated)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 287.05759170
• Heavy Atom Count: 19
• Complexity: 467

Purity/Quality:

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

Nifurtimox ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CS(=O)(=O)CCN1N=CC2=CC=C(O2)[N+](=O)[O-]
• Isomeric SMILES: CC1CS(=O)(=O)CCN1/N=C\C2=CC=C(O2)[N+](=O)[O-]
• Indications: Treatment of American trypanosomiasis (Chagas’ disease) due to Trypanosoma cruzi. The drug may also be used in patients with Trypanosoma brucei gambiense sleeping sickness who are refractory to other treatments. Nifurtimox (Lampit) is a nitrofuran derivative whose likely mechanism of action for killing of trypanosomes is through the production of activated forms of oxygen. Nifurtimox is reduced to the nitro anion radical, which reacts with oxygen to produce superoxide and hydrogen peroxide. The free radical metabolites, an absence of parasite catalase, and a peroxide deficiency lead to lipid peroxidation and cell damage. This production of activated oxygen results in toxicity to the protozoal cells.
• Description: Nifurtimox is manufactured by Bayer and marketed under the trade name Lampits.It is a nitrofuran derivative that was developed specifically for the treatment of American trypanosomiasis (Chagas'disease) (Packachanian, 1957). Nifurtimox is one of two drugs approved for use in treatment of Chagasdisease. It was shown to be the most active and least toxic of this group of agents in preclinical studies and was evaluated in clinical trials in the 1960s and subsequently marketed for use in Chagas’ disease in Latin America in the late 1960s and early 1970s. Although the use of nifurtimox for Chagas’ disease has decreased with the availability of benznidazole, a potentially more active and less toxic agent, there has been a resurgence of interest in and use of nifurtimox for the treatment of second-stage human African trypanosomiasis (HAT)caused by Trypanosoma brucei gambiense.
• Uses: Antiprotozoal (Trypanosoma). Showing anti-Trypanosoma cruzi activity. The nitrofuran nifurtimoxis the most effective drug against T. cruzi, being cidal against the trypomastigote and amastigote forms. It is active against both the extra- and intracellular form of the parasite. In combination with corticosteroids it has prevented myocardial inflammation and destroyed the parasites within the heart. Side effects of the drug tend to be mild and include nausea, vomiting, insomnia, nervous excitation, vertigo, and skin rashes. Cardiac symptoms are treated symptomatically. Benznidazole (2, C12H12N4O3, N-benzyl-2-nitro-1 imidazoleacetamide, RO 7-1051), an alternative drug, can prevent the spread of the parasites from one tissue to another although relapses are common. Primaquine can destroy the extracellular trypanosomes in the blood, but is not effective against the intracellular forms of the parasite.
• Clinical Use: Nifurtimox is trypanocidal and exerts an effect on the trypomastigote and amastigote forms of T. cruzi. It is effective in the treatment of the acute form of Chagas’ disease but is less effective once the disease becomes chronic. The drug is moderately well tolerated, and treatment generally lasts 3 to 4 months. Cure rates of 80 to 90% have been reported. Since much of the tissue damage caused by the disease is irreversible, early diagnosis and treatment are important. Nifurtimox has also been used in T. gambiense infection with meningoencephalopathic involvement.

Technology Process of (Z)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine

There total 3 articles about (Z)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine 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:

methyl-3 amino-4 thiomorpholine dioxyde-1,1 (26494-77-9) + 5-nitrofurane-2-carboxaldehyde (698-63-5) → nifurtimox (23256-30-6,39072-15-6,39072-16-7)

Guidance literature:

In ethanol; for 24h; Heating / reflux;

Reference yield:

2-hydroxypropyl 2-hydroxyethyl sulfide (6713-03-7) → nifurtimox (23256-30-6,39072-15-6,39072-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: dihydrogen peroxide / phosphoric acid / Heating / reflux

2: sodium hydroxide; t-butoxycarbonylhydrazine / water / Heating / reflux

3: ethanol / 24 h / Heating / reflux

With sodium hydroxide; t-butoxycarbonylhydrazine; dihydrogen peroxide; phosphoric acid; In ethanol; water;

Reference yield:

→ nifurtimox (23256-30-6,39072-15-6,39072-16-7)

Guidance literature:

upstream raw materials:

methyl-3 amino-4 thiomorpholine dioxyde-1,1

5-nitrofurane-2-carboxaldehyde

2-hydroxypropyl 2-hydroxyethyl sulfide

Refernces

• 1、 Bock,Haberkorn,Herlinger,Mayer,Petersen. "The structure-activity relationship of 4-(5'-nitrofurfurylidene-amino)-tetrahydro-4H-1,4-thiazine-1,1-dioxides active against Trypanosoma cruzi.". . p. 1564 - 1569. Retrieved 2007/10/04.