Sulindac sulfone

Base Information

• Chemical Name: Sulindac sulfone
• CAS No.: 59973-80-7
• Molecular Formula: C20H17 F O4 S
• Molecular Weight: 372.417
• Hs Code.: 2930902000
• NSC Number: 719619
• UNII: K619IIG2R9
• DSSTox Substance ID: DTXSID6040246
• Wikipedia: Exisulind
• Wikidata: Q5420370
• NCI Thesaurus Code: C1239
• Metabolomics Workbench ID: 63239
• ChEMBL ID: CHEMBL488025
• Mol file: 59973-80-7.mol

Synonyms:(5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-(N-benzyl)-indene)-acetamide;1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-((4-(methylsulfonyl)phenyl)methylene)-, (Z)-;Aptosyn;CP 248;CP248;exisulind;FGN-1;OSIP 486823;OSIP-486823;OSIP486823;sulindac sulfone;sulindac sulfone, (Z)-isomer

Chemical Property of Sulindac sulfone

Chemical Property:

• Melting Point: 248-250°C
• PSA: 79.82000
• LogP: 5.11240
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: >25 mg/mL
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 372.08315835
• Heavy Atom Count: 26
• Complexity: 723

Purity/Quality:

99% ^*data from raw suppliers

Sulindac Sulfone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C1=CC3=CC=C(C=C3)S(=O)(=O)C)C=CC(=C2)F)CC(=O)O
• Isomeric SMILES: CC\1=C(C2=C(/C1=C\C3=CC=C(C=C3)S(=O)(=O)C)C=CC(=C2)F)CC(=O)O
• Recent ClinicalTrials: Combination Chemotherapy in Treating Patients With Advanced Non-Small Cell Lung Cancer
• Uses: An active metabolite of Sulindac. Inducer of apoptosis independent of cyclooxygenase inhibition. Inhibits cell growth by inducing apoptosis.

Technology Process of Sulindac sulfone

There total 5 articles about Sulindac sulfone 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: 100.0%

Sulindac (38194-50-2) → sulindac sulfone (59973-80-7)

Guidance literature:

With Oxone; In tetrahydrofuran; methanol; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.12.014

Reference yield:

sulindac sulfide (49627-27-2) → (R)-Sulindac sulfoxide + (S)-Sulindac sulfoxide + sulindac sulfone (59973-80-7)

Guidance literature:

With 2-methylimidazole; C₈₄H₇₂ClFeN₄O₁₂S₄^(4-)*4Na⁽¹⁺⁾; dihydrogen peroxide; In methanol; aq. phosphate buffer; at -20 ℃; for 1h; Overall yield = 100 %Spectr.; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.molcata.2012.12.016

Reference yield:

(R)-Sulindac sulfoxide → sulindac sulfone (59973-80-7)

Guidance literature:

With glucose-6-phosphate dehydrogenase; D-glucose 6-phosphate; recombinant rat 1A₂ P₄₅₀ enzyme; NADPH; magnesium chloride; pH=7.4; aq. phosphate buffer;

DOI:10.1124/dmd.110.037663

upstream raw materials:

Sulindac

sulindac sulfide

Downstream raw materials:

(Z)-5-fluoro-2-methyl-1-[[4-(methylsulfone)phenyl]methylene]-1H-indene-3-acetic acid 4-(thioxo-5H-[1,2]dithiol-3-yl)-phenyl ester

(Z)-5-fluoro-2-methyl-1-[[4-(methylsulfone)phenyl]methylene]-1H-indene-3-acetic acid 2-methanesulfonylsulfanylethyl ester

methyl 2-((1Z)-1-(4-(methylsulfonyl)benzylidene)-5-fluoro-2-methyl-1H-inden-3-yl)acetate

(Z)-4-(3-(2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetoxy)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Refernces

• 1、 Srour, Hassan,Jalkh, Joanna,Le Maux, Paul,Chevance, Soizic,Kobeissi, Marwan,Simonneaux, Gérard. "Asymmetric oxidation of sulfides by hydrogen peroxide catalyzed by chiral manganese porphyrins in water/methanol solution". . p. 75 - 79. Retrieved 2013/05/22.
• 2、 Fogli, Stefano,Banti, Irene,Stefanelli, Fabio,Picchianti, Luca,Digiacomo, Maria,MacChia, Marco,Breschi, Maria Cristina,Lapucci, Annalina. "Therapeutic potential of sulindac hydroxamic acid against human pancreatic and colonic cancer cells". experimental part. p. 5100 - 5107. Retrieved 2010/12/24.