Sulindac sulfide

Base Information

• Chemical Name: Sulindac sulfide
• CAS No.: 49627-27-2
• Molecular Formula: C20H17 F O2 S
• Molecular Weight: 340.418
• Hs Code.: 2930902000
• European Community (EC) Number: 250-892-2,256-403-9
• NSC Number: 747692
• UNII: 6UVA8S2DEY
• DSSTox Substance ID: DTXSID0049078
• Wikidata: Q27145288
• NCI Thesaurus Code: C29854
• Pharos Ligand ID: KBWF1V6KAKGW
• ChEMBL ID: CHEMBL18797
• Mol file: 49627-27-2.mol

Synonyms:sulindac sulfide;sulindac sulfide, (E)-isomer;sulindac sulfide, (Z)-isomer;sulindac sulfide, sodium salt

Chemical Property of Sulindac sulfide

Chemical Property:

• Melting Point: 189-191°C
• Boiling Point: 526.3°Cat760mmHg
• Flash Point: 272.1°C
• PSA: 62.60000
• Density: 1.3g/cm³
• LogP: 5.35000
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: >22 mg/mL
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 340.09332912
• Heavy Atom Count: 24
• Complexity: 546

Purity/Quality:

98%min ^*data from raw suppliers

Sulindac sulfide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-42/43-63

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C1=CC3=CC=C(C=C3)SC)C=CC(=C2)F)CC(=O)O
• Isomeric SMILES: CC\1=C(C2=C(/C1=C\C3=CC=C(C=C3)SC)C=CC(=C2)F)CC(=O)O
• Uses: An active metabolite of Sulindac. Inhibits cyclooxygenase, but induces apoptosis by a cyclooxygenase-independent mechanism. Inhibition of Ras activation of Ref-1. Impairs nucleotide exchange on Ras by CDC25 and accelerates Ras hydrolysis of GTP by p120GAP. An active metabolite of Sulindac. Inhibits cyclooxygenase, but induces apoptosis by a cyclooxygenase-independent mechanism. Inhibition of Ras activation of Ref-1. Impairs nucleotide exchange on Ras by CDC25 and accelerates Ras hydrolysis of GTP by p120GAP.

Technology Process of Sulindac sulfide

There total 14 articles about Sulindac sulfide 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 sulfide (49627-27-2)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; for 2.5h; Cooling with acetone-dry ice; Inert atmosphere;

DOI:10.1016/j.bmc.2013.12.014

Reference yield: 85.0%

ethyl 2-(5-fluoro-2-methyl-1H-inden-3-yl)acetate (53077-50-2) + 4-(Methylthio)benzaldehyde (3446-89-7) → sulindac sulfide (49627-27-2) + sulindac sulfide (61812-45-1)

Guidance literature:

ethyl 2-(5-fluoro-2-methyl-1H-inden-3-yl)acetate; With sodium methylate; In methanol; at 20 ℃; for 0.333333h;

4-(Methylthio)benzaldehyde; at 80 ℃; for 3.5h;

Reference yield:

4-methylthiobenzaldehyde (146857-81-0) + 5-fluoro-2-methyl-1H-indene-3-acetic acid (32004-66-3) → 5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid (49627-27-2,61812-45-1,32004-67-4)

Guidance literature:

With sodium methylate; In methanol;

upstream raw materials:

4-methylthiobenzaldehyde

5-fluoro-2-methyl-1H-indene-3-acetic acid

6-fluoro-2-methylindanone

Sulindac

Downstream raw materials:

Sulindac

(Z)-N-(2-(dimethylamino)ethyl)-2-(5-fluoro-2-methyl-1-(4-(methylsulfonyl)benzylidene)-1H-inden-3-yl)acetamide

(Z)-2-(6-fluoro-2-methyl-3-(4-(methylthio)benzylidene)-3H-inden-1-yl)acetic acid O-(tert-butyldimethylsilyl)hydroxyamide

5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl acetic acid

Refernces

• 1、 -. "Green synthesis method of sulindac". . . Retrieved 2020/06/20.
• 2、 Nortcliffe, Andrew,Ekstrom, Alexander G.,Black, James R.,Ross, James A.,Habib, Fouad K.,Botting, Nigel P.,O'Hagan, David. "Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment". supporting information. p. 756 - 761. Retrieved 2014/01/23.