Salirasib

Base Information

• Chemical Name: Salirasib
• CAS No.: 162520-00-5
• Molecular Formula: C22H30O2S
• Molecular Weight: 358.53700
• European Community (EC) Number: 878-362-1
• NSC Number: 685986
• UNII: MZH0OM550M
• DSSTox Substance ID: DTXSID501025654
• Nikkaji Number: J1.216.035F,J653.317E
• Wikidata: Q27088685
• NCI Thesaurus Code: C71146
• Pharos Ligand ID: HYYK22GDJQDN
• Metabolomics Workbench ID: 153627
• ChEMBL ID: CHEMBL23293
• Mol file: 162520-00-5.mol

Synonyms:Farnesyl thiosalicylate;Farnesyl thiosalicylic acid;Farnesylthiosalicylic acid;2-(((2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl)sulfanyl)benzoic acid;FTS;Lopac-F-8175;2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylbenzoic acid;S-Farnesylthiosalicylic acid;

Chemical Property of Salirasib

Chemical Property:

• Melting Point: 64-66°C
• Boiling Point: 486.0±45.0 °C(Predicted)
• PKA: 3.50±0.36(Predicted)
• PSA: 62.60000
• Density: 1.05
• LogP: 6.89610
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 358.19665137
• Heavy Atom Count: 25
• Complexity: 498

Purity/Quality:

99% ^*data from raw suppliers

Salirasib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCSC1=CC=CC=C1C(=O)O)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CSC1=CC=CC=C1C(=O)O)/C)/C)C
• Recent ClinicalTrials: Study of Salirasib to Treat Non-Small Cell Lung Cancer
• Recent NIPH Clinical Trials: Phase 1 study of ONO-7056
• Description: Association of Ras protein with the inner surface of the plasma membrane is required for Ras signaling activity. Farnesyl thiosalicylic acid (FTS) is an inhibitor of Ras-mediated signaling that functions by dislodging Ras from the cell membrane thereby rendering it susceptible to proteolytic degradation. FTS inhibits the growth of human Ha-ras-transformed Rat1 fibroblasts with an IC50 value of 7.5 μM. It does not inhibit Ras farnesylation in vitro and although FTS does inhibit prenylated protein methyltransferase (PPMTase) in cell-free systems with a Ki value of 2.6 μM, it is relatively ineffective at inhibiting methylation in whole cells. Treatment of chow-fed ApoE-deficient mice with 5 mg/kg FTS three times per week for six weeks reduces early atherosclerotic lesion development by 52% compared to controls.
• Uses: It is a new specific nontoxic drug with a mild hydrophobic nature, which acts as a Ras antagonist and can therefore be used for stent applications as well as for local cancer treatment. Salirasib is a new specific nontoxic drug with a mild hydrophobic nature, which acts as a Ras antagonist and can therefore be used for stent applications as well as for local cancer treatment. Salirasib has been used as a farnesyltransferase inhibitor.

Technology Process of Salirasib

There total 17 articles about Salirasib 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: 98.0%

methyl 2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzoate → salirasib (162520-00-5)

Guidance literature:

methyl 2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzoate; With sodium hydroxide; In methanol;

In methanol; at 60 ℃; for 3h; Acidic conditions;

Reference yield: 90.0%

farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7) → salirasib (162520-00-5)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 10h; Reflux;

DOI:10.1016/j.bmc.2013.11.013

Reference yield: 85.0%

farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7) + Thiosalicylic acid (147-93-3) → salirasib (162520-00-5)

Guidance literature:

With guanidine hydrogen carbonate; In acetone; Ambient temperature;

DOI:10.1021/jm00008a004

upstream raw materials:

farnesyl bromide

Thiosalicylic acid

ethyl farnesoate

Farnesol

Downstream raw materials:

N-(2-(diethylamino)ethyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide

N-(3-(dimethylamino)propyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide

N-(3-(diethylamino)propyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide

N-(4-(diethylamino)butyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide

Refernces

• 1、 -. "Protein degradation targeting chimeric compound, preparation method and medical application thereof". . . Retrieved 2021/03/31.
• 2、 Porta, Exequiel O. J.,Bofill Verdaguer, Ignasi,Perez, Consuelo,Banchio, Claudia,Ferreira De Azevedo, Mauro,Katzin, Alejandro M.,Labadie, Guillermo R.. "Repositioning Salirasib as a new antimalarial agent". supporting information. p. 1599 - 1605. Retrieved 2019/09/30.