Varespladib

Base Information

• Chemical Name: Varespladib
• CAS No.: 172732-68-2
• Molecular Formula: C21H20N2O5
• Molecular Weight: 380.398
• UNII: 2Q3P98DATH
• DSSTox Substance ID: DTXSID50169378
• Nikkaji Number: J1.099.228A
• Wikipedia: Varespladib
• Wikidata: Q7915613
• NCI Thesaurus Code: C152832
• Pharos Ligand ID: V7VQ1F4YMSQS
• Metabolomics Workbench ID: 152989
• ChEMBL ID: CHEMBL148674
• Mol file: 172732-68-2.mol

Synonyms:((3-(aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetate;LY 315920;LY-315920;LY315920;LY315920-NA;S 5920;S-5920;varespladib;varespladib sodium

Chemical Property of Varespladib

Chemical Property:

• Vapor Pressure: 9.53E-19mmHg at 25°C
• Melting Point: 230-234 °C
• Boiling Point: 667.9°C at 760 mmHg
• PKA: 3.12±0.40(Predicted)
• Flash Point: 357.7°C
• PSA: 111.62000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 3.08370
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 380.13722174
• Heavy Atom Count: 28
• Complexity: 589

Purity/Quality:

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

LY 315920 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1=C(C2=C(N1CC3=CC=CC=C3)C=CC=C2OCC(=O)O)C(=O)C(=O)N
• Recent ClinicalTrials: A Study of Bortezomib, Lenalidomide and Dexamethasone (VRd) Followed by BCMA CAR-T Therapy in Transplant-Ineligible Patients With New-diagnosed Multiple Myeloma
• Recent EU Clinical Trials: PONV – Histamin - Vitamin C
• Uses: VARESPLADIB is used as a PLA2 inhibitor (Phospholipase A2 Enzyme inhibitor). Varespladib has been used as a secretory phospholipase A (sPLA2) inhibitor: to test its effect on the human astrocytes subjected to psychosine-induced toxicityto test its neutralization functionality on the black snake species P. colletti?venom in combination with snake venom metalloproteinases (SVMP)-inhibitor, marimastat to test its protective functionality on envenoming by vipers

Technology Process of Varespladib

There total 22 articles about Varespladib 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%

tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate (889675-08-5) → ((3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid (172732-68-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h;

DOI:10.1021/jo070643y

Reference yield: 74.0%

[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester (172733-08-3) → ((3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid (172732-68-2)

Guidance literature:

With sodium hydroxide; In methanol; for 0.666667h; Heating;

DOI:10.1021/jm960487f

Reference yield:

4-(benzyloxy)-2-ethyl-1H-indole (39843-70-4) → ((3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid (172732-68-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.08 h / 0 °C

1.2: 83 percent / dimethylformamide / 2 h

2.1: 68 percent / H₂ / Pd/C / methanol / 2 h / 2068.59 Torr

3.1: NaH / dimethylformamide / 0.08 h / 20 °C

3.2: 87 percent / dimethylformamide / 0.5 h

4.1: CH₂Cl₂ / 2 h / 20 °C

5.1: 0.505 g / NH₃ / CH₂Cl₂ / 0.17 h / 20 °C

6.1: trifluoroacetic acid / CH₂Cl₂ / 1 h

With ammonia; hydrogen; sodium hydride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm060136t

upstream raw materials:

[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester

tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

3-chloro-2-iodophenyl N,N-dimethyl O-carbamate

tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

Refernces

• 1、 Smart, Brian P.,Oslund, Rob C.,Walsh, Laura A.,Gelb, Michael H.. "The first potent inhibitor of mammalian group X secreted phospholipase A2: Elucidation of sites for enhanced binding". . p. 2858 - 2860. Retrieved 2007/10/03.
• 2、 -. "Indole sPLA2 inhibitors". . . Retrieved 2008/06/13.