Vadimezan

Base Information

• Chemical Name: Vadimezan
• CAS No.: 117570-53-3
• Molecular Formula: C17H14O4
• Molecular Weight: 282.296
• Hs Code.: 2932999099
• European Community (EC) Number: 700-141-4
• UNII: 0829J8133H
• DSSTox Substance ID: DTXSID2040949
• Nikkaji Number: J360.785B
• Wikipedia: Vadimezan
• Wikidata: Q7908310
• NCI Thesaurus Code: C2504
• Metabolomics Workbench ID: 149694
• ChEMBL ID: CHEMBL71263
• Mol file: 117570-53-3.mol

Synonyms:5,6-dimethyl xanthenone acetic acid;5,6-dimethyl-9-oxo-9H-xanthene-4-acetic acid;5,6-dimethylxanthenone-4-acetic acid;5,6-dimethylxanthenoneacetic acid;5,6-dimethylxanthenoneacetic acid, sodium salt;5,6-MeXAA;AS1404;ASA 404;ASA-404;ASA404;dimethyloxoxanthene acetic acid;DMXAA;NSC 640488;vadimezan

Chemical Property of Vadimezan

Chemical Property:

• Vapor Pressure: 1.12E-11mmHg at 25°C
• Melting Point: 259-261 °C
• Refractive Index: 1.633
• Boiling Point: 520.9 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 197.1 °C
• PSA: 67.51000
• Density: 1.321 g/cm³
• LogP: 3.19010
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 17 mg/mL, soluble
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 282.08920892
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

99.9% ^*data from raw suppliers

Vadimezan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C2=C(C=C1)C(=O)C3=CC=CC(=C3O2)CC(=O)O)C
• Recent ClinicalTrials: ASA404 or Placebo in Combination With Paclitaxel and Carboplatin as First-Line Treatment for Stage IIIb/IV Non-Small Cell Lung Cancer
• Recent EU Clinical Trials: An open-label, multi-center, continued access trial of investigational drug ASA404 for patients in previous ASA404 clinical trials
• Description: DMXAA (117570-53-3) is a STING (Stimulator of Interferon Genes) agonist selective for mouse STING.1,2 Intratumoral administration of DMXAA resulted in tumor regression and complete rejection in mouse xenografts.3 Tumor regression induced by DMXAA results from a cascade of cellular events which include disruption of tumor vasculature followed by the release of chemokines which trigger the recruitment of immune cells.4 DMXAA induced expression of IFN-β resulting in a striking expansion of leukemia-specific T cells extending survival in two acute myeloid leukemia models.5
• Uses: Vadimezan is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models. Vadimezan is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models. It is a substrate for the immune adaptor protein STING in mice.

Technology Process of Vadimezan

There total 22 articles about Vadimezan 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: 99.0%

2-(7-bromo-5,6-dimethyl-9-oxo-9H-xanthene-4-yl) acetic acid (1021381-69-0) → vadimezan (117570-53-3)

Guidance literature:

With palladium on activated charcoal; hydrogen;

DOI:10.1016/j.tetlet.2009.04.074

Reference yield: 95.0%

2-<2-(carboxymethyl)phenoxy>-3,4-dimethylbenzoic acid (117570-93-1) → vadimezan (117570-53-3)

Guidance literature:

With sulfuric acid; In water; at 80 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2009.04.074

Reference yield: 83.0%

3,4-dimethyl-2-nitrobenzaldehyde + 2-Hydroxyphenylacetic acid (614-75-5) → vadimezan (117570-53-3)

Guidance literature:

With potassium phosphate; triphenylphosphine; copper dichloride; In toluene; at 110 ℃; for 24h; Reagent/catalyst;

upstream raw materials:

2-<2-(carboxymethyl)phenoxy>-3,4-dimethylbenzoic acid

(2-hydroxyphenyl)acetic acid disodium salt

6,7-dimethylisatin

2,3-dimethyl-α-isonitrosoacetanilide

Downstream raw materials:

2-(7-bromo-5,6-dimethyl-9-oxo-9H-xanthene-4-yl) acetic acid

4-(2-(5,6-dimethylxanthone-4-yl)acetamido)benzoic acid ethyl ester

2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)-N-(4-nitro-3-(trifluoromethyl)phenyl)acetamide

N-(3-chloro-4-fluorophenyl)-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetamide

Refernces

• 1、 -. "Compound as DMXAA-Pyranoxanthone well as preparation method and application thereof". Paragraph 0041; 0043; 0049; 0050. . Retrieved 2020/02/19.
• 2、 -. "Preparation method of DMXAA". . . Retrieved 2020/10/21.