5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide

Base Information

• Chemical Name: 5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide
• CAS No.: 747412-49-3
• Molecular Formula: C26H31N3O5
• Molecular Weight: 465.549
• Hs Code.: 2934999090
• Mol file: 747412-49-3.mol

Synonyms:NVP-AUY922;VER 52296;5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide;

Chemical Property of 5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide

Chemical Property:

• Vapor Pressure: 5.54E-17mmHg at 25°C
• Refractive Index: 1.597
• Boiling Point: 640.1°C at 760 mmHg
• PKA: 8.47±0.48(Predicted)
• Flash Point: 340.9°C
• PSA: 108.06000
• Density: 1.234 g/cm³
• LogP: 4.45390
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (>25 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

NVP-AUY 922 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Luminespib (AUY-922, NVP-AUY922) is a highly potent HSP90 inhibitor for HSP90α/β with IC50 of 13 nM /21 nM in cell-free assays, weaker potency against the HSP90 family members GRP94 and TRAP-1, exhibits the tightest binding of any small-molecule HSP90 ligand. Phase 2. Hsp90 is a molecular chaperone of many different kinases, transcription factors, and hormone receptors involved in signal transduction, cell cycle regulation, and apoptosis. In addition to its important function in normal cell homeostasis, a high affinity form of Hsp90 is prevalent in tumor cells. Hsp90 inhibition has been associated with the degradation of oncogenic client proteins. NVP-AUY922 is a Hsp90 inhibitor (IC50 = 21 nM in a FP binding assay) that prevents the proliferation of a range of human cancer cell lines in vitro with GI50s averaging 9 nM. In a human colon cancer xenograft model, 50 mg/kg NVP-AUY922 inhibits tumor growth by ~50% compared to vehicle controls. Unlike some first generation Hsp90 inhibitors that are quickly glucuronidated, NVP-AUY922 is retained in tumors in vivo when administered at 4 mg/kg i.p. by cassette dosing in tumor-bearing mice.
• Uses: NVP-AUY 922 is a potent inhibitor of heat shock protein 90 (Hsp90) that prevents the proliferation of a range of human cancer cell lines. NVP-AUY 922 has been shown to enhance the radiation sensitivity of tumor cell lines under hypoxia. Potent Hedgehog inhibitor.

Technology Process of 5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide

There total 1 articles about 5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide 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:

5-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide → 5-(2,4-dihydroxy-5-isopropylphenyl)-4-(4-morpholin-4-ylmethylphenyl)isoxazole-3-carboxylic acid ethylamide (747412-49-3)

Guidance literature:

With boron trichloride; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jm701018h

Reference yield: 85.0%

5-(2,4-dihydroxy-5-isopropylphenyl)-4-(4-morpholin-4-ylmethylphenyl)isoxazole-3-carboxylic acid ethylamide (747412-49-3) + methanesulfonic acid (75-75-2,98527-29-8) → 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide mesylate

Guidance literature:

In tert-butyl methyl ether; water; acetone; at 0 - 45 ℃; for 26 - 26.5833h; Product distribution / selectivity;

Reference yield: 24.0%

cholesteryl hemi-4-oxaglutarate + 5-(2,4-dihydroxy-5-isopropylphenyl)-4-(4-morpholin-4-ylmethylphenyl)isoxazole-3-carboxylic acid ethylamide (747412-49-3) → AUY922-diglycolate-cholesterol

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 19 ℃; for 4.25h; Inert atmosphere;

Refernces

• 1、 -. "ISOXAZOLE COMPOUNDS AS INHIBITORS OF HEAT SHOCK PROTEINS". Page 110. . Retrieved 2010/02/08.