Onalespib

Base Information

• Chemical Name: Onalespib
• CAS No.: 912999-49-6
• Molecular Formula: C24H31N3O3
• Molecular Weight: 409.528
• Hs Code.: 2933990090
• UNII: Q7Y33N57ZZ
• DSSTox Substance ID: DTXSID80238485
• Nikkaji Number: J3.146.978C
• Wikidata: Q27287092
• NCI Thesaurus Code: C85454
• Pharos Ligand ID: W9TP9BN7UBYB
• Metabolomics Workbench ID: 149732
• ChEMBL ID: CHEMBL1214827
• Mol file: 912999-49-6.mol

Synonyms:(2,4-dihydroxy-5-isopropylphenyl)-(5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl)methanone;AT 13387;AT-13387;AT13387;onalespib

Chemical Property of Onalespib

Chemical Property:

• Boiling Point: 605.7±55.0 °C(Predicted)
• PKA: 8.50±0.48(Predicted)
• PSA: 67.25000
• Density: 1.237
• LogP: 2.93830
• Solubility.: insoluble in H2O; ≥13.25 mg/mL in DMSO; ≥47.7 mg/mL in EtOH with ultrasonic
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 409.23654186
• Heavy Atom Count: 30
• Complexity: 592

Purity/Quality:

99.0%, ^*data from raw suppliers

Onalespib（AT13387,ATI13387X） >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC(=C(C=C1O)O)C(=O)N2CC3=C(C2)C=C(C=C3)CN4CCN(CC4)C
• Recent ClinicalTrials: Onalespib in Treating Patients With Locoregionally Advanced Squamous Cell Carcinoma of the Head and Neck Receiving Radiation Therapy and Cisplatin
• Recent EU Clinical Trials: A Study of HSP90 Inhibitor AT13387 Alone and in Combination with
• Description: Onalespib is a selective inhibitor of Hsp90 (IC50 = 18 nM). It induces the degradation of specific Hsp90 client proteins, including mutant EGFR, for up to seven days in tumor cell lines in vitro and up to three days in vivo. Onalespib is retained in tumor xenografts and is efficacious in a range of xenograft models.

Technology Process of Onalespib

There total 17 articles about Onalespib 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: 94.0%

2-(2,4-bis-benzyloxy-5-isopropenylphenyl)-[5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl]methanone (1019890-18-6) → (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone (912999-49-6)

Guidance literature:

With hydrogen; potassium carbonate; palladium 10% on activated carbon; In water; isopropyl alcohol; for 1 - 1.16667h; under 2250.23 Torr;

Reference yield: 90.0%

(2,4-dihydroxy-5-(2-hydroxyprop-2-yl)-phenyl)-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindol-2-yl]-methanone (1019890-25-5) → (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone (912999-49-6)

Guidance literature:

(2,4-dihydroxy-5-(2-hydroxyprop-2-yl)-phenyl)-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindol-2-yl]-methanone; With acetic anhydride; In toluene; at 100 ℃; for 16h;

With hydrogenchloride; In methanol; water; for 5h; Heating / reflux;

With potassium carbonate; In water; pH=8; Purification / work up;

Reference yield: 70.0%

5-((4-methylpiperazin-1-yl)methyl)iso-indoline trihydrochloride + 7-hydroxy-6-iso-propyl-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1415742-78-7) → (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone (912999-49-6)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; at -20 - 20 ℃; for 15h;

DOI:10.1021/jo302406w

upstream raw materials:

2-(2,4-bis-benzyloxy-5-isopropenylphenyl)-[5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl]methanone

(2,4-dihydroxy-5-(2-hydroxyprop-2-yl)-phenyl)-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindol-2-yl]-methanone

(2,4-bis-benzyloxy-5-isopropyl-phenyl)-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindol-2-yl]-methanone

5-bromoisoindoline

Downstream raw materials:

(2,4-dihydroxy-5-isopropyl-phenyl)-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindol-2-yl]-methanone L-lactate salt

carbonic acid 5-tert-butoxycarbonyloxy-4-isopropyl-2-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindole-2-carbonyl]-phenyl ester tert-butyl ester

diethyl-carbamic acid 5-diethylcarbamoyloxy-2-isopropyl-4-[5-(4-methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindole-2-carbonyl]-phenyl ester

Refernces

• 1、 -. "COMBINATION THERAPY FOR TREATING CANCER". Page/Page column 63; 77. . Retrieved 2019/02/02.
• 2、 -. "PHARMACEUTICAL COMPOUNDS". Page/Page column 103. . Retrieved 2010/06/22.