9H-Purine-9-propanamine, 6-amino-8-((6-iodo-1,3-benzodioxol-5-yl)thio)-N-(1-methylethyl)-

Base Information

• Chemical Name: 9H-Purine-9-propanamine, 6-amino-8-((6-iodo-1,3-benzodioxol-5-yl)thio)-N-(1-methylethyl)-
• CAS No.: 873436-91-0
• Molecular Formula: C₁₈H₂₁IN₆O₂S
• Molecular Weight: 512.374
• NSC Number: 752199
• UNII: 06IVK87M04
• DSSTox Substance ID: DTXSID20236288
• Nikkaji Number: J3.119.979D
• Wikidata: Q27236209
• NCI Thesaurus Code: C101227
• Pharos Ligand ID: P97S8J2LK4BD
• Metabolomics Workbench ID: 153589
• ChEMBL ID: CHEMBL200102
• Mol file: 873436-91-0.mol

Synonyms:9H-purine-9-propanamine, 6-amino-8-((6-iodo-1,3-benzodioxol-5-yl)thio)-N-(1-methylethyl)-;PU H71;PU-H71

Chemical Property of 9H-Purine-9-propanamine, 6-amino-8-((6-iodo-1,3-benzodioxol-5-yl)thio)-N-(1-methylethyl)-

Chemical Property:

• Boiling Point: 650.6±65.0 °C(Predicted)
• PKA: 10.16±0.29(Predicted)
• PSA: 125.41000
• Density: 1.84
• LogP: 4.25320
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 512.04914
• Heavy Atom Count: 28
• Complexity: 521

Purity/Quality:

98%Min ^*data from raw suppliers

PUH71 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)NCCCN1C2=NC=NC(=C2N=C1SC3=C(C=C4C(=C3)OCO4)I)N
• Recent ClinicalTrials: The First-in-human Phase I Trial of PU-H71 in Patients With Advanced Malignancies
• Uses: Trifluoroacetic Acid of PU-H71 is a potent Hsp90 inhibitor (IC50 = 50 nM). Hsp90 plays a critical role in modulating the activity of many cell signaling proteins and are an attractive target for anti-cancer therapeutics. Studies indicate that Hsp90 inhibitors may serve as potential anti-Parkinson′s disease.

Technology Process of 9H-Purine-9-propanamine, 6-amino-8-((6-iodo-1,3-benzodioxol-5-yl)thio)-N-(1-methylethyl)-

There total 10 articles about 9H-Purine-9-propanamine, 6-amino-8-((6-iodo-1,3-benzodioxol-5-yl)thio)-N-(1-methylethyl)- 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: 90.0%

9-(3-bromopropyl)-8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio)-9H-purin-6-amine (1240419-78-6) + isopropylamine (75-31-0) → 8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine (873436-91-0)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1002/jlcr.1689

Reference yield:

{3-[6-amino-8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-purin-9-yl]-propyl}-isopropyl-carbamic acid tert-butyl ester (873437-14-0) → 8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine (873436-91-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/jm0508078

Reference yield:

tert-butyl N-(3-hydroxypropyl)-N-(isopropyl)carbamate (873437-13-9) → 8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine (873436-91-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / pyridine / CH₂Cl₂ / 20 °C

2: Cs₂CO₃ / dimethylformamide / 24 h / 80 °C

3: 30 mg / TFA / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; caesium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0508078

upstream raw materials:

{3-[6-amino-8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-purin-9-yl]-propyl}-isopropyl-carbamic acid tert-butyl ester

tert-butyl N-(3-hydroxypropyl)-N-(isopropyl)carbamate

3-(tert-butoxycarbonyl-isopropylamino)propyl tosylate

8-(benzo[1,3]dioxol-5-ylsulfanyl)adenine

Refernces

• 1、 He, Huazhong,Zatorska, Danuta,Kim, Joungnam,Aguirre, Julia,Llauger, Laura,She, Yuhong,Wu, Nian,Immormino, Robert M.,Gewirth, Daniel T.,Chiosis, Gabriela. "Identification of potent water soluble purine-scaffold inhibitors of the heat shock protein 90". . p. 381 - 390. Retrieved 2007/10/03.