Triciribine

Base Information

• Chemical Name: Triciribine
• CAS No.: 35943-35-2
• Molecular Formula: C13H16 N6 O4
• Molecular Weight: 320.308
• UNII: 2421HMY9N6
• DSSTox Substance ID: DTXSID6045743
• Nikkaji Number: J1.370.732D
• Wikipedia: Triciribine
• Wikidata: Q25326616
• NCI Thesaurus Code: C142998
• Metabolomics Workbench ID: 63785
• ChEMBL ID: CHEMBL331237
• Mol file: 35943-35-2.mol

Synonyms:3-amino-1,5-dihydro-5-methyl-I-beta-D-ribofuranosyl-1,4,5,6,8- pentaazaacenaphthylene;6-amino-4-methyl-8-(beta-D-ribofuranosyl)-(4H,8H)pyrrolo(4,3,2-de)pyrimido(4,5-c)pyridazine;6-ARPPP;NSC 154020;NSC 154120;NSC-154020;triciribine

Chemical Property of Triciribine

Chemical Property:

• Vapor Pressure: 1.15E-21mmHg at 25°C
• Melting Point: 207 °C (decomp)
• Refractive Index: 1.7000 (estimate)
• Boiling Point: 718.5°Cat760mmHg
• PKA: 12.35±0.70(Predicted)
• Flash Point: 388.3°C
• PSA: 144.47000
• Density: 2.02g/cm³
• LogP: -0.90710
• Storage Temp.: Store at RT
• Solubility.: DMSO: >10mg/mL
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 320.12330301
• Heavy Atom Count: 23
• Complexity: 507

Purity/Quality:

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

Triciribine ^*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: CN1C2=NC=NC3=C2C(=CN3C4C(C(C(O4)CO)O)O)C(=N1)N
• Isomeric SMILES: CN1C2=NC=NC3=C2C(=CN3[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)C(=N1)N
• Recent ClinicalTrials: PTX-200 and Carboplatin in Ovarian Cancer
• Uses: Triciribine is an antitumor tricyclic nucleoside. Triciribine acts as a potent, small-molecule inhibitor of AKT phosphorylation in subjects with solid tumors contining activated AKT. Triciribine is al so a selective inhibitor of HIV-1 and HIV-2, including strains known to be resistant to AZT or TIBO. Triciribine is an antitumor tricyclic nucleoside. Triciribine acts as a potent, small-molecule inhibitor of AKT phosphorylation in subjects with solid tumors contining activated AKT. Triciribine is also a selective inhibitor of HIV-1 and HIV-2, including strains known to be resistant to AZT or TIBO. Triciribine hydrate has been used to study the effect of diethyldithiocarbamate (DDC) on matrix metalloproteinase-1 (MMP-1) in hepatic stellate cells1. It has also been used to analyze ADAM 10 activation by (-)-epigallocatechin-3-gallate (EGCG) in N2a cells overexpressing Swedish mutant APP (SweAPP N2a cells)2.

Technology Process of Triciribine

There total 10 articles about Triciribine 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: 92.0%

C34H28N6O7 → triciribine (35943-35-2)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 2h;

DOI:10.3390/molecules22040643

Reference yield: 74.0%

4-(1-methylhydrazino)-5-cyano-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine (699011-59-1) → triciribine (35943-35-2)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 19h; Inert atmosphere; Reflux;

DOI:10.1080/00397911.2010.524342

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → triciribine (35943-35-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.25 h / 20 °C

1.2: 73 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / 60 °C

2.1: 72 percent / CHCl₃; ethanol / 0.5 h

3.1: 97 percent / ammonium formate / Pd/C / ethanol / 1 h / Heating

4.1: sodium methoxide / methanol / 1 h / 20 °C

5.1: 0.44 g / methanol / 18 h / Heating

With N,O-bis-(trimethylsilyl)-acetamide; sodium methylate; ammonium formate; palladium on activated charcoal; In methanol; ethanol; chloroform; acetonitrile;

DOI:10.1081/NCN-120027815

upstream raw materials:

4-(N-methyl-hydrazino)-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

4-(1-methylhydrazino)-5-cyano-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

6-bromo-4-chloro-5-cyano-7-[2,3,5-tri-O-benzoyl-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

Downstream raw materials:

4-methyl-6-amino-8-[5'-O-(phenylphosphoryl (P->N)-L-methyl ester valine)-β-D-ribofuranosyl]pyrrolo[4,3,2-d]pyrimidino[4,5-c]pyridazine

4-methyl-6-amino-8-[5'-O-(phenylphosphoryl (P->N)-L-valine methyl ester)-2',3'-O-dilevylinyl-β-D-ribofuranosyl]pyrrolo[4,3,2-d]pyrimidino[4,5-c]pyridazine

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(3-benzoylamino-5-methyl-5H-1,4,5,6,8-pentaaza-acenaphthylen-1-yl)-tetrahydro-furan-3-yl ester

Refernces

• 1、 Schram,Townsend. "". . p. 4757. Retrieved 1971.
• 2、 Shen, Wei,Kim, Jae-Seung,Hilfinger, John. "Expedient total synthesis of triciribine and its prodrugs". experimental part. p. 358 - 374. Retrieved 2011/12/02.