35943-35-2

Usage

Uses

Used in Anticancer Applications:
API-2 is used as an antitumor agent for inhibiting AKT phosphorylation in subjects with solid tumors containing activated AKT. This action contributes to the suppression of tumor growth and progression.
Used in Antiviral Applications:
API-2 is used as a selective inhibitor for HIV-1 and HIV-2, including strains known to be resistant to AZT or TIBO. Its antiviral properties make it a valuable compound in the fight against HIV.
Used in Research Applications:
API-2 is used as a research tool for studying the effects of various compounds on matrix metalloproteinase-1 (MMP-1) in hepatic stellate cells and analyzing ADAM 10 activation by (-)-epigallocatechin-3-gallate (EGCG) in N2a cells overexpressing Swedish mutant APP (SweAPP N2a cells). This application aids in understanding the underlying mechanisms of certain diseases and the development of targeted therapies.
Used in Pharmaceutical Industry:
API-2 is used as a key compound in the development of novel drug delivery systems and therapeutic strategies for cancer and HIV treatment. Its multifaceted applications make it a promising candidate for further research and development in the pharmaceutical sector.

Biological Activity

Selective inhibitor of Akt (protein kinase B) signaling; displays minimal inhibition of PKC, PKA, SGK and p38 pathways. Inhibits phosphorylation and activation of downstream targets of Akt including Bad, GSK-3 β and AFX. In vitro, induces apoptosis and growth arrest preferentially in human cancer cells with elevated levels of Akt. In mice, potently and selectively inhibits growth of Akt-overexpressing tumors. Inhibits DNA synthesis and displays antiviral activity against HIV-1 and -2.

Biochem/physiol Actions

Triciribine is a highly selective Akt/PKB inhibitor, that selectively inhibits the cellular phosphorylation/activation of Akt1/2/3.

InChI:InChI=1/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)

Upstream product

• 35943-36-3 4-(N-methyl-hydrazino)-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 699011-59-1 4-(1-methylhydrazino)-5-cyano-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 699011-57-9 6-bromo-4-chloro-5-cyano-7-[2,3,5-tri-O-benzoyl-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine 
• 699011-58-0 6-bromo-5-cyano-4-(1-methylhydrazino)-7-[2,3,5-tri-O-benzoyl-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine 
• 24391-39-7 6-bromo-4-chloro-5-cyanopyrrolo[2,3-d]pyrimidin-4-one 
• 24391-40-0 6-Bromo-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 19393-83-0 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine 

Downstream Products

• 1065474-61-4 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 
• 1065474-31-8 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 
• 1054635-69-6 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 

Relevant academic research and scientific papers

An expedient total synthesis of triciribine

In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) group and ring closure reaction together to give a tricyclic nucleobase motif.

An Improved Total Synthesis of Triciribine: A Tricyclic Nucleoside with Antineoplastic and Antiviral Properties

We describe an efficient total synthesis of triciribine, a tricyclic nucleoside with antineoplastic and antiviral properties, starting from 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine.

Expedient total synthesis of triciribine and its prodrugs

Triciribine (TCN, 1) and its monophosphate (TCNP, 2) are ricyclic nucleotide derivatives that have potential antineoplastic activity. Triciribine inhibits the phosphorylation, activation, and signaling of Akt-1, -2, and -3, which may result in the inhibition of Akt-expressing tumor cell proliferation. Both TCN and TCNP have very low bioavailability, and the development of both drugs as intravenous (IV) treatments was halted because of the toxicity induced by the high doses needed for their use as general cytotoxic agents. This publication describes an expedient and straightforward total synthesis of amino acid prodrugs (3, 4) of TCN and TCNP. In our study, both the prodrugs significant improved the plasma exposure of the parent drugs and the prodrugs.Copyright TSRL Inc.