681281-88-9

Basic information

• Product Name: 5-(2-BENZOTHIAZOLYL)-3-ETHYL-2-(-(METHY
• Synonyms: 5-(2-BENZOTHIAZOLYL)-3-ETHYL-2-(-(METHY;6-(2-Benzothiazolyl)-1-ethyl-2-[2-(methylphenylamino)ethenyl]-3-phenyl-1H-benzimidazolium iodide;(E)-5-(benzo[d]thiazol-2-yl)-3-ethyl-2-(2-(methyl(phenyl)amino)vinyl)-1-phenyl-1H-benzo[d]imidazol-3-ium iodide;6-benzothiazol-2-yl-1-ethyl-2-[2-(methyl-phenyl-amino)-vinyl]-3-phenyl-3H-benzoimidazol-1-ium iodide;5-(Benzo[d]thiazol-2-yl)-3-ethyl-2-(2-(methyl(phenyl)amino)vinyl)-1-phenyl-1H-benzo[d]imidazol-3-ium iodide
• CAS NO: 681281-88-9
• Molecular Formula: C₃₁H₂₇N₄S*I
• Molecular Weight: 614.548
• Mol File: 681281-88-9.mol
• Article Data: 1

Chemical Properties

• Appearance: orange/solid
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥10 mg/mL
• CAS DataBase Reference: 5-(2-BENZOTHIAZOLYL)-3-ETHYL-2-(-(METHY(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-BENZOTHIAZOLYL)-3-ETHYL-2-(-(METHY(681281-88-9)
• EPA Substance Registry System: 5-(2-BENZOTHIAZOLYL)-3-ETHYL-2-(-(METHY(681281-88-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 681281-88-9(Hazardous Substances Data)

Usage

Biological Activity

akt inhibitor iv is an inhibitor of akt activation that inhibits akt-mediated nuclear export of forkhead box class o transcription factor 1a (foxo1a; ic50 = 625 nm) and reduces phosphorylation of akt at ser473 and thr308 in a dose-dependent manner. akt inhibitor iv inhibits replication of parainfluenza virus 5 (piv5) in hela cells (ic50 = 520 nm). it also reduces the growth of cancer cells (ic50 = 0.3 μm for both jurkat and hela cells) via a reduction in mitochondrial polarization and increased production of reactive oxygen species (ros).

Upstream product

• 1268527-46-3 [(E)-2-(5-benzothiazol-2-yl-1-phenyl-1H-benzoimidazol-2-yl)ethenyl]methyl phenylamine 
• 75-03-6 ethyl iodide 
• 1268527-43-0 (4-benzothiazol-2-yl-2-nitrophenyl)phenylamine 
• 1268527-45-2 4-benzothiazol-2-yl-N¹-phenylbenzene-1,2-diamine 
• 34900-01-1 3-(N-methyl-N-phenylamino)acrolein 
• 137-07-5 2-amino-benzenethiol 
• 100-61-8 N-methylaniline 
• 16588-34-4 4-chloro-3-nitro-benzaldehyde 

Relevant articles and documents

Synthesis and biological evaluation of analogues of AKT (protein kinase B) inhibitor-IV

Inhibitors of the PI3-kinase/AKT (protein kinase B) pathway are under investigation as anticancer and antiviral agents. The benzimidazole derivative AKT inhibitor-IV (ChemBridge 5233705) affects this pathway and exhibits potent anticancer and antiviral activity. To probe its biological activity, we synthesized AKT inhibitor-IV and 21 analogues using a novel six-step route based on ZrCl4-catalyzed cyclization of 1,2-arylenediamines with α,β-unsaturated aldehydes. We examined effects on viability of HeLa carcinoma cells, viability of normal human cells (NHBE), replication of recombinant parainfluenza virus 5 (PIV5) in HeLa cells, and replication of the intracellular bacterium Mycobacterium fortuitum in HeLa cells. Replacement of the benzimidazole N-ethyl substitutent of AKT inhibitor-IV with N-hexyl and N-dodecyl groups enhanced antiviral activity and cytotoxicity against the cancer cell line, but these compounds showed substantially lower toxicity (from 6-fold to >20-fold) against NHBE cells and no effect on M. fortuitum, suggesting inhibition of one or more host protein(s) required for proliferation of cancer cells and PIV5. The key structural elements identified here may facilitate identification of targets of this highly biologically active scaffold.