1355361-72-6

Basic information

• Product Name: 8-(cyclohexyloxy)-1-oxo-2-phenyl-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid
• Synonyms: 8-(cyclohexyloxy)-1-oxo-2-phenyl-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid
• CAS NO: 1355361-72-6
• Molecular Weight: 419.501
• Mol File: 1355361-72-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 8-(cyclohexyloxy)-1-oxo-2-phenyl-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(cyclohexyloxy)-1-oxo-2-phenyl-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid(1355361-72-6)
• EPA Substance Registry System: 8-(cyclohexyloxy)-1-oxo-2-phenyl-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid(1355361-72-6)

Safety Data

• Hazardous Substances Data: 1355361-72-6(Hazardous Substances Data)

Upstream product

• 1355361-81-7 5-(cyclohexyloxy)-2-methyl-1,3-benzothiazole 
• 1355361-83-9 ethyl [5-(cyclohexyloxy)-1,3-benzothiazol-2-yl]acetate 
• 1355361-91-9 ethyl 8-(cyclohexyloxy)-1-oxo-2-phenyl-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate 
• 1355361-85-1 ethyl (2E/Z)-2-[5-(cyclohexyloxy)-1,3-benzothiazol-2-yl]-3-(dimethylamino)acrylate 
• 108-93-0 cyclohexanol 
• 1555-80-2 phenylacetic anhydride 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 68867-14-1 2-methyl-5-benzothiazolol 

Relevant articles and documents

Pyridobenzothiazolones Exert Potent Anti-Dengue Activity by Hampering Multiple Functions of NS5 Polymerase

Treatment of dengue virus (DENV) and other flavivirus infections is an unmet medical need. The highly conserved flaviviral NS5 RNA-dependent RNA polymerase (RdRp) is an attractive antiviral target that interacts with NS3 and viral RNA within the replicati

Sustainable, three-component, one-pot procedure to obtain active anti-flavivirus agents

The mosquito-borne viruses belonging to the genus Flavivirus such as Dengue virus (DENV) and Zika virus (ZIKV) cause human infections ranging from mild flu-like symptoms to hemorrhagic fevers, hepatitis, and neuropathies. To date, there are vaccines only for few flaviviruses while no effective treatments are available. Pyridobenzothiazole (PBTZ) derivatives are a class of compounds endowed with a promising broad-spectrum anti-flavivirus activity and most of them have been reported as potent inhibitors of the flaviviral NS5 polymerase. However, synthesis of PBTZ analogues entails a high number of purification steps, the use of hazardous reagents and environmentally unsustainable generation of waste. Considering the promising antiviral activity of PBTZ analogues which require further exploration, in this work, we report the development of a new and sustainable three-component reaction (3CR) that can be combined with a basic hydrolysis in a one-pot procedure to obtain the PBTZ scaffold, thus reducing the number of synthetic steps, improving yields and saving time. 3CR was significantly explored in order to demonstrate its wide scope by using different starting materials. In addition, taking advantage of these procedures, we next designed and synthesized a new set of PBTZ analogues that were tested as anti-DENV-2 and anti-ZIKV agents. Compound 22 inhibited DENV-2 NS5 polymerase with an IC50 of 10.4 μM and represented the best anti-flavivirus compound of the new series by inhibiting DENV-2- and ZIKV-infected cells with EC50 values of 1.2 and 5.0 μM, respectively, that translates into attractive selectivity indexes (SI - 83 and 20, respectively). These results strongly reaffirm PBTZ derivatives as promising anti-flavivirus agents that now can be synthesized through a convenient and sustainable 3CR in order to obtain more potent compounds for further pre-clinical development studies.