247-92-7

Basic information

• Product Name: 1,2,4-Triazolo[3,4-b]benzothiazole
• Synonyms: 1,2,4-Triazolo[3,4-b]benzothiazole;7-thia-2,4,5-triazatricyclo[6.4.0.0^{2,6}]dodeca-1(8),3,5,9,11-pentaene;1,2,4-triazolobenzothiazole
• CAS NO: 247-92-7
• Molecular Formula: C8H5N3S
• Molecular Weight: 175
• Mol File: 247-92-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 175-176 °C
• Appearance: /
• Density: 1.58g/cm³
• Refractive Index: 1.857
• PKA: 2.11±0.30(Predicted)
• CAS DataBase Reference: 1,2,4-Triazolo[3,4-b]benzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Triazolo[3,4-b]benzothiazole(247-92-7)
• EPA Substance Registry System: 1,2,4-Triazolo[3,4-b]benzothiazole(247-92-7)

Safety Data

• Hazardous Substances Data: 247-92-7(Hazardous Substances Data)

Usage

General Description

1,2,4-Triazolo[3,4-b]benzothiazole is a heterocyclic compound that consists of a triazole ring fused with a benzothiazole ring. It has potential applications in medicinal chemistry, specifically as a scaffold for drug development. The compound has been investigated for its antibacterial, antifungal, and anti-inflammatory properties. 1,2,4-Triazolo[3,4-b]benzothiazole has also been studied for its potential as an anticancer agent and has shown promising activity against various cancer cell lines. Its unique chemical structure and biological activities make it an interesting target for further research in the development of new medicinal compounds.

InChI:InChI=1/C8H5N3S/c1-2-4-7-6(3-1)11-5-9-10-8(11)12-7/h1-5H

Upstream product

• 615-21-4 1,3-benzothiazol-2-ylhydrazine 
• 64-18-6 formic acid 
• 149-73-5 trimethyl orthoformate 
• 180967-55-9 3-chloro-1,2,4-triazolo[3,4-b]benzothiazol-4(H)-one 
• 116577-86-7 3,4-dihydro-2H-as-triazino<3,4-b>benzothiazole-3,4-dione 
• 2740-81-0 2-chlorophenylisothiocyanate 
• 624-84-0 formic acid hydrazide 
• 122-51-0 orthoformic acid triethyl ester 
• 137-07-5 2-amino-benzenethiol 
• 82725-45-9 2-(4-methoxy-phenylmethylthio)-aniline 
• 1404101-25-2 4-[2-(4-methoxybenzylthio)phenyl]-1,2,4-4H-triazole 

Downstream Products

• 3028-06-6 2-Acetylaminobenzothiazole 

Relevant articles and documents

Synthesis of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazole Derivatives via C-H Bond Functionalization of Disulfide Intermediates

Many nitrogen-and sulfur-containing heterocyclic compounds exhibit biological activity. Among these heterocycles are benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles for which two main synthetic approaches exist. Here we report a new synthetic protocol that allows the preparation of these tricyclic compounds via the oxidation of a mercaptophenyl moiety to its corresponding disulfide. Subsequent C-H bond functionalization is thought to enable an intramolecular ring closure, thus forming the desired benzo[4,5]thiazolo[2,3-c][1,2,4]triazole. This method combines a high functional group tolerance with short reaction times and good to excellent yields.

Synthesis and benzodiazepine receptor binding of some imidazo- and pyrimido[2,1-b]benzothiazoles

A series of substituted imidazo[2,1-b]benzothiazoles 2a-u was synthesized and the compounds evaluated for their affinity at the central benzodiazepine receptors. Substitution at the 7-position generally resulted in a decreased ligand affinity whereas a significant increase was observed for 5-substituted compounds. The intrinsic efficacy of selected high-affinity ligands 2j,k,q, as well as some previously reported pyrimido[2,1-b]benzothiazoles 1, was measured in vitro through the determination of the GABA ratio and [35S]TBPS displacement. Consistent with a partial inverse agonist profile, the benzothiazole derivatives 2j,k,q increased [35S]TBPS binding. For compounds 1c and 1d, a discrepancy between GABA ratio and [35S]TBPS binding data was observed. Only the latter assay was in full agreement with the pharmacological data, which indicated an inverse agonist and a partial agonist profile for 2k,q and 1c,d respectively. The affinity and intrinsic activity data of compounds 1c,d and 2j,k,q are discussed in the light of the recently proposed pharmacophore model by Skolnick/Cook; in particular, the agonistic activity of 1c,d is interpreted on the basis of a possible interaction of substitutents in position 6 with the receptors lipophilic area L3 of Skolnick/Cook, whereas the observed inverse agonist profile of 2j,k,q is explained taking into account their structural analogy with the well known proconvulsant β-CCE.

Agent for the control of plant-pathogenic organisms

Methods employing and compositions comprising, for the control of plant-pathogenic organisms, specified triazolobenzoxazole and triazolobenzothiazole compounds; and novel methods for the preparation of the compounds.