103845-98-3

Usage

InChI:InChI=1/C9H5BrN4S/c10-4-1-2-6-5(3-4)7-8(11-6)12-9(15)14-13-7/h1-3,13H,(H,14,15)

Upstream product

• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 79-19-6 thiosemicarbazide 
• 66475-83-0 N-(4-bromophenyl)-2-(hydroxyimino) acetamide 
• 106-40-1 4-bromo-aniline 
• 4553-11-1 2-(5-bromo-2,3-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarbothioamide 
• 129951-97-9 5-oxo-6-(2-amino-5-bromophenyl)-1,2,4-triazine-3-thione 

Downstream Products

• 1338362-74-5 C₁₇H₁₁BrN₆O 
• 1338362-72-3 C₁₇H₁₁BrN₆O 
• 1338362-70-1 C₁₇H₁₁BrN₆ 
• 1338362-68-7 C₁₆H₈BrClN₆ 
• 1338362-66-5 C₁₆H₈BrClN₆ 
• 499783-55-0 C₁₆H₉BrN₆ 
• 1338362-51-8 C₁₇H₁₃BrN₆O 
• 1338362-50-7 C₁₇H₁₃BrN₆O 
• 1338362-48-3 C₁₇H₁₃BrN₆ 
• 1338362-47-2 C₁₆H₁₀BrClN₆ 
• 1338362-46-1 C₁₆H₁₀BrClN₆ 
• 878285-92-8 C₁₆H₁₁BrN₆ 
• 1338362-40-5 C₁₇H₁₃BrN₆O 
• 1338362-39-2 C₁₇H₁₃BrN₆ 

Relevant academic research and scientific papers

Further Studies on Triazinoindoles as Potential Novel Multitarget-Directed Anti-Alzheimer's Agents

The inadequate clinical efficacy of the present anti-Alzheimer's disease (AD) drugs and their low impact on the progression of Alzheimer's disease in patients have revised the research focus from single targets to multitarget-directed ligands. A novel series of substituted triazinoindole derivatives were obtained by introducing various substituents on the indole ring for the development of multitarget-directed ligands as anti-AD agents. The experimental data indicated that some of these compounds exhibited significant anti-AD properties. Among them, 8-(piperidin-1-yl)-N-(6-(pyrrolidin-1-yl)hexyl)-5H-[1,2,4]triazino[5,6-b]indol-3-amine (60), the most potent cholinesterase inhibitor (AChE, IC50 value of 0.32 μM; BuChE, IC50 value of 0.21 μM), was also found to possess significant self-mediated Aβ1-42 aggregation inhibitory activity (54% at 25 μM concentration). Additionally, compound 60 showed strong antioxidant activity. In the PAMPA assay, compound 60 exhibited blood-brain barrier penetrating ability. An acute toxicity study in rats demonstrated no sign of toxicity at doses up to 2000 mg/kg. Furthermore, compound 60 significantly restored the cognitive deficits in the scopolamine-induced mice model and Aβ1-42-induced rat model. In the in silico ADMET prediction studies, the compound satisfied all the parameters of CNS acting drugs. These results highlighted the potential of compound 60 to be a promising multitarget-directed ligand for the development of potential anti-AD drugs.

Triazino indole-quinoline hybrid: A novel approach to antileishmanial agents

A novel series of 1,2,4-triazino-[5,6b]indole-3-thione covalently linked to 7-chloro-4-aminoquinoline have been synthesized and evaluated for their in vitro activity against extracellular promastigote and intracellular amastigote form of Leishmania donovani. Among all tested compounds, compounds 7a and 7b were found to be the most active with IC50 values 1.11, 0.36 μM and selectivity index (SI) values 67, >1111, respectively, against amastigote form of L. donovani which is several folds more potent than the standard drugs, miltefosine (IC50 = 8.10 μM, SI = 7) and sodium stibo-gluconate (IC50 = 54.60 μM, SI ≥ 7).

Indole derivative and application thereof

The invention discloses an indole derivative. The indole derivative is an indole structure-containing derivative with a novel structure. Through test of the in-vitro anti-tumor activity, it is found that the indole derivative has a remarkable anti-tumor effect and can be applied to preparation of medicine for treating or preventing cancer diseases and other proliferative diseases, so that treatment or prevention of cancer diseases and other proliferative diseases is achieved. Therefore, the indole derivative has an excellent application prospect in the aspect of development of anti-tumor medicine.

Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists

The cannabinoid receptor 2 (CB2R) has been linked with the regulation of inflammation, and selective receptor activation has been proposed as a target for the treatment of a range of inflammatory diseases such as atherosclerosis and arthritis.

Triazino indole-quinoline hybrid: A novel approach to antileishmanial agents

A novel series of 1,2,4-triazino-[5,6b]indole-3-thione covalently linked to 7-chloro-4-aminoquinoline have been synthesized and evaluated for their in vitro activity against extracellular promastigote and intracellular amastigote form of Leishmania donovani. Among all tested compounds, compounds 7a and 7b were found to be the most active with IC50 values 1.11, 0.36 μM and selectivity index (SI) values 67, >1111, respectively, against amastigote form of L. donovani which is several folds more potent than the standard drugs, miltefosine (IC50 = 8.10 μM, SI = 7) and sodium stibo-gluconate (IC50 = 54.60 μM, SI ≥ 7).

Aqua mediated one pot facile synthesis of novel thioxo-1,2,4-triazin-5(2H)- one and [1,2,4] triazino[5,6-b]indole derivatives and their biological activities

Rapid and highly efficient one pot green chemical synthesis of substituted 6-(2-aminophenyl)-4-(4-substitutedphenyl)-3-thioxo-3,4-dihydro-1,2, 4-triazin-5(2H)-one and 8-substituted-3,5-dihydro-2H-[1,2,4]triazino[5,6-b] indole is carried out in aqueous medium under microwave irradiation. Improved synthesis of potent bioactive Schiff and N-Mannich bases of hexahydro-1H-indole- 2,3-dione is also reported. The title compounds are easily accessible by various approaches; even waste free approaches have been developed. The operational simplicity, environmentally benign conditions and high yield achieved in a very short reaction time are major benefits that meet the requirements of green production, including saving energy and high efficiency. The results obtained under microwaves are compared with that of conventional heating. Structural assignments are based on spectroscopic data. Compounds have also been screened for antibacterial and antifungal activities.

Synthesis and characterization of some halogen containing triazolo triazinoindoles as possible fungicides

Certain 6H-5-aryl-9-halo-1,2,4-triazolo[3′,4′:3,4]·1,2, 4-triazino [5,6-b]-lndoles (4a-1) and 5H-1-aryl-8-halo-1,2,4-triazolo [4′,3′:3,4]-1,2,4-Triazino [5,6-b]-indoles (5a-1) have been prepared in good yields, characterization of new compounds has been done means of spectral data and elemental analysis. The fungicidal activity of synthesized compounds have been evaluated against A. niger and F. oxysporium.

Heterocyclic systems containing bridgehead nitrogen atom : Part LXXII - Reaction of 5H-2,3-dihydro-1,2,4-triazinoindole-3-thiones with phenacyl bromide, 1,2-dibromomethane and chloroacetic acid

8-Bromo-5H-dihydro-1,2,4-triazinoindole-3-thione (III), obtained by the reaction of 5-bromoisatin (I) with thiosemicarbazide followed by cyclization of the intermediate 5-bromoisatin-3-thiosemicarbazone (II) with alkali, on condensation with phenacyl bromide gives 8-bromo-3-phenacylthio-5H-1,2,4-triazinoindole (IV).The ketone IV on polyphosphoric acid-catalyzed cyclization furnishes 7-bromo-3-phenylthiazolotriazinoindole (Va) and not 7-bromo-1-phenylthiazolotriazinoindole (VIIa) which has been obtained through unequivocal synthesis.The reaction of III with 1,2-dibromoethane, on the other hand, yields7-bromo-1,2-dihydrothiazolotriazinoindole (VIII), identical with the authentic compound obtained by the reaction II with 1,2-dibromoethane. 5H-6-Methyl-1,2,4-triazinoindole-3-thiolacetic acid (XI), obtained by the reacvtion of 5H-2,3-dihydro-6-methyl-1,2,4-triazinoindole-3-thione (X) with chloroacetic acid, on cyclization with acetc anhydride in the presence or absence of pyridine gave 2-acetyl-3-hydroxy-9-methylthiazolotriazinoindole (XIII).All structures have been established by IR, 1H NMR and mass spectral data.

SEMICARBAZONES AND THIOSEMICARBAZONES OF THE HETEROCYCLIC SERIES LIV. DERIVATIVES OF 1,2,4-TRIAZINE, 1,2,4-TRIAZOLE, AND 1,3,4-THIADIAZOLE FROM 1-ACETYL-5-BROMOISATIN AND THIOSEMICARBAZIDE

The reaction of 1-acetyl-5-bromoisatin with thiosemicarbazide and the transformations of the products of this reaction have special features due to the introduction of the bromine atom into the indole ring.In alcohol the reaction leads to the formation of

Heterocyclic Systems Containing Bridgehead Nitrogen Atom: Synthesis of 2,3-Dihydrothiazolotriazinoindole, 4H-2,3-Dihydrothiazinotriazinoindole and Related Heterocycles

8-Bromo-5H-2,3-dihydro-1,2,4-triazinoindole-3-thione (II) on condensation with 1,2-dibromoethane and 1,3-dibromopropane gives the cyclized products 7-bromo-2,3-dihydrothiazolotriazinoindole (III) and 4H-8-bromo-2,3-dihydrothiazinotriazinoindole (IV) respectively, and not the angular isomers VI and VII.The unequivocal synthesis of the latter (VI and VII) has been accomplished by the reaction of 5-bromoisatin-3-thiosemicarbazone (I) with 1,2-dibromoethane and 1,3-dibromopropane respectively.Condensation of II with 2,3-dichloroquinoxaline on the other hand, yields the angular isomer 3-bromoquinoxalinothiazoloindolotriazine (V), identical with a sample obtained unambigously by the reaction of I with 2,3-dichloroquinoxaline.