36047-55-9

Usage

Uses

Used in Pharmaceutical Industry:
5-ETHYL-5H-[1,2,4]TRIAZINO[5,6-B]INDOLE-3-THIOL is used as a potential pharmaceutical agent for its unique molecular structure, which may offer specific therapeutic benefits. The presence of the thiol group could provide antioxidant properties or interact with biological systems in ways that are beneficial for treating certain conditions.
Used in Materials Science:
In the field of materials science, 5-ETHYL-5H-[1,2,4]TRIAZINO[5,6-B]INDOLE-3-THIOL may be utilized as a component in the development of new materials with specialized properties. Its unique molecular structure could contribute to the creation of materials with enhanced stability, reactivity, or other desirable characteristics.
Used in Research Applications:
5-ETHYL-5H-[1,2,4]TRIAZINO[5,6-B]INDOLE-3-THIOL serves as a subject of research in chemical and biological studies. Its synthesis and properties are of interest to scientists who aim to understand its behavior and potential applications in various contexts, including drug discovery and material development.

InChI:InChI=1/C11H10N4S/c1-2-15-8-6-4-3-5-7(8)9-10(15)12-11(16)14-13-9/h3-6H,2H2,1H3,(H,12,14,16)

Upstream product

• 4290-94-2 N-ethylisatin 
• 79-19-6 thiosemicarbazide 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 112800-90-5 10-Ethyl-1-(4-nitro-phenyl)-1,2-dihydro-10H-2,3,4,5,10,10b-hexaaza-cyclopenta[a]fluorene 
• 112800-92-7 10-Ethyl-1-(4-methoxy-phenyl)-1,2-dihydro-10H-2,3,4,5,10,10b-hexaaza-cyclopenta[a]fluorene 
• 112800-91-6 1-(4-Chloro-phenyl)-10-ethyl-1,2-dihydro-10H-2,3,4,5,10,10b-hexaaza-cyclopenta[a]fluorene 
• 112800-93-8 10-Ethyl-1-phenyl-1,2-dihydro-10H-2,3,4,5,10,10b-hexaaza-cyclopenta[a]fluorene 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of 1,2,3-triazole-linked triazino[5,6-b]indole-benzene sulfonamide conjugates as potent carbonic anhydrase I, II, IX, and XIII inhibitors

A series of 1,2,3-triazole-linked triazino[5,6-b]indole-benzene sulfonamide hybrids (6a– 6o) was synthesized and evaluated for carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity against the human (h) isoforms hCA I, II, XIII (cytosolic isoforms), and hCA IX (transmembrane tumor-associated isoform). The results revealed that the compounds 6a–6o exhibited Ki values in the low to medium nanomolar range against hCA II and hCA IX (Kis ranging from 7.7 nM to 41.3 nM) and higher Ki values against hCA I and hCA XIII. Compound 6i showed potent inhibition of hCA II (Ki = 7.7nM), being more effective compared to the standard inhibitor acetazolamide (AAZ) (Ki = 12.1 nM). Compounds 6b and 6d showed moderate activity against hCA XIII (Ki= 69.8 and 65.8 nM). Hence, compound 6i could be consider as potential lead candidate for the design of potent and selective hCA II inhibitors.

Novel Multitarget Directed Triazinoindole Derivatives as Anti-Alzheimer Agents

The multifaceted nature of Alzheimer's disease (AD) demands treatment with multitarget-directed ligands (MTDLs) to confront the key pathological aberrations. A novel series of triazinoindole derivatives were designed and synthesized. In vitro studies revealed that all the compounds showed moderate to good anticholinesterase activity; the most active compound 23e showed an IC50 value of 0.56 ± 0.02 μM for AChE and an IC50 value of 1.17 ± 0.09 μM for BuChE. These derivatives are also endowed with potent antioxidant activity. To understand the plausible binding mode of the compound 23e, molecular docking studies and molecular dynamics simulation studies were performed, and the results indicated significant interactions of 23e within the active sites of AChE as well as BuChE. Compound 23e successfully diminished H2O2-induced oxidative stress in SH-SY5Y cells and displayed excellent neuroprotective activity against H2O2 as well as Aβ-induced toxicity in SH-SY5Y cells in a concentration dependent manner. Furthermore, it did not show any significant toxicity in neuronal SH-SY5Y cells in the cytotoxicity assay. Compound 23e did not show any acute toxicity in rats at doses up to 2000 mg/kg, and it significantly reversed scopolamine-induced memory deficit in mice model. Additionally, compound 23e showed notable in silico ADMET properties. Taken collectively, these findings project compound 23e as a potential balanced MTDL in the evolution process of novel 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).

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).

TRIAZINE COMPOUNDS AND THEIR USE

A compound of formula (I) wherein R1 is hydrogen, alkyl, -alkyl-aryl, -alkyl-heterocycloalkyl or -alkyl-0-heterocycloalkyl; R2 is hydrogen, hydroxy, amino, nitro, alkoxy, alkyl, aryl or heteroaryl; R3 is hydrogen, alkyl or

Synthesis of Triazolotriazinoindole, Tetrazolotriazinoindole and their Derivatives

Reactions of 5-ethyl-5H-1,2,4-triazinoindol-3-thione (1) with various reagents have been studied. 1 and hydrazine hydrate in anhydrous ethanol gave 5-ethyl-3-hydrazino-5H-1,2,4-triazinoindole (2).This compound was condensed with formic acid and acetic acid to give 10-ethyl-10H-triazolotriazinoindole (4, R=H) and 10-ethyl-1-methyl-10H-triazolotriazinotriazinoindole (7).Interaction of 2 with acetylacetone in alcoholic KOH gave the pyrazole 8, whereas reaction of 2 with ethyl acetoacetate in anhydrous ethanol led to the expected hydrazone 9, which on reflux with alcoholic KOH gives 1-(5-ethyl-5H-1,2,4-triazinoindol-3-yl)-3-methyl-2-pyrazolin-5-one 10.Treatment of 2 with ethyl chloroformate gives 11, which can be converted to 10-ethyl-2,10-dihydro-1H-triazolotriazino-indol-1-one 12 by fusion.