4046-70-2

Usage

Uses

Used in Pharmaceutical Industry:
5-METHYL-1,2,4-TRIAZINO[5,6-B]INDOLE-3-THIOL is used as a chemical intermediate for the synthesis of various organic compounds and drug candidates. Its unique structure and electronic properties make it a promising candidate for drug development, potentially leading to the creation of new therapeutic agents.
Used in Materials Science:
In the field of materials science, 5-METHYL-1,2,4-TRIAZINO[5,6-B]INDOLE-3-THIOL is used for its potential to contribute to the development of novel materials with specific properties. Its sulfur-containing nature may allow it to participate in various chemical reactions, which could be harnessed to create new materials with tailored characteristics.
Used as a Catalyst in Chemical Processes:
5-METHYL-1,2,4-TRIAZINO[5,6-B]INDOLE-3-THIOL is used as a catalyst in certain chemical reactions due to its sulfur-containing nature. This property may enable it to facilitate specific transformations, enhancing the efficiency and selectivity of various industrial processes.

InChI:InChI=1/C10H8N4S/c1-14-7-5-3-2-4-6(7)8-9(14)11-10(15)13-12-8/h2-5H,1H3,(H,11,13,15)

Upstream product

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 79-19-6 thiosemicarbazide 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 1064666-90-5 C₂₁H₁₆BrN₇OS₂ 
• 121998-33-2 (2-Fluoro-benzyl)-(5-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)-amine 
• 121998-34-3 (4-Fluoro-benzyl)-(5-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)-amine 
• 3994-69-2 benzyl-(5-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)-amine 
• 4091-89-8 9-Methyl-2-methylmercapto-1,3,4-triaza-carbazol 

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).

Synthesis and biological evaluation of new [1,2,4]triazino[5,6-b]indol-3-ylthio-1,3,5-triazines and [1,2,4]triazino[5,6-b]indol-3-ylthio-pyrimidines against Leishmania donovani

A series of [1,2,4]triazino[5,6-b]indol-3-ylthio-1,3,5-triazines and [1,2,4]triazino[5,6-b]indol-3-ylthio-pyrimidines were synthesized and screened for their in vitro antileishmanial activity against Leishmania donovani. Among all, 8 compounds have shown more than 90% inhibition against promastigotes and IC50 in the range of 4.01-57.78 μM against amastigotes. Compound 5, a triazino[5,6-b]indol-3-ylthio-1,3,5-triazine derivative was found to be the most active and least toxic with 20- & 10-fold more selectivity (S.I. = 56.61) as compared to that of standard drugs pentamidine and sodium stibogluconate (SSG), respectively.

1,2,4-TRIAZIN-3-YL-HYDRAZINE OR 5H-1,2,4-TRIAZINO’5,6-B!INDOL-3-YL-HYDRAZINE COMPOUNDS AS INHIBITORS OF BACE USEFUL IN THE TREATMENT OF ALZHEIMER

A compound of formula (I) wherein R1 is aryl and R2 is hydrogen; or R1 and R2 taken together form a group of formula (i) wherein R6 is alkyl or -alkyl-aryl; and R7 is hydrogen, halogen, alk

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