67458-38-2

Usage

General Description

6-CHLORO-3-METHYL-[1,2,4]TRIAZOLO[3,4-A]-PHTHALAZINE is a chemical compound that belongs to the phthalazine family, which consists of a six-membered ring system containing two nitrogen atoms and two carbon atoms. The compound has a chlorine atom and a methyl group attached to the triazolo ring, giving it a chloro and methyl substitution. This chemical may have various applications in the fields of pharmaceuticals, agrochemicals, or materials science due to its unique structure and potential pharmacological or biological activities. Further research and studies are needed to fully understand the properties and uses of 6-CHLORO-3-METHYL-[1,2,4]TRIAZOLO[3,4-A]-PHTHALAZINE.

Upstream product

• 6145-55-7 4-hydrazino-1-chlorophthalazine hydrochloride 
• 75-36-5 acetyl chloride 
• 51935-42-3 1-chloro-4-hydrazinophthalazine 
• 108-24-7 acetic anhydride 
• 4752-10-7 1,4-dichlorophthalazine 
• 64-17-5 ethanol 
• 85-44-9 phthalic anhydride 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 1068-57-1 acetic acid hydrazide 

Downstream Products

• 1527471-40-4 6-(2-chloro-5-nitrophenyl)-3-methyl-[1,2,4]triazolo[3,4-a]phthalazine 
• 1567843-83-7 N-(4-methoxyphenyl)-3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-amine 
• 1567843-84-8 3-methyl-N-(p-tolyl)-1,2,4-triazolo[3,4-a]phthalazin-6-amine 
• 1567843-85-9 N-(2-chlorophenyl)-3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-amine 
• 1621388-44-0 N-(4-fluorophenyl)-2-(4-(3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-yl) piperazin-1-yl) acetamide 
• 1621388-45-1 N-(4-chlorophenyl)-2-(4-(3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-yl) piperazin-1-yl) acetamide 
• 1621388-46-2 N-(4-methoxyphenyl)-2-(4-(3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-yl) piperazin-1-yl) acetamide 
• 1621388-47-3 2-(4-(3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-yl)piperazin-1-yl)-N-(3-(trifluoromethyl) phenyl) acetamide 
• 1621388-48-4 N-(2-fluorophenyl)-2-(4-(3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-yl) piperazin-1-yl) acetamide 

Relevant academic research and scientific papers

Discovery of novel triazolophthalazine derivatives as DNA intercalators and topoisomerase II inhibitors

A new series of triazolophthalazine derivatives was designed and synthesized as topoisomerase II (Topo II) inhibitors and DNA intercalators. The synthesized derivatives were evaluated in vitro for their cytotoxic activities against three human cancer cell lines: HepG2, MCF-7, and HCT-116 cells. Compound IXb was the most potent counterpart with IC50 values of 5.39 ± 0.4, 3.81 ± 0.2, and 4.38 ± 0.3 μM, as it was about 1.47, 1.77, and 1.19 times more active than doxorubicin (IC50 = 7.94 ± 0.6, 6.75 ± 0.4, and 5.23 ± 0.3 μM) against HepG2, MCF-7, and HCT-116 cells, respectively. Additionally, the binding affinity of the synthesized compounds toward the DNA molecule was assessed using the DNA/methyl green assay. Compound?IXb showed an excellent DNA binding affinity with an IC50 value of 27.16 ± 1.2 μM, which was better than that of the reference drug doxorubicin (IC50 = 31.02 ± 1.80 μM). Moreover, compound IXb was the most potent member among the tested compounds when investigated for their Topo II inhibitory activity. Furthermore, compound IXb induced apoptosis in HepG2 cells and arrested the cell cycle at the G2/M phase. Additionally, compound IXb showed Topo II poisoning effects at 2.5 μM and Topo II catalytic inhibitory effects at 5 and 10 μM. Finally, molecular docking studies were carried out against the DNA–Topo II complex and DNA, to investigate the binding patterns of the designed compounds.

TRIAZOLOPHTHALAZINE COMPOUNDS, USE AS ANTI-HUMAN IMMUNODEFICIENCY VIRUS INHIBITORS OF HIV VIF-DEPENDENT DEGRADATION OF APOBEC3

The present disclosure is concerned with triazolophthalazine compounds that are capable of inhibiting infection by the Human Immunodeficiency Virus (HIV) by inhibiting HIV Vif-dependent degradation of the APOBEC3 innate immune system. The present disclosu

Discovery of a PCAF Bromodomain Chemical Probe

The p300/CBP-associated factor (PCAF) and related GCN5 bromodomain-containing lysine acetyl transferases are members of subfamily I of the bromodomain phylogenetic tree. Iterative cycles of rational inhibitor design and biophysical characterization led to the discovery of the triazolopthalazine-based L-45 (dubbed L-Moses) as the first potent, selective, and cell-active PCAF bromodomain (Brd) inhibitor. Synthesis from readily available (1R,2S)-(?)-norephedrine furnished L-45 in enantiopure form. L-45 was shown to disrupt PCAF-Brd histone H3.3 interaction in cells using a nanoBRET assay, and a co-crystal structure of L-45 with the homologous Brd PfGCN5 from Plasmodium falciparum rationalizes the high selectivity for PCAF and GCN5 bromodomains. Compound L-45 shows no observable cytotoxicity in peripheral blood mononuclear cells (PBMC), good cell-permeability, and metabolic stability in human and mouse liver microsomes, supporting its potential for in vivo use.

Synthesis and antimicrobial activities of novel 1,2,4-triazolo [3,4-a] phthalazine derivatives

A series of novel 1,2,4-triazolo [3,4-a] phthalazine derivatives were synthesized in five steps from a common precursor, phthalic anhydride. Most of synthesized phthalazine derivatives showed inhibitory activity against Staphylococcus aureus. One of phthalazine derivatives 5l showed inhibitory activity against all tested bacterial and fungal strains.

Synthesis and anticancer activities of novel 1,2,4-triazolo[3,4-a] phthalazine derivatives

Trying to develop potent and selective anticancer agents, two series of novel 1,2,4-triazolo[3,4-a]phthalazine derivatives were designed and synthesized. Their antitumor activities were evaluated by MTT method against four selected human cancer cell lines (MGC-803, EC-9706, HeLa and MCF-7). Our results showed that compound 11h exhibited good anticancer activities compared to 5-fluorouracil against the four tested cell lines, with IC50 values ranging from 2.0 to 4.5 μM. Flow cytometry analysis indicated that compound 11h induced the cellular early apoptosis and cell cycle arrest at G2/M phase in EC-9706.

[1,2,4]Triazolo[4,3-a]phthalazines: Inhibitors of diverse bromodomains

Bromodomains are gaining increasing interest as drug targets. Commercially sourced and de novo synthesized substituted [1,2,4]triazolo[4,3-a]phthalazines are potent inhibitors of both the BET bromodomains such as BRD4 as well as bromodomains outside the BET family such as BRD9, CECR2, and CREBBP. This new series of compounds is the first example of submicromolar inhibitors of bromodomains outside the BET subfamily. Representative compounds are active in cells exhibiting potent cellular inhibition activity in a FRAP model of CREBBP and chromatin association. The compounds described are valuable starting points for discovery of selective bromodomain inhibitors and inhibitors with mixed bromodomain pharmacology.

TRIAZOLO-PYRIDAZINE COMPOUNDS AND DERIVATIVES THEREOF USEFUL IN THE TREATMENT OF NEUROPATHIC PAIN

The present invention is directed to a method of use of triazolo-pyridazine compounds in the treatment of neuropathic pain. The present invention is also directed to the use of triazolo-pyridazine compounds in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorders, and panic, as well as in the treatment of pain, Parkinson’s disease, cognitive dysfunction, epilepsy, circadian rhythm and sleep disorders - such as shift-work induced sleep disorder and jet-lag, drug addiction, drug abuse, drug withdrawal and other diseases. The present invention is also directed to novel triazolo-pyridazine compounds that selectively bind to α2δ-1 subunit of Ca channels.

Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ -1 subunit of voltage gated calcium channel

We have identified and synthesized a series of [1,2,4]triazolo[3,4-a] phthalazine derivatives as high-affinity ligands to α2δ-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50=15nM) and (S)-22 (IC50=30nM). A potent and selective radioligand, [3H]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin.