67458-38-2

Basic information

• Product Name: 6-CHLORO-3-METHYL-[1,2,4]TRIAZOLO[3,4-A]-PHTHALAZINE
• Synonyms: 6-CHLORO-3-METHYL-[1,2,4]TRIAZOLO[3,4-A]-PHTHALAZINE;AKOS BBS-00002556;TIMTEC-BB SBB011399
• CAS NO: 67458-38-2
• Molecular Formula: C₁₀H₇ClN₄
• Molecular Weight: 218.64
• Mol File: 67458-38-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-CHLORO-3-METHYL-[1,2,4]TRIAZOLO[3,4-A]-PHTHALAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-3-METHYL-[1,2,4]TRIAZOLO[3,4-A]-PHTHALAZINE(67458-38-2)
• EPA Substance Registry System: 6-CHLORO-3-METHYL-[1,2,4]TRIAZOLO[3,4-A]-PHTHALAZINE(67458-38-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 67458-38-2(Hazardous Substances Data)

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 this compound.

Upstream product

• 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 
• 75-36-5 acetyl chloride 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 1068-57-1 acetic acid hydrazide 
• 6145-55-7 4-hydrazino-1-chlorophthalazine hydrochloride 

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 
• 1621388-48-4 N-(2-fluorophenyl)-2-(4-(3-methyl-1,2,4-triazolo[3,4-a]phthalazin-6-yl) piperazin-1-yl) acetamide 

Relevant articles and documents

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.

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 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.