6775-78-6

Usage

Physical State

White to Gray to Brown powder to crystal

Uses

6-chloroimidazo[1,2-b]pyridazine (cas# 6775-78-6) is a useful research chemical.

Safe handling

Handling is performed in a well ventilated place.Wear suitable protective equipment.Prevent dispersion of dust.Wash hands and face thoroughly after handling. Use a local exhaust if dust or aerosol will be generated. Avoid contact with skin,eyes and clothing.

InChI:InChI=1/C6H4ClN3/c7-5-1-2-6-8-3-4-10(6)9-5/h1-4H

Upstream product

• 5469-69-2 6-chloro-pyridazin-3-ylamine 
• 17157-48-1 bromoacetaldehyde 
• 97-97-2 chloroacetaldehyde dimethyl acetal 
• 1453176-84-5 6-chloro-1,2-diazinan-3-amine 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 107-20-0 2-chloroethanal 
• 51947-89-8 3-(2-Hydroxy-ethylamino)-6-chlor-pyridazin 

Downstream Products

• 132846-42-5 6-Chloro-9-methyl-9-phenyl-9H-imidazo<1,2-b>pyrazolo<4,3-d>pyridazine 
• 132846-41-4 6-Chloro-9-methyl-9-phenyl-7,8-dihydro-9H-imidazo<1,2-b>pyrazolo<4,3-d>pyridazine 
• 13526-66-4 3-bromo-6-chloro-imidazo[1,2-b]pyridazine 
• 18087-76-8 6-chloro-3-nitroimidazo<1,2-b>pyridazine 
• 17240-33-4 6-methoxyimidazo<1,2-b>pyridazine 
• 6653-96-9 6-aminoimidazo[1,2-b]pyridazine 
• 40972-42-7 3,6-dichloroimidazo<1,2-b>pyridazine 
• 137384-34-0 6-[(4-sulfamoylmethylcyclohexane-1-yl) methyloxy]imidazo[1,2-b]pyridazine hydrochloric acid salt 
• 57470-53-8 6-Ethoxyimidazo[1,2-b]pyridazine 
• 1084953-09-2 4-(imidazo[1,2-b]pyridazin-6-yl)benzoic acid 
• 1005781-45-2 3-(imidazo[1,2-b]pyridazin-6-yloxy)aniline 
• 1005781-42-9 4-(imidazo[1,2-b]pyridazin-6-yloxy)aniline 
• 1005787-67-6 methyl 3-(imidazo[1,2-b]pyridazin-6-yloxy)benzoate 
• 1005787-61-0 2-(imidazo[1,2-b]pyridazin-6-yloxy)aniline 

Relevant academic research and scientific papers

Synthesis and in vitro evaluations of 6-(hetero)-aryl-imidazo[1,2-b]pyridazine-3-sulfonamide's as an inhibitor of TNF-α production

Tumor necrosis factor-α is an important pro-inflammatory cytokine having a key role in hosts defensive process of immune systems and its over expression led to a diverse range of inflammatory diseases such as Rheumatoid arthritis, Cronh's disease, psoriasis, etc. This paper describes our medicinal chemistry efforts on imidazo[1,2-b]pyridazine scaffold: design, synthesis and biological evaluation. By the introducing sulfonamide functionality at 3 positions and substituting 6 positions with (hetero)-aryl groups’, a small library of compounds was prepared. All synthesized compounds were screened for lipopolysaccharide (LPS) mediated TNF-α production inhibitory activity. Biological data revealed that the majority of the compounds of this series showed moderate to potent TNF-α production inhibitory activity. Compound 5u and 5v are the most potent compounds from the series with activity of IC50 = 0.5 μM and 0.3 μM respectively. A short SAR demonstrates that 3-sulfonyl-4-arylpiperidine-4-carbonitrile moiety on imidazo[1,2-b]pyridazine showed better activity compared to the 3-(4-aryllpiperazin-1-yl) sulfonyl) in hPBMC assay. The molecular modeling studies revealed that the potent TNF-α production inhibitory activity 5v due to the extra stability of complex because of an extra pi-pi (π-π) stacking, hydrogen-bonding interactions.

Design, synthesis and biological evaluation of imidazopyridazine derivatives containing isoquinoline group as potent MNK1/2 inhibitors

Mitogen-activated protein kinase (MAPK)-interacting kinases (MNKs) are located at the meeting-point of ERK and p38 MAPK signaling pathways, which can phosphorylate eukaryotic translation initiation factor 4E (eIF4E) at the conserved serine 209 exclusively. MNKs modulate the translation of mRNA involved in tumor-associated signaling pathways. Consequently, selective inhibitors of MNK1/2 could reduce the level of phosphorylated eIF4E. Series of imidazopyrazines, imidazopyridazines and imidazopyridines derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against diffuse large B-cell lymphoma (DLBCL) cell lines. In particular, compound II-5 (MNK1 IC50 = 2.3 nM; MNK2 IC50 = 3.4 nM) exhibited excellent enzymatic inhibitory potency and proved to be the most potent compound against TMD-8 and DOHH-2 cell lines with IC50 value of 0.3896 μM and 0.4092 μM respectively. These results demonstrated that compound II-5 could be considered as a potential MNK1/2 inhibitor for further investigation.

INHIBITORS OF LIN28 AND METHODS OF USE THEREOF

The present disclosure relates to compounds of formula (I) and compositions comprising the same. The disclosure further relates to methods of treating cancers.

Synthesis and antifungal activity of imidazo[1,2-b]pyridazine derivatives against phytopathogenic fungi

A series of 3,6-disubstituted imidazo[1,2-b]pyridazine derivatives have been synthesized and characterized with spectroscopic analyses. The antifungal activities of these compounds against nine phytopathogenic fungi were evaluated by the mycelium growth rate method. The in vitro antifungal bioassays indicated that most of compounds displayed excellent and broad-spectrum antifungal activities. Especially, compounds 4a, 4c, 4d, 4l and 4r exhibited 1.9–25.5 fold more potent than the commercially available fungicide hymexazol against Corn Curvalaria Leaf Spot (CL), Alternaria alternate (AA), Pyricularia oryzae (PO) and Alternaria brassicae (AB) strains. Structure-activity relationship analysis showed that the enhanced antifungal activity is significantly affected by the substituents on the benzene ring and pyridazine ring.

Application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides

The invention belongs to the technical field of farm chemicals, and specifically relates to application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides. The 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives are prepared and applied in farm chemical preparation. The inhibition activity of the derivatives on nine common plant pathogenic fungi is testedby adopting a hypha growth rate inhibition method; some of the derivatives show excellent fungistat activity, and are expected to be used for preventing and treating plant diseases caused by pathogenic fungi such as wheat scab, rice blast, cotton blight, tobacco brown spot, cabbage black spot, pumpkin blight, apple ring spot, Curvularia lunata(Walk) Boed and potato dry rot.

Synthesis, characterization, and antidiabetic activity of 6-methoxyimidazo[1,2-b]pyridazine derivatives

The present article describes the synthesis, characterization, and antidiabetic activity of 6-methoxyimidazo[1,2-b]pyridazine derivatives 7a-l. The synthetic sequence for the preparation of these derivatives involves the following prominent reactions: (a) Step 1: involves the high-pressure amination reaction; (b) Step 2: involves the Zinc oxide nanoparticle-catalyzed cyclization reaction; (c) Step 3: involves the methoxylation; (d) Step 4: involves the bromination reaction; (e) Step 5: involves the Suzuki coupling reaction; (f) Step 6: involves the reduction of the –NO2 group; (g) Step 7: involves Boc protection of the 1o amino group (h) Step 8: involves diazotization of the amine group and finally the last of the synthesis (i) Step 9: involves the saponification of the ethyl ester group. Furthermore, the structures of the newly synthesized 6-methoxyimidazo[1,2-b]pyridazine derivatives 7a–l were determined using 1H NMR, 13C NMR, and Mass and IR spectroscopic analyses. These derivatives were evaluated for their antidiabetic property and the results revealed that most of the compounds exhibited significant potency. It is worth mentioning that compounds 7b (69.87%), 7f (69.0%), 7h (68.79%), and 7l (68.61%) with substitution R = para-NH2, para-COOH, meta-NH2, and meta-COOH, respectively, showed significant (good) hypoglycemic activity when compared to the standard drug insulin (50 mg/kg b.w) in reducing the blood glucose level.

Aromatic heterocyclic compound serving as PI3K/mTOR kinase regulator and preparation method and application of aromatic heterocyclic compound

The invention discloses 6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-a]pyridines shown as a formula (I) or 6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-b]pyridazine derivatives or pharmaceutically acceptable salts thereof and a preparation method. The invention also discloses application of 6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-a]pyridines or6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-b]pyridazine derivatives or pharmaceutically acceptable salts thereof to preparation of medicines for resisting tumors, treating cerebral ischemia and treating diabetes mellitus as a PI3K/mTOR inhibitor.

Antiplasmodial imidazopyridazines: structure-activity relationship studies lead to the identification of analogues with improved solubility and hERG profiles

3,6-Diarylated imidazopyridazines have recently been shown to possess good in vitro antiplasmodial and in vivo antimalarial activity. However, frontrunner compounds have been associated with poor solubility and a hERG (human ether-a-go-go-related gene) inhibition liability raising concerns for potential cardiotoxicity risks. Herein, we report the synthesis and structure-activity relationship studies of new imidazopyridazines aimed at improving aqueous solubility and countering hERG inhibition while maintaining antiplasmodial potency. While we identified new analogues with potent antiplasmodial activity (IC50 = 0.031 μM against the NF54 drug-sensitive strain, and IC50 = 0.0246 μM against the K1 multidrug resistant strain), hERG inhibition remained an issue. Excitingly, on the other hand, new analogues with a substantially improved hERG inhibition profile (IC50 = 7.83-32.3 μM) with sub-micromolar antiplasmodial activity (NF54, IC50 = 0.151-0.922 μM) were identified. Similarly, the introduced molecular features also resulted in analogues with moderate to high solubility (60-200 μM) while also displaying sub-micromolar antiplasmodial potency (NF54, IC50 = 0.136-0.99 μM).

COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.

Exploration of the imidazo[1,2-b]pyridazine scaffold as a protein kinase inhibitor

3,6-Disubstituted imidazo[1,2-b]pyridazine derivatives were synthesized to identify new inhibitors of various eukaryotic kinases, including mammalian and protozoan kinases. Among the imidazo[1,2-b]pyridazines tested as kinase inhibitors, several derivatives were selective for DYRKs and CLKs, with IC50?50?=?82?nM), CLK4 (IC50?=?44?nM), DYRK1A (IC50?=?50?nM), and PfCLK1 (IC50?=?32?nM). The compounds were also tested against Leishmania amazonensis. Several compounds showed anti-leishmanial activity at rather high (10?μM) concentration, but were not toxic at 1?μM or 10?μM, as judged by viability assays carried out using a neuroblastoma cell line.