18794-95-1

Upstream product

• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 141-97-9 ethyl acetoacetate 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 77336-02-8 4-[(4-Methoxy-phenyl)-hydrazono]-5-methyl-2-(pyridine-4-carbonyl)-2,4-dihydro-pyrazol-3-one 
• 132577-12-9 4-[(4-Methoxy-phenyl)-hydrazono]-5-methyl-2-phthalazin-1-yl-2,4-dihydro-pyrazol-3-one 
• 123565-82-2 ethyl 5-cyano-1-(4-methoxyphenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate 
• 112517-60-9 2-(3,5-Dinitro-benzoyl)-4-[(4-methoxy-phenyl)-hydrazono]-5-methyl-2,4-dihydro-pyrazol-3-one 
• 84384-61-2 2-[2-(2,4-Dinitro-phenyl)-acetyl]-4-[(4-methoxy-phenyl)-hydrazono]-5-methyl-2,4-dihydro-pyrazol-3-one 
• 131628-04-1 3-{4-[(4-Methoxy-phenyl)-hydrazono]-3-methyl-5-oxo-4,5-dihydro-pyrazol-1-yl}-N-naphthalen-2-yl-3-oxo-propionamide 
• 136920-71-3 8-Methoxy-3-methyl-1-phenyl-1H-pyrazolo[4,3-c]cinnoline 
• 136920-59-7 6-Methoxy-3-(1-{[4-phenyl-3H-thiazol-(2Z)-ylidene]-hydrazono}-ethyl)-cinnolin-4-ol 
• 128639-59-8 4-Cyano-5-methyl-2-(4'-methoxyphenyl)pyridazin-3(2H)-one 
• 128639-57-6 5-cyano-1-(4-methoxy-phenyl)-4-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid 

Relevant academic research and scientific papers

Design, synthesis and anti-tumor evaluation of 1,2,4-triazol-3-one derivatives and pyridazinone derivatives as novel CXCR2 antagonists

Chemokine receptor 2 (CXCR2) is the receptor of glutamic acid–leucine–arginine sequence-contained chemokines CXCs (ELR+ CXCs). In recent years, CXCR2-target treatment strategy has come a long way in cancer therapy. CXCR2 antagonists could block

Design, synthesis and biological evaluation of novel N-[4-(2-fluorophenoxy)pyridin-2-yl]cyclopropanecarboxamide derivatives as potential c-Met kinase inhibitors

Three series of novel 4-phenoxypyridine derivatives containing 4-methyl-6-oxo-1,6-dihydropyridazine- 3-carboxamide, 5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide and 4-methyl-3,5-dioxo-2,3,4,5- tetrahydro-1,2,4-triazine-6-carboxamide moieties were synthesized and evaluated for their in vitro inhibitory activitives against c-Met kinase and cytotoxic activitives against A549, H460, HT-29 cancer cell lines. The results indicated that most of the compounds showed moderate to good antitumor activitives. The most promising compound 26a (with c-Met IC50 value of 0.016 μM) showed remarkable cytotoxicity against A549, H460, and HT-29 cell lines with IC50 values of 1.59 μM, 0.72 μM and 0.56 μM, respectively. Their preliminary structure-activity relationships (SARs) studies indicate that 4-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxamide was more preferred as linker part, and electron-withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activitives. Furthermore, the colony formation, acridine orange/ethidium bromide (AO/EB) staining, apoptosis, and wound-healing assay of 26a were performed on HT-29 and/or A549 cell lines.

Discovery of novel 7-azaindole derivatives bearing dihydropyridazine moiety as c-Met kinase inhibitors

A series of 7-azaindole derivatives bearing the dihydropyridazine scaffold were synthesized and evaluated for their c-Met kinase inhibitory, and antiproliferative activity against 4 cancer cell lines (HT29, A549, H460, U87MG) were evaluated in?vitro. Most compounds showed moderate to excellent potency. Compared to foretinib, the most promising analog 34 (c-Met IC50: 1.06?nM, a multitarget tyrosine kinase inhibitor) showed a 6.4-, 7.8-, and 3.2-fold increase in activity against HT29, A549, and H460?cell lines, respectively. Structure activity relationship studies indicated that mono-EWGs (such as R2?=?F) at 4-position of moiety D was a key factor in improving the antitumor activity.

Discovery of novel pyrrolo-pyridine/pyrimidine derivatives bearing pyridazinone moiety as c-Met kinase inhibitors

In continue to our previous research, eight series of pyrrolo[2,3-b]pyridine and pyrrolo[2,3-d]pyrimidine derivatives bearing pyridazinone moiety were designed, synthesized, and the in vitro antitumor activity was evaluated against four cancer cell lines (A549, HepG2, MCF-7 and PC-3). Some selected compounds (22f, 22g, 26c and 26e) were evaluated for the activity against c-Met kinase, and according to the results of kinase inhibitory activity, the compound 22g was further evaluated for other four tyrosine kinases (Flt-3, VEGFR-2, c-Kit and EGFR) to test the enzyme-based selectivity. The most promising compound 22g showed excellent activity than lead compound Foretinib against A549, HepG2, MCF-7 and PC-3 cell lines, with the IC50 values of 2.19 ± 0.45 μM, 1.32 ± 0.26 μM, 6.27 ± 1.04 μM and 4.63 ± 0.83 μM. The structure–activity relationships (SARs) and docking studies indicated that the pyrrolo[2,3-b]pyridine derivatives bearing 4-oxo-pyridazinone moiety was superior to the pyrrolo[2,3-d]pyrimidine derivatives bearing 6-oxo-pyridazinone moiety. What's more, the target compounds modified with X and Y (X = H, Y = H) were favorable to the activity. And electron drawing groups (EWGs) of 4-Cl-3CF3 on the aryl group show the best activity.

Microwave assisted synthesis and biological activity of 4-(2-(aryl substituted) hydrazono)-1-(2-(p-tolyloxyacetyl)-3-methyl-1H-pyrazol- 5-one

A novel series of 4-(2-(aryl substituted) hydrazono)-1-(2-(p-tolyloxy) acetyl)-3-methyl- 1H-pyrazol-5-ones 3(a-j) was prepared by the reaction of ethyl-2-arylhydrazono -3- oxobutyrate and p-tolyloxyacethydrazide under microwave irradiation. The structures of the synthesized compounds were established by their spectral and analytical data. All the new compounds were screened for their antibacterial and antifungal activity.

Synthesis and antibacterial activity of some novel 4-aryl hydrazono-2,5-disubstituted-2,4-dihydro-3H-pyrazol-3-ones

4-Aryl hydrazono-2,4-dihydro-3H-pyrazol-2,5-disubstituted-3-ones were prepared by the reaction of ethyl-2-arylhydrazono-3-oxybutyrates with substituted hydrazines in the presence of glacial acetic acid at reflux temp. The synthesized compounds have been c

Design, synthesis and structure-activity relationships of novel 4-phenoxyquinoline derivatives containing pyridazinone moiety as potential antitumor agents

A series of novel 4-phenoxyquinoline derivatives containing pyridazinone moiety were synthesized and evaluated for their in vitro cytotoxic activity against five cancer cell lines (HT-29, H460, A549, MKN-45, and U87MG). Most of the compounds exhibited moderate-to-significant cytotoxicity and high selectivity against one or more cell lines. Compounds 15a, 20a, 15b, 15c, 20d, and 16e were further examined for their inhibitory activity against c-Met kinase. The most promising compound 15a (c-Met half-maximal inhibitory concentration [IC50] = 2.15 nM) showed remarkable cytotoxicity against HT-29, H460, and A549 cell lines with IC50 values of 0.10 μM, 0.13 μM, and 0.05 μM, respectively, and thus it was 1.5- to 2.3-fold more potent than foretinib. Their preliminary structure-activity relationships (SARs) studies indicate that electron-withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activity.

Type II diabetes-related enzyme inhibition and molecular modeling study of a novel series of pyrazolone derivatives

Inhibitors of alpha-Amylase are targets for the development of novel drugs for the treatment of diabetes and obesity. Alpha amylase is an enzyme which increases the bio availability of glucose in the blood. Hence, the inhibition effects of alpha amylase of 2-[1-(4-isobutylphenyl)ethyl]-5-methyl-4-[2-(aryl- substituted)hydrazinylidene]-2,4-dihydro-3H-pyrazol-3-one (4a-l) were investigated, among them compounds 4d, 4f, 4a, and 4g have displayed good inhibitory activity. The compounds with significant results were further evaluated for their molecular modeling study using in silico method. The new series of compounds were synthesized by solvent-free microwave irradiation method and were characterized by spectral and analytical data.

HETEROCYCLIC COMPOUNDS AS IMAGING PROBES OF TAU PATHOLOGY

Pyridazinone compounds of Formula I: (I) wherein: R' is alkyl or Ar, optionally substituted with at least one alkyl, halo? gen, hydroxyl, alkoxy, haloalkoxy, acid, ester, amino, nitro, amide, or alkoxyhalo; 2 R is independently alkyi, alkynyl, ester, amino, amide, acid, aryl, heteroaryl, aminoalkyl, -C(=0)alkyl, -C(=0)aryl, -C(=0)heteroaryl, -C(=0)heterocycloalkyl, - C(=0)heterocycloalkylAr, -C(=0)(CH2)nhalo, -C(=0)(CH2)nheterocyclyl, or -SC^Ar, optionally substituted with at least one alkyi, alkylhalo, halogen, nitro, aryl, heteroaryl, or heteroaryl(CH2)nhalo; R 3 and R4 are independently hydrogen, alkyi, alkenyl, alkynyl, aryl, heteroaryl; Ar is an aryl, heteroaryl, cycloalkyl, heterocycloalkyl group; n is an integer from 0-10; or a radiolabeled derivative thereof. The compounds are useful as imaging probes of Tau pathology in Alzheimer's disease are described. Compositions and methods of making such compounds are also described.

Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety

A new class of 4-arylhydrazono-1-benzothiazolyl-3-methylpyrazolin-5-ones (3a-j) and 4-arylazo-1-benzothiazolyl-3,5-dimethylpyrazoles (4a-j) were designed as pharmacophore hybrids between pyrazolinone/pyrazole and benzothiazole moiety. The target molecules were efficiently synthesized by the cyclization of various oxobutyrates/pentane-2,4-dione derivatives with 6-chloro-2- hydrazinobenzothiazole in the presence of glacial acetic acid. The compounds were evaluated for their in vitro antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electron-withdrawing groups in phenyl ring had a promising effect on the antimicrobial activity. Also, correlation study has been used to establish the relationships between the antibacterial activity and physicochemical parameter clogP. Springer Science+Business Media, LLC 2011.