(6-OXO-1,6-DIHYDRO-PYRIDAZIN-3-YLOXY)-ACETIC ACID - CAS 34173-61-0
Catalog number: 34173-61-0
Category: Main Product
Molecular Formula:
C6H6N2O4
Molecular Weight:
170.12284;g/mol
COA:
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Purity:
95%
Synonyms:
2-[(6-oxo-1H-pyridazin-3-yl)oxy]aceticacid;34173-61-0;2-((6-Oxo-1,6-dihydropyridazin-3-yl)oxy)aceticacid;(6-Oxo-1,6-dihydro-pyridazin-3-yloxy)-aceticacid;ST50984604;Aceticacid,2-[(1,6-dihydro-6-oxo-3-pyridazinyl)oxy]-
MSDS:
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InChIKey:
FEDJGPQLLNQAIY-UHFFFAOYSA-N
InChI:
InChI=1S/C6H6N2O4/c9-4-1-2-5(8-7-4)12-3-6(10)11/h1-2H,3H2,(H,7,9)(H,10,11)
Canonical SMILES:
C1=CC(=NNC1=O)OCC(=O)O
1.Synthesis, anticonvulsant and neurotoxicity evaluation of some new pyrimidine-5-carbonitrile derivatives.
Shaquiquzzaman M1, Khan SA, Amir M, Alam MM. Saudi Pharm J. 2012 Apr;20(2):149-54. doi: 10.1016/j.jsps.2011.09.007. Epub 2011 Sep 24.
A series of 2-[2-(substituted benzylidene) hydrazinyl]-4-(4-methoxyphenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile (3-16) were synthesized by refluxing 2-hydrazino-4-(4-methoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile (2) with different substituted aromatic aldehydes in glacial acetic acid and absolute alcohol mixture (8:2). The compounds were evaluated for their anticonvulsant and neurotoxicity effect. In MES test compounds 2-[2-(4-bromo-benzylidene)-hydrazinyl]-4-(4-methoxyphenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile (5), 2-[2-(4-hydroxy-benzylidene)-hydrazinyl]-4-(4-methoxyphenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile (9), and 2-[2-(3-fluoro-benzylidene)-hydrazinyl]-4-(4-methoxyphenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile (16) were found to be highly active at a dose level of 30 mgkg(-1) at 0.5 h time interval, indicating their ability to prevent seizure spread at a relatively low dose.
2.Synthesis and oral hypoglycemic properties of two 4-oxo-4,5,6,7-tetrahydroindole-3-acetic acids.
Nagarajan K1, Talwalker PK, Goud AN, Shah RK, Shenoy SJ. Arzneimittelforschung. 1989 May;39(5):548-50.
Condensation of beta-acetyl-2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexene-1-propionic acid (3) with n-butyl and isobutylamines affords the title acids 4 and 5, respectively, which show good oral hypoglycemic activity in normal rats. Acids 4 and 5, are also active in streptozocin-induced diabetic rats. Results of extensive pharmacological and acute toxicity tests are reported.
3.Inotropic effects of OR-1896, an active metabolite of levosimendan, on canine ventricular myocardium.
Takahashi R1, Talukder MA, Endoh M. Eur J Pharmacol. 2000 Jul 14;400(1):103-12.
We performed experiments in dog ventricular trabeculae loaded with aequorin to elucidate the mechanism of positive inotropic effect of (R)-N-[4-(4-methyl-6-oxo-1,4,5, 6-tetrahydro-pyridazin-3-yl)-phenyl]-acetamide (OR-1896), an active metabolite of (R)-([4-(1,4,5, 6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]-hydrazono)-pr opaned initrile (levosimendan). Concentration-response curve for OR-1896 was biphasic: positive inotropic effect of OR-1896 reached a plateau at 10(-5) M (1st phase) and the concentration-response curve became steeper at 10(-3) M and higher (2nd phase). Maximum response of the 1st phase was 29% of maximal response to isoproterenol and associated with an increase in Ca(2+) transients of 13% of the maximal response to isoproterenol. For a given increase in force, the increase in Ca(2+) transients by OR-1896 was lower than that induced by elevation of [Ca(2+)](o). The positive inotropic effect of OR-1896 was not associated with impairment of relaxation and it was abolished by carbachol.
4.Anti-inflammatory and antimicrobial activity of 4,5-dihydropyrimidine-5-carbonitrile derivatives: their synthesis and spectral elucidation.
Alam MM1, Akhter M, Husain A, Marella A, Tanwar OP, Ali R, Hasan SM, Kumar H, Haider R, Shaquiquzzaman M. Acta Pol Pharm. 2012 Nov-Dec;69(6):1077-85.
Thirteen new 6-(1-H-indole-2-yl)-4-oxo-2-[2-(substituted-benzylidene)-hydrazinyl]-4,5-dihydropy-rimidine-5-carbonitrile derivatives were synthesized. The title compounds, hydrazones, were synthesized by reaction of hydrazine group of 2-hydrazinyl-4-(1-H-indole-2-yl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile (2) with different substituted aromatic aldehydes using a mixture (2:8, v/v) of glacial acetic acid and alcohol. The required intermediate compound 2 was synthesized from 2-mercapto-4-(1-H-indole-2-yl)-6-oxo-1,6-dihy-dropyrimidine-5-carbonitrile 1 upon nucleophilic attack by the hydrazine hydrate. Compound 1 was synthesized by modified Biginelli condensation method using indole-3-carbaldehyde, ethyl cyanoacetate and thiourea. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and antimicrobial actions. Among the newer derivatives, one compound i.e., 6-(1-H-indole-2-yl)-4-oxo-2-[2-(2,6-dichlorobenzylidene)-hydrazinyl]-4,5-dihydropyrimidine-5-carbonitrile (7) emerged as lead compound having 71.
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CAS 34173-61-0 (6-OXO-1,6-DIHYDRO-PYRIDAZIN-3-YLOXY)-ACETIC ACID

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