2-Substituted-8-methyl-3,6-dihydroimidazo[4,5-c]pyrazolo[3,4-e]pyridazine as an anti-inflammatory agent

Tewari, Ashish Kumar; Dubey, Rajeev K.; Mishra, Anil K.

doi:10.1007/s00044-009-9290-9

Cited by 13 publications

(4 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pyridazine-based frameworks are widely distributed in biologically active products with anti-viral [ 15 , 16 , 17 , 18 , 19 , 20 ], anti-inflammatory [ 21 , 22 , 23 , 24 , 25 ], anti-microbial [ 26 , 27 , 28 ], anti-cancer [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ], anti-convulsant [ 37 , 38 , 39 , 40 ], anti-analgesic [ 41 , 42 ], anti-tubercular [ 43 , 44 , 45 ], anti-hypertensive [ 3 , 46 ], anti-diabetic [ 47 ], anti-depressant [ 48 , 49 ], anti-Alzheimer’s [ 50 , 51 ], phosphodiesterase [ 52 , 53 ], platelet aggregation [ 54 , 55 , 56 , 57 ], and cholesterol acyl transferase inhibitor properties [ 58 ]. Peptide nucleic acids (PNAs) with new pyridazine-type nucleobases were reported as replacements for the DNA duplex bases instead of thymine, adenine, guanine and cytosine to form novel DNA or RNA duplexes [ 59 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation

et al. 2017

View full text Add to dashboard Cite

4-(2-(4-Halophenyl)hydrazinyl)-6-phenylpyridazin-3(2H)-ones 1a,b were prepared and treated with phosphorus oxychloride, phosphorus pentasulphide and ethyl chloroformate to give the corresponding chloropyridazine, pyridazinethione, oxazolopyridazine derivatives 2–4, respectively. Compound 2 reacted with hydrazine hydrate to afford hydrazinylpyridazine 7. The reaction of 4-(2-(4-chlorophenyl)hydrazinyl)-3-hydrazinyl-6-phenylpyridazine (7) with acetic anhydride, p-chlorobenzaldehyde and carbon disulphide gave the corresponding pyridazinotriazine derivatives 8–10. On the other hand, 5-(4-chlorophenylamino)-7-(3,5-dimethoxybenzylidene)-3-phenyl-5H-pyridazino[3,4-b][1,4]thiazin-6(7H)-one (11) was prepared directly from the reaction of compound 3 with chloroacetic acid in presence of p-chlorobenzaldehyde. Compound 11 reacted with nitrogen nucleophiles (hydroxylamine hydrochloride, hydrazine hydrate) and active methylene group-containing reagents (malononitrile, ethyl cyanoacetate) to afford the corresponding fused compounds 12–15, respectively. Pharmacological screening for antiviral activity against hepatitis A virus (HAV) was performed for the new compounds. 4-(4-Chlorophenylamino)-6-phenyl-1,2-dihydropyridazino[4,3-e][1,2,4]triazine-3(4H)-thione (10) showed the highest effect against HAV.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Pyridazines are of great organic , and inorganic − interests as well as an important intermediate in the synthesis of pharmaceuticals. − 4-Amino-3,6-dichloropyridazine (C 4 H 3 N 3 Cl 2 , CAS registry no. 823-58-5, molecular weight 164.0), with its chemical structure shown in Figure , is synthesized from the amination of 3,4,6-trichloropyridazine in ethanol solution saturated with NH 3 .…”

Section: Introductionmentioning

confidence: 99%

Measurement and Correlation of Solubilities of 4-Amino-3,6-dichloropyridazine in Ethanol + Water Mixtures from (303.15 to 323.15) K

et al. 2014

View full text Add to dashboard Cite

The solubilities of 4-amino-3,6-dichloropyridazine (ADCP) in an ethanol + water mixture were determined from (303.15 to 323.15) K with an interval of 2.5 K at atmospheric pressure using the synthetic method with a laser monitoring observation technique. The solubility of ADCP was found to increase with the rise of temperature and the mole fraction of ethanol. The experimental solubilities were regressed with different models including the modified Apelblat equation, combined nearly ideal binary solvent/Redlich−Kister (CNIBS/R-K) model, and the hybrid model. For the six mixture solvents studied, all of the mean percentage deviations with Apelblat equation are less than 1.7 %.

show abstract

“…The synthetic strategies used to obtain the target compounds are represented in Schemes . The starting compound, 5‐hydrazineyl‐3‐methyl‐1 H ‐pyrazole ( 1 ) was synthesized according to the previously reported method . Thus, treatment of 1 with acetylacetone in absolute ethanol catalyzed by TEA under reflux gave 3,4,6‐trimethyl‐1,8‐dihydropyrazolo[3,4‐ c ][1,2]diazepine ( 3 ) rather than the expected product 3,5,5′‐trimethyl‐2′ H ‐1,3′‐bipyrazole ( 2 ) (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Antioxidant Evaluation of Some Novel Pyrazolo[3,4‐c][1,2]diazepine and Pyrazolo[3,4‐c]pyrazole Derivatives

Mohammed

Elbeily

El‐Taweel

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

5‐Hydrazineyl‐3‐methyl‐1H‐pyrazole (1) was used as a starting material for the synthesis of novel pyrazolo[3,4‐c][1,2]diazepine derivatives 3, 4, and 6a,b by its reaction with acetylacetone, ethyl acetoacetate, and isatylidene derivatives 5a,b, respectively. Also, pyrazolo[3,4‐c][1,2]diazepine derivative 11 was synthesized via multicomponent reaction of 1, benzaldehyde, and malononitrile. Moreover, compound 1 was used for synthesis novel pyrazolo[3,4‐c]pyrazole derivative 7 by its reaction with isatin. In addition, pyrazolo[3,4‐c]pyrazole derivatives 18a–c were synthesized by treatment of 2‐cyano‐N′‐(3‐methyl‐1H‐pyrazol‐5‐yl)acetohydrazide (13) with aromatic aldehydes 16a–c. The newly synthesized compounds were valeted by means of analytical and spectral data. All newly synthesized compounds were screened for their antioxidant activities. Compounds 3, 13, 18b, and 18c showed higher radical‐scavenging activities.

show abstract

2-Substituted-8-methyl-3,6-dihydroimidazo[4,5-c]pyrazolo[3,4-e]pyridazine as an anti-inflammatory agent

Cited by 13 publications

References 19 publications

Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation

Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation

Measurement and Correlation of Solubilities of 4-Amino-3,6-dichloropyridazine in Ethanol + Water Mixtures from (303.15 to 323.15) K

Synthesis, Characterization, and Antioxidant Evaluation of Some Novel Pyrazolo[3,4‐c][1,2]diazepine and Pyrazolo[3,4‐c]pyrazole Derivatives

Contact Info

Product

Resources

About