2-Phenylimidazo[1,2-b]pyridazine derivatives highly active against Haemonchus contortus

Ali, Abdelselam; Cablewski, Teresa; Francis, Craig L.; Ganguly, Ashit K.; Sargent, Roger M.; Sawutz, David G.; Winzenberg, Kevin N.

doi:10.1016/j.bmcl.2011.05.096

Cited by 15 publications

(7 citation statements)

References 25 publications

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“…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

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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 %.

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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

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“…Tabuchi and co-workers [105,106] In 2011, Ali and co-workers synthesized a series of 2phenylimidazo[1,2-b]pyridazine derivatives and evaluated their in vitro anthelmintic activity against Haemonchus contortus. [107] Thus, Ni-…”

Section: Kumada Cross-couplingmentioning

confidence: 95%

Synthesis and Functionalization of Imidazo[1,2‐b]Pyridazine by Means of Metal‐Catalyzed Cross‐Coupling Reactions

et al. 2021

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This review surveys the recent developments in organometallic-chemistry-based methods for the preparation of imidazo [1,2-b]pyridazines by cyclization as well as their functionalization by means of cross-coupling reactions such as Sonogashira, Heck, Negishi, Suzuki-Miyaura, Kumada and Stille. In addition, the advances made on the CÀ H activation of imidazo[1,2-b] pyridazines using C-arylation, C-benzylation and C-alkylation are also reviewed. Furthermore, the recent reports on the Narylation of this heterocyclic system are discussed and highlighted. The sequential couplings as well as the one-pot functionalization of two different positions on the imidazo[1,2b]pyridazine systems are also reviewed. Procedures in which metal-based catalysis is not involved in the functionalization of imidazo [1,2-b]pyridazines are not included in this review.(MTCC 3382), Staphylococcus aureus (MTCC 3160), Bacillus subtilis (MTCC 297), and Gram-negative bacteria: Pseudomonas aeruginosa (MTCC 1034), Klebsiella pneumoniae (MTCC).

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“…The excessive and uncontrolled use of these anthelmintics has provoked the development of drug resistant worms. , The two newer groups of anthelmintics, namely amino-acetonitrile derivatives (e.g., monepantel) and derquantel (Figure ), have been effective at combating multiresistant nematodes, but emerging resistance is proving problematic. − Recent reports disclose selenophene and thiophene derivatives, acrylonitrile-based compounds, and 2-phenylimidazo[1,2- b ]pyridazine derivatives, each with potent in vitro activity against H. contortus, but drug development has yet to be undertaken. − Thus, given the expansion of resistance to existing anthelmintics, the search for new chemical entities with nematocidal or nematostatic activity remains crucial.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Novel 1-Methyl-1H-Pyrazole-5-carboxamides Leads to High Potency Larval Development Inhibitors of the Barber’s Pole Worm

Kundu

Ghoshal

et al. 2018

J. Med. Chem.

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A phenotypic screen of a diverse library of small molecules for inhibition of the development of larvae of the parasitic nematode Haemonchus contortus led to the identification of a 1-methyl-1H-pyrazole-5-carboxamide derivative with an IC 50 of 0.29 μM. Medicinal chemistry optimization targeted modifications on the left-hand side (LHS), middle section, and right-hand side (RHS) of the scaffold in order to elucidate the structure−activity relationship (SAR). Strong SAR allowed for the iterative and directed assembly of a focus set of 64 analogues, from which compound 60 was identified as the most potent compound, inhibiting the development of the fourth larval (L4) stage with an IC 50 of 0.01 μM. In contrast, only 18% inhibition of the mammary epithelial cell line MCF10A viability was observed, even at concentrations as high as 50 μM.

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2-Phenylimidazo[1,2-b]pyridazine derivatives highly active against Haemonchus contortus

Cited by 15 publications

References 25 publications

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

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

Synthesis and Functionalization of Imidazo[1,2‐b]Pyridazine by Means of Metal‐Catalyzed Cross‐Coupling Reactions

Optimization of Novel 1-Methyl-1H-Pyrazole-5-carboxamides Leads to High Potency Larval Development Inhibitors of the Barber’s Pole Worm

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