Late-stage diversification of biologically active pyridazinones via a direct C–H functionalization strategy

Li, Wei; Fan, Zhoulong; Geng, Kaijun; Xu, Youjun; Zhang, Ao

doi:10.1039/c4ob02061h

Cited by 6 publications

(3 citation statements)

References 62 publications

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“…Presently we have investigated the high-pressure effects on a high- Z ′ structure of 3-hydroxy-4,5-dimethyl-1-phenylpyridazin-6-one, i.e., 4,5-dimethyl-1-phenylmaleic hydrazide, C 12 H 12 N 2 O 2 , denoted 1 (Figure ). It is a derivative of maleic hydrazide, known in three polymorphic forms, an analogue of nucleic bases, applied as the growth inhibitor in agriculture; derivatives of 1 are used as antiviral drugs. − …”

Section: Introductionmentioning

confidence: 99%

High-Pressure Preference for the Low Z′ Polymorph of a Molecular Crystal

Roszak

Katrusiak

2016

Crystal Growth & Design

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High pressure destabilizes the high Z′ polymorph of 3-hydroxy-4,5-dimethyl-1-phenylpyridazin-6-one (1α); however, recrystallization is needed for obtaining a low Z′, more dense polymorph. Three polymorphs α, β, and γ can be monotonically compressed to 2.0 GPa at least. At ambient pressure 1 crystallizes in space group C2/c, Z′ = 4 as polymorph 1α, or as lower-density polymorph 1β, of space group P21/c and Z′ = 1. Polymorph β is metastable, and after about one year, it transforms to phase α. The isochoric recrystallization above 0.40 GPa yields a new polymorph γ of space group P21/a and Z′ reduced to 1. The γ polymorph retrieved to ambient conditions for months has showed no signs of transformations. The main motif of OH···O bonded chains is retained in all three phases, but high pressure enforced identical conformation of closely packed molecules and their identical crystal environment in phase γ.

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Section: Introductionmentioning

confidence: 99%

High-Pressure Preference for the Low Z′ Polymorph of a Molecular Crystal

Roszak

Katrusiak

2016

Crystal Growth & Design

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“…The ortho-selective diversification of a biologically active pyridazinone scaffold,series of pyridazinone analogues were synthesized conveniently as the synthetic precursors of potential sortase A (SrtA) inhibitors (Li at al., 2015). A series of phenyl substituted pyridazin-3-ones substituted with morpholino-pyrimidines, SAR of the phenyl was explored and their c-Met kinase and cell-based inhibitory activity toward c-Met driven cell lines were tested.…”

Section: Biological Activitiesmentioning

confidence: 99%

Diverse chemical and biological potentials of various pyridazine and pyridazinone derivatives

Int¹

2019

Preprint

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A series of heterocyclic compounds incorporating pyridazine moiety were for diverse biological activities. Pyridazines and pyridazinones derivatives showed wide spectrum of biological activities such as vasodialator, cardiotonic, anticonvulsant, antihypertensive, antimicrobial, anti-inflammatory, analgesic, anti-feedant, herbicidal, and various other biological, agrochemical and industrial chemical activities. The results illustrated that the synthesized pyridazine/pyridazine compounds have diverse and significant biological activities. Mechanistic insights into the biological properties of pyridazinone derivatives and various synthetic techniques used for their synthesis are also described.

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“…N-Phenyl lactams 1g-1h proceeded smoothly in the reaction but afforded product 3a in much lower yields. For the five-membered (1i) or six-membered (1j) heterocycle-bearing TDGs, such as pyrazolones 11 and pyridazi-nones, 12 the corresponding product 3a was obtained in 15% and 70% yields, respectively, suggesting that the pyridazinonyl-TDG has a higher inductive effect. Interestingly, 1-acetyl-2phenylhydrazine (1k) took part in the reaction as well, though in a lower yield (17%).…”

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confidence: 99%