Pyrazol-3-ones. Part III: Reactivity of the Ring Substituents

Varvounis, George; Fiamegos, Yiannis C.; Pilidis, George

doi:10.1016/s0065-2725(07)95002-3

Cited by 23 publications

(7 citation statements)

References 130 publications

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“…Pyrazole derivatives are known to exhibit a wide spectrum of biological activities such as anti‐inflammatory, antipyretic, analgesic, peroxisome proliferator‐activated receptor gammaPPAR γ partial agonistic, antitumor, antibacterial, antiviral, and antiprion activities . There have been many attempts to develop alternative methods for the synthesis of pyrazole derivatives .…”

Section: Introductionmentioning

confidence: 99%

A Divergent Synthesis of Spiropyrazole Derivatives Containing Iminolactone and/or Cyclic Imide Moiety

Masumoto

Maruoka

Okabe

et al. 2014

Journal of Heterocyclic Chem

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An approach to spiropyrazole derivatives containing iminolactone and/or cyclic imide moiety starting from 1H‐pyrazole‐4‐acetic acid derivative is described. Hydrolysis of C‐cyanomethylated 1H‐pyrazole‐4‐acetic acid methyl ester (1), which was easily prepared from 1H‐pyrazole‐4‐acetic acid derivative by a C‐cyanomethylation, led to the C‐cyanomethylated 1H‐pyrazole‐4‐acetic acid (2). Compound 2 was reacted with ethanol in the presence of tin(IV) chloride in refluxing chloroform to give the key intermediate ethyl imidate (3). Sodium hydride‐assisted lactonization of 3 in N,N‐dimethylformamide afforded the spiropyrazole derivative containing iminolactone moiety (4). On the other hand, thermal treatment of 3 with sodium acetate in the absence of solvent caused another intramolecular cyclization to yield the spiropyrazole derivative containing cyclic imide moiety (6).

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Section: Introductionmentioning

confidence: 99%

A Divergent Synthesis of Spiropyrazole Derivatives Containing Iminolactone and/or Cyclic Imide Moiety

Masumoto

Maruoka

Okabe

et al. 2014

Journal of Heterocyclic Chem

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“…These derivatives are the subject of many research studies due to their widespread potential pharmacological activities such as antitumor, analgesic, antidepressant, antibacterial, plant growth regulatory, anti‐inflammatory, and antihyperglycemic activities [1–8]. Various methods have been reported for the synthesis of pyrazole derivatives [9–14].…”

Section: Introductionmentioning

confidence: 99%

A Novel Synthesis of 4‐Pyridazineacetic Acids viaRing Expansion of N‐Cyanomethylated 3‐Pyrazoline‐4‐acetic Acids

Masumoto

Maruoka

Okabe

et al. 2012

Journal of Heterocyclic Chem

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A novel synthetic route to 4‐pyridazineacetic acids 10–12 has been achieved by the ring‐expansion reaction of N‐cyanomethylated 3‐pyrazoline‐4‐acetic acids 7–9. 1H‐Pyrazole‐4‐acetic acids 1–3 were reacted with iodoacetonitrile in the presence of triethylamine in refluxing acetonitrile to give the corresponding C‐cyanomethylated 1H‐pyrazole‐4‐acetic acids 4–6 as major products together with N‐cyanomethylated 3‐pyrazoline‐4‐acetic acids 7 and 8 as minor products. On the other hand, reactions of 1 and 3 with chloroacetonitrile in the presence of triethylamine in refluxing chloroform afforded the corresponding N‐cyanomethylated 3‐pyrazoline‐4‐acetic acids 7 and 9 as major products. Thermal treatment of 7–9 with sodium hydride in N,N‐dimethylformamide caused ring expansion to yield the corresponding 4‐pyridazineacetic acids 10–12.

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“…In this respect, the incorporation of heterocyclic residues into perspective pharmaceutical lead candidates constitutes an important strategy which provides activity and safety features. Thus, a broad variety of azaheterocycles compounds have been considered as potent antitumor agents, while pyrazoles belong among the most representative five-membered heterocyclic systems [5,6]. Particularly, over the past two decades, pyrazolecontaining compounds have received considerable attention, owing to their diverse chemotherapeutic potentials, including versatile antineoplastic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro Biological Evaluation of Novel Pyrazole Derivatives as Potential Antitumor Agents

Christodoulou

Fokialakis²,

Nam³

et al. 2012

med chem

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The synthesis of twenty seven novel pyrazole derivatives bearing aryl substituted groups at positions 1 and 3 of the pyrazole structural motif and various functional groups at position 4 is presented. The critical step for their synthesis is the TCT/DMF promoted cyclization of the corresponding hydrazine precursors, which provided the desired pyrazole skeleton. The anticancer properties of the novel pyrazole derivatives were evaluated in vitro against human prostate (DU145), melanoma (A2058) and breast cancer (MCF-7) cell lines. Among the compounds tested, pyrazole 5a and its methoxy derivatives 3d,e were assayed as the most potent, displaying selective activity against the MCF-7 cell line with IC(50) values of 14, 10 and 12 µM respectively. Results herein indicate that the reported backbone represents a promising structural lead for further development as antitumor agents.

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Pyrazol-3-ones. Part III: Reactivity of the Ring Substituents

Cited by 23 publications

References 130 publications

A Divergent Synthesis of Spiropyrazole Derivatives Containing Iminolactone and/or Cyclic Imide Moiety

A Divergent Synthesis of Spiropyrazole Derivatives Containing Iminolactone and/or Cyclic Imide Moiety

A Novel Synthesis of 4‐Pyridazineacetic Acids viaRing Expansion of N‐Cyanomethylated 3‐Pyrazoline‐4‐acetic Acids

Synthesis and In Vitro Biological Evaluation of Novel Pyrazole Derivatives as Potential Antitumor Agents

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