Biological activities of pyrazoline derivatives--a recent development.
31 Oct 2009-Recent Patents on Anti-infective Drug Discovery (Recent Pat Antiinfect Drug Discov)-Vol. 4, Iss: 3, pp 154-163
TL;DR: The present review provides an insight view to pyrazolines synthesis and its biological activities along with the compilation of recent patents on pyrazoline derivatives.
Abstract: Pyrazolines are well known and important nitrogen containing 5-membered heterocyclic compounds and various methods have been worked out for their synthesis. Numerous pyrazoline derivatives have been found to possess considerable biological activities, which stimulated the research activity in this field. They have several prominent effects, such as antimicrobial, antimycobacterial, antifungal, antiamoebic, anti-inflammatory, analgesic, antidepressant and anticancer activities. They also possess some potent receptor selective biological activity like Nitric oxide synthase (NOS) inhibitor and Cannabinoid CB1 receptor antagonists activity. 4,5-dihydro-1H- pyrazolines seem to be the most frequently studied pyrazoline type compounds. As a result, a large number of such pyrazolines using different synthetic methods for their preparation have been described in the chemistry literature. The present review provides an insight view to pyrazolines synthesis and its biological activities along with the compilation of recent patents on pyrazolines.
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TL;DR: The most effective anticancer compound 10 was found to be active with mean GI₅₀ and TGI values of 0.071 μM and 0.76 μM, respectively and demonstrated the highest antiproliferative influence on the non-small-cell lung cancer cell line HOP-92.
Abstract: The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-...
186 citations
TL;DR: A highly regioselective cycloaddition procedure of electron-deficient allenes with trifluorodiazoethane (CF3CHN2) is described, in absence of bases, where the reaction proceeded smoothly to give 5-(trifloromethyl)pyrazolines, whereas the utility of Et3N led to the formation of 3-pyrazoles.
108 citations
TL;DR: The present review sheds light on the recent therapeutic patent literature describing the applications of pyrazolines and their derivatives on selected activities, including antimicrobial effects, anti-inflammatory, analgesic, antidepressant and anticancer.
Abstract: Introduction: Pyrazolines are well-known and important nitrogen-containing five-membered ring heterocyclic compounds. Various methods have been worked out for their synthesis. Several pyrazoline derivatives have been found to possess diverse biological properties, which has stimulated research activity in this field. Areas covered: The present review sheds light on the recent therapeutic patent literature (2000 – 2011) describing the applications of pyrazolines and their derivatives on selected activities. Many of the therapeutic applications of pyrazoline derivatives have been discussed, either in the patent or in the general literature areas in this review. In addition to selected biological data, a wide range of pharmaceutical applications and pharmaceutical compositions are also summarized. Expert opinion: Pyrazoline derivatives have numerous prominent pharmacological effects, such as antimicrobial (antibacterial, antifungal, antiamoebic, antimycobacterial), anti-inflammatory, analgesic, antidepressan...
106 citations
TL;DR: The [3+2] cycloaddition of CF3CHN2, generated in situ, with electron-deficient alkenes/alkynes affords CF3-substituted pyrazolines/pyrazoles in quantitative yields as discussed by the authors.
98 citations
TL;DR: Diversely substituted pyrazoles, embedded with a variety of functional groups, are important biological agents and a significant amount of research activity has been directed towards this chemical class.
Abstract: Monoamine oxidase plays a significant role in the control of intracellular concentration of monoaminergic neurotransmitters or neuromodulators and dietary amines. The rapid degradation of these molecules ensures the proper functioning of synaptic neurotransmission and is critically important for the regulation of emotional and other brain functions. The development of human MAO inhibitors led to important breakthroughs in the therapy of several neuropsychiatric disorders. Different families of heterocycles containing 2 or 4 nitrogen atoms have been used as scaffolds for synthesizing selective monoamine oxidase inhibitors, but the early period of the MAO-inhibitors started with hydrazine derivatives. Pyrazole, pyrazoline, and pyrazolidine derivatives can be considered as a cyclic hydrazine moiety. This scaffold also displayed promising antidepressant and anticonvulsant properties as demonstrated by different and established animal models. Diversely substituted pyrazoles, embedded with a variety of functional groups, are important biological agents and a significant amount of research activity has been directed towards this chemical class.
91 citations
Cites background from "Biological activities of pyrazoline..."
...As a consequence, a large number of 2-pyrazolines have been described in the chemical literature [16], using different synthetic methods for their preparation....
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References
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TL;DR: Anticonvulsant activities of the compounds were determined by maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (metrazol) (scMet.) tests, neurotoxicities was determined by rotarod toxicity test on albino mice.
344 citations
"Biological activities of pyrazoline..." refers background in this paper
...42% duration of immobility times at 10 mg kg 1 dose level [21]....
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TL;DR: It was found that the compounds possessing electron-releasing groups such as dimethyl amino, methoxy and hydroxyl substituents, on both the aromatic rings at positions 3 and 5 of pyrazolines, considerably enhanced the antidepressant activity when compared to the pyrazlines having no substituent on the phenyl rings.
328 citations
"Biological activities of pyrazoline..." refers background in this paper
...05) in the Porsolt behavioral despair test [20]....
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TL;DR: The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that N-acetyl 4,5-dihydropyrazole 7 was the only active one at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with a 50% effective concentration (EC(50) value of 7 microg/ml.
289 citations
"Biological activities of pyrazoline..." refers background in this paper
...The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that some of compounds were the most active derivatives whereas Nacetyl 4,5-dihydropyrazole was the only active at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with an EC50 value of 7μg/ml [29]....
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TL;DR: The most efficient anticancer compound 16 was found to be active with selective influence on colon cancer cell lines, especially on HT 29 (logGI(50)=-6.37) and in vitro anticancer activity of synthesized compounds were tested by the National Cancer Institute.
246 citations
Additional excerpts
...37) [14]....
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TL;DR: In general, the oxidized pyrazoles displayed better antitumor activity than their parent pyrazoline analogs, whereas the benzenesulfonamides and the N1, N3-disubstituted sulfonylureas showed significant better antitUMor spectrum than the sulfonyLthioureido and the derived thiazole analogs.
224 citations
"Biological activities of pyrazoline..." refers background in this paper
...Eight compounds showed promising broad spectrum antitumor activity against most of the tested sub panel tumor cell lines [19]....
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