Synthesis and Anticonvulsant Activity of 6‐Alkoxy‐[1,2,4]Triazolo[3,4‐<i>a</i>]Phthalazines

Zhang, Lei; Guan, Liping; Sun, Xuerong; Wei, Cheng‐Xi; Chai, Kyu Yun; Quan, Zhe‐Shan

doi:10.1111/j.1747-0285.2009.00776.x

Cited by 117 publications

(48 citation statements)

References 24 publications

(43 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…triazolo [3,4-a]phthalazine; was first recognized for anticonvulsant activity with an ED 50 value of 7.1 mg/kg against ME 1,2 S-induced seizures. The anticonvulsant activity of compound I was slightly higher than that of the reference drug (Carbamazepine) in the MES test, but the adverse effects of compound I were marked with a TD of 36.7 mg/kg.…”

Section: O M P O U N D I ( 6 -( 4 -C H L O R O P H E N O X Y ) -mentioning

confidence: 99%

“…The QUAN-0808 had positive effects in both electrical and chemical tests. These animal models are usually considered suitable for identifying anticonvulsant 1,9 activity againsta variety of seizures. The chemical models of seizure, such as PTZinduced seizures, represent models of'myoclonic seizure' that produce clonic and tonic seizures.…”

Section: Anticonvulsant Activitymentioning

confidence: 99%

See 1 more Smart Citation

A Mini Review on Biological Activities of 6-(4-Chlorophenyoxy)-Tetrazolo [5,1-A] Phthalazine (Quan-0808) Compound

Asif¹

2017

Journal of Pharmaceutical Research

View full text Add to dashboard Cite

Abstract:Purpose: Approaches:Findings: Conclusions:Key words:QUAN-0808 (6-(4-chlorophenoxy)-tetrazolo[5,1-a]phthalazine) was tested for the anticonvulsant, anti-inflammatory, analgesic, anticoagulant, antithrombotic and antidepressant effects.Anticonvulsant activity was testedby electroshock seizure model and neurotoxicity was tested by the rotarod neurotoxicity test in mice. In chemically induced models of seizure like pentylenetetrazole, isoniazid, thiosemicarbazide and 3-mercaptopropionic acid were further tested for the anticonvulsant activity.QUAN-0808 caused significant anticonvulsant activity against all types of seizures. It appreciably reduced xylene-induced ear edema, reduced the prostaglandin E2 and nitric oxide levels on the edema and reduced acetic acid-induced capillary permeability hyperactivity and reduced acetic acid-induced writhing response. It exhibited anti-inflammatory and antinociceptiveeffect in a dose-dependent manner.The peripheral effect mechanisms of QUAN-0808 may be related to a reduced in the formation of PGE2, NO, bradykinin and additional inflammatory mediators. The anticoagulant and antithrombotic effects of Q808 delayed bleeding and clotting time in mice. QUAN-0808 exerts anticoagulant, antithrombotic and antidepressant effect, exhibited a significant reduction in immobility as antidepressant. anticonvulsant, antidepressive, antinociceptive, antithrombotic. Tetrazolo

show abstract

Section: O M P O U N D I ( 6 -( 4 -C H L O R O P H E N O X Y ) -mentioning

confidence: 99%

Section: Anticonvulsant Activitymentioning

confidence: 99%

A Mini Review on Biological Activities of 6-(4-Chlorophenyoxy)-Tetrazolo [5,1-A] Phthalazine (Quan-0808) Compound

Asif¹

2017

Journal of Pharmaceutical Research

View full text Add to dashboard Cite

show abstract

“…13 Moreover, fused phthalazine derivatives were found to possess multiple biological activities such as anticonvulsant, 14 activities. Many methods are available for the synthesis of phthalazine derivatives, [19][20][21][22] however, some of these methods suffered from several drawbacks such as hazardous organic solvents, high cost, long reaction times, excess amounts of acids, and harsh reaction conditions with non-recyclable catalysts.…”

Section: 11mentioning

confidence: 99%

“…12 Among a large variety of N-containing heterocyclic compounds, heterocycles containing hydrazine moiety as 'fusion site' have received considerable attention due to their pharmacological properties and clinical applications. 13 Moreover, fused phthalazine derivatives were found to possess multiple biological activities such as anticonvulsant, 14 cardiotonic, 15 vasorelaxant, 16 antifungal, 17 and anticancer 18 activities. Many methods are available for the synthesis of phthalazine derivatives, [19][20][21][22] however, some of these methods suffered from several drawbacks such as hazardous organic solvents, high cost, long reaction times, excess amounts of acids, and harsh reaction conditions with non-recyclable catalysts.…”

Section: Introductionmentioning

confidence: 99%

Sulfonic Acid Functionalized Nanoporous Silica (Sba-Pr-So3h) as an Efficient Catalyst for the One-Pot Synthesis of 2h-Indazolo[1,2-B]phthalazine-Triones

Ziarani

Badiei

Mohtasham

et al. 2014

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

Sulfonic acid functionalized SBA-15 (SBA-Pr-SO 3 H) with a pore size of 6 nm is an efficient catalyst in the green three-component condensation of phthalhydrazide, dimedone and aldehydes to give 2H-indazolo[1,2-b]phthalazine-triones under solvent-free conditions in excellent yields and short reaction times.Keywords: Sulfonic acid functionalized SBA-15; Phthalhydrazide; Dimedone; Nano-reactor; One-pot reaction. INTRODUCTIONIn recent years, heterogeneous catalysts have gained great importance due to economic and environmental considerations.1-3 Among the various heterogeneous catalysts, particularly, Santa Barbara Amorphous (SBA-15) is significant mesoporous silica with exclusive and important properties such as thick walls, profusely large surface area, huge pore volume and hydrothermal stability which render it as a promising catalyst for wide applications. Moreover, functionalization and modification of SBA-15 could enhance and optimize its catalytic activity. 4 Applications of these nano catalysts in organic synthesis and one-pot reactions under green conditions are significant and growing. In continuation of our studies, on the application of nanoporous heterogeneous solid catalysts to organic synthesis, 5-9 herein, we want to report a suitable method for the preparation of 2H-indazolo[1,2-b]phthalazine-trione derivatives using SBA-Pr-SO 3 H as a nanoporous heterogeneous acid catalyst.The development of simple synthetic routes for construction of complex organic molecules from readily available reagents is an important task in organic synthesis. Multi-component reactions (MCRs) are powerful and valuable tools for the rapid and efficient synthesis of a wide variety of organic molecules. 10, 11In the past few decades, the synthesis of nitrogen-containing heterocyclic compounds has gained prominence as they are widespread in nature.12 Among a large variety of N-containing heterocyclic compounds, heterocycles containing hydrazine moiety as 'fusion site' have received considerable attention due to their pharmacological properties and clinical applications.13 Moreover, fused phthalazine derivatives were found to possess multiple biological activities such as anticonvulsant, 14 activities. Many methods are available for the synthesis of phthalazine derivatives, [19][20][21][22] however, some of these methods suffered from several drawbacks such as hazardous organic solvents, high cost, long reaction times, excess amounts of acids, and harsh reaction conditions with non-recyclable catalysts. Therefore, the development of a new, efficient, and environmentally benign procedure which allows the simple synthesis of heterocycles containing phthalazine ring fragment is necessary. In this paper, we want to report the application of SBA-Pr-SO 3 H as a highly active nanoporous heterogeneous acid catalyst in the preparation of 2H-indazolo[1,2-b] phthalazine-trione derivatives. EXPERIMENTAL Materials and MethodsAll chemicals were obtained commercially and used without further purification. The IR spectra were recorded ...

show abstract

“…1 Such compounds express a broad spectrum of biological activities, such as anticancer, 2 anticonvulsant, 3 anti-inamma-tory, 1b,4 vasorelaxant, 5 antitubercular, 6 antihypertensive, 7 and antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products

et al. 2018

View full text Add to dashboard Cite

Pyrazolyl-phthalazine-dione derivatives (PPDs) were synthetized in the ionic liquid catalyzed one-pot multicomponent reaction of acetylacetone, 2,3-dihydrophthalazine-1,4-dione, and different aldehydes in moderate to good yields. Six new PPDs were obtained, and the crystal structure of 2-acetyl-1-(4-fluorophenyl)-3-methyl-1H-pyrazolo[1,2-b]phthalazine-5,10-dione (PPD-4) was determined. The most interesting structural features of the novel PPD-4 is the formation of a rather short intermolecular distance between the F atom of one molecule and the midpoint of the neighbouring six-membered heterocyclic ring. This interaction arranges all molecules into parallel supramolecular chains. UV-Vis spectra of all PPDs were acquired and compared to the simulated ones obtained with TD-DFT. All synthetized compounds were subjected to evaluation of their in vitro antioxidative activity using a stable DPPH radical. It was shown that PPD-7, with a catechol motive, is the most active antioxidant, while PPD-9, with two neighbouring methoxy groups to the phenolic OH, exerted a somewhat lower, but significant antioxidative potential. The results of DFT thermodynamical study are in agreement with experimental findings that PPD-7 and PPD-9 should be considered as powerful radical scavengers. In addition, the obtained theoretical results (bond dissociation and proton abstraction energies) specify SPLET as a prevailing radical scavenging mechanism in polar solvents, and HAT in solvents with lower polarity. On the other hand, the obtained reaction enthalpies for inactivation of free radicals suggest competition between HAT and SPLET mechanisms, except in the case of the cOH radical in polar solvents, where HAT is labeled as prefered.

show abstract

Synthesis and Anticonvulsant Activity of 6‐Alkoxy‐[1,2,4]Triazolo[3,4‐a]Phthalazines

Cited by 117 publications

References 24 publications

A Mini Review on Biological Activities of 6-(4-Chlorophenyoxy)-Tetrazolo [5,1-A] Phthalazine (Quan-0808) Compound

A Mini Review on Biological Activities of 6-(4-Chlorophenyoxy)-Tetrazolo [5,1-A] Phthalazine (Quan-0808) Compound

Sulfonic Acid Functionalized Nanoporous Silica (Sba-Pr-So3h) as an Efficient Catalyst for the One-Pot Synthesis of 2h-Indazolo[1,2-B]phthalazine-Triones

A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products

Contact Info

Product

Resources

About