Synthesis, Nematicidal and Antimicrobial Properties of Bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4-methylphenyl)-2(aryl)-tetrahydro-2&lt;i&gt;H&lt;/i&gt;-pyrazolo[3,4-&lt;i&gt;d&lt;/i&gt;]thiazol-5-yl]phenyl]methanes

Reddy, Cherkupally Sanjeeva; Srinivas, A.; Nagaraj, A.

doi:10.1248/cpb.57.685

Cited by 17 publications

(6 citation statements)

References 42 publications

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“…7) However, to date there has been no phytochemical investigation into a related plant, A. quinquegona. From the n-hexane-and EtOAc-soluble fractions of the leaves of A. quinquegona, eight alkylated benzoquinones, named ardisiaquinones A-H (1)(2)(3)(4)(5)(6)(7)(8) were isolated along with four known compounds (9)(10)(11)(12) (Fig. 1).…”

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confidence: 99%

Alkylated Benzoquinones: Ardisiaquinones A–H from the Leaves of Ardisia quinquegona and Their Anti-Leishmania Activity

Asaumi

Kawakami

Sugimoto

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Eight alkylated benzoquinone derivatives, named ardisiaquinones A-H, were isolated together with four known compounds from the leaves of Ardisia quinquegona using a combination of different chromatography techniques. Their structures were elucidated by spectroscopy and by the preparation of methyl ethers. Anti-Leishmania activity and cytotoxicity of the isolated compounds were assayed. Some compounds showed moderate anti-Leishmania activity, however, always associated with cytotoxicity.

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confidence: 99%

Alkylated Benzoquinones: Ardisiaquinones A–H from the Leaves of Ardisia quinquegona and Their Anti-Leishmania Activity

Asaumi

Kawakami

Sugimoto

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Following the successful introduction of antimicrobial and nematicidal agents, inspired by the biological profile of triazoles, thiazolidenones, and in the continuation of our work on biologically active heterocycles, [27][28][29][30][31][32][33][34][35][36][37][38][39] we have developed a series of novel triazole linked thiazolidenone derivatives, and evaluated their nematicidal activity along with antibacterial activity.…”

Section: Srinivas Et Al: Synthesis and Biological Evaluation mentioning

confidence: 99%

Synthesis and Biological Evaluation of Triazole linked Thiazolidenone Glycosides

Srinivas

Madavarapu²,

Sunitha³

et al. 2016

ACSi

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In a one pot procedure a series of novel triazole linked thiazolidinone derivatives 8a-g and 9a-g was prepared by condensation of (3aR,5S,6R,6aR]dioxole-5-carbaldehyde 7 with mercapto acids and primary amines in the presence of ZnCl 2 under both microwave irradiation and conventional heating conditions. Compound 7 was prepared from diacetone D-glucose with oxidation followed by reduction, click reaction, primary acetonide deprotection and with oxidative cleavage. Characterization of new compounds has been done by means of IR, NMR, MS and elemental analysis. The nematicidal and antibacterial activity of the compounds has also been evaluated.

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“…23) In addition, it has been reported that thiadiazoles exhibit a broad spectrum of biological effectiveness such as anti-parkinsonism, 24) hypoglycaemic, 25) anticancer, 26) anti-inflammatory, 27) anti-asthmatic 28) and anti-hypertensive 29) activities. Inspired by the biological profile of pyrazole, triazole, thiadiazole, and in continuation of our research on biologically active heterocycles, [30][31][32][33][34][35] it was thought worthwhile to synthesize some new heterocyclic compounds containing pyrazole, triazole and thiadiazol rings in one molecular frame work. We report herein the synthesis of a new series of 1,2,4-triazole [3,4-b] [1,3,4]thiadiazoles bearing pyrazole and their antimicrobial activity.…”

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confidence: 99%

Synthesis of New 1,2,4-Triazole[3,4-b][1,3,4]thiadiazoles Bearing Pyrazole as Potent Antimicrobial Agents

Reddy

Rao

Kumar

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Pyrazole and its derivatives represent one of the most active classes of compounds possessing a wide spectrum of biological activities, including antibacterial, 1) antifungal, 2) herbicidal, 3) insecticidal 4) and other biological activities. 5-7)Similarly, the biological activities of various 1,2,4-triazole derivatives and their N-bridged heterocyclic analogs have been widely investigated as antitumor, 8) antiviral, 9) anti-inflammatory, 10) analgesic 11) and antidepressant. 12) 1,2,4-Triazole system is also an important starting material in the synthesis of biologically active heterocycles, which constitute an important class of organic compounds with diverse biological activities, including antiparasitic, analgesic, antibacterial and anti-inflammatory activities. [13][14][15][16][17][18] Further, triazole fused with other heterocyclic rings is also found to possess diverse applications in the field of medicine. [19][20][21][22] The commonly known systems are triazolo-pyridines, 19) triazolo-pyridazines, 20) triazolo-pyrimidines, 21) triazolo-pyrazines, 22) triazolo-triazines 21) and triazolo-thiadiazines. 23) In addition, it has been reported that thiadiazoles exhibit a broad spectrum of biological effectiveness such as anti-parkinsonism, 24) hypoglycaemic, 25) anticancer, 26) anti-inflammatory, 27) anti-asthmatic 28) and anti-hypertensive 29) activities. Inspired by the biological profile of pyrazole, triazole, thiadiazole, and in continuation of our research on biologically active heterocycles, [30][31][32][33][34][35] it was thought worthwhile to synthesize some new heterocyclic compounds containing pyrazole, triazole and thiadiazol rings in one molecular frame work. We report herein the synthesis of a new series of 1,2,4-triazole [3,4-b][1,3,4]thiadiazoles bearing pyrazole and their antimicrobial activity. Results and DiscussionSynthesis The starting material, (E)-2-acetyl-3-(dimethylamino)-2-propenoate (2), was obtained via condensation of ethyl acetoacetate (1) with N,N-dimethyldimethoxymethanamine, 36) which on cyclo-condensation with phenyl hydrazine resulted 5-methyl-1-phenyl-1H-4-pyrazolecarboxylate (3).36) The 5-methyl-1-phenyl-1H-4-pyrazolecarbohydrazide (4) was obtained in 72% yield via hydrazinolysis of compound 3 with hydrazine hydrate. The hydrazide 4 on reaction with carbon disulfide and potassium hydroxide, in ethanol, followed by acidification gave 5-(5-methyl-1-phenyl-1H-4-pyrazolyl)-1,3,4-oxadiazol-2-yl-hydrosulfide (5) in 70% yield. Reaction of 5 with hydrazine hydrate under reflux for 6 h resulted 4-amino-5-(5-methyl-1-phenyl-1H-4-pyrazolyl)-4H-1,2,4-triazol-3-yl-hydrosulfide (6) in 69% yield. The final compounds, 6-(aryl/heteryl)-3-(5-methyl-1-phenyl-1H-4-pyrazolyl)[1,2,4]triazolo [3,4-b] [1,3,4]thiadiazole (7a-j), were synthesized in 66-78% via the reaction of 6 with POCl 3 and the corresponding aryl/heteryl carboxylic acids, in ethanol at reflux temperature for 12 h (Chart 1). The structures of all the newly synthesized compounds were confirmed by their elemental analyses, electron...

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Synthesis, Nematicidal and Antimicrobial Properties of Bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4-methylphenyl)-2(aryl)-tetrahydro-2<i>H</i>-pyrazolo[3,4-<i>d</i>]thiazol-5-yl]phenyl]methanes

Cited by 17 publications

References 42 publications

Alkylated Benzoquinones: Ardisiaquinones A–H from the Leaves of <i>Ardisia quinquegona</i> and Their Anti-<i>Leishmania</i> Activity

Alkylated Benzoquinones: Ardisiaquinones A–H from the Leaves of <i>Ardisia quinquegona</i> and Their Anti-<i>Leishmania</i> Activity

Synthesis and Biological Evaluation of Triazole linked Thiazolidenone Glycosides

Synthesis of New 1,2,4-Triazole[3,4-b][1,3,4]thiadiazoles Bearing Pyrazole as Potent Antimicrobial Agents

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