The synthesis of 3-(alditol-1-yl)-1,2,4-triazolo[3,4-a]phthalazines

Shaban, Μ. A. E.; Ali, Raafat S.; El-Badry, Sousan M.

doi:10.1016/s0008-6215(00)85294-5

Cited by 12 publications

(2 citation statements)

References 16 publications

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“…Hydralazine glucose conjugate (aldehydo-D-glucose phthalazin-1-ylhydrazone) was prepared by incubating 0.51 mmole of D-glucose and hydralazine hydrochloride with sodium acetate (1.02 mmole) in water: methanol (1:3)46. The reaction mixture was kept at boiling water bath for 10 min.…”

Section: Methodsmentioning

confidence: 99%

Proteome wide reduction in AGE modification in streptozotocin induced diabetic mice by hydralazine mediated transglycation

Kesavan

Bhat

Golegaonkar

et al. 2013

Sci Rep

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The non-enzymatic reaction between glucose and protein can be chemically reversed by transglycation. Here we report the transglycation activity of hydralazine using a newly developed MALDI-TOF-MS based assay. Hydralazine mediated transglycation of HbA1c, plasma proteins and kidney proteins was demonstrated in streptozotocin (STZ) induced diabetic mice, as evidenced by decrease in protein glycation, as well as presence of hydralazine-glucose conjugate in urine of diabetic mice treated with hydralazine. Hydralazine down regulated the expression of Receptor for Advanced Glycation End products (RAGE), NADPH oxidase (NOX), and super oxide dismutase (SOD). These findings will provide a new dimension for developing intervention strategies for the treatment of glycation associated diseases such as diabetes complications, atherosclerosis, and aging.

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Section: Methodsmentioning

confidence: 99%

Proteome wide reduction in AGE modification in streptozotocin induced diabetic mice by hydralazine mediated transglycation

Kesavan

Bhat

Golegaonkar

et al. 2013

Sci Rep

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“…3 Under certain conditions, the hydrazones were found to undergo cyclization and autodehydrogenation to produce sugar-substituted s-triazolo [3,4-a]phthalazine IIIa. 3 Under certain conditions, the hydrazones were found to undergo cyclization and autodehydrogenation to produce sugar-substituted s-triazolo [3,4-a]phthalazine IIIa.…”

Section: Introductionmentioning

confidence: 99%

Interactions between Drug Substances and Excipients. 1. Fluorescence and HPLC Studies of Triazolophthalazine Derivatives from Hydralazine Hydrochloride and Starch††Presented at the PharmAnalysis Conference ’95, Atlantic City, NJ, June 1995

Lesse¹,

Zhao²

1996

Journal of Pharmaceutical Sciences

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The strength of hydralazine hydrochloride (I) 10 mg tablets, containing starch as an excipient, decreases significantly with time. An investigation to determine the basis for the drop in strength showed that starch exposed to the drug exhibited fluorescence at 414 nm. As model compounds IIIa and V, which contain a triazolophthalazinyl moiety, also fluoresce at about 414 nm, it is proposed that the emission is due to a triazolophthalazine derivative (IIIc) resulting from hydralazine hydrochloride and starch. Degradation of IIIc generates s-triazolo[3,4-a]phthalazine (IIIb), and a small amount of IIIb is detected in aged tablets. IIIc in aged tablets can be converted to IIIb by acid-catalyzed hydrolysis. The quantity of IIIb determined by HPLC amounts to most of the "missing" hydralazine hydrochloride. The reaction between hydralazine hydrochloride and starch is believed to cause the unexpected drop in the strength of hydralazine hydrochloride tablets.

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Reactions of Aroylhydrazones, IV: Synthesis of Nitrogen Heterocycles from Opianic Acid Hydrazones

Nassr

El-Badry

Smaban

1985

J Chinese Chemical Soc

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Opianic acid reacts with various hydrazines to yield either hydrazone (3, 6) or phthalazinone (4) derivatives depending upon the electronic properties of the substituent attached to the hydrazine molecule. Oxidative cyclization of opianic acid aroylhydrazones with iodine and yellow mercuric oxide gave the 1,3,4‐oxadiazole derivatives 21. The aroylhydrazones were also condensatively cyclized by heating with acetic anhydride to give the 1,3,4‐oxadiazoline derivatives 24. Structures assigned to the prepared compounds were corroborated by studying their chemical as well as their spectral characteristics.

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The synthesis of 3-(alditol-1-yl)-1,2,4-triazolo[3,4-a]phthalazines

Cited by 12 publications

References 16 publications

Proteome wide reduction in AGE modification in streptozotocin induced diabetic mice by hydralazine mediated transglycation

Proteome wide reduction in AGE modification in streptozotocin induced diabetic mice by hydralazine mediated transglycation

Interactions between Drug Substances and Excipients. 1. Fluorescence and HPLC Studies of Triazolophthalazine Derivatives from Hydralazine Hydrochloride and Starch††Presented at the PharmAnalysis Conference ’95, Atlantic City, NJ, June 1995

Reactions of Aroylhydrazones, IV: Synthesis of Nitrogen Heterocycles from Opianic Acid Hydrazones

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