122665-86-5

Usage

Uses

Used in Pharmaceutical Research and Development:
ETHYL 2-[3-(CYANOMETHYL)-4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL]ACETATE is utilized as a potential drug candidate due to its distinctive molecular structure and functional groups, which may contribute to its bioactivity and therapeutic potential.
Used in Chemical Synthesis:
As a reagent in chemical synthesis, ETHYL 2-[3-(CYANOMETHYL)-4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL]ACETATE is employed to facilitate the creation of new compounds or the modification of existing ones, potentially leading to advancements in various chemical and material sciences.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, ETHYL 2-[3-(CYANOMETHYL)-4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL]ACETATE is used as a starting material or intermediate in the synthesis of novel pharmaceutical agents, aiming to discover new drugs with improved efficacy and safety profiles.
Used in Drug Discovery:
ETHYL 2-[3-(CYANOMETHYL)-4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL]ACETATE is used in drug discovery processes to identify new lead compounds or optimize existing ones, leveraging its structural features to target specific biological pathways or receptors.
Used in Bioactive Compound Screening:
In the search for bioactive compounds, ETHYL 2-[3-(CYANOMETHYL)-4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL]ACETATE is employed as a subject for screening assays to evaluate its potential interactions with biological targets, which could reveal new applications in therapeutics or diagnostics.
Used in Chemical Biology:
ETHYL 2-[3-(CYANOMETHYL)-4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL]ACETATE is utilized in chemical biology to study the interactions between small molecules and biological systems, providing insights into molecular mechanisms and potential applications in disease treatment or prevention.
Note: The specific applications listed above are hypothetical and based on the compound's description as a potential drug candidate and reagent. Actual uses would depend on the outcomes of research and development efforts in these areas.

InChI:InChI=1/C14H13N3O3/c1-2-20-13(18)9-12-10-5-3-4-6-11(10)14(19)17(16-12)8-7-15/h3-6H,2,8-9H2,1H3

Upstream product

• 107-14-2 chloroacetonitrile 
• 25947-13-1 ethyl 1,2-dihydro-1-oxophthalazin-4-ylacetate 
• 122665-88-7 ethyl 3,4-dihydro-4-oxo-3-(hydroxymethyl)-1-phthalazineacetate 
• 151-50-8 potassium cyanide 
• 122665-90-1 ethyl 3,4-dihydro-4-oxo-3-(bromomethyl)-1-phthalazineacetate 

Relevant academic research and scientific papers

Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (zopolrestat) and congeners

A new working hypothesis that there is a hitherto unrecognized binding site on the aldose reductase (AR) enzyme with strong affinity for benzothiazoles was pursued for the design of novel, potent aldose reductase inhibitors (ARIs). The first application of this hypothesis led to a novel series of 3,4-dihydro-4-oxo-3-(benzothiazolylmethyl)-1-phthalazineacetic acids. The parent of this series (207) was a potent inhibitor of AR from human placenta (IC50 = 1.9 x 10-8 M) and was orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications (ED50 = 18.5 mg/kg). Optimization of this lead through medicinal chemical rationale, including analogy from other drug series, led to more potent congeners of 207 and culminated in the design of 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (216, CP-73,850, zopolrestat). Zopolrestat was found to be more potent than 207, both in vitro and in vivo. Its IC50 against AR and ED50 in the acute test were 3.1 x 10-9 M and 3.6 mg/kg, respectively. Its ED50s in reversing already elevated sorbitol accumulation in rat sciatic nerve, retina, and lens in a chronic test were 1.9, 17.6, and 18.4 mg/kg, respectively. It was well absorbed in diabetic patients, resulting in high blood level, showed a highly favorable plasma half-life (27.5 h), and is undergoing further clinical evaluation. An assortment of synthetic methods used for the construction of benzothiazoles, including an efficient synthesis of zopolrestat, is described. Structure-activity relationships in the new series are discussed.

HETEROCYCLIC OXOPHTHALAZINYL ACETIC ACIDS

A heterocyclic oxophthalazinyl acetic acid having aldose reductast inhibitory activity of the formula, wherein X is oxygen or sulfur; Z is a covalent bond, O, S, NH or CH2 or CHR5Z is vinyl; R1 is hydroxy, or a prodrug group; R2 is a heterocyclic group, R3 and R4 are hydrogen or the same or a different substituent, and R5 is hydrogen, methyl or trifluoromethyl. The pharmaceutically acceptable acid addition salts of the above compounds wherein R1 is di(C1-C4)alkylamino or (C1-C4)alkoxy substituted by N-morpholino or di(Cl-C4)alkylamino and the pharmaceutically active base addition salts of the above compounds wherein R1 is hydroxy are also aldose reductase inhibitors