25947-13-1

Basic information

• Product Name: (4-OXO-3,4-DIHYDRO-PHTHALAZIN-1-YL)-ACETIC ACID ETHYL ESTER
• Synonyms: ETHYL 3,4-DIHYDRO-4-OXO-1-PHTHALAZINEACETATE;2-(4-keto-3H-phthalazin-1-yl)acetic acid ethyl ester;2-(4-oxo-3H-phthalazin-1-yl)acetic acid ethyl ester;ethyl 2-(4-oxo-3H-phthalazin-1-yl)acetate;ethyl 2-(4-oxo-3H-phthalazin-1-yl)ethanoate;ETHYL (4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL)ACETATE;ETHYL 2-(4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL)ACETATE;(4-OXO-3,4-DIHYDRO-PHTHALAZIN-1-YL)-ACETIC ACID ETHYL ESTER
• CAS NO: 25947-13-1
• Molecular Formula: C₁₂H₁₂N₂O₃
• Molecular Weight: 232.24
• Mol File: 25947-13-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 177-179 °C
• Boiling Point: 472.9 °C at 760 mmHg
• Flash Point: 239.8 °C
• Appearance: /
• Density: 1.3 g/cm³
• Vapor Pressure: 1.45E-09mmHg at 25°C
• Refractive Index: 1.608
• PKA: 11.87±0.40(Predicted)
• CAS DataBase Reference: (4-OXO-3,4-DIHYDRO-PHTHALAZIN-1-YL)-ACETIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (4-OXO-3,4-DIHYDRO-PHTHALAZIN-1-YL)-ACETIC ACID ETHYL ESTER(25947-13-1)
• EPA Substance Registry System: (4-OXO-3,4-DIHYDRO-PHTHALAZIN-1-YL)-ACETIC ACID ETHYL ESTER(25947-13-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 25947-13-1(Hazardous Substances Data)

Usage

General Description

"(4-oxo-3,4-dihydro-phthalazin-1-yl)-acetic acid ethyl ester" is a chemical compound with a molecular formula of C12H14N2O4. It is an organic compound and an ester derivative of acetic acid. (4-OXO-3,4-DIHYDRO-PHTHALAZIN-1-YL)-ACETIC ACID ETHYL ESTER is used in research and development as a precursor for the synthesis of various pharmaceuticals and agrochemicals. It is also used in the production of dyes and pigments. The chemical structure of this compound consists of a phthalazine ring with an attached acetic acid ester group, which gives it unique properties and allows it to be used in a variety of applications.

InChI:InChI=1/C12H12N2O3/c1-2-17-11(15)7-10-8-5-3-4-6-9(8)12(16)14-13-10/h3-6H,2,7H2,1H3,(H,14,16)

Upstream product

• 85-44-9 phthalic anhydride 
• 122665-82-1 ethyl 1,3-dihydro-1-hydroxy-3-oxo-1-isobenzofuranacetate 

Downstream Products

• 138129-07-4 [3-(4,5-Diphenyl-oxazol-2-ylmethyl)-4-oxo-3,4-dihydro-phthalazin-1-yl]-acetic acid ethyl ester 
• 110722-39-9 {3-[3-(2-Bromo-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 110703-81-6 [4-Oxo-3-(3-phenyl-isothiazol-4-ylmethyl)-3,4-dihydro-phthalazin-1-yl]-acetic acid ethyl ester 
• 138129-24-5 {3-[(3,5-Bis-trifluoromethyl-phenylcarbamoyl)-methyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 138129-04-1 {4-Oxo-3-[5-(2-trifluoromethyl-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 110704-54-6 Ethyl 3-[3-(2-trifluoromethylphenyl)-1,2,4-oxadiazol-5-ylmethyl]-4-oxo-3H-phthalazin-1-ylacetate 
• 110722-38-8 {3-[3-(2-Chloro-6-fluoro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 138129-03-0 {3-[3-(2,4-Difluoro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 138128-94-6 [4-Oxo-3-(5-phenyl-benzooxazol-2-ylmethyl)-3,4-dihydro-phthalazin-1-yl]-acetic acid ethyl ester 
• 138129-01-8 {3-[3-(2-Methoxy-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 131105-68-5 ethyl 3-<2-<<2-bromo-3,5-bis(trifluoromethyl)phenyl>amino>-2-oxoethyl>-3,4-dihydro-4-oxo-1-phthalazineacetate 
• 157097-01-3 {3-[(2-Bromo-4-methoxy-5-trifluoromethyl-phenylcarbamoyl)-methyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 138129-23-4 3-[2-[N-[2-Bromo-5-(trifluoromethyl)phenyl]-amino]-2-oxoethyl]-3, 4-dihydro-4-oxo-1-phthalazineacetic acid ethyl ester 
• 138129-25-6 {4-Oxo-3-[(3,4,5-trimethoxy-phenylcarbamoyl)-methyl]-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 

Relevant articles and documents

Evaluation of anti-depressant effects of phthalazinone-based triple-acting small molecules against 5-HT2A, 5-HT2C, and the serotonin transporter

Development of highly effective, safe, and fast-acting anti-depressants is urgently required for the treatment of major depressive disorder. It has been suggested that targeting 5-HT2A and 5-HT2C in addition to inhibition of serotonin reuptake may be beneficial in generating anti-depressant agents with better pharmacology and less adverse effects. We have developed phthalazinone-based compounds that potently bind to 5-HT2A, 5-HT2C, and the serotonin transporter. The representative compounds 11j and 11l displayed strong binding affinities against these targets, and showed favorable toxicity profiles as determined by hERG binding and CYP inhibition assays. Furthermore, these compounds presented promising anti-depressant effects comparable to fluoxetine and also synergistic effects with fluoxetine in forced swimming test, which implicates these compounds can be developed to help the treatment of major depressive disorder.

NOVEL IL-2/IL-15 RECEPTOR ANTAGONIST COMPOUNDS AND USES THEREOF FOR THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISEASES OR GRAFT REJECTION

Novel IL-2/IL-15 Receptor antagonist compounds and uses thereof for the treatment of autoimmune and inflammatory diseases or graft rejection Novel IL-2/IL-15 Receptor antagonist compounds and uses thereof for the treatment of autoimmune and inflammatory diseases or graft rejection. The invention relates to a compound of general formula (1) wherein X represents O, S or NR 4, wherein R4 is alkyl; A is selected from S, SO, SO2, NH and O; Y represents (CR5R6)n or (CR5 R6 O)n, wherein R5 and R6 identical or different are H or alkyl and n represents an integer from 1 to 15; R1 represents a 5 to 10 membered aromatic or non-aromatic mono-or bicyclic, 1 optionally bridged ring, R2 is C1-C4 alkyl; R3 is H or alkyl; p is 0 or 1; or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of the interactions of IL-2/15 to IL-2/15Rβand hence useful in the treatment of an autoimmune or an inflammatory diseases and graft rejection.

Phthalazinone inhibitors of inosine-5′-monophosphate dehydrogenase from Cryptosporidium parvum

Cryptosporidium parvum (Cp) is a potential biowarfare agent and major cause of diarrhea and malnutrition. This protozoan parasite relies on inosine 5′-monophosphate dehydrogenase (IMPDH) for the production of guanine nucleotides. A CpIMPDH-selective N-aryl-3,4-dihydro-3-methyl-4-oxo-1- phthalazineacetamide inhibitor was previously identified in a high throughput screening campaign. Herein we report a structure-activity relationship study for the phthalazinone-based series that resulted in the discovery of benzofuranamide analogs that exhibit low nanomolar inhibition of CpIMPDH. In addition, the antiparasitic activity of select analogs in a Toxoplasma gondii model of C. parvum infection is also presented.