102072-84-4

Basic information

• Product Name: PHTHALAZIN-5-AMINE
• Synonyms: 5-AMINO-PHTHALAZINE;PHTHALAZIN-5-AMINE;Quinoxalin-5-ylamine
• CAS NO: 102072-84-4
• Molecular Formula: C₈H₇N₃
• Molecular Weight: 145.16
• Mol File: 102072-84-4.mol

Chemical Properties

• Melting Point: 223-224 °C(Solv: methanol (67-56-1))
• Boiling Point: 423.2 °C at 760 mmHg
• Flash Point: 239.3 °C
• Appearance: /
• Density: 1.292 g/cm³
• Vapor Pressure: 2.28E-07mmHg at 25°C
• Refractive Index: 1.723
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.32±0.30(Predicted)
• CAS DataBase Reference: PHTHALAZIN-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: PHTHALAZIN-5-AMINE(102072-84-4)
• EPA Substance Registry System: PHTHALAZIN-5-AMINE(102072-84-4)

Safety Data

• Hazardous Substances Data: 102072-84-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PHTHALAZIN-5-AMINE is used as a building block for the synthetic preparation of ezrin inhibitors. These inhibitors are specifically designed to target metastatic osteosarcoma, a highly aggressive and malignant bone cancer. By inhibiting the function of the ezrin protein, which plays a critical role in cancer cell migration and invasion, PHTHALAZIN-5-AMINE-based ezrin inhibitors can potentially suppress the metastatic spread of osteosarcoma, offering a promising therapeutic strategy for this devastating disease.

InChI:InChI=1/C8H7N3/c9-8-3-1-2-6-4-10-11-5-7(6)8/h1-5H,9H2

Upstream product

• 89898-86-2 5-nitrophthalazine 
• 253-52-1 PHTHALAZINE 
• 484-23-1 1,4-bis(hydrazino)phthalazine 
• 91-15-6 phthalonitrile 

Downstream Products

• 147088-71-9 phthalazine-5,8-dione 
• 102072-85-5 DA 3044 

Relevant articles and documents

Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones

6-Arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones were synthesized and tested for in vitro antifungal activity against two pathogenic strains of fungi. Among those tested, many compounds showed good antifungal activity. The results suggest that phthalazine-5,8-diones would be potent antifungal agents.

Ezrin inhibitors and methods of making and using

The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growth of a cancer cell.

Design, synthesis and biological evaluation of ezrin inhibitors targeting metastatic osteosarcoma

Respiratory failure due to pulmonary metastasis is the major cause of death for patients with osteosarcoma. However, the molecular basis for metastasis of osteosarcoma is poorly understood. Recently, ezrin, a member of the ERM family of proteins, has been associated with osteosarcoma metastasis to the lungs. The small molecule NSC 668394 was identified to bind to ezrin, inhibit in vitro and in vivo cell migration, invasion, and metastatic colony survival. Reported herein are the design and synthesis of analogues of NSC 668394, and subsequent functional ezrin inhibition studies. The binding affinity was characterized by surface plasmon resonance technique. Cell migration and invasion activity was determined by electrical cell impedance methodology. Optimization of a series of heterocyclic-dione analogues led to the discovery of compounds 21k and 21m as potential novel antimetastatic agents.

4-Piperidinecarboxamide modulators of vanilloid VR1 receptor

This invention is directed to vanilloid receptor VR1 ligands. More particularly, this invention relates to hetero isonipecotic amides that are potent modulators of VR1 which are useful for the treatment and prevention of disease conditions in mammals.

Novel transient receptor potential vanilloid 1 receptor antagonists for the treatment of pain; Structure-activity relationships for ureas with quinoline, isoquinoline, quinazoline, phthalazine, quinoxaliue, and cinnoline moieties

Novel transient receptor potential vanilloid 1 (TRPV1) receptor antagonists with various bicyclic heteroaromatic pharmacophores were synthesized, and their in vitro activity in blocking capsaicin activation of TRPV1 was assessed. On the basis of the contribution of these pharmacophores to the in vitro potency, they were ranked in the order of 5-isoquinoline > 8-quinoline = 8-quinazoline > 8-isoquinoline ≥ cinnoline ≈ phthalazine ≈ quinoxaline ≈ 5-quinoline. The 5-isoquinoline-containing compound 14a (hTRPV1 IC50 = 4 nM) exhibited 46% oral bioavailability and in vivo activity in animal models of visceral and inflammatory pain. Pharmacokinetic and pharmacological properties of 14a are substantial improvements over the profile of the high-throughput screening hit 1 (hTRPV1 IC50 = 22 nM), which was not efficacious in animal pain models and was not orally bioavailable.