5784-45-2

Basic information

• Product Name: 1-CHLOROPHTHALAZINE
• Synonyms: 1-Chlorophthalazine;NSC 71104;1-Chlorophthalazine Discontinued See C379660;Hydralazine IMpurity 02;Hydralazine Chloro IMpurity;1-Chloro-2,3-benzodiazine;Phthalazine, 1-chloro-
• CAS NO: 5784-45-2
• Molecular Formula: C₈H₅ClN₂
• Molecular Weight: 164.59
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 5784-45-2.mol

Chemical Properties

• Melting Point: 109-112°C
• Boiling Point: 364.3 °C at 760 mmHg
• Flash Point: 205.6 °C
• Appearance: Brown Solid
• Density: 1.349g/cm³
• Vapor Pressure: 4.43E-07mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 1.74±0.10(Predicted)
• Water Solubility: Insoluble in water. Soluble in dichloromethane, ethanol and methanol.
• Sensitive: Moisture Sensitive
• Stability: Moisture Sensitive
• CAS DataBase Reference: 1-CHLOROPHTHALAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLOROPHTHALAZINE(5784-45-2)
• EPA Substance Registry System: 1-CHLOROPHTHALAZINE(5784-45-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 5784-45-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Chlorophthalazine is used as a pharmaceutical intermediate for the synthesis of various drugs. Its chemical structure allows it to be a key component in the development of new medications, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Medical Isotopes Production:
1-Chlorophthalazine is also employed in the production of medical isotopes, which are essential for diagnostic and therapeutic applications in the field of nuclear medicine. These isotopes play a crucial role in the detection and treatment of various diseases, including cancer, cardiovascular conditions, and neurological disorders.

InChI:InChI=1/C10H11N3/c1-7-4-2-3-5-8(7)9-6-10(11)13-12-9/h2-6H,1H3,(H3,11,12,13)

Upstream product

• 119-39-1 phthalazone 
• 10025-87-3 trichlorophosphate 
• 119-67-5 o-carboxybenzaldehyde 
• 253-52-1 PHTHALAZINE 
• 119-39-1 1-hydroxy-2,3-benzodiazine 

Downstream Products

• 24953-56-8 1-methoxyphthalazine 
• 90915-02-9 1-ethoxyphthalazine 
• 24953-63-7 α-Phenyl-1-phthalazinacetonitril 
• 109127-95-9 sulfanilic acid phthalazin-1-ylamide 
• 109516-21-4 toluene-4-sulfonic acid-(N'-phthalazin-1-yl-hydrazide); hydrochloride 
• 100537-30-2 1-Phenoxy-phthalazin 
• 253-52-1 PHTHALAZINE 
• 496-12-8 isoindoline 
• 19064-69-8 phthalazin-1-ylamine 
• 119-39-1 phthalazone 
• 85236-43-7 1-(4-hydroxyanilino)phthalazine 
• 13969-11-4 10-Oxo-3,4-benzo-dihydropyridazino-chinazolin 
• 7134-95-4 1'H-1,2'-biphthalazinyl-1'-one 

Relevant articles and documents

Design and Synthesis of 1,2-Bis(hydroxymethyl)pyrrolo[2,1- a]phthalazine Hybrids as Potent Anticancer Agents that Inhibit Angiogenesis and Induce DNA Interstrand Cross-links

Hybrid molecules are composed of two pharmacophores with different biological activities. Here, we conjugated phthalazine moieties (antiangiogenetic pharmacophore) and bis(hydroxymethyl)pyrrole moieties (DNA cross-linking agent) to form a series of bis(hydroxymethyl)pyrrolo[2,1-a]phthalazine hybrids. These conjugates were cytotoxic to a variety of cancer cell lines by inducing DNA damage, arresting cell cycle progression at the G2/M phase, triggering apoptosis, and inhibiting vascular endothelial growth factor receptor 2 (VEGFR-2) in endothelial cells. Among them, compound 29d encapsulated in a liposomal formulation (e.g., 29dL) significantly suppressed the growth of small-cell lung cancer cell (H526) xenografts in mice. Based on immunohistochemical staining, the tumor xenografts in mice treated with 29dL showed time-dependent decreases in the intensity of CD31, a marker of blood vessels, whereas the intensity of γ-H2AX, a marker of DNA damage, increased. The present data revealed that the conjugation of antiangiogenic and DNA-damaging agents can generate potential hybrid agents for cancer treatment.

Design and synthesis of phthalazine-based compounds as potent anticancer agents with potential antiangiogenic activity via VEGFR-2 inhibition

In the designed compounds, either a biarylamide or biarylurea moiety or an N-substituted piperazine motif was linked to position 1 of the phthalazine core. The anti-proliferative activity of the synthesised compounds revealed that eight compounds (6b, 6e, 7b, 13a, 13c, 16a, 16d and 17a) exhibited excellent broad spectrum cytotoxic activity in NCI 5-log dose assays against the full 60 cell panel with GI50 values ranging from 0.15 to 8.41 μM. Moreover, the enzymatic assessment of the synthesised compounds against VEGFR-2 tyrosine kinase showed the significant inhibitory activities of the biarylureas (12b, 12c and 13c) with IC50s of 4.4, 2.7 and 2.5 μM, respectively, and with 79.83, 72.58 and 71.6% inhibition of HUVEC at 10 μM, respectively. Additionally, compounds (7b, 13c and 16a) were found to induce cell cycle arrest at S phase boundary. Compound 7b triggered a concurrent increase in cleaved caspase-3 expression level, indicating the apoptotic-induced cell death.

TOLL-LIKE RECEPTOR 8 (TLR8)-SPECIFIC ANTAGONISTS AND METHODS OF MAKING AND USES THEREOF

Toll-like receptor 8 (TLR8)-specific inhibitors and methods of using the same in individuals having an autoimmune disease or an inflammatory disorder.

BIS(HYDROXYMETHYL) PYRROLOPHTHALAZINE HYBRIDS, PREPARATION METHODS AND USES THEREOF

Disclosed herein are novel bifunctional compounds and their uses for the treatment and/or prophylaxis of cancers. The bifunctional compound disclosed herein has the structure of formula (I).

Identification of new potent phthalazine derivatives with VEGFR-2 and EGFR kinase inhibitory activity

Efforts to develop new antitumor agents are now directed towards multitarget therapies that are believed to have high potency and low tendency to resistance compared to conventional drugs. Herein, we highlighted the synthesis and antitumor activity of five series of phthalazine-based compounds featuring a variety of bioactive chemical fragments at position 1 of the phthalazine nucleus. The antitumor activity of the target compounds was performed against fourteen cancer cell lines where all compounds were active in the nanomolar level. In addition, the mechanism of action of the target compounds was investigated through an enzymatic inhibitory assay against VEGFR-2 and EGFR kinases, revealing potent and preferential activity toward VEGFR-2. Binding mode of the most active compounds was studied using docking experiment.

Synthesis and in vitro evaluation of hydrazinyl phthalazines against malaria parasite, Plasmodium falciparum

In this report, we describe the synthesis of 1-(Phthalazin-4-yl)-hydrazine using bronsted acidic ionic liquids and demonstrate their ability to inhibit asexual stage development of human malaria parasite, Plasmodium falciparum. Through computational studies, we short-listed chemical scaffolds with potential binding affinity to an essential parasite protein, dihydroorotate dehydrogenase (DHODH). Further, these compounds were synthesized in the lab and tested against P. falciparum. Several compounds from our library showed inhibitory activity at low micro-molar concentrations with minimal cytotoxic effects. These results indicate the potential of hydralazine derivatives as reference scaffolds to develop novel antimalarials.

Synthesis, vasorelaxant activity, and molecular modeling study of some new phthalazine derivatives

New phthalazine-based vasodilators were synthesized through the chloroacylation of the starting compound 1-hydrazinophthalazine 4 to give the two key intermediates 5 and 7. These intermediates were used to alkylate various cyclic amines to furnish the final compounds 6a-h and 8a-h. Compounds were tested for their vasorelaxant activities against nor-adrenaline-induced spasm on thoracic rat aorta rings and compared to the reference drug, prazosin. Seven compounds showed higher activity than prazosin, especially compound 8d having an IC50 = 0.10 mM. Molecular modeling studies, including fitting of the synthesized compounds to a 3D-pharmacophore and their docking into optimized homology model as α1-AR antagonists showed high docking score and fit values. Most vasodilation activities of tested compounds are consistent with their molecular modeling results.

Manufacture of pure hydralazine salts

The present invention provides an improved process of preparing hydralazine hydrochloride, which involves the preparation of 1-chlorophthalazine salt and further reacting with hydrazine followed by purification of hydralazine hydrochloride, which is free of phosphate, does not contain any individual impurities more than 0.05%, total impurities less than 0.5%, and a hydrazine content of not more than 0.001%, and preferably less than 0.0003%. One benefit of improved purity is enhanced storage stability.

PHARMACEUTICAL COMPOUNDS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF

Disclosed are 1-arylamino-phthalazines, 4-arylamino-benzo[d][1,2,3]triazines, and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

Synthesis of hydrazine derivatives of pyridazine

The present invention relates to both a novel method of preparing hydralazine hydrochloride and to a novel method of preparing hydrazine derivatives of compounds containing a pyridazine ring, including, for example, pyridazines, phthalazines and other compounds containing the pyridazine ring.