256443-12-6

Basic information

• Product Name: 1-(3,5-Dichloropyridin-4-ylmethyl)-6-methoxy-4-(1H-1,2,4-triazol-1-yl)phthalazine
• Synonyms: Z-15370A
• CAS NO: 256443-12-6
• Molecular Formula: C₁₇H₁₂Cl₂N₆O
• Molecular Weight: 387.23079
• Mol File: 256443-12-6.mol

Chemical Properties

• CAS DataBase Reference: 1-(3,5-Dichloropyridin-4-ylmethyl)-6-methoxy-4-(1H-1,2,4-triazol-1-yl)phthalazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,5-Dichloropyridin-4-ylmethyl)-6-methoxy-4-(1H-1,2,4-triazol-1-yl)phthalazine(256443-12-6)
• EPA Substance Registry System: 1-(3,5-Dichloropyridin-4-ylmethyl)-6-methoxy-4-(1H-1,2,4-triazol-1-yl)phthalazine(256443-12-6)

Safety Data

• Hazardous Substances Data: 256443-12-6(Hazardous Substances Data)

Usage

Chemical class

Phthalazine derivatives

Contains a 1,2,4-triazole ring

Commonly found in various pharmaceutical compounds

Potential pharmacological applications

As an inhibitor or modulator of specific enzymes or receptors in the body

Novel chemical compound

Makes it a potential candidate for further medicinal chemistry research and drug development

Unique chemical features

Of interest to scientists and researchers studying its potential therapeutic effects in various disease conditions

Upstream product

• 256443-02-4 1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-2H-phthalazin-1-one 
• 288-88-0 1,2,4-Triazole 
• 256443-81-9 4-chloro-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxyphthalazine 

Relevant articles and documents

Phthalazine PDE IV inhibitors: Conformational study of some 6-methoxy-1,4-disubstituted derivatives

This report describes the detailed conformational analysis and synthesis of a series of phthalazine phosphodiesterase-type (IV) (PDE IV) inhibitors bearing either mono- or dichloro 4-methylenepyridine at the 'down' position of the phthalazine nucleus or different heterocycles at the 'top' position 4 of the phthalazine moiety. Both the mono- and dichloro 4-methylenepyridine units linked at carbon C1 of the phthalazine nucleus show identical conformational behaviour with the substituent preferentially oriented towards the external part of the molecule and the pyridine plane almost orthogonal to that of phthalazine ring. The heterocyclic five-membered rings linked at carbon C4 of phthalazine show quite different conformational behaviour. The 1,3-thiazole ring exists in a well-defined conformation almost coplanar with respect to the phthalazine nucleus while the 1,2,4-triazole and the 1,3-diazole heterocycles show a great conformational freedom with large torsion angles. Compound 3 bearing the thiazole ring at C4 displays the major biological activity, thus suggesting that a planar and rather rigid conformation of the pentacycle should favour the PDE IV inhibition capacity of this class of compounds.

Phthalazine derivatives phosphodiesterase 4 inhibitors

The present invention provides a compound selected from the group including: 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-phenyl-phthalazine; 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazin-2-carboxylic acid methyl ester; benzyl-{3-{1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl}-prop-2-ynyl}-methyl-amine; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-5-(5-morpholin-4-yl-pent-1-ynyl)-phthalazine dihydrochloride; 3-{1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl}-prop-2-yn-1-ol; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-morpholin-4-yl-phthalazine; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-(1,2,4)triazol-1-yl-phthalazine; N→O derivatives thereof; and pharmaceutically acceptable salts thereof. The invention also provides a pharmaceutical composition which includes a therapeutically effective amount of the above compound in admixture with a suitable carrier.

Phthalazine PDE4 inhibitors. Part 2: The synthesis and biological evaluation of 6-methoxy-1,4-disubstituted derivatives

This communication describes the synthesis and in vitro evaluation of a novel and potent series of phosphodiesterase type IV (PDE4) inhibitors. The compounds described present substituents in position 4 of the phthalazine ring to replace the commonly obse