7-(Ethoxycarbonyl)-6,8-dimethyl-2-phenyl-1(2H)-phthalazinone derivatives: synthesis and inhibitory effects on platelet aggregation

Sugimoto, Akihiro; Tanaka, Hiromichi; Eguchi, Y.; Ito, Shigeru; Takashima, Yoshimi; Ishikawa, Masayuki

doi:10.1021/jm00376a013

Cited by 27 publications

(7 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Mono-arylhydrazines I are important intermediates in the synthesis of a number of heterocycles, including indoles [1] and some azoles (for example [2–3]), many of which exhibit biological activity and are used in drug development [4–6]. Arylhydrazines are also key intermediates in the preparation of stable radicals such as verdazyl [7–9] and benzo[1,2,4]triazinyls [10–12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of oleophilic electron-rich phenylhydrazines

Jankowiak

Kaszyński

2012

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryPhenylhydrazines 1 substituted with two or three long-chain alkyl, alkoxy or alkylsulfanyl groups were successfully prepared by acid-induced removal of the Boc group in hydrazides 2. The reaction is carried out with 5 equivalents of TfOH in CF3CH2OH/CH2Cl2 at −40 °C for 1.5 min. Under these conditions, the deprotected hydrazine 1 is fully protonated, which increases its stability in the reaction medium. The hydrazines were isolated in 60–86% yields and purities >90%. The hydrazides 2 were obtained in 43–71% yields from aryl bromides 5, which were lithiated with t-BuLi and subsequently reacted with di-tert-butyl azodicarboxylate (DTBAD).

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of oleophilic electron-rich phenylhydrazines

Jankowiak

Kaszyński

2012

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…All synthesized compounds were showed no appreciable effect on platelet aggregation induced by adenosine diphosphate, but most of them inhibited effectively the arachidonic acid (AA) induced platelet aggregation. The 2-phenyl derivatives, and ortho-substituted 2-phenyl derivatives showed the most potent inhibition of all compounds (Sugimoto et al, 1984). Antihypersensitivity agent is a 4-(p-chlorobenzyl)-2-[Nmethyl-perhydroazepinyl-(4)]-1-(2H)phthalazinone hydrochloride (azelastine) (Inoue.…”

Section: Azelastinmentioning

confidence: 99%

Pharmacological activities of various phthalazine and phthalazinone derivatives

Int¹

2019

Preprint

View full text Add to dashboard Cite

Various pthalazine derivatives have been synthesized and tested for their diverse biological activities. Pthalazine derivatives have been exhibited pharmacological activities like antitumor, PARP-1 inhibitors, antimicrobial, antivirus, antihistamine-H1, antiallergic rhinitis, antifungal, anti-inflammatory, anti-proliferative, COX-2 inhibitor, LOX-5 inhibitor, antidiabetes, and other biological activities like imaging agent. Pthalazine derivatives were also used as agrochemicals and chemicals. Various synthetic aspects indicate that pthalazines derivatives are easy to synthesize which can produce a wide variety of activity.

show abstract

“…This compound provided to be an in vitro inhibitor of platelet aggregation induced by ADP and arachidonic acid (AA) [114]. Subsequent studies showed that the inclusion of phenyl groups at N2 of 87 resulted in derivatives which inhibited platelet aggregation induced by AA without affecting aggregation induced by ADP (compound 88) [115] and that this activity was markedly increased when the hydroxymethyl group at C4 was replaced by a hydrogen atom (compound 89, Figure 16) or by an ortho- …”

Section: Antiplatelet Agentsmentioning

confidence: 99%