Synthesis and c-Src inhibitory activity of imidazo[1,5-a]pyrazine derivatives as an agent for treatment of acute ischemic stroke

Mukaiyama, Harunobu; Nishimura, Toshihiro; Kobayashi, Satoko; Ozawa, Tomonaga; Kamada, Noboru; Komatsu, Yoshimitsu; Kikuchi, Shinji; Oonota, Hideki; Kusama, Hiroshi

doi:10.1016/j.bmc.2006.10.041

Cited by 51 publications

(33 citation statements)

References 29 publications

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“…16) Therefore, the formation of imidazo [1,5-a] pyrazin-8(7H)-one derivatives (4) could be explained by the further reaction of the 3 with excessive TosMIC. Indeed, the reaction of 3a with TosMIC was reported to give 4a in high yield.…”

Section: Resultsmentioning

confidence: 99%

A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1<i>H</i>)-Pyrazinones of Biological Interest

Saijo

Sekiya

Tamai

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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In this report, we describe a new method for the synthesis of densely functionalized 2(1H)-pyrazinones. Treatment of mesoionic 1,3-oxazolium-5-olates with carbanions derived from activated methylene isocyanides (p-toluenesulfonylmethyl isocyanide (TosMIC) and ethyl isocyanoacetate) causes a novel ring transformation affording 2(1H)-pyrazinones in moderate to high yields. The cytotoxicity and antibacterial activity of some of the obtained products were studied and some of the products exhibited tumor-specific cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1<i>H</i>)-Pyrazinones of Biological Interest

Saijo

Sekiya

Tamai

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Previously, we reported that electron-donating substituents on the phenyl ring, especially the methoxy group, enhanced the c-Src inhibitory activity. 17) A single methoxy group at either the 3Ј-(7g) or 4Ј-position (7h) reduced the inhibitory activity against c-Src kinase compared to the dimethoxy derivative 7f. Removing the methoxy group on the aniline phenyl ring (7i) resulted in activity similar to that of monomethoxy derivatives 7g and 7h.…”

Section: Discovery Of Novel 2-anilinopyrazolo[15-a]pyrimidine Derivamentioning

confidence: 99%

Discovery of Novel 2-Anilinopyrazolo[1,5-a]pyrimidine Derivatives as c-Src Kinase Inhibitors for the Treatment of Acute Ischemic Stroke

Mukaiyama

Nishimura

Shiohara

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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We synthesized a series of novel 2-anilinopyrazolo[1,5-a]pyrimidine derivatives and evaluated their ability to inhibit c-Src kinase; 7-(2-amino-2-methylpropylamino)-5-cyclopropyl-2-(3,5-dimethoxyphenylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide 7o and 7-(2-amino-2-methylpropylamino)-2-(3,5-dimethoxyphenylamino)-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide 7f showed potent inhibitory activity. Compound 7f inhibited c-Src selectively and exhibited satisfactory central nervous system (CNS) penetration. Furthermore, 7f.HCl reduced the infarct volume in vivo in a rat middle cerebral artery (MCA) occlusion model when administrated intraperitoneally.

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“…Fused aromatic heterocycles are among the most important compound classes in drug discovery and also play a pivotal role in living organisms . In particular, such scaffolds can be found as building blocks for DNA (guanine and adenine) and also in many approved drugs, including sildenafil, zolpidem, and trazodone, and in medicinal chemistry studies (i.e., tyrosine kinase c‐Src inhibitors or P38α inhibitors ) (Fig. ).…”

Section: Introductionmentioning

confidence: 99%

A Convenient One‐pot Synthesis of N‐Fused 1,2,4‐Triazoles via Oxidative Cyclization Using Trichloroisocyanuric Acid

Bhatt

Singh

Kant

2019

Journal of Heterocyclic Chem

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A facile one‐pot synthesis of N‐fused 1,2,4‐triazoles from heterocyclic hydrazines and aldehydes is reported. The reaction is efficiently promoted by trichloroisocyanuric acid to afford the desired products mostly in high yields and in relatively short time. The mild nature of the synthesis and short reaction time are notable advantages of the developed protocol. This protocol is effective toward various substrates having different functionalities.

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Synthesis and c-Src inhibitory activity of imidazo[1,5-a]pyrazine derivatives as an agent for treatment of acute ischemic stroke

Cited by 51 publications

References 29 publications

A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1<i>H</i>)-Pyrazinones of Biological Interest

A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1<i>H</i>)-Pyrazinones of Biological Interest

Discovery of Novel 2-Anilinopyrazolo[1,5-a]pyrimidine Derivatives as c-Src Kinase Inhibitors for the Treatment of Acute Ischemic Stroke

A Convenient One‐pot Synthesis of N‐Fused 1,2,4‐Triazoles via Oxidative Cyclization Using Trichloroisocyanuric Acid

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