Synthesis and biological evaluation of nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide as potential antiplatelet agents

Wang, Xiaoli; Wang, Linna; Huang, Zhangjian; Sheng, Xiao; Li, Tingting; Ji, Hui; Xu, Jinyi; Zhang, Yihua

doi:10.1016/j.bmcl.2013.02.035

Cited by 19 publications

(14 citation statements)

References 15 publications

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“…Furthermore, they produced better neurobehavioral improvement coupled with higher levels of antioxidant SOD, GSH, GSH-Px, and optimal blood-brain barrier (BBB) penetration compared to NBP [16, 17]. This could be crucial for future improvement of poststroke cerebral circulation [16, 18]. Other H 2 S releasing compounds, such as 6-amino-3-n-butylphthalide (Figure 1) and (±)-6-(4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy)hexyl 2-(1-acetoxypentyl) benzoate, also showed superior antiplatelet aggregation and antithrombotic properties compared to NBP, aspirin, or ticlopidine hydrochloride [19], with an additional protection against collagen and adrenaline induced thrombosis [18, 19].…”

Section: Nbp and Ischemic Strokementioning

confidence: 99%

A Review of Recent Advances in Neuroprotective Potential of 3-N-Butylphthalide and Its Derivatives

Abdoulaye

Guo

2016

BioMed Research International

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The research of alternative treatment for ischemic stroke and degenerative diseases has always been a priority in neurology. 3-N-Butylphthalide (NBP), a family of compounds initially isolated from the seeds of Apium graveolens Linn., has shown significant neuroprotective effects. Previous extensive studies have demonstrated that NBP promotes a better poststroke outcome and exerts a multitargeted action on several mechanisms, from oxidative stress to mitochondrial dysfunction to apoptosis to inflammation. Additionally, recent findings on several neurological disorders have shown that NBP's beneficial effects extend beyond the management of stroke. However, despite the increasing number of studies toward a better understanding and the rapid advances made in therapeutic options, to date, dl-3-N-butylphthalide, a synthetic variation of l-3-N-butylphthalide, remains the only clinically approved anti-ischemic agent in China, stressing the difficulties for a viable and effective transition from experimental to clinical practice. Events indicate that NBP, due to its multitargeted effect and the adaptability of its basic structure, can be an important game changer and a precursor to a whole new therapeutic approach to several neurological conditions. The present review discusses recent advances pertaining to the neuroprotective mechanisms of NBP-derived compounds and the possibility of their clinical implementation in the management of various neurological conditions.

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Section: Nbp and Ischemic Strokementioning

confidence: 99%

A Review of Recent Advances in Neuroprotective Potential of 3-N-Butylphthalide and Its Derivatives

Abdoulaye

Guo

2016

BioMed Research International

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“…Then compound 2 was obtained by the treatment of compound 1 with Pd/C in 94.5% yield [17]. Afterward, compound 2 was nitrated using potassium nitrate in H 2 SO 4 to obtain the corresponding nitro compound 3, which was reduced with iron powder and NH 4 Cl in THF/H 2 O to give amino compound 4 [18]. Compound 4 was subjected to standard Sandmeyer reactions to give the 6-bromobutylphthalide (5).…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of novel n-butyphthalide derivatives as promising botanical fungicides

Luo

et al. 2020

Zeitschrift Für Naturforschung C

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In order to obtain novel botanical fungicides, three series of novel 6-substituted n-butyphthalide derivatives have been designed and synthesized via nucleophilic addition, reduction, nitrification, amination, sulfonation, Sandmeyer and Suzuki reaction. The mycelium growth rate method was used to evaluate the inhibition activity against eight phytopathogenic fungi in vitro. Preliminary bioassay tests showed that compounds 6f, 6n, 6p, 6r and 7a exhibited better activity for some fungi at 50 μg/mL than the positive drug hymexazol and lead compound n-butyphthalide (NBP). The preliminary structure–activity relationships indicated that the antifungal activity is significantly affected by the substituents on the benzene ring.

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“…The structural basis on which NBP exerts its bioactivities has not yet been elucidated clearly, but some derivatives with substituted groups at position 6 of NBP have been reported to have similar activities as NBP 19,20 (4,5). In particular, the ring-opening prodrug (6) of 6-bromo-3-n-butylphthalide (5) had been approved by CFDA for clinical trials in China in 2016.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of 3-n-Butylphthlide-Edaravone Hybrids as Potential Agents for the Treatment of Cerebral Ischemia

2019

Chem Sci Trans

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A series of 3-n-butylphthlide-edaravone hybrids was synthesized and their structures were elucidated on the basis of analytical and spectral (IR, 1 H NMR, 13 C NMR, MS and elemental analyses) data. These synthesized compounds were evaluated for their in vitro antiplatelet by the turbidimetric method and antioxidant activities by the Fenton method. The results indicated that compound 11a showed similar potency of antiplatelet aggregation as 3-n-butylphthlide and stronger ·OH scavenging activity (IC 50 value of 2.87 mM) than edaravone (IC 50 value of 3.57 mM).

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Synthesis and biological evaluation of nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide as potential antiplatelet agents

Cited by 19 publications

References 15 publications

A Review of Recent Advances in Neuroprotective Potential of 3-N-Butylphthalide and Its Derivatives

A Review of Recent Advances in Neuroprotective Potential of 3-N-Butylphthalide and Its Derivatives

Design and synthesis of novel n-butyphthalide derivatives as promising botanical fungicides

Design, Synthesis and Biological Evaluation of 3-n-Butylphthlide-Edaravone Hybrids as Potential Agents for the Treatment of Cerebral Ischemia

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