Total Synthesis of Natural Product Piperodione and Its Analogues

Tiwari, Praveen Kumar; Ballav, Hemkalyan; Aidhen, Indrapal Singh

doi:10.1002/slct.201801427

Cited by 3 publications

(5 citation statements)

References 30 publications

(11 reference statements)

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“…Our study has demonstrated that piperine is not the active constituent responsible for the observed neurotrophic activity of P. retrofractum fruits. Recently, the total synthesis of piperodione ( 83 ) was reported from two groups, and 83 was verified to have NGF-potentiating activity but not cytotoxicity at all [ 147 , 148 ]. Now, with large quantities of 83 in hand, further pharmacological studies of 83 are in progress.…”

Section: Miscellaneous Natural Products With Neurotrophic Effectsmentioning

confidence: 99%

The search for, and chemistry and mechanism of, neurotrophic natural products

Kubo

Harada

2020

J Nat Med

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Neurotrophic factors, now termed neurotrophins, which belong to a class of polypeptidyl agents, have been shown to potentially be beneficial for the treatment of neurodegenerative diseases such as Alzheimer's disease, because endogenous neurotrophic factors (NGF, BDNF, NT3, NT4) have been recognized to play critical roles in the promotion of neurogenesis, differentiation, and neuroprotection throughout the development of the central nervous system. However, high-molecular weight proteins are unable to cross the blood-brain barrier and are easily decomposed by peptidase under physiological conditions. To address this issue, small molecules that can mimic the functions of neurotrophic factors would be promising alternatives for the treatment of neurodegenerative disease. We have continued to search for natural products having typical neurotrophic properties, which can cause neurogenesis, enhance neurite outgrowth, and protect neuronal death using three cellular systems (PC12, rat cortical neurons, and MEB5 cells). In this review, we summarize the neurotrophic activities and synthesis of dimeric isocuparane-type sesquiterpenes from the liverwort, Mastigophora diclados, the mechanism of neurotrophic neolignans, magnolol, honokiol and their sesquiterpene derivatives, and introduce unique neurotrophin-mimic natural products, including seco-prezizaane-type sesquiterpenes from the Illicium species, vibsane-type diterpenes from Viburnum awabuki, and miscellaneous natural products with neurotrophic effects discovered by us.

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Section: Miscellaneous Natural Products With Neurotrophic Effectsmentioning

confidence: 99%

The search for, and chemistry and mechanism of, neurotrophic natural products

Kubo

Harada

2020

J Nat Med

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“…Structure−activity relationship analysis showed that when R is an unsubstituted phenyl, the corresponding compound 1 did not show notable antiviral activity. Nevertheless, when R was a phenyl with substituents of difluoromethoxy (28) and trifluoromethyl (34) at the position 4 of benzene, the anti-TMV activity was enhanced desirably. Interestingly, compound 34 also showed the best inactivation activity (90.1%), which was similar to that of ningnanmycin (91.9%).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Amide, as one of the crucial active motifs in organic synthesis, ubiquitously exists in a large number of bioactive molecules, such as herbicidal, bactericidal, antiviral, and insecticidal molecules. , For a specific example in 2013, the methyl thiazide bearing an amide unit, as a plant activator, can be applied in many cash crops such as tobacco, rice, and cucumber to mainly control viral diseases including TMV . Notably, among the amide derivatives, α-ketoamide is a considerably special amide derivative, which not only has excellent biological activity, existing in many natural products, − polypeptides, , and many biologically active molecules, , but also serves as a precursor for a variety of transformations in the chemical synthesis. , Interestingly, our previous work has indicated that a series of synthesized α-ketoamide derivatives exhibited good anti-TMV activities for potential use in plant protection, which is rarely reported in the pesticide area.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, and Bioactivity of α-Ketoamide Derivatives Bearing a Vanillin Skeleton for Crop Diseases

Luo

Guo

et al. 2020

J. Agric. Food Chem.

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A series of novel α-ketoamide derivatives bearing a vanillin skeleton were designed and synthesized. Bioactivity tests on virus and bacteria were performed. The results indicated that some compounds exhibited excellent antitobacco mosaic virus (TMV) activities, such as compound 34 exhibited an inactivation activity of 90.1% and curative activity of 51.8% and compound 28 exhibited a curative activity of 54.8% at 500 μg mL −1 , which is equivalent to that of the commercial ningnanmycin (inactivation of 91.9% and curative of 51.9%). Moreover, the in vitro antibacterial activity test illustrated that compounds 2, 22, and 33 showed much higher activities than commercial thiodiazole copper, which could be used as lead compounds or potential candidates. The findings of transmission electron microscopy and molecular docking indicated that the synthesized compounds exhibited strong and significant binding affinity to the TMV coat protein and could obstruct the self-assembly and increment of TMV particles. This study revealed that α-ketoamide derivatives bearing a vanillin skeleton could be used as a novel potential pesticide for controlling the plant diseases.

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“…Synthesis of Starting Material 1-Morpholinopropane-1,2dione (4f). 25 SOCl 2 (0.76 mL, 10.5 mmol, 2.1 equiv) and triethylamine (1.45 mL, 10.5 mmol, 2.1 equiv) were added to a solution of pyruvic acid (0.35 mL, 5 mmol, 1.0 equiv) in dry CH 2 Cl 2 (10 mL) in turn at 0 °C. The reaction mixture was stirred for 1 h at room temperature under N 2 .…”

Section: ■ Conclusionmentioning

confidence: 99%

Modular Approach to Highly Substituted 3-Methylpyridones

Zhang,

Chen,

Zheng

et al. 2024

J. Org. Chem.

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A method has been developed for the rapid synthesis of highly substituted 3-methylpyridones via the condensation of Baylis− Hillman amines and ketones under benzoic acid catalysis. The process features readily available starting materials, broad substrate scope, high functional group tolerance, excellent regioselectivity, and gram-scale synthesis. We envision that this on-demand construction of 3-methylpyridones will provide exciting opportunities in biological research, therapeutics, and material sciences

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Total Synthesis of Natural Product Piperodione and Its Analogues

Cited by 3 publications

References 30 publications

The search for, and chemistry and mechanism of, neurotrophic natural products

The search for, and chemistry and mechanism of, neurotrophic natural products

Design, Synthesis, and Bioactivity of α-Ketoamide Derivatives Bearing a Vanillin Skeleton for Crop Diseases

Modular Approach to Highly Substituted 3-Methylpyridones

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