Stereoselective synthesis of spirotryprostatin A

Kitahara, Katsushi; Shimokawa, Jun; Fukuyama, Tohru

doi:10.1039/c3sc52525b

Cited by 33 publications

(13 citation statements)

References 35 publications

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“…Fortunately, the synthesis of indole DKPs has attracted attention from chemists. Various synthetic methods of these compounds have been explored, such as the synthesis of spirotryprostatin A (Figure 1) (Cheng et al, 2011; Kitahara et al, 2014). Moreover, developing new, harmless antimicrobial agents for foods and plants that are derived from natural compounds has attracted widespread attention (Zhao et al, 2017; Alejo-Armijo et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activity, Structure-Activity Relationship, and Molecular Docking Studies of Indole Diketopiperazine Alkaloids

Jia

Liu

et al. 2019

Front. Chem.

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Strategies for the synthesis of indole diketopiperazine alkaloids (indole DKPs) have been described and involve three analogs of indole DKPs. The antimicrobial activity and structure-activity relationship (SAR) of 24 indole DKPs were explored. Compounds 3b and 3c were found to be the most active, with minimum inhibitory concentrations (MIC) values in the range of 0.94–3.87 μM (0.39–1.56 μg/mL) against the four tested bacteria (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli). Furthermore, compounds 4a and 4b displayed broad-spectrum antimicrobial activity with MIC values of 1.10–36.9 μM (0.39–12.5 μg/mL) against all tested bacteria and plant pathogenic fungi (Colletotrichum gloeosporioides, Valsa mali, Alternaria alternata and Alternaria brassicae). According to the in silico study, compounds 3c showed significant binding affinity to the FabH protein from Escherichia coli, which has been identified as the key target enzyme of fatty acid synthesis (FAS) in bacteria. Therefore, these compounds are not only promising new antibacterial agents but also potential FabH inhibitors.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activity, Structure-Activity Relationship, and Molecular Docking Studies of Indole Diketopiperazine Alkaloids

Jia

Liu

et al. 2019

Front. Chem.

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“…Changing the palladium source to Pd2(dba)3 and heating in dimethylacetamide (DMA) [12] forced the cyclization and led to the desired 7-membered ring carbamate 9a in reasonable yield as a E/Z mixture of isomers (Table 3, Conditions B, entry 2). Addition of P(o-Tol)3 (60 mol%) to the previous conditions had a dramatic effect, [13] leading to the same carbamate 9a but in a 94% yield as a single Z-isomer (Table 3, Conditions C, entry 3). When these conditions were applied to 8b, the same observations were made and better yield and selectivities were obtained using the combination Pd2(dba)3/P(o-Tol)3/NEt3 in DMA (entry 5).…”

Section: Resultsmentioning

confidence: 99%

A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates

et al. 2017

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Free-radical carbo-alkenylation of N-aryl, N-benzyl, and N-phenethyl-ene-carbamates with a disulfone provides vinylsulfones which may then be functionalized and engaged in Heck-type coupling to furnish highly substituted 5-, 6-and 7-membered nitrogen heterocycles. Grignardmediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the aspidosperma family.

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“…Ultimately deprotection of the silyl ether was carried out using HF-pyridine complex and compound 4 were obtained in 85% yields. 10 Final cleavage of the acetyl group was done by using a methanolic solution of ammonia, to afford quantitatively compound 5.…”

Section: Resultsmentioning

confidence: 99%

Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate: Towards new carbonic anhydrase glycoinhibitors

Ombouma¹,

Vullo²,

Supuran³

et al. 2014

Bioorganic & Medicinal Chemistry

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a b s t r a c tFerrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate allowed the preparation of hydroxysulfamide glycosides in good yields with a good a stereoselectivity. A variety of monosaccharide derivatives was synthesized using this new methodology leading to selective and powerful glycoinhibitors of the tumor associated carbonic anhydrases (CA, EC 4.2.1.1) isoforms CA IX and CA XII.

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Stereoselective synthesis of spirotryprostatin A

Cited by 33 publications

References 35 publications

Synthesis, Antimicrobial Activity, Structure-Activity Relationship, and Molecular Docking Studies of Indole Diketopiperazine Alkaloids

Synthesis, Antimicrobial Activity, Structure-Activity Relationship, and Molecular Docking Studies of Indole Diketopiperazine Alkaloids

A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates

Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate: Towards new carbonic anhydrase glycoinhibitors

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