A Total Synthesis of the Cyclic Depsipeptide Chaiyaphumine‐A

Gholap, Somnath S.; Ugale, Sandip R.

doi:10.1002/slct.201701520

Cited by 5 publications

(3 citation statements)

References 25 publications

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“…Gholap and Ugale (2017) reported the synthesis of chaiyaphumine-A (130) by convergent-based solution phase synthesis involving protection, deprotection, coupling and cyclization reactions [18]. This novel class of peptide will the subject of much research to develop new antimalarial drugs.…”

Section: Chaiyaphuminementioning

confidence: 99%

“…Chloroquine was less effective against strains resistant to Dd2 and K1, whereas compounds 16 and 17 showed the same in vitro antimalarial activities against chloroquinesensitive 3D7 and chloroquine-resistant Dd2 and K1 strains, with no antimicrobial activity up to 30 µM [7]. The antimalarial activity of the isolated kakeromamide B peptide (18) was evaluated against asexual blood-stage and liver-stage P. falciparum (Table 19). Compound 18 exhibited moderate activity against the blood stage of P. falciparum with an EC 50 value of 8.9 µM as well as moderate liver-stage antimalarial activity against P. berghei liver schizonts with EC 50 values of 11 µM.…”

Section: Biology Activity Of Isolated and Synthesized Compoundsmentioning

confidence: 99%

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An Overview on Antimalarial Peptides: Natural Sources, Synthetic Methodology and Biological Properties

Kurniaty,

Maharani,

Hidayat

et al. 2023

Molecules

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Peptide compounds play a significant role in medicinal chemistry as they can inhibit the activity of species that cause malaria. This literature review summarizes the isolation of antimalarial peptides, the synthesis method with the detailed structure and sequences of each peptide, and discusses the biological activity of the isolated and synthesized compounds. The synthetic routes and reactions for cyclic and linear antimalarial peptides are systematically highlighted in this review including preparing building blocks, protection and deprotection, coupling and cyclization reactions until the target compound is obtained. Based on the literature data and the results, this review’s aim is to provide information to discover and synthesize more antimalarial peptide for future research.

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Section: Chaiyaphuminementioning

confidence: 99%

Section: Biology Activity Of Isolated and Synthesized Compoundsmentioning

confidence: 99%

An Overview on Antimalarial Peptides: Natural Sources, Synthetic Methodology and Biological Properties

Kurniaty,

Maharani,

Hidayat

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

“…Unfortunately, all attempts at cyclization with this reagent of 17a and 18a (entries 3 and 11) as well as using cesium chloride as an additive to promote carbonyl coordination (entries 4 and 12) failed to provide 1 in any increased yield. Uronium-based coupling reagents are well reported for their success in macrocyclizations, and as such, N,N,N ′ ,N ′ -tetramethyl- O -(1 H -benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) − and N,N,N ′ ,N ′ -tetramethyl- O -(1 H -benzotriazol-1-yl)uronium tetrafluoroborate (TBTU) − were both attempted with 17a and 18a in the absence and presence of 4-(dimethylamino)pyridine (DMAP). , In all attempted cyclizations, these uronium-based reagents provided either none or low yields of 1 . Employing HBTU with DMAP to cyclize 18a provided a 13% yield of 1 (entry 14), but in our hands, EDC·HCl with HOBt gave the best, albeit low, 15% yield of the natural product.…”

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confidence: 99%

Total Synthesis of Reniochalistatin E

et al. 2017

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Reniochalistatin E (1) is one of the five related cyclic peptides isolated from the marine sponge Reniochalina stalagmitis. The discovery of these compounds resulted from a screening program directed toward the identification of proline-rich bioactive compounds. Reniochalistatin E is the only member of the family to possess a tryptophan amino acid residue. Given the cytotoxicity observed for 1, efforts were directed toward developing a synthetic route to 1. The first total synthesis of 1 has been accomplished in a 15-step route in an overall 5.0% yield. The synthetic sample of reniochalistatin E was shown to have similar activity toward HeLa and RPMI-8226 cell lines compared to the natural sample, with IC values of 16.9 vs 17.3 μM and 4.5 vs 4.9 μM, respectively. Interestingly, both of the fully deprotected octapeptides constructed toward the synthesis of reniochalistatin E were shown to have cytotoxicity. The route provides a means to probe the structure-activity relationship of 1 and further biological investigations.

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Design, Synthesis and Biological Screening of Novel 1,3,4‐Oxadiazoles as Antitubercular Agents

Tambe¹,

Choudhari

Sarkar

et al. 2018

ChemistrySelect

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A series of novel 2,5‐disubstitued 1,3,4‐oxadiazole derivatives bearing 2,2‐dimethyl‐2,3‐dihydrobenzofuran scaffold has been synthesized and screened for antitubercular activity. All the synthesized compounds were characterized by IR, 1H NMR, 13C‐NMR and Mass spectral study. The in vitro antitubercular activity of the synthesized compounds was evaluated against Mycobacterium tuberculosis H37Ra(ATCC 25177) strain. Among the synthesized compounds, four compound displayed good antitubercular activity IC50 values in low micro‐gram range (<10 μg/mL). The antitubercular data suggested that growth inhibition MTB can be imparted by the introduction of a 4‐ trifluoromethyl phenyl acetylene substituent. Specificity of these compounds was checked by screening them for their anti‐bacterial activity against four bacterial strains (Gram‐negative strains: E. coli, S. aureus; Gram‐positive strains: P. aeruginosa and B. subtilis). None of the compound displayed antibacterial activity against any of the seleted strain. Molecular docking studies were carried out on InhA (FabI/ENR) which shows that the synthesized compounds bind at the catalytic site in a most favourable manner suggesting their potential as anti‐mycobacterial agents. The research presented here was found to be adventitious for the development of new therapeutic agents against Mycobacterium infection.

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A Total Synthesis of the Cyclic Depsipeptide Chaiyaphumine‐A

Cited by 5 publications

References 25 publications

An Overview on Antimalarial Peptides: Natural Sources, Synthetic Methodology and Biological Properties

An Overview on Antimalarial Peptides: Natural Sources, Synthetic Methodology and Biological Properties

Total Synthesis of Reniochalistatin E

Design, Synthesis and Biological Screening of Novel 1,3,4‐Oxadiazoles as Antitubercular Agents

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