Stereoselective Synthesis of (+)-Nephrosteranic Acid by Ring-Closing Metathesis and Its Biological Evaluation

Perepogu, Arun Kumar; Raman, D.; Murty, U. S. N.; Rao, V. Jayathirtha

doi:10.1080/00397910903011337

Cited by 17 publications

(10 citation statements)

References 21 publications

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“…[38][39][40][41] Another drawback of such an approach would be that butenolide is expensive and prone to polymerisation, whereas the compounds used in our method (maleic or citraconic anhydride) are cheap and stable. through a copper-catalysed 1,4-addition to the stem compound butenolide followed by direct trapping of the enolate with an alkyl iodide.…”

Section: Resultsmentioning

confidence: 99%

A Diels–Alder/Retro‐Diels–Alder Approach for the Enantioselective Synthesis of Microbial Butenolides

et al. 2012

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Several volatile lactones have been identified from the endophytic fungus Geniculosporium sp. isolated from the rockrose Cistus monspeliensis, commonly known as Montpelier cistus. The fungal volatiles were collected from agar‐plate cultures by using a closed‐loop stripping apparatus and the headspace extracts were analysed by GC–MS. Structures for these lactones were proposed from their mass spectral data. The suggested structures were verified by synthesis of reference compounds through a Diels–Alder/retro‐Diels–Alder approach. This synthetic method was also successfully applied in the synthesis of butenolides that are signalling molecules from streptomycetes. For the enantioselective synthesis of these butenolides a modified route including an enantioselective Diels–Alder reaction was used.

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Section: Resultsmentioning

confidence: 99%

A Diels–Alder/Retro‐Diels–Alder Approach for the Enantioselective Synthesis of Microbial Butenolides

et al. 2012

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“…[4e] Nephrosteranic acid (4 a) showed potent antibacterial activity against Gram-positive bacterial strains Staphylococcus aureus (MTCC 737), Staphylococcus epidermidis (MTCC 435), and Gram-negative strains Escherichia coli (MTCC 1687) and Pseudomonas aeruginosa (MTCC 1688). [9] It also showed antifungal activity, which was more than 80% against Aspergillus niger and more than 60% against other fungal strains in comparison with Clotrimazole as reference drug. When tested for cytotoxic activity against human acute monocytic leukemia and human leukemic monocyte lymphoma cell lines, nephrosteranic acid (4 a) showed IC 50 of 27.66 and 24.45 μg/mL, respectively, in comparison to Etoposide drug with IC 50 = 1.4 and 1.2 μg/mL activity, respectively.…”

Section: Introductionmentioning

confidence: 92%

“…Rao and co-workers [66] in 2010 reported the synthesis of (+)-nephrosteranic acid (4 a) based on asymmetric epoxidation as key step (Scheme 39). The α,β-unsaturated ester 192 (88 : 12 E/Z) obtained from 191 on ester reduction gave allyl alcohol 193.…”

Section: Nephrosteranic Acid (4 A) and Roccellaric Acid (4 B)mentioning

confidence: 99%

“…When tested for cytotoxic activity against human acute monocytic leukemia and human leukemic monocyte lymphoma cell lines, nephrosteranic acid (4 a) showed IC 50 of 27.66 and 24.45 μg/mL, respectively, in comparison to Etoposide drug with IC 50 = 1.4 and 1.2 μg/mL activity, respectively. [9] Protolichesterinic acid (2 b) along with other lichen metabolites has been indicated for antistaphylococcic activity. It and also dihydroprotolichesterinic acid (5) inhibit the growth of Gram negative bacteria.…”

Section: Introductionmentioning

confidence: 99%

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Evolution of Strategies in Paraconic Acids Synthesis

2020

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Various syntheses of different paraconic acids over the last seventeen years have been abstracted here. Paraconic acids have either a methylene or methyl group at the 4-position of the γ-butyrolactone with a common C-3 carboxylic acid group and a long alkyl chain. Several possibilities of relative configurations give rise to distinct set of paraconic acids, which are also categorized in this review. Various strategies based on chiral catalytic methods, chiral pool, chiral auxiliary, resolution and other methods were engaged in the synthesis of different paraconic acids. A few members are yet to be synthesized and this compilation might entice future synthetic attempts on them.

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“…Briefly, it began with the preparation of hydroxyl lactones 1a-e where the enantiocontrol was imposed by the asymmetric dihydroxylation of trans-configured -unsaturated carboxylic ester with AD mix-® or AD mix-®. The resulting lactones were deshydrated giving butenolides 2a-e. For the two next steps we modified the approach according to Perepogu et al 18 A Gilman addition of a vinyl group was added trans-selectively to the C=C bond giving vinyl lactones 3a-e, followed by an oxidation of the double bond allowing access to HO 2 C-substituted lactones 4a-e. Activation by Stiles' reagent, followed by amino-methylation in situ fragmentation provided the -methylene butyrolactones 5a-e. Then, the target enantiopure lichesterinic acid derivatives 6a-e were obtained by isomerization of the double bond using NEt 3 in DMF. This synthesis is achieved in seven steps and around 10% overall yield with good enantioselective excess determined by chiral HPLC.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis and biological evaluation of potential antibacterial butyrolactones

Sweidan¹,

Chollet-Krugler²,

Weghe³

et al. 2016

Bioorganic & Medicinal Chemistry

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Novel butyrolactone analogues were designed and synthesized based on the known lichen antibacterial compounds, lichesterinic acids (B-10 and B-11), by substituting different functional groups on the butyrolactone ring trying to enhance its activity. All synthesized butyrolactone analogues were evaluated for their in vitro antibacterial activity against Streptococcus gordonii. Among the derivatives, B-12 and B-13 had the lowest MIC of 9.38μg/mL where they have shown to be stronger bactericidals, by 2-3 times, than the reference antibiotic, doxycycline. These two compounds were then checked for their cytotoxicity against human gingival epithelial cell lines, Ca9-22, and macrophages, THP-1, by MTT and LDH assays which confirmed their safety against the tested cell lines. A preliminary study of the structure-activity relationships unveiled that the functional groups at the C position had an important influence on the antibacterial activity. An optimum length of the alkyl chain at the C position registered the best antibacterial inhibitory activity however as its length increased the bactericidal effect increased as well. This efficiency was attained by a carboxyl group substitution at the C position indicating the important dual role contributed by these two substituents which might be involved in their mechanism of action.

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Stereoselective Synthesis of (+)-Nephrosteranic Acid by Ring-Closing Metathesis and Its Biological Evaluation

Cited by 17 publications

References 21 publications

A Diels–Alder/Retro‐Diels–Alder Approach for the Enantioselective Synthesis of Microbial Butenolides

A Diels–Alder/Retro‐Diels–Alder Approach for the Enantioselective Synthesis of Microbial Butenolides

Evolution of Strategies in Paraconic Acids Synthesis

Design, synthesis and biological evaluation of potential antibacterial butyrolactones

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