A short synthesis of (±)-cherylline dimethyl ether

Kale, Bhima Y.; Shinde, Ananta; Sonar, Swapnil S.; Shingate, Bapurao B.; Kumar, Sanjeev; Ghosh, Samir; Soodamani, Venugopal; Shingare, Murlidhar S.

doi:10.3762/bjoc.5.80

Cited by 7 publications

(5 citation statements)

References 17 publications

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“…Although cherylline can be extracted from several Amaryllidaceae species, mostly from the Crinum genus ( 62 – 64 ), it is considered a rare alkaloid. Fortunately, cherylline chemical synthesis has been successfully performed through several methods ( 65 – 67 ), as reviewed in reference 68 , providing an alternative method of production. AA’s biosynthesis pathway is beginning to be uncovered ( 15 ); once the enzymes responsible for cherylline synthesis are confirmed, exogenous introduction of encoding genes into yeasts or microalgae will be an interesting strategy to produce AAs.…”

Section: Discussionmentioning

confidence: 99%

Amaryllidaceae Alkaloid Cherylline Inhibits the Replication of Dengue and Zika Viruses

Mérindol

Sow

et al. 2021

Antimicrob Agents Chemother

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Dengue fever, caused by dengue virus (DENV) is the most prevalent arthropod-borne viral disease, and is endemic in many tropical and sub-tropical parts of the world with an increasing incidence in temperate regions. The closely related flavivirus Zika virus (ZIKV) can be transmitted vertically in utero and causes congenital Zika syndrome and other birth defects. In adults, ZIKV is associated with Guillain-Barré syndrome. There are no approved antiviral therapies against neither viruses. Effective antiviral compounds are urgently needed. Amaryllidaceae alkaloids (AAs) are a specific class of nitrogen-containing compounds produced by plants of the Amaryllidaceae family with numerous biological activities. Recently, the AA lycorine was shown to present strong antiflaviviral properties. Previously, we demonstrated that Crinum jagus contained lycorine and several alkaloids of cherylline, crinine and galanthamine-types with unknown antiviral potential. In this study, we explored their biological activities. We show that C. jagus crude alkaloid extract inhibited DENV infection. Among the purified AAs, cherylline inhibited efficiently both DENV (EC 50 =8.8 μM) and ZIKV replication (EC 50 =20.3 μM), but had no effect on HIV-1 infection. Time-of-drug-addition and -removal experiments identified a post-entry step as the one targeted by cherylline. Consistently, using subgenomic replicons and replication-defective genomes, we demonstrate that cherylline specifically hinders the viral RNA-synthesis step but not viral translation. In conclusion, AAs are an underestimated source of antiflavivirus compounds, including the effective inhibitor cherylline that could be optimized for new therapeutic approaches.

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Section: Discussionmentioning

confidence: 99%

Amaryllidaceae Alkaloid Cherylline Inhibits the Replication of Dengue and Zika Viruses

Mérindol

Sow

et al. 2021

Antimicrob Agents Chemother

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“…Cherylline (125) and latifine (126) ( Figure 5) are the two tetrahydroisoquinoline alkaloids isolated from Amaryl-lidaceae plants and they show various pharmacological activities. In 2009, Shingare and co-workers 70 and Tilve and co-workers 71 independently reported efficient synthesis of (±)-cherylline dimethyl ether (130) (Scheme 39).…”

Section: Synthesis Of Tetrahydroisoquinoline Skeletonmentioning

confidence: 99%

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles

Balcı

2018

Synthesis

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Carbon–nitrogen bond formation is one of the most important reactions in organic chemistry. Various synthetic strategies for the generation of C–N bonds are described in the literature. For example, primary amines can be easily synthesized by the thermal decomposition of an acyl azide to an isocyanate, i.e. the Curtis rearrangement, followed by hydrolysis; the Curtius rearrangement has been used extensively. Furthermore, the advantage of the Curtius rearrangement is the isolation of acyl azides as well as the corresponding isocyanates. The isocyanates can be converted into various nitrogen-containing compounds upon reaction with various nucleophiles that can be used as important synthons for cyclization, in other words, for the synthesis of heterocycles. Therefore, this review demonstrates the importance of acyl azides not only in the synthesis acyclic systems, but also in the synthesis of various nitrogen-containing heterocycles.1 Introduction2 Synthesis of Acyl Azides2.1 Acyl Azides from Carboxylic Acid Derivatives2.2 Acyl Azides by Direct Transformation of Carboxylic Acids2.3 Acyl Azides from Aldehydes2.4 Carbamoyl Azides from Haloarenes, Sodium Azide, and N-Formylsaccharin3 Mechanism of Formation of Isocyanates4 Synthesis of Diacyl Azides5 Synthetic Applications5.1 Synthesis of Pyrimidinone Derivatives5.2 Dihydropyrimidinone and Isoquinolinone Derivatives5.3 Synthesis of Tetrahydroisoquinoline Skeleton5.4 Synthesis of Five-Membered Heterocycles5.5 Heterocycles Synthesized Starting from Homophthalic acid5.6 Heterocycles Synthesized from 2-(Ethoxycarbonyl)nicotinic Acid5.7 Formation of Aza-spiro Compounds5.8 Parham-Type Cyclization5.9 Diazepinone Derivatives5.10 Synthesis of Pyridine Derivatives5.11 Synthesis of Indole Derivatives6 Miscellaneous7 Conclusion

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“…[122][123][124][125] A practical strategy based on Weinreb amides has been presented for the synthesis of 4-aryl-1,2,3,4tetrahydroisoquinoline skeletons 180. 4-Aryl-1,2,3,4-tetrahydroisoquinoline skeletons, representatively cherylline 176 and latifine 177, are another small subgroup of the Amaryllidaceae alkaloids.…”

Section: Cherylline-typementioning

confidence: 99%

“…Various methodologies for the synthesis of (AE)-cheryllinen and (AE)-latifine dimethyl ethers 178 and 179 have been recently developed. [122][123][124][125] A practical strategy based on Weinreb amides has been presented for the synthesis of 4-aryl-1,2,3,4tetrahydroisoquinoline skeletons 180. 126 3 Sceletium alkaloids It was claimed that alkaloids from the Sceletium plant species have mood elevation and anti-anxiety properties, especially after the plant material has been fermented.…”

Section: 36mentioning

confidence: 99%

Amaryllidaceae and Sceletium alkaloids

Jin

2011

Nat. Prod. Rep.

104

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A short synthesis of (±)-cherylline dimethyl ether

Abstract: SummaryA synthesis of (±)-cherylline dimethyl ether is reported. The key steps involved are Michael-type addition, radical azidonation of an aldehyde, Curtius rearrangement, and reduction of an isocyanate intermediate followed by Pictet–Spengler cyclization.

Cited by 7 publications

References 17 publications

Amaryllidaceae Alkaloid Cherylline Inhibits the Replication of Dengue and Zika Viruses

Amaryllidaceae Alkaloid Cherylline Inhibits the Replication of Dengue and Zika Viruses

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles

Amaryllidaceae and Sceletium alkaloids

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A short synthesis of (±)-cherylline dimethyl ether

Abstract: SummaryA synthesis of (±)-cherylline dimethyl ether is reported. The key steps involved are Michael-type addition, radical azidonation of an aldehyde, Curtius rearrangement, and reduction of an isocyanate intermediate followed by Pictet–Spengler cyclization.

Cited by 7 publications

References 17 publications

Amaryllidaceae Alkaloid Cherylline Inhibits the Replication of Dengue and Zika Viruses

Amaryllidaceae Alkaloid Cherylline Inhibits the Replication of Dengue and Zika Viruses

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles­

Amaryllidaceae and Sceletium alkaloids

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Product

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Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles