Spruce budworm (<i>Choristoneura</i> <i>fumiferana</i>) antifeedants 4. Synthesis of specionin and biological studies

Mohammad‐Ali, A. K.; Chan, T. H.; Thomas, A. W.; Jewett, B.; Strunz, George M.

doi:10.1139/v94-271

Cited by 23 publications

(12 citation statements)

References 17 publications

(29 reference statements)

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“…Reagents were purchased and used as received unless otherwise noted. p ‐Benzyloxybenzoyl chloride, bis(5‐bromomethyl‐1,3‐phenylene)‐32‐crown‐10 ( 4 ) and p ‐benzyloxybenzonitrile were prepared via literature procedures.…”

Section: Methodsmentioning

confidence: 99%

An Inhospitable Cryptand: The Importance of Conformational Freedom in Host‐Guest Complexation

et al. 2019

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Two new cryptands were synthesized from bis(5‐bromomethyl‐1,3‐phenylene)‐32‐crown‐10 (4). The third arms, containing 19 or 21 atoms, were installed via Williamson ether syntheses with bisphenols containing 2,6‐disubstituted pyridines. 2,6‐Diaminopyridine was converted into the bis(p‐hydroxybenzoyl) derivative 3 for the first cryptand (5) and 2,6‐dicarboxypyridine was converted into the bis(p‐hydroxybenzylamide) 9 for the second cryptand (10). Cryptand 5 did not complex viologen derivatives 11–13 to an extent detectable by 1H NMR. We attribute the lack of complexation between viologen derivatives and 5 to its lack of conformational flexibility that prevents π‐stacking, a necessary component for complexation of viologens. In contrast longer and more flexible cryptand 10 did complex dimethyl paraquat (11) with Ka = 1.6 (±0.2) × 103 m–1 in acetone at 23 °C, probably by π‐stacking with the p‐oxybenzyl moieties of the host, made available by its enhanced flexibility.

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Section: Methodsmentioning

confidence: 99%

An Inhospitable Cryptand: The Importance of Conformational Freedom in Host‐Guest Complexation

et al. 2019

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“…Can [14]) or the L parameter (eqs. [8], [9], [lo], and [12]) greatly lowers the correlation coefficient. The results of the Hansch analysis suggest therefore that the biological activity correlates mainly with .rr value (lipophilic character) and L value (steric effect).…”

Section: Preliminary Studiesmentioning

confidence: 99%

Structure–activity relationship study of synthetic hydrazines as ecdysone agonists in the control of spruce budworm (Choristoneurafumiferana)

Mohammed-Ali¹,

Chan²,

Thomas³

et al. 1995

Can. J. Chem.

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A quantitative structure-activity relationship study was performed for a number of aroylhydrazine compounds with respect to their biological activity against spruce budworm. It was found that the biological activity can be modulated by substituents on the aromatic rings. Substituents with high .ir value and small L value lead to increase in biological activity. Molecular mechanics calculations were used to explain how the active compounds may mimic the strong-binding Y region of ecdysone.Key words: spruce budworm, ecdysone, agonist, hydrazines, quantitative structure-activity relationship.RCsumC : On a effectuC une Ctude de la relation quantitative structure-activiti d'un certain nombre de composCs aroylhydrazines par rapport 2 leur activitC biologique contre tordeuse d'kpinette. On a trouvC que l'activitt peut Etre modulCe par les substituants attachts au noyaux aromatiques. Les substituants avec des valeurs ClevCes de .ir et des valeurs de L faibles augmentent llactivitC biologique. On a utilisC des calculs de mCcanique molCculaire pour expliquer comment les composts actifs peuvent mimer la rCgion Y de forte liaison de l'ecdysone.

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“…Grimshaw in 1960, 4 this naturally occurring material devoid of cytotoxic activity, [5][6][7] is used for several decades by organic chemists for the synthesis of chiral building blocks or scaffolds. [8][9][10][11][12][13][14][15][16] Aucubin permitted the synthesis of various classes of biologically interesting chiral compounds: insect antifeedants, 17 carbocyclic nucleoside analogues, cytotoxic cyclopentenone glucosides, [21][22] chiral rigid -amino acid glucosides 23 and polyaminoiridoids whose have similar polarity with aminoside antibiotics. 24 For those syntheses, functional or skeletal modifications were applied to aucubin and sometimes with an innovative chemistry.…”

Section: Introductionmentioning

confidence: 99%

Influence of solvents and catalysts on the formation and hydrolysis of polyfunctional enoxysilanes derived from aucubin

Lémus¹,

Koch²,

Michel³

et al. 2014

Arkivoc

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Aucubin, a natural iridoid widely extracted from Aucuba japonica presents a strong interest as semisynthetic raw substantial, thanks to its numerous features. In this study, we describe an unprecedented reaction between trimethylsilyldiazomethane and the aldehyde-derived aucubin (3a) leading to different original non-natural skeletons exemplified by the tricyclic compounds 6 and 9 (Figure 1). The influence of catalysts, solvents and temperature on the formation of the products together with the hydrolysis of enoxysilane 4 will be presented.

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Spruce budworm (Choristoneura fumiferana) antifeedants 4. Synthesis of specionin and biological studies

Abstract: Specionin (1) was synthesized in seven steps from aucubin (2), an abundant iridoid form aucuba japonica. In a "no-choice" bioassay, specionin and several of its derivatives showed only modest antifeedant activity against the spruce budworm, while other derivatives were devoid of activity.

Cited by 23 publications

References 17 publications

An Inhospitable Cryptand: The Importance of Conformational Freedom in Host‐Guest Complexation

An Inhospitable Cryptand: The Importance of Conformational Freedom in Host‐Guest Complexation

Structure–activity relationship study of synthetic hydrazines as ecdysone agonists in the control of spruce budworm (Choristoneurafumiferana)

Influence of solvents and catalysts on the formation and hydrolysis of polyfunctional enoxysilanes derived from aucubin

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