Synthesis of Sulfur-Containing Morphinane Dienes

Berényi, Sándor; Sepsi, A.; Gyulai, Susanna; Szilágyi, László

doi:10.1080/00397919508013849

Cited by 7 publications

(2 citation statements)

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“…Berényi and his colleagues conducted parallel study aiming to investigate the differences of the reactivity of 14 -bromo-(65) and 14 -chlorocodeine tosylate (52) in the presence of potassium thiocyanate [107]. From the 14 -chloro derivative a mixture of 6-and 7-thiocyanato morphinandienes 66, 67 were isolated; while the 14 -bromo-counterpart yielded a mixture of 6-tosyloxy-(68) and 7-thiocyanato-6-demethoxythebaine (67, Scheme 26).…”

Section: Pseudohalo Analogues Of Thebainementioning

confidence: 99%

Recent Developments in the Chemistry of Thebaine and its Transformation Products as Pharmacological Targets

Berényi¹,

Csutorás²,

Sipos

2009

CMC

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The most practical synthetic routes to the preparation of as important pharmaceuticals as oxycodone, naloxone, naltrexone, nalbuphine and buprenorphine have utilized the alkaloid, thebaine, as a starting material. This review intends to focus on chemical transformations of morphinans which resulted in morphinandiene derivatives with well-established and novel pharmacological potencies. These chemical transformations were mainly associated with the formation and substitution of the unique diene structure of the ring C of the morphinan backbone.

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Section: Pseudohalo Analogues Of Thebainementioning

confidence: 99%

Recent Developments in the Chemistry of Thebaine and its Transformation Products as Pharmacological Targets

Berényi¹,

Csutorás²,

Sipos

2009

CMC

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“…The normal β-face adduct (56) was isolated in low yield (10%) when 5-β-TMS-thebaine (12g) was reacted with p-benzoquinone (45 • C, 7 days). Removal of the trimethylsilyl group with tetrabutylammonium fluoride resulted in the quinol (57).…”

Section: β-Alkylthebainesmentioning

confidence: 99%

Diels–Alder Adducts of Morphinan-6,8-Dienes and Their Transformations

et al. 2022

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6,14-ethenomorphinans are semisynthetic opiate derivatives containing an ethylene bridge between positions 6 and 14 in ring-C of the morphine skeleton that imparts a rigid molecular structure. These compounds represent an important family of opioid receptor ligands in which the 6,14-etheno bridged structural motif originates from a [4 + 2] cycloaddition of morphinan-6,8-dienes with dienophiles. Certain 6,14-ethenomorphinans having extremely high affinity for opioid receptors are often non-selective for opioid receptor subtypes, but this view is now undergoing some revision. The agonist 20R-etorphine and 20R-dihydroetorphine are several thousand times more potent analgesics than morphine, whereas diprenorphine is a high-affinity non-selective antagonist. The partial agonist buprenorphine is used as an analgesic in the management of post-operative pain or in substitution therapy for opiate addiction, sometimes in combination with the non-selective antagonist naloxone. In the context of the current opioid crisis, we communicated a summary of several decades of work toward generating opioid analgesics with lesser side effects or abuse potential. Our summary placed a focus on Diels–Alder reactions of morphinan-6,8-dienes and subsequent transformations of the cycloadducts. We also summarized the pharmacological aspects of radiolabeled 6,14-ethenomorphinans used in molecular imaging of opioid receptors.

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