Bromination of codeine and its derivatives: Revisiting a 95 year old process

Barmaki, Samira; Ali, Arlene; Desaulniers, Jean-Paul; Bolshan, Yuri

doi:10.1016/j.tetlet.2020.152234

Cited by 1 publication

(1 citation statement)

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“…Moreover, a facile, safe, and yield-improving method has been developed for the synthesis of 1-bromocodeine 10 with N -bromoacetamide reagent in the presence of trifluoroacetic anhydride ( Scheme 2 ) [ 27 ].…”

Section: Modifications On Ring Amentioning

confidence: 99%

Synthesis and Modification of Morphine and Codeine, Leading to Diverse Libraries with Improved Pain Relief Properties

Zarin,

Dehaen,

Salehi

et al. 2023

Pharmaceutics

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Morphine and codeine, two of the most common opioids, are widely used in the clinic for different types of pain. Morphine is one of the most potent agonists for the μ-opioid receptor, leading to the strongest analgesic effect. However, due to their association with serious side effects such as respiratory depression, constriction, euphoria, and addiction, it is necessary for derivatives of morphine and codeine to be developed to overcome such drawbacks. The development of analgesics based on the opiate structure that can be safe, orally active, and non-addictive is one of the important fields in medicinal chemistry. Over the years, morphine and codeine have undergone many structural changes. The biological investigation of semi-synthetic derivatives of both morphine and codeine, especially morphine, shows that studies on these structures are still significant for the development of potent opioid antagonists and agonists. In this review, we summarize several decade-long attempts to synthesize new analogues of morphine and codeine. Our summary placed a focus on synthetic derivatives derived from ring A (positions 1, 2, and 3), ring C (position 6), and N-17 moiety.

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Section: Modifications On Ring Amentioning

confidence: 99%