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Design and synthesis of selective orexin 1 receptor antagonists with a morphinan skeleton and novel rearrangement reaction of morphinan skeleton

谷田, 誠浩 筑波大学 DOI:10.15068/00160440

2020.07.21

概要

1.1 Overview of morphinan derivatives
Morphinan is a general name for compounds containing a heterocyclic skeleton 1 composed of A-, B-, C-, and D-rings (Figure 1). Natural products with the morphinan skeleton include morphine (2) and thebaine (3), which are extracted from the unripe seed pods of opium poppy.1 These morphinan compounds with an oxygen-containing ring (E-ring) are called 4,5-epoxymorphinans. Morphinan derivatives typically bind with opioid receptors, which are classified into μ, δ, and κ opioid receptor types abbreviated MOR, DOR, and KOR, respectively.2 For example, 2, which shows agonistic activity for MOR, is a clinically used analgesic drugs. Naltrexone (4), a semi-synthetic opioid, shows antagonistic activity for MOR and is used as a therapeutic agent for drug addiction to morphine and their related drugs.

Other examples include hydromorphone (5), oxymorphone (6), and levorphanol (7), which are MOR agonists used as opioid analgesics. Naloxone (8), an MOR antagonist, is used to improve respiratory depression caused by overdose of opioid analgesics (Figure 2). These drugs exert pharmacological effects by acting on opioid receptors in the central nervous system (CNS).

Unlike drugs acting on the peripheral nervous system, CNS drugs must have proper physicochemical and pharmacokinetic properties to penetrate the blood–brain barrier (BBB).3 Thus, morphinan derivatives can be applied to study and develop CNS drugs.

The unique structures of morphinan derivatives can be utilized in organic synthesis and medicinal chemistry. For instance, naltrexone (4) has four consecutive asymmetric centers and five reactive functional groups: 3-phenolic hydroxy, 4,5-epoxy, 6-carbonyl, 14-hydroxy, and 17-basic tertiary amino groups (Figure 3). These structural features enable to arrange the functional groups to proper three-dimensional directions, which are essential for an adequate interaction with target receptors and enzymes. Thus, 4 is often used as an starting material or intermediate for the synthesis of drugs with the morphinan skeleton.

For the above reasons, various researchers reported the conversion of the naltrexone into other morphinan derivatives.

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63. Synthesis of 128 was performed to determine the stereochemistry of the major diastereomer of the compound 120 as follows. The recrystallization of the approximately 5:1 diastereomixture of 128 (12.3 mg) from refluxing MeOH afforded only 128a (5.0 mg) as a needle-like crystal and the stereochemistry of the 128a was determined by the NOESY experiments. As a result, the stereochemistry of the major isomer of 128 should be the same as that of 128a.

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