Über Alkaloide IX. Über die Struktur von Vincamin

Trojánek, J.; Štrouf, O.; Holubek, J.; Čekan, Z.

doi:10.1135/cccc19640433

Cited by 8 publications

(3 citation statements)

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“…Note: 81 is a known compound (apovincamine, CAS No. 4880-92-6), , and this procedure converting vincamine to 81 was adapted from the literature …”

Section: Methodsmentioning

confidence: 99%

“…[α] D 20 : +112° ( c 0.61 g/100 mL, CH 2 Cl 2 ), lit. +98 ( c 0.51 g/100 mL, MeOH) . Note: Compound 81 is an intermediate en route to 10 .…”

Section: Methodsmentioning

confidence: 99%

“…Note: 81 is a known compound (apovincamine, CAS No. 4880-92-6), 44,45 and this procedure converting vincamine to 81 was adapted from the literature. 44 1 H NMR: (600 MHz, CDCl 3 ) δ 7.47 (d, J = 7.7 Hz, 1H), 7.23 (d, J = 8.3 Hz, 1H), 7.17 (td, J = 7.1, 1.1 Hz, 1H), 7.13 (td, J = 7.2, 0.9 Hz, 1H), 6.14 (s, 1H), 4.17 (s, 1H), 3.95 (s, 3H), 3.38 (dd, J = 13.9, 6.2 Hz, 1H), 3.27 (td, J = 11.7, 5.5 Hz, 1H), 3.03 (m, 1H), 2.70−2.60 (m, 2H), 2.54 (dd, J = 16.4, 3.4 Hz, 1H), 2.00−1.86 (m, 2H), 1.75 (m, 1H), 1.52 (d, J = 13.7 Hz, 1H), 1.42 (dt, J = 13.2, 2.9 Hz, 1H), 1.06− 0.98 (m, 4H).…”

Section: Synthesis Procedures For the Generation Of 2 Methyl 2-[(7s8r...mentioning

confidence: 99%

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Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine’s Biological Activity

et al. 2020

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Innovative discovery strategies are essential to address the ongoing opioid epidemic in the United States. Misuse of prescription and illegal opioids (e.g., morphine, heroin) has led to major problems with addiction and overdose. We used vincamine, an indole alkaloid, as a synthetic starting point for dramatic structural alterations of its complex, fused ring system to synthesize 80 diverse compounds with intricate molecular architectures. A select series of vincamine-derived compounds were screened for both agonistic and antagonistic activities against a panel of 168 G protein-coupled receptor (GPCR) drug targets. Although vincamine was without an effect, the novel compound 4 (V2a) demonstrated antagonistic activities against hypocretin (orexin) receptor 2. When advanced to animal studies, 4 (V2a) significantly prevented acute morphine-conditioned place preference (CPP) and stress-induced reinstatement of extinguished morphine-CPP in mouse models of opioid reward and relapse. These results demonstrate that the ring distortion of vincamine offers a promising way to explore new chemical space of relevance to opioid addiction.

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“…Note: 81 is a known compound (apovincamine, CAS No. 4880-92-6), , and this procedure converting vincamine to 81 was adapted from the literature …”

Section: Methodsmentioning

confidence: 99%

“…[α] D 20 : +112° ( c 0.61 g/100 mL, CH 2 Cl 2 ), lit. +98 ( c 0.51 g/100 mL, MeOH) . Note: Compound 81 is an intermediate en route to 10 .…”

Section: Methodsmentioning

confidence: 99%