Efficient one-pot synthetic approaches for cannabinoid analogues and their application to biologically interesting (−)-hexahydrocannabinol and (+)-hexahydrocannabinol

Lee, Yong Rok; Xia, Likai

doi:10.1016/j.tetlet.2008.03.075

Cited by 56 publications

(29 citation statements)

References 24 publications

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“…For this reason, Brønsted acids were employed in our new methodology for the preparation of various benzopyrans [25][26][27][28][29][30][31][32][33][34]. As a part of our ongoing evaluation of the synthetic efficacy of Brønsted acids, we first investigated the reaction of b-enaminone 1a with 3-methyl-2-butenal using several Brønsted acids, but also Lewis acids and other reagents ( Table 1).…”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition

Lee

Kim

2012

Monatsh Chem

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Section: Resultsmentioning

confidence: 99%

Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition

Lee

Kim

2012

Monatsh Chem

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“…11) Therefore, HIF-1α and other factors interacting with HIF-1α have been suggested as therapeutic targets for anti-cancer drug development. 12,13) We recently synthesized and evaluated the anti-cancer effects of a novel series of hexahydrocannabinol analogs. [14][15][16] Of these analogs, LYR-8, a cannabinoid-like compound with no affinity for conventional cannabinoid receptors (CB 1 and CB 2 ), was found to directly inhibit the growth, induce apoptosis of cancer cells and inhibit endothelial cell proliferation and angiogenesis.…”

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confidence: 99%

Anti-tumor Activity of the Novel Hexahydrocannabinol Analog LYR-8 in Human Colorectal Tumor Xenograft Is Mediated through the Inhibition of Akt and Hypoxia-Inducible Factor-1α Activation

Thapa

Kang

Park

et al. 2012

Biological & Pharmaceutical Bulletin

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Cannabinoid compounds have been shown to exert anti-tumor effects by affecting angiogenesis, invasion, and metastasis. In the present study, we examined the action mechanism by which LYR-8, a novel hexahydrocannabinol analog, exerts anti-angiogenic and anti-tumor activity in human cancer xenografts. In the xenografted tumor tissues, LYR-8 significantly reduced the expression of hypoxia-inducible factor-1 alpha (HIF-1α), a transcription factor responsible for induction of angiogenesis-promoting factors, and its target genes, vascular endothelial growth factor (VEGF) and cyclooxygenase-2 (COX-2). In HT-29 human colon cancer cells treated with a hypoxia-inducing agent (CoCl(2)), LYR-8 dose-dependently suppressed the induction of HIF-1α and subsequently its targets, VEGF and COX-2. In addition, highly elevated prostaglandin E(2) (PGE(2)) concentrations in CoCl(2)-treated HT-29 cells were also significantly suppressed by LYR-8. However, LYR-8 alone in the absence of CoCl(2) did not alter the basal expression of VEGF and COX-2, or PGE(2) production. Furthermore, LYR-8 effectively suppressed Akt signaling, which corresponded to the suppression of CoCl(2)-induced HIF-1α accumulation. Taken together, LYR-8 exerts anti-tumor effects through the inhibition of Akt and HIF-1α activation, and subsequently suppressing factors regulating tumor microenvironment, such as VEGF and COX-2. These results indicate a novel function of cannabinoid-like compound LYR-8 as an anti-tumor agent with a HIF-1α inhibitory activity.

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“…11 As an expansion of the synthesis of benzopyrans and cannabinoid, (±)-perrottetinene (4) was concisely synthesized in this study.…”

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Concise Synthesis of (±)-Perrottetinene with Bibenzyl Cannabinoid

Park¹,

Lee²

2010

Bulletin of the Korean Chemical Society

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Efficient one-pot synthetic approaches for cannabinoid analogues and their application to biologically interesting (−)-hexahydrocannabinol and (+)-hexahydrocannabinol

Cited by 56 publications

References 24 publications

Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition

Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition

Anti-tumor Activity of the Novel Hexahydrocannabinol Analog LYR-8 in Human Colorectal Tumor Xenograft Is Mediated through the Inhibition of Akt and Hypoxia-Inducible Factor-1α Activation

Concise Synthesis of (±)-Perrottetinene with Bibenzyl Cannabinoid

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