合成和CBD芳香衍生物的抗增殖活性
Kang Li1, Xiaomei Ge1, Xinye Lv1
1Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha, Hunan, China.
Natural product research
|July 15, 2024
概括
新型大麻 (CBD) 衍生物被合成并测试其抗癌作用. 化合物2f对肝癌细胞表现出显著的抗增殖活性,表现优于CBD.
科学领域:
- 药用化学 医学化学
- 有机合成 有机合成
- 癌症生物学 癌症生物学
背景情况:
- 大麻素 (CBD) 是一种非精神活性化合物,具有潜在的治疗应用.
- 开发新的CBD衍生物可以增强其药理特性.
- 向肝癌和胰腺癌仍然是一个重大的临床挑战.
研究的目的:
- 合成新型香精衍生物的大麻 (CBD).
- 评估这些衍生物对人类肝脏和胰腺癌细胞系的体外抗增殖活性.
- 为了确定强效的CBD衍生物,提高抗癌效果.
主要方法:
- 合成CBD-8,12-二芳衍生物 (化合物2a-2t) 和CBD-8,12-二乙烯-21-芳衍生物 (化合物5a-5c).
- 使用CCK-8试验进行体外抗繁殖活性评估.
- 对人类肝癌细胞系 (HePG2,HeP3B) 和胰腺癌细胞系 (ASPC-1,BXPC-3) 的评估.
主要成果:
- 化合物2f对HePG2细胞具有显著的抗增殖活性,IC50为2.75μM.
- 化合物2f的活性是CBD对HePG2细胞的5.32倍.
- 化合物2b和5b对HePG2细胞 (IC50 5.95-9.21μM) 的抗癌活性也得到改善.
结论:
- 成功合成了CBD的新型芳香衍生物.
- 化合物2f代表了开发新的抗癌药物来对抗肝癌的有前途的头.
- 对这些CBD衍生物的进一步研究可能会为特定类型的癌症提供有效的治疗方法.
相关概念视频
01:25Aromatic Compounds: Overview
10.5K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
In 1825, Faraday...
10.5K
01:21Chemotherapy-Induced Nausea and Vomiting: Cannabinoids
211
Tetrahydrocannabinol (THC) is a phytocannabinoid that primarily interacts with the CB1 receptor, a type of G protein-coupled receptor (GPCR) predominantly in and around the chemoreceptor trigger zone (CTZ) and emetic center. THC also blocks the serotonin receptor activity in the dorsal vagal complex (DVC) by inhibiting serotonin release. THC exerts its anti-emetic effects through these interactions, which are beneficial for patients undergoing chemotherapy.
Two synthetic agonists of THC,...
Two synthetic agonists of THC,...
211
01:14π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
1.2K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.2K
01:34NMR Spectroscopy of Benzene Derivatives
8.0K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
8.0K
01:23Nomenclature of Aromatic Compounds with a Single Substituent
8.1K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
8.1K
01:18Frost Circles for Different Conjugated Systems
2.7K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
2.7K