(7R)-7,8-dihydrosinomenine | 65120-75-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: (7R)-7,8-dihydrosinomenine
• 英文别名: 4-hydroxy-3,7β-dimethoxy-17-methylmorphinan-6-one；4-hydroxy-3,7b-dimethoxy-17-methylmorphinan-6-one；ent-4-hydroxy-3,7α-dimethoxy-17-methyl-morphinan-6-one；ent-4-Hydroxy-3,7α-dimethoxy-17-methyl-morphinan-6-on；(1R,9S,10S,12R)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
• CAS: 65120-75-4
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: QAVNAPIOJZCYAH-UESRRSCYSA-N

物化性质

• 沸点：
  489.8±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (7R)-7,8-dihydrosinomenine 在 铂 作用下， 生成 (4bR,8aS,9S)-3,7-dimethoxy-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-4,6-diol
  参考文献：
  名称：

  Liquid–liquid phase separation and crystallization behavior of poly(ethylene terephthalate)/poly(ether imide) blend

  摘要：

  The liquid-liquid (L-L) phase separation and crystallization behavior of poly(ethylene terephthalate) (PET)/poly(ether imide) (PEI) blend were investigated with optical microscopy, light scattering, and small angle X-ray scattering (SAXS). The thermal analysis showed that the concentration fluctuation between separated phases was controllable by changing the time spent for demixing before crystallization. The L-L phase-separated specimens at 130 C for various time periods were subjected to a temperature-jump of 180 C for the isothermal crystallization and then effects of L-L phase separation on crystallization were investigated. The crystal growth rate decreased with increasing L-L phase-separated time (t(s)). The slow crystallization for a long t(s) implied that the growth path of crystals was highly distorted by the rearrangement of the spinodal domains associated with coarsening. The characteristic morphological parameters at the lamellar level were determined by the correlation function analysis on the SAXS data. The blend had a larger amorphous layer thickness than the pure PET, indicating that PEI molecules in the PET-rich phase were incorporated into the interlamellar regions during crystallization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0032-3861(02)00054-x
• 作为产物：
  描述：

  青藤碱 在 palladium 10% on activated carbon 、 氢气 作用下， 以 水 为溶剂， 以79%的产率得到(7R)-7,8-dihydrosinomenine
  参考文献：
  名称：

  Sinomenine derivatives with embedment of nitrogen-containing heterocycles exhibiting potent TNF-αinhibitory activity

  摘要：

  本研究探讨了含有小型药物类氮杂环基团的盐酸缬草碱衍生物对肿瘤坏死因子-α（TNF-α）产生的抑制作用。发现几种具有氯苯基取代基的新型盐酸缬草碱衍生物展现出比天然盐酸缬草碱及其他衍生物更强的TNF-α抑制活性。

  DOI：

  10.1007/s11426-012-4588-8

文献信息

• Anti-osteoclastogenic effects of isoquinoline alkaloids from the rhizome extract of Sinomenium acutum
  作者：Ji Young Lee、Kwang-Jin Kim、Jinhee Kim、Sang Un Choi、Seong Hwan Kim、Shi Yong Ryu

  DOI：10.1007/s12272-016-0734-8

  日期：2016.5

  A phytochemical investigation for the rhizome extract from Sinomenium acutum (Menispermaceae) resulted in the isolation of several active principles responsible for the anti-osteoclastogenic property of the extract, together with related isoquinoline alkaloids (1–13) including two new compounds, 1 and 2. Among isolated compounds, salutaridine (7), dauricumine (10), cheilanthifoline (12), and dauriporphine

  对青蒿（Menispermaceae）的根茎提取物进行植物化学研究，结果分离出几种负责该提取物抗破骨细胞特性的活性成分，以及相关的异喹啉生物碱 (1-13)，包括两种新化合物 1 和 2 . 在分离的化合物中，salutaridine (7)、dauricumine (10)、cheilanthifoline (12) 和 dauriporphine (13) 被观察到对核因子-κB 配体诱导的小鼠骨髓源巨噬细胞分化的受体激活剂产生显着抑制分别进入多核破骨细胞。两种新分离的化合物 1 和 2 的化学结构通过光谱分析（包括 2D NMR 实验）确定为 8-脱甲氧基头孢酮 (1) 和 7(R)-7,8-二氢青藤碱 (2)。
• Synthesis and antitumor activities of sinomenine derivatives on rings A and C
  作者：Can-Jing Wei、Fang Xu、Meng-Jiao Shi、Jia-Wen Hu、Jia-Jia Wang、Bo Zhen、Xue Wang、Teng-Fei Ji、Jin-Hua Wang、Guan-Hua Du

  DOI：10.1080/10286020.2017.1386659

  日期：2018.3.4

  A series of new sinomenine derivatives were designed, synthesized, and evaluated in tumor inhibitory activity, such as human triple negative breast cancer cell line (MDA-MB-231), glioma cell line (A172), human lung cancer cell line (A549), human colon cancer cell line (HCT-8). The modifications were carried out on rings A and C of the sinomenine by esterificating on phenolic hydroxyl with good yields

  设计，合成并评估了一系列新的青藤碱衍生物，例如人三阴性乳腺癌细胞系（MDA-MB-231），神经胶质瘤细胞系（A172），人肺癌细胞系（A549） ，人类结肠癌细胞系（HCT-8）。通过以良好的产率在酚羟基上酯化在青藤碱的环A和C上进行修饰。这项工作的重点是合成步骤简明扼要，青藤碱衍生物具有良好的抗肿瘤活性。
• Design, synthesis, and pharmacological evaluation of sinomenine derivatives on rings A and C: Novel compounds screening for aplastic anemia targeting on cytotoxic T lymphocyte
  作者：Ziqian Zhang、Hongjian Wang、Jiqiao Yuan、Xuyu Li、Nan Fang、Mingbao Lin、Qi Hou、Tengfei Ji

  DOI：10.1016/j.ejmech.2021.113791

  日期：2021.12

  Cytotoxic T lymphocyte (CTL), a key effector cell in aplastic anemia (AA) immune injury, is shown to be a potential target for AA drug therapy. However, there is no candidate for this target till now. Oriented by the inhibition activity of CTL and macrophage derived nitric oxide (NO), a series of novel sinomenine derivatives on rings A and C are designed, synthesized and screened. Among them, compound

  细胞毒性 T 淋巴细胞 (CTL) 是再生障碍性贫血 (AA) 免疫损伤中的关键效应细胞，被证明是 AA 药物治疗的潜在靶点。然而，到目前为止，还没有这个目标的候选人。以CTL和巨噬细胞衍生的一氧化氮（NO）的抑制活性为导向，设计、合成和筛选了一系列新型青藤碱衍生物在A环和C环上。其中，化合物3a对CTL的抑制活性最好，IC 50值为2.3 μM，对巨噬细胞NO产生的抑制率为97.1%，无明显细胞毒性。此外，化合物3a通过改善贫血症状和BM造血功能对AA模型小鼠免疫介导的BM衰竭具有显着的治疗效果，并且在改善生活质量方面比环孢素A（CsA）更具优势。其对 AA 的功效至少部分来自于靶向活化的分化簇 (CD)8 + T 细胞。此外，在小鼠的初步急性毒性评估中， 3a的毒性 (LD 50  > 10.0 g/kg) 也比青藤碱 (LD 50  = 1.1 g/kg) 低得多，并且抑制 hERG
• Goto, Justus Liebigs Annalen der Chemie, 1931, vol. 489, p. 86,93
  作者：Goto

  DOI：——

  日期：——
• On the Reduction of 1-Bromo-sinomeneine
  作者：Kakuji Goto、Tatsuo Arai、Tetsuro Kono

  DOI：10.1246/bcsj.23.17

  日期：1950.1