cleomiscosin A methyl ether

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 香豆素木脂素
• 英文名称: cleomiscosin A methyl ether
• 英文别名: (2R,3R)-3-(3,4-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• 化学式: C₂₁H₂₀O₈
• 分子量: 400.385
• InChiKey: YJINBIPHZOTKQM-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cleomiscosin A methyl ether 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以67%的产率得到5-bromocleomiscosin A methyl ester
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of derivatives of coumarino-lignoid, cleomiscosin A and its methyl ether

  摘要：

  Six novel cleomiscosin A (a coumarino-lignoid), derivatives have been synthesized for the first time by using electrophilic substitution reaction to give nuclear nitrated and halogenated derivatives of cleomiscosin A in good yields. Structures of these compounds were established on the basis of IR, H-1 NMR, C-13 NMR and Mass spectral data. Some of the synthesized derivatives were tested for in-vitro target based anti-inflammatory study using primary macrophages cell culture bioassay system. The results showed that the compounds 1a, 3a and 4a (1 and 10 mu g/mL) exhibited potent anti-inflammatory activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.027
• 作为产物：
  描述：

  重氮甲烷 、 6-methoxy-5′′-demethoxydaphneticin 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以13 mg的产率得到cleomiscosin A methyl ether
  参考文献：
  名称：

  Study of anti-inflammatory, analgesic and antipyretic activities of seeds of Hyoscyamus niger and isolation of a new coumarinolignan

  摘要：

  A chemical and biological validation of the traditional use of Hyoscyamus niger seeds as anti-inflammatory drug has been established The methanolic extract of seeds of H niger (MHN) was evaluated for its analgesic, anti-inflammatory and antipyretic activities in experimental animal models at different doses MHN produced significant increase in hot plate reaction time, while decreasing writhing response in a close-dependent manner indicating its analgesic activity It was also effective in both acute and chronic inflammation evaluated through carrageenin-induced paw oedema and cotton pellet granuloma methods In addition to its analgesic and anti-inflammatory activity, it also exhibited antipyretic activity in yeast-induced pyrexia model Furthermore, the bioactive MHN tinder chemical investigation showed the presence of coumarinolignans as major chemical constituent and yielded a new coumarinolignan, cleomiscosin A methyl ether (1) along with four known coumarinolignans, cleomiscosin A (2), cleomiscosin B (3), cleomiscosin A-9'-acetate (4) and cleomiscosin B-9'-acetate (5) The structure elucidation of 1 was done by spectroscopic data interpretation and comparative HPLC analysis Cleomiscosin A, but not its isomer cleomiscosin B, reduced dry and wet weight of cotton pellet granuloma in mice This suggests that cleomiscosin A is all important constituent of MHN responsible for anti-inflammatory activity (C) 2009 Elsevier B V All rights reserved

  DOI：

  10.1016/j.fitote.2009.08.024

文献信息

• QSAR, docking and in vitro studies for anti-inflammatory activity of cleomiscosin A methyl ether derivatives
  作者：Shelly Sharma、Sunil Kumar Chattopadhyay、Dharmendra Kumar Yadav、Feroz Khan、Shilpa Mohanty、Anil Maurya、Dnyaneshwar Umrao Bawankule

  DOI：10.1016/j.ejps.2012.09.008

  日期：2012.12

  A series of five (6a-8b) novel polyhalogenated derivatives and an interesting ester (9a) derivative have been synthesized from cleomiscosin A methyl ether. All the six derivatives were subjected to in silico QSAR modeling and docking studies and later the predicted results were confirmed through in vitro experiments. QSAR modeling results showed that compounds 6a and 9a possessed anti-inflammatory activity comparable or even higher than diclofenac sodium. Docking results revealed that compounds 9a and 6a showed very good anti-inflammatory activity due to low docking energies of viz., IL6 (-92.45 and -81.993 kcal mol(-1)), TNF-alpha (-94.992 and -69.235 kcal mol(-1)) and IL1 beta (-67.462 and -65.985 kcal mol(-1)). Further all the six novel derivatives were subjected for in vitro anti-inflammatory activity using primary macrophages cell culture bioassay system. At the initial doses of 1 mu g/ml and 10 mu g/ml, the pro-inflammatory cytokines (IL-1 beta, IL-6 and TNF-alpha) were quantified from cell culture supernatant using enzyme linked immunosorbent assay (ELISA). The in vitro effect of 6a-9a on cell viability in mouse peritoneal macrophage cells isolated from mice was evaluated using MTT assay. The in silico and in vitro data suggested that all the derivatives might be considered as potential anti-inflammatory drug-like molecules. (C) 2012 Elsevier B.V. All rights reserved.