12,13-dihydroandrographolide | 496848-48-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 12,13-dihydroandrographolide
• 英文别名: (4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-4-hydroxyoxolan-2-one
• CAS: 496848-48-7
• 化学式: C₂₀H₃₂O₅
• 分子量: 352.471
• InChiKey: IVXCEOGAEAIXET-YCCRBALFSA-N

物化性质

• 沸点：
  541.4±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12,13-dihydroandrographolide 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Synthesis and In Vivo Hepatoprotective Activity of Some Novel Andrographolide Derivatives

  摘要：

  在本研究中，组合原则被报道能够提高穿心莲酯的护肝活性。合成了十种穿心莲酯衍生物，并在CCl4诱导的肝损伤小鼠中评估其体内护肝活性。药理学结果显示，有六种衍生物表现出显著的护肝活性。最有前景的化合物6b在肝酶（ALT和AST）活性方面显著优于穿心莲酯，具有成为新药物先导化合物的高效能。

  DOI：

  10.2174/1570180810666131123002409
• 作为产物：
  描述：

  穿心莲内酯 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以46%的产率得到12,13-dihydroandrographolide
  参考文献：
  名称：

  Synthesis and In Vivo Hepatoprotective Activity of Some Novel Andrographolide Derivatives

  摘要：

  在本研究中，组合原则被报道能够提高穿心莲酯的护肝活性。合成了十种穿心莲酯衍生物，并在CCl4诱导的肝损伤小鼠中评估其体内护肝活性。药理学结果显示，有六种衍生物表现出显著的护肝活性。最有前景的化合物6b在肝酶（ALT和AST）活性方面显著优于穿心莲酯，具有成为新药物先导化合物的高效能。

  DOI：

  10.2174/1570180810666131123002409

文献信息

• Synthesis and biological evaluation of andrographolide derivatives as potent anti-HIV agents
  作者：Bin Wang、Jing Li、Wen Long Huang、Hui Bin Zhang、Hai Qian、Yong Tang Zheng

  DOI：10.1016/j.cclet.2011.01.015

  日期：2011.7

  Abstract A series of Andro derivatives were described and evaluated for their anti-HIV activity in vitro . Compound 10 and 16b , of which TI were >10, had some anti-HIV-1 activity in vitro . Therein, compound 10 which was the best potent compound, could serve as a new lead for further development of anti-AIDS agents.

  摘要描述了一系列Andro衍生物并对其体外抗HIV活性进行了评估。TI> 10的化合物10和16b在体外具有一定的抗HIV-1活性。其中，最有效的化合物10可以作为抗艾滋病药物进一步开发的新先导。
• Synthesis and evaluation of andrographolide derivatives as potent anti-osteoporosis agents in vitro and in vivo
  作者：Songxuan Zhang、Yuting Zhang、Yuying Fang、Hao Chen、Mengjiao Hao、Qingyun Tan、Chen Hu、Huihao Zhou、Jun Xu、Qiong Gu

  DOI：10.1016/j.ejmech.2021.113185

  日期：2021.3

  In this work, we found that 14-deoxy-11,12-didehydroandrographolide (2), a derivative of andrographolide (AP, 1), had greatly reduced cytotoxicity compared with AP and exhibited moderate anti-osteoclastogenesis activity. Thirty compounds were synthesized by introducing anti-osteoporosis chemotypes at C-19 of 2. Six of them exhibited stronger inhibition of osteoclastogenesis than AP. Of note, compound

  在这项工作中，我们发现穿心莲内酯的衍生物（AP，1）14-脱氧-11,12-二氢加氢穿心莲内酯（2）与AP相比具有大大降低的细胞毒性，并表现出中等的抗破骨细胞生成活性。通过在2的C-19处引入抗骨质疏松症的化学型，合成了30种化合物。他们中的六个表现出比AP更强的破骨细胞抑制作用。值得注意的是，化合物12g表现出最强的活性，IC 50值为0.35μM。通过12g处理，破骨细胞特异性基因（例如TRAcP，CTSK，NFATc1和MMP-9）的表达水平也降低了。此外，蛋白质印迹和免疫荧光分析表明该化合物12g通过下调RANKL诱导的NF-κB信号通路抑制破骨细胞分化。在卵巢切除（OVX）雌性小鼠模型中，化合物12g显着改善了骨质流失。因此，化合物12g显示出有希望的体内功效和低毒性，表明其治疗骨质疏松症的治疗潜力。
• Studies on the novel α-glucosidase inhibitory activity and structure–activity relationships for andrographolide analogues
  作者：Gui-Fu Dai、Hai-Wei Xu、Jun-Feng Wang、Feng-Wu Liu、Hong-Min Liu

  DOI：10.1016/j.bmcl.2006.02.011

  日期：2006.5

  A series of analogues of andrographolide were synthesized and evaluated as novel alpha-glucosidase inhibitors. Among them compound 23, 15-p-methoxylbenzylidene 14-deoxy-11, 12-didehydroandrographolide, was a potent inhibitor against alpha-glucosidase Whose IC50 value was 16 mu M. The structure-activity relationships were also discussed. (C) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents
  作者：Srinivas Nanduri、Vijay Kumar Nyavanandi、Siva Sanjeeva Rao Thunuguntla、Sridevi Kasu、Mahesh Kumar Pallerla、P. Sai Ram、Sriram Rajagopal、R. Ajaya Kumar、Rajagopalan Ramanujam、J. Moses Babu、Krishnamurthi Vyas、A. Sivalakshmi Devi、G. Om Reddy、Venkateswarlu Akella

  DOI：10.1016/j.bmcl.2004.06.090

  日期：2004.9

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• Pal, Mahesh; Singh, Meenakshi; Sharma, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 9, p. 1915 - 1918
  作者：Pal, Mahesh、Singh, Meenakshi、Sharma

  DOI：——

  日期：——