19-O-acetyl-14-deoxy-11,12-didehydroandrographolide

• 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: 19-O-acetyl-14-deoxy-11,12-didehydroandrographolide
• 英文别名: 19-O-acetyl dehydroandrographolide
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: LEZFQUGXNJHTGD-NGVUMRSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  穿心莲内酯 在 吡啶 、 aluminum oxide 作用下， 反应 28.5h， 生成 19-O-acetyl-14-deoxy-11,12-didehydroandrographolide 、 3,19-O-diacetyl-14-deoxy-11,12-didehydroandrographolide
  参考文献：
  名称：

  合成14-脱氧11,12-二氢脱水穿心莲内酯类似物作为胆管癌的潜在细胞毒剂

  摘要：

  从天然存在的穿心莲内酯中合成了一系列的14-脱氧-11,12-二氢-穿心莲内酯类似物，并评估了它们对包括胆管癌在内的9种癌细胞系的细胞毒性。类似物5a和5b表现出最强的细胞毒性，在KKU-M213细胞系上ED 50分别为3.37和3.08μM，在KKU-100细胞系上为2.93和3.27μM。在这项研究中确定的胆管癌细胞系的选择性细胞毒性突显了结构修饰在该癌症药物开发中的重要性。

  DOI：

  10.1016/j.bmcl.2017.10.063

文献信息

• Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma
  作者：Sudarat Sombut、Rada Bunthawong、Uthaiwan Sirion、Teerapich Kasemsuk、Pawinee Piyachaturawat、Kanoknetr Suksen、Apichart Suksamrarn、Rungnapha Saeeng

  DOI：10.1016/j.bmcl.2017.10.063

  日期：2017.12

  A series of 14-deoxy-11,12-didehydroandrographolide analogues were synthesized from naturally occurring andrographolide and their cytotoxicity evaluated against nine cancer cell lines including cholangiocarcinoma. Analogues 5a and 5b exhibited the most potent cytotoxicity with ED50s of 3.37 and 3.08 μM on KKU-M213 cell lines and 2.93 and 3.27 μM on KKU-100 cell lines, respectively. Selective cytotoxicity

  从天然存在的穿心莲内酯中合成了一系列的14-脱氧-11,12-二氢-穿心莲内酯类似物，并评估了它们对包括胆管癌在内的9种癌细胞系的细胞毒性。类似物5a和5b表现出最强的细胞毒性，在KKU-M213细胞系上ED 50分别为3.37和3.08μM，在KKU-100细胞系上为2.93和3.27μM。在这项研究中确定的胆管癌细胞系的选择性细胞毒性突显了结构修饰在该癌症药物开发中的重要性。
• Synthesis, structure–activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents
  作者：Hao Chen、Yun-Bao Ma、Xiao-Yan Huang、Chang-An Geng、Yong Zhao、Li-Jun Wang、Rui-Hua Guo、Wen-Juan Liang、Xue-Mei Zhang、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2014.03.060

  日期：2014.5

  Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07 mu M and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values. Structureactivity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of andrographolide-related esters as insecticidal and acaricidal agents
  作者：Xiaobo Huang、Bingchuan Zhang、Hui Xu

  DOI：10.1016/j.bmcl.2017.12.038

  日期：2018.2

  In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of andrographolide-related esters, such as 3,19-dialkyl(aryl) carbonyloxy andrographolide (3a-g), 3-alkyl(aryl)carbonyloxyandrographolide (4a-g), and 19-alkyl(aryl) carbonyloxyandrographolide (5a-g), were prepared. Their structures were well characterized by H-1 NMR, IR, optical rotation, HRMS and mp. Especially three-dimensional structures of compounds 3a, 4g, and 5g were unambiguously confirmed by single-crystal X-ray diffraction. Compounds 3a and 5a exhibited good insecticidal and acaricidal activities against Mythimna separata and Tetranychus cinnabarinus. Their structure-activity relationships were also discussed. (C) 2017 Elsevier Ltd. All rights reserved.