ent-8β-cyanomethyl-13-methyl-12-podocarpen-19-oic acid | 1191993-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: ent-8β-cyanomethyl-13-methyl-12-podocarpen-19-oic acid
• 英文别名: (1R,4aS,4bR,8aR,10aS)-8a-(cyanomethyl)-1,4a,7-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• CAS: 1191993-58-4
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: FHXVTNZYELINAI-UFHDJZAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨甲基吡啶 、 ent-8β-cyanomethyl-13-methyl-12-podocarpen-19-oic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  从甜菊醇和异甜菊醇衍生的支架合成面向多样性的图书馆。

  摘要：

  容易获得的天然产物甜菊糖苷提供了独特的二萜核心结构，可通过面向多样性的合成和官能团转换来探索小分子文库的开发。验证阵列由甜菊醇、异甜菊醇和衍生自甜菊苷的相关类似物制备，以产生 90 多种化合物。这些化合物已提交给 NIH 分子库小分子存储库，以便在分子库筛选中心网络中进行筛选。在多个文库成员的多个高通量分析中确定了微摩尔命中。对化合物进行了化学信息学分析，验证了这组化合物的预期多样性和复杂性。

  DOI：

  10.1021/acscombsci.9b00186
• 作为产物：
  描述：

  4α-carboxy-13α-amino-13,16-seco-ent-19-norbeyeran-16-oic acid lactam 在 Aspergillus niger BCRC 32720 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以28 mg的产率得到ent-8β-cyanomethyl-7α-hydroxy-13-methyl-13-podocarpen-19-oic acid
  参考文献：
  名称：

  Transformation of Isosteviol Lactam by Fungi and the Suppressive Effects of Its Transformed Products on LPS-Induced iNOS Expression in Macrophages

  摘要：

  From the screening of 21 microbial strains, Absidia pseudocylindrospora ATCC 24169 and Aspergillus niger BCRC 32720 were found to reproducibly transform isosteviollactam (4 alpha-carboxy-13 alpha-amino-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactam) (3) into various compounds. Preparative-scale transformation of 3 with Abs. pseudocylindrospora yielded two new hydroxylated compounds (4 and 5), with conservation of the lactam ring. Preparative-scale transformation of 3 with Asp. niger afforded seven new compounds, 6 and 9-14, together with the known compounds 7 and 8. A single-crystal X-ray diffraction experiment confirmed the structure of 14. The suppressive effects of compounds 1-14 on the lipopolysaccharide-induced expression of the inducible nitric oxide synthase gene in RAW 264.7 macrophages were examined by a reverse-transcription real-time PCR analysis. With the exception of 7, all other compounds significantly reduced levels of iNOS mRNA relative to control cells, which were induced by LPS alone. Compounds 2, 3, and 5 were similar in activity to dexamethasone, while 9 was more potent.

  DOI：

  10.1021/np100915q

文献信息

• Diversity-Oriented Library Synthesis from Steviol and Isosteviol-Derived Scaffolds
  作者：Trinh A. D. Holth、Michael A. Walters、Oliver E. Hutt、Gunda I. Georg

  DOI：10.1021/acscombsci.9b00186

  日期：2020.3.9

  for small molecule library development by diversity-oriented synthesis and functional group transformations. Validation arrays were prepared from steviol, isosteviol, and related analogues, derived from stevioside, to produce over 90 compounds. These compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for screening in the Molecular Libraries Screening Center Network. Micromolar

  容易获得的天然产物甜菊糖苷提供了独特的二萜核心结构，可通过面向多样性的合成和官能团转换来探索小分子文库的开发。验证阵列由甜菊醇、异甜菊醇和衍生自甜菊苷的相关类似物制备，以产生 90 多种化合物。这些化合物已提交给 NIH 分子库小分子存储库，以便在分子库筛选中心网络中进行筛选。在多个文库成员的多个高通量分析中确定了微摩尔命中。对化合物进行了化学信息学分析，验证了这组化合物的预期多样性和复杂性。
• Transformation of Isosteviol Lactam by Fungi and the Suppressive Effects of Its Transformed Products on LPS-Induced iNOS Expression in Macrophages
  作者：Bo-Hon Chou、Li-Ming Yang、Shwu-Fen Chang、Feng-Lin Hsu、Li-Hsuan Wang、Wen-Kuang Lin、Pan-Chun Liu、Shwu-Jiuan Lin

  DOI：10.1021/np100915q

  日期：2011.6.24

  From the screening of 21 microbial strains, Absidia pseudocylindrospora ATCC 24169 and Aspergillus niger BCRC 32720 were found to reproducibly transform isosteviollactam (4 alpha-carboxy-13 alpha-amino-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactam) (3) into various compounds. Preparative-scale transformation of 3 with Abs. pseudocylindrospora yielded two new hydroxylated compounds (4 and 5), with conservation of the lactam ring. Preparative-scale transformation of 3 with Asp. niger afforded seven new compounds, 6 and 9-14, together with the known compounds 7 and 8. A single-crystal X-ray diffraction experiment confirmed the structure of 14. The suppressive effects of compounds 1-14 on the lipopolysaccharide-induced expression of the inducible nitric oxide synthase gene in RAW 264.7 macrophages were examined by a reverse-transcription real-time PCR analysis. With the exception of 7, all other compounds significantly reduced levels of iNOS mRNA relative to control cells, which were induced by LPS alone. Compounds 2, 3, and 5 were similar in activity to dexamethasone, while 9 was more potent.