dimethyl (2S,4R)-2-hydroxy-2-[(2S)-5-hydroxy-7-methyl-4-oxo-2,3-dihydrothieno[2,3-b]chromen-2-yl]-4-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxypentanedioate | 1391971-83-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: dimethyl (2S,4R)-2-hydroxy-2-[(2S)-5-hydroxy-7-methyl-4-oxo-2,3-dihydrothieno[2,3-b]chromen-2-yl]-4-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxypentanedioate
• CAS: 1391971-83-7
• 化学式: C₂₉H₂₇F₃O₁₁S
• 分子量: 640.588
• InChiKey: XCRAJLXVQINLIG-XWTFPBBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  oxalicumone A 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 生成 dimethyl (2S,4R)-2-hydroxy-2-[(2S)-5-hydroxy-7-methyl-4-oxo-2,3-dihydrothieno[2,3-b]chromen-2-yl]-4-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxypentanedioate
  参考文献：
  名称：

  Cytotoxic Dihydrothiophene-Condensed Chromones from Marine-Derived Fungus Penicillium oxalicum

  摘要：

  Two new dihydrothiophene-condensed chromones and a new natural chromone, namely oxalicumones A-C (1-3), respectively, were isolated from a culture broth of a marine-derived fungus Penicillium oxalicum SCSGAF 0023, Meripilaceae family. The structures of 1-3 and acetylated derivatives of 1 (4-7) were elucidated on the basis of spectroscopic methods and chemical reactions. The absolute configuration of 1 was established by using the modified Mosher ester method and circular dichroism data of in situ formed [Rh-2(OCOCF3)(4)] and [Mo-2(OAc)(4)] complexes. (R)-MTPA ester of 1 showed cytotoxicity against A375, SW-620, and HeLa carcinoma cell lines with IC50 values of 8.9, 7.8, and 18.4 mu M, respectively. Compound 1 displayed cytotoxicity against A375 and SW-620 cell lines with IC50 values of 11.7 and 22.6 mu M, respectively. The structure-biological activity relationship of 1 is discussed.

  DOI：

  10.1055/s-0032-1327874

文献信息

• Cytotoxic Dihydrothiophene-Condensed Chromones from Marine-Derived Fungus Penicillium oxalicum
  作者：Yu-Lin Sun、Fei He、Kai-Sheng Liu、Xiao-Yong Zhang、Jie Bao、Yi-Fei Wang、Xu-Hua Nong、Xin-Ya Xu、Shu-Hua Qi

  DOI：10.1055/s-0032-1327874

  日期：——

  Two new dihydrothiophene-condensed chromones and a new natural chromone, namely oxalicumones A-C (1-3), respectively, were isolated from a culture broth of a marine-derived fungus Penicillium oxalicum SCSGAF 0023, Meripilaceae family. The structures of 1-3 and acetylated derivatives of 1 (4-7) were elucidated on the basis of spectroscopic methods and chemical reactions. The absolute configuration of 1 was established by using the modified Mosher ester method and circular dichroism data of in situ formed [Rh-2(OCOCF3)(4)] and [Mo-2(OAc)(4)] complexes. (R)-MTPA ester of 1 showed cytotoxicity against A375, SW-620, and HeLa carcinoma cell lines with IC50 values of 8.9, 7.8, and 18.4 mu M, respectively. Compound 1 displayed cytotoxicity against A375 and SW-620 cell lines with IC50 values of 11.7 and 22.6 mu M, respectively. The structure-biological activity relationship of 1 is discussed.