oxalicumone A | 1391971-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: oxalicumone A
• 英文别名: dimethyl (2S,4R)-2,4-dihydroxy-2-[(2S)-5-hydroxy-7-methyl-4-oxo-2,3-dihydrothieno[2,3-b]chromen-2-yl]pentanedioate
• CAS: 1391971-76-8
• 化学式: C₁₉H₂₀O₉S
• 分子量: 424.428
• InChiKey: ICIIHDQGIKEFTE-RGIROJJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  165
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  oxalicumone A 、 2-硝基苯甲酰氯 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成
  参考文献：
  名称：

  Dihydrothiophene-condensed chromones from a marine-derived fungus Penicillium oxalicum and their structure–bioactivity relationship

  摘要：

  Four dihydrothiophene-condensed chromones including two new compounds oxalicumones D-E (1-2) and known oxalicumones A-B (3-4), along with five other known chromones were isolated from a culture broth of the marine gorgonian-associated fungus Penicillium oxalicum SCSGAF 0023. The structures of 1-2 were elucidated by spectroscopic analysis. Eleven derivatives 3a-3i and 4a-4b were obtained from the acylation of 3 and 4, respectively. Compounds 1-4, 3a-3e, 3g-3h, and 4b showed significant cytotoxicity against several carcinoma cell lines with IC50 <= 10 mu M. And their structure-bioactivity relationship was discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.028

文献信息

• 一类色酮类化合物及其制备方法和在制备抗肿 瘤与酶抑制剂药物中的应用
  申请人：中国科学院南海海洋研究所

  公开号：CN103483354B

  公开（公告）日：2016-01-20

  本发明公开了一类色酮类化合物及其制备方法和在制备抗肿瘤与酶抑制剂药物中的应用。本发明的如式（Ⅰ）所示的含硫色酮类化合物对肺腺癌细胞、组织细胞淋巴瘤细胞、白血病细胞、胃癌细胞、急性淋巴母细胞白血病细胞、急性粒细胞白血病细胞或肝癌细胞的生长有较强的抑制作用，对JAK3，AuroraA和ABL有抑制作用，在制备抗肿瘤以及酶抑制剂药物方面有良好的应用前景。
• Cytotoxic Dihydrothiophene-Condensed Chromones from the Marine-Derived Fungus Penicillium oxalicum
  作者：Yu-Lin Sun、Jie Bao、Kai-Sheng Liu、Xiao-Yong Zhang、Fei He、Yi-Fei Wang、Xu-Hua Nong、Shu-Hua Qi

  DOI：10.1055/s-0033-1350805

  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. 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 and 2 were established by using the modified Mosher ester method and circular dichroism data of an in situ formed [Rh-2(OCOCF3)(4)] and [Mo-2(OAc)(4)] complex. (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 was discussed.
• 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.
• Dihydrothiophene-condensed chromones from a marine-derived fungus Penicillium oxalicum and their structure–bioactivity relationship
  作者：Jie Bao、Jin-Feng Luo、Xiao-Chu Qin、Xin-Ya Xu、Xiao-Yong Zhang、Zheng-Chao Tu、Shu-Hua Qi

  DOI：10.1016/j.bmcl.2014.04.028

  日期：2014.6

  Four dihydrothiophene-condensed chromones including two new compounds oxalicumones D-E (1-2) and known oxalicumones A-B (3-4), along with five other known chromones were isolated from a culture broth of the marine gorgonian-associated fungus Penicillium oxalicum SCSGAF 0023. The structures of 1-2 were elucidated by spectroscopic analysis. Eleven derivatives 3a-3i and 4a-4b were obtained from the acylation of 3 and 4, respectively. Compounds 1-4, 3a-3e, 3g-3h, and 4b showed significant cytotoxicity against several carcinoma cell lines with IC50 <= 10 mu M. And their structure-bioactivity relationship was discussed. (C) 2014 Elsevier Ltd. All rights reserved.