denigrin A | 1593821-37-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: denigrin A
• 英文别名: 3,4-Bis(4-hydroxyphenyl)-1-[2-(4-hydroxyphenyl)ethyl]pyrrole-2,5-dione；3,4-bis(4-hydroxyphenyl)-1-[2-(4-hydroxyphenyl)ethyl]pyrrole-2,5-dione
• CAS: 1593821-37-4
• 化学式: C₂₄H₁₉NO₅
• 分子量: 401.419
• InChiKey: REWIMHIVGDGBBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  denigrin A 、 乙酸酐 在 吡啶 作用下， 以3 mg的产率得到
  参考文献：
  名称：

  Denigrins A–C: new antitubercular 3,4-diarylpyrrole alkaloids fromDendrilla nigra

  摘要：

  Chemical diversity is vital to antitubercular drug discovery as it ensures a novel bioactivity profile. Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds denigrins A-C, with potent antitubercular activity. Spectral and chemical analyses confirmed that these three compounds belong to the 3,4-diaryl pyrrole alkaloid category. The presence of monohydroxy substitution on benzene rings is not very common in lamellarin and related 3,4-diaryl pyrrole alkaloids isolated from marine invertebrates. Among these, denigrin C showed highest potency (minimum inhibitory concentration 4g/mL) against Mycobacterium tuberculosis H37Rv.

  DOI：

  10.1080/14786419.2014.891112
• 作为产物：
  描述：

  苯甲醚 在 碘 、 sodium acetate 、 palladium diacetate 、 三溴化硼 、 溶剂黄146 、 苯甲醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 38.4h， 生成 denigrin A
  参考文献：
  名称：

  抗结核海洋生物碱洋地黄素A和B的合成

  摘要：

  抗结核海洋生物碱洋地精A和B的第一次合成分三步和五步完成，马来酸酐的总收率分别为62％和31％。合成的关键特征包括有效的Mizoroki-Heck反应，几何学控制的乙烯基醇醛缩合和一锅内酰胺化。该合成首先证明了马来酸酐在钯催化的与二芳基碘鎓盐的交叉偶联反应中的适用性。

  DOI：

  10.1016/j.tetlet.2018.06.013

文献信息

• 10.1021/acs.jnatprod.3c01177
  作者：Yi, Liangguang、Tan, Shen、White, Lorenzo V.、Liang, Min-Yi、Banwell, Martin G.

  DOI：10.1021/acs.jnatprod.3c01177

  日期：——

  The title marine natural products have been prepared by total synthesis and in the case of congeners 3, 6, and 7 for the first time. Each of these was obtained by manipulation of readily prepared denigrin B (2). The structure, 3, assigned to denigrin C is shown to be incorrect. Reaction of compound 2 with DDQ has led, in high yield, to the related natural product spirodactylone (16), while treating

  标题海洋天然产物是通过全合成方法制备的，同系物3、6和7是首次制备。这些都是通过操作容易制备的 denigrin B ( 2 ) 获得的。分配给 denigrin C 的结构3被证明是不正确的。化合物2与DDQ的反应以高产率产生相关的天然产物螺缩酮( 16 )，同时用PIFA/BF 3 ·Et 2 O处理相应的全甲基醚15 ，得到具有异构骨架的化合物20 。
• Synthesis of anti-tubercular marine alkaloids denigrins A and B
  作者：Milandip Karak、Tohru Oishi、Kohei Torikai

  DOI：10.1016/j.tetlet.2018.06.013

  日期：2018.7

  The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride

  抗结核海洋生物碱洋地精A和B的第一次合成分三步和五步完成，马来酸酐的总收率分别为62％和31％。合成的关键特征包括有效的Mizoroki-Heck反应，几何学控制的乙烯基醇醛缩合和一锅内酰胺化。该合成首先证明了马来酸酐在钯催化的与二芳基碘鎓盐的交叉偶联反应中的适用性。
• Denigrins A–C: new antitubercular 3,4-diarylpyrrole alkaloids from<i>Dendrilla nigra</i>
  作者：Muthyala Murali Krishna Kumar、Jarpula Devilal Naik、Kancherla Satyavathi、Hechhu Ramana、Pemmadi Raghuveer Varma、Kurre Purna Nagasree、Desaraju Smitha、Desaraju Venkata Rao

  DOI：10.1080/14786419.2014.891112

  日期：2014.6.18

  Chemical diversity is vital to antitubercular drug discovery as it ensures a novel bioactivity profile. Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds denigrins A-C, with potent antitubercular activity. Spectral and chemical analyses confirmed that these three compounds belong to the 3,4-diaryl pyrrole alkaloid category. The presence of monohydroxy substitution on benzene rings is not very common in lamellarin and related 3,4-diaryl pyrrole alkaloids isolated from marine invertebrates. Among these, denigrin C showed highest potency (minimum inhibitory concentration 4g/mL) against Mycobacterium tuberculosis H37Rv.