Diethyl <<1-(phenylsulfonyl)-3-(β-carbethoxyvinyl)indol-2-yl>methyl>phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Diethyl <<1-(phenylsulfonyl)-3-(β-carbethoxyvinyl)indol-2-yl>methyl>phosphonate
• 英文别名: diethyl-1-phenylsulfonyl-(3-((E)-2-(ethoxycarbonyl)vinyl)-indol-2-yl)methylphosphonate；(E)-ethyl 3-{2-[(diethoxyphosphoryl)methyl]-1-(phenylsulfonyl)1H-indol-3-yl}acrylate；diethyl [1-phenylsulfonyl-3-(β-carbethoxyvinyl)indol-2-yl]methylphosphonate；ethyl (E)-3-[1-(benzenesulfonyl)-2-(diethoxyphosphorylmethyl)indol-3-yl]prop-2-enoate
• 化学式: C₂₄H₂₈NO₇PS
• 分子量: 505.529
• InChiKey: WDXSNEMVSOHUPJ-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Diethyl <<1-(phenylsulfonyl)-3-(β-carbethoxyvinyl)indol-2-yl>methyl>phosphonate 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 ethyl 4-[2-(4-methoxystyryl)-1-phenylsulfonyl-indol-3-yl]-1-phenylsulfonyl-pyrrole-3-carboxylate
  参考文献：
  名称：

  双齿菌类的合成方法：吡咯并[2,3-c]咔唑，吡咯二苯并噻吩和苯并[e]吲哚的简便合成方法

  摘要：

  通过使用三烯前体的分子内环化反应，可以轻松合成双齿yo草的吡咯并[2,3- c ]咔唑核心单元。该方法还应用于吡咯二苯并噻吩和苯并[ e ]吲哚衍生物的合成。

  DOI：

  10.1002/ejoc.201600674
• 作为产物：
  描述：

  2-甲基吲哚-3-甲醛 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 17.0h， 生成 Diethyl <<1-(phenylsulfonyl)-3-(β-carbethoxyvinyl)indol-2-yl>methyl>phosphonate
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.

  DOI：

  10.1021/jo00112a011

文献信息

• Synthesis and Biological Evaluation of Calothrixins B and their Deoxygenated Analogues
  作者：Bose Muthu Ramalingam、Nachiappan Dhatchana Moorthy、Somenath Roy Chowdhury、Thiyagarajan Mageshwaran、Elangovan Vellaichamy、Sourav Saha、Karthikeyan Ganesan、B. Navin Rajesh、Saleem Iqbal、Hemanta K. Majumder、Krishnasamy Gunasekaran、Ramamoorthy Siva、Arasambattu K. Mohanakrishnan

  DOI：10.1021/acs.jmedchem.7b01797

  日期：2018.2.8

  A series of calothrixin B (2) analogues bearing substituents at the ‘E’ ring and their corresponding deoxygenated quinocarbazoles lacking quinone unit were synthesized. The cytotoxicities of calothrixins 1, 2, and 15b–p and quinocarbazole analogues were investigated against nine cancer cell lines. The quinocarbazoles 21a and 25a inhibited the catalytic activity of human topoisomerase II. The plasmid

  合成了一系列在“ E”环上带有取代基的邻氨基吡啶B（2）类似物及其缺少醌单元的脱氧喹咔唑。calothrixins的细胞毒性1，2，和15B - p和quinocarbazole类似物针对9个癌细胞系进行了研究。喹咔唑21a和25a抑制人拓扑异构酶II的催化活性。质粒DNA calothrixins裂解能力1，2，和15B - p确定的化合物15H导致DNA裂解的效果与calothrixin A（1）相当。Calothrixin A（1），3-fluorocalothrixin 15h和4- fluoroquino咔唑21b诱导了广泛的DNA损伤，随后凋亡的细胞死亡。光谱和质粒解旋研究证明了喹咔唑结合的插入模式。我们确定了两种有前途的候选药物，即在动物模型中具有低毒性的3-氟calothrixin B 15h及其脱氧衍生物4-氟喹咔唑21b对GI 50为1 nM的NCI-H460细胞系具有有效的细胞毒性。
• Lewis Acid-Mediated Michaelis−Arbuzov Reaction at Room Temperature: A Facile Preparation of Arylmethyl/Heteroarylmethyl Phosphonates
  作者：Ganesan Gobi Rajeshwaran、Meganathan Nandakumar、Radhakrishnan Sureshbabu、Arasambattu K Mohanakrishnan

  DOI：10.1021/ol1029436

  日期：2011.3.18

  A facile preparation of arylmethyl and heteroarylmethyl phosphonate esters was achieved involving a Lewis acid mediated Michaelis-Arbuzov reaction at room temperature. Interaction of arylmethyl halides/alcohols with triethyl phosphite in the presence of Lewis acid at room temperature afforded phosphonate esters in good yields.
• Ethyl β-{2-[4-(dimethylamino)phenyliminomethyl]-1-(phenylsulfonyl)indol-3-yl}acrylate
  作者：K. Sethu Sankar、S. Kannadasan、D. Velmurugan、P. C. Srinivasan、S. Shanmuga Sundara Raj、H.-K. Fun

  DOI：10.1107/s0108270102005152

  日期：2002.5.15

  The title compound, C28H27N3O4S, crystallizes in the centro-symmetric space group P2(1)/n, with one molecule in the asymmetric unit. In the indole ring, the dihedral angle between the fused rings is 3.6 (1)degrees. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 79.2 (1)degrees with the best plane of the indole moiety. The phenyl ring of the dimethylaminophenyl group is orthogonal to the phenyl ring of the phenylsulfonyl group. The dihedral angle formed by the weighted least-squares planes through the pyrrole ring and the phenyl ring of the dimethylaminophenyl group is 7.8 (1)degrees. The molecular structure is stabilized by C-H...O and C-H...N interactions.
• A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder
  作者：Arasambattu K. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1021/jo00112a011

  日期：1995.4

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.
• Synthetic Approach to Dictyodendrins: A Facile Synthesis of Pyrrolo[2,3-<i>c</i>]carbazole, Pyrrolodibenzothiophene, and Benzo[<i>e</i>]indole
  作者：Potharaju Raju、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201600674

  日期：2016.9

  A facile synthesis of the pyrrolo[2,3‐c]carbazole core unit of dictyodendrins has been achieved by using an intramolecular cyclization reaction of a triene precursor. The method was also applied to the syntheses of pyrrolodibenzothiophene and benzo[e]indole derivatives.

  通过使用三烯前体的分子内环化反应，可以轻松合成双齿yo草的吡咯并[2,3- c ]咔唑核心单元。该方法还应用于吡咯二苯并噻吩和苯并[ e ]吲哚衍生物的合成。