(2-((4-chlorophenyl)amino)-2-oxoethyl)triphenylphosphonium

• 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: (2-((4-chlorophenyl)amino)-2-oxoethyl)triphenylphosphonium
• 英文别名: (4-Chlor-anilinocarbonylmethyl)-triphenyl-phosphonium；4-chlorophenylaminocarbonylmethyl triphenylphosphonium chloride；[2-(4-Chloroanilino)-2-oxoethyl]-triphenylphosphanium;chloride
• 化学式: C₂₆H₂₂ClNOP*Cl
• 分子量: 466.347
• InChiKey: TZPVWFMQKLNMNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-((tert-butyldimethylsilyl)oxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde 、 (2-((4-chlorophenyl)amino)-2-oxoethyl)triphenylphosphonium 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以73%的产率得到(E)-4-(4-((tert-butyldimethylsilyl)oxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-N-(4-chlorophenyl)but-2-enamide
  参考文献：
  名称：

  Mycophenolic anilides as broad specificity inosine-5’-monophosphate dehydrogenase (IMPDH) inhibitors

  摘要：

  Inosine-5'-monophosphate dehydrogenase (IMPDH) is a potential target for microorganisms. However, identifying inhibitor design determinants for IMPDH orthologs continues to evolve. Herein, a series of mycophenolic anilide inhibitors of Cryptosporidium parvum and human IMPDHs are reported. Furthermore, molecular docking of 12 (e.g. SH-19; CpIMPDH Ki,app = 0.042 ± 0.015 µM, HsIMPDH2 Ki,app = 0.13 ± 0.05 µM) supports different binding modes with the two enzymes. For CpIMPDH the inhibitor extends into a pocket in an adjacent subunit. In contrast, docking suggests the inhibitor interacts with Ser276 in the NAD binding site in HsIMPDH2, as well as an adjacent pocket within the same subunit. These results provide further guidance for generating IMPDH inhibitors for enzymes found in an array of pathogenic microorganisms, including Mycobacterium tuberculosis.

  DOI：

  10.1016/j.bmcl.2020.127543
• 作为产物：
  描述：

  对氯苯胺 在 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 33.5h， 生成 (2-((4-chlorophenyl)amino)-2-oxoethyl)triphenylphosphonium
  参考文献：
  名称：

  One-Pot Synthesis of Indolo[2,3-c]quinolin-6-ones by Sequential Photocyclizations of 3-(2-Azidophenyl)-N-phenylacrylamides

  摘要：

  A one-pot synthesis of indolo[2,3-c]quinolin-6(7H)-ones was achieved by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides in moderate to high yields. The reactions proceeded via photochemical cyclization of aryl azides to form N-phenylindol-2-carbamides and subsequent 6 pi-electrocyclic reaction and oxidative aromatization to afford the corresponding indolo[2,3-c]quinolin-6(7H)-ones.

  DOI：

  10.1055/s-0032-1317703

文献信息

• Fuerst,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1962, vol. 17, p. 299 - 313
  作者：Fuerst,H. et al.

  DOI：——

  日期：——
• One-Pot Synthesis of Indolo[2,3-c]quinolin-6-ones by Sequential Photocyclizations of 3-(2-Azidophenyl)-N-phenylacrylamides
  作者：Wei Zhang、Zhanshan Li、Weixia Wang、Xiaotian Zhang、Congcong Hu

  DOI：10.1055/s-0032-1317703

  日期：——

  A one-pot synthesis of indolo[2,3-c]quinolin-6(7H)-ones was achieved by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides in moderate to high yields. The reactions proceeded via photochemical cyclization of aryl azides to form N-phenylindol-2-carbamides and subsequent 6 pi-electrocyclic reaction and oxidative aromatization to afford the corresponding indolo[2,3-c]quinolin-6(7H)-ones.
• US3972928A
  申请人：——

  公开号：US3972928A

  公开（公告）日：1976-08-03
• Mycophenolic anilides as broad specificity inosine-5’-monophosphate dehydrogenase (IMPDH) inhibitors
  作者：Seungheon Lee、Angela F. Ku、Mohana Rao Vippila、Yong Wang、Minjia Zhang、Xingyou Wang、Lizbeth Hedstrom、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2020.127543

  日期：2020.12

  Inosine-5'-monophosphate dehydrogenase (IMPDH) is a potential target for microorganisms. However, identifying inhibitor design determinants for IMPDH orthologs continues to evolve. Herein, a series of mycophenolic anilide inhibitors of Cryptosporidium parvum and human IMPDHs are reported. Furthermore, molecular docking of 12 (e.g. SH-19; CpIMPDH Ki,app = 0.042 ± 0.015 µM, HsIMPDH2 Ki,app = 0.13 ± 0.05 µM) supports different binding modes with the two enzymes. For CpIMPDH the inhibitor extends into a pocket in an adjacent subunit. In contrast, docking suggests the inhibitor interacts with Ser276 in the NAD binding site in HsIMPDH2, as well as an adjacent pocket within the same subunit. These results provide further guidance for generating IMPDH inhibitors for enzymes found in an array of pathogenic microorganisms, including Mycobacterium tuberculosis.